Not “do you have smart people?” Every founder says yes to that. I mean: do you believe the organization, as a system, can perceive reality more accurately than you can alone?

That answer tells me a lot. The CEO’s job changes when the company starts to know things the CEO does not. Early on, the founder is often the company’s best source of judgment. They have the most customer context, the clearest product intuition, and the deepest sense of urgency. But as the company grows, knowledge spreads. Sales knows things product does not. Finance sees risks the founder cannot feel. Legal, compliance, research, security, and people teams start solving problems the founder cannot see from the CEO’s desk.

The founder’s job is no longer to be the company’s intelligence. It is to build an organization whose intelligence exceeds their own. This transition is difficult because it requires shifting between two very different leadership modes.

Operator mode

Operator-CEOs are the company’s brain, and employees are the hands. They’re expected to be deeply involved in strategy, to hold the anxiety for all outcomes, to be the most central person in almost every important decision. They delegate execution, not thinking.

This model works beautifully at a certain scale. The early-stage startup is essentially designed for it. When you’re ten people trying to figure out product-market fit, you want a founder who is in every customer conversation, reviewing every design decision, opinionated about everything. Intense involvement is a feature, not a bug. Speed, coherence, and conviction are what you need, and one brain calling the shots provides exactly that.

The fatal flaw of operator mode, though, is a specific kind of blind spot. As companies grow, more and more mission-critical work becomes invisible to the founder.

Because an operator cannot personally evaluate the quality of work in specialized areas like finance or legal, they struggle to distinguish between a function that’s genuinely bureaucratic and one that’s doing vital work outside their line of sight. They tend to misread “I can’t evaluate this” as “this is probably unimportant.”

You see it in the small moments. The founder rolls their eyes at the legal review. The new VP of Finance keeps raising risks that feel like “process.” The head of People says the hiring loop is broken, and everyone nods, and then nothing changes because the CEO can’t quite tell whether this is real work or HR theater.

The result is underinvestment in exactly the capabilities the company needs as it scales. Beyond that, the operator is a bottleneck by design. Every significant decision goes through one person, so the organization can only move as fast as that person can. Strong employees figure this out quickly and quit (they want to think, not just execute). Over time, an organization stuck in operator mode ends up with a team optimized for loyalty and execution rather than judgment. (If this sounds familiar, hold that thought.)

Orchestrator mode

The orchestrator accepts, as a baseline, that the organization knows things they don’t. Their job is to set direction, create the conditions for good decisions to happen without them in the room, and hold the whole thing together when those decisions start to conflict.

But orchestration is not abdication. They build the machinery by which judgment improves: clear strategy, explicit decision rights, strong executives, fast feedback loops, and enough direct contact with reality that they can still tell when the system is fooling itself.

Satya Nadella is the obvious contemporary example. He came in with deep technical and organizational credibility, especially from Microsoft’s cloud business, but he did not try to be the smartest person in every Microsoft business. His achievement was not personally out-thinking every division; it was making those divisions add up to something coherent.

The orchestrator has their own failure modes. Strategy can become a collage - the sum of what smart people in each domain want to do - rather than genuine direction. The leader can lose ground truth, becoming so abstracted from execution that they can’t tell when the organization is drifting or, worse, lying to them. And accountability diffuses: when everyone owns a piece of a decision, hard tradeoffs have a way of falling through the cracks (and usually right onto the plates of incredibly frustrated middle managers).

John Sculley at Apple is the classic example of that failure mode. He brought professional management discipline to early Apple, but lacked the unifying product judgment to force hard choices. Under his tenure, Apple’s strategy became a sprawling collage of overlapping product lines designed to appease internal divisions rather than serve a clear vision. He built the machine, but forgot to drive it.

The startup fork

Successful founders are almost always operators, and they should be. The hard part is that the same founder behavior can be exactly right at one stage and exactly wrong at the next. At ten employees, being in every important decision creates coherence. At a hundred, it teaches the company not to think until you enter the room.

If a company is successful, it eventually creates more context than one founder can hold. At some point, a founder hits an inflection point where they have a choice to make - often without fully realizing they’re making it (usually right after a great VP rage-quits).

One option is to become an orchestrator: to genuinely change how you conceive of your role, to hire people who will push back on you, to accept that important decisions are being made every day of which you’re not aware, and to recognize that this is correct. This is hard. It requires a kind of ego flexibility that founders are not typically selected for. It means sitting in a product review, watching a team make a choice you wouldn’t make, and keeping your mouth shut - not because you suddenly agree, but because stepping in to “fix” it would teach them to stop thinking for themselves. (Finding a good coach can also help.)

The other option is to restructure the company to stay small enough for the operator model (aka, “founder mode”). One way to read Brian Chesky’s recent Airbnb reorganization is as a deliberate choice to preserve more operator leverage at scale. After a period of growth into genuine organizational complexity, Chesky reorganized back into something tighter - something he could run the way he ran it when it was small.

When is this a legitimate strategic choice versus a refusal to adapt? Well, product-market fit buys time (though it doesn’t repeal complexity). With extreme PMF, an undisputed market leader can afford the bottlenecks of an overgrown operator because the product’s momentum covers for organizational drag. Given Airbnb’s market dominance, Chesky had the luxury to make that choice.

Steve Jobs is perhaps the best historical example of a founder who successfully built a massive company around his operator mode. When he returned to Apple, he famously slashed the product line to a simple grid - cleaning up the exact collage Sculley had created. He actively constrained the company’s surface area so his operator intuition could still touch everything that mattered. Crucially, though, in the one critical area he knew he couldn’t add value (global manufacturing and supply chain), he handed it to Tim Cook and let him build a machine. Jobs found a third mode: stay close to the parts where your judgment is unusually good, and get out of the way where it isn’t.

Contrast that with Travis Kalanick at Uber. Kalanick had brilliant product and market intuition, but he is the clearest example of the operator’s blind spot. He devalued the specialized functions he couldn’t personally evaluate - HR, legal, compliance, corporate culture. Under his leadership, “I don’t understand why this matters” became functionally identical to “this does not matter.” Uber didn’t implode because the product lacked PMF. It imploded because PMF created a bigger, more dangerous company than Kalanick’s operating model could safely contain.

The scale problem

This is not only a startup problem. The bigger and older the institution, the less forgiving this gets.

The United States federal government is not a startup (tech-exec posts on X notwithstanding). It manages massive complexity across domains where expertise takes decades to develop. Yet the current administration looks a lot like operator logic pushed past its useful range: a small circle of trusted executors is being stacked with more and more responsibilities, not because the work consolidates naturally but because the operator needs people he trusts rather than people with depth. Rubio has been asked to serve simultaneously as Secretary of State and National Security Adviser, while Bill Pulte has been moved into the acting Director of National Intelligence role while retaining his existing housing-finance responsibilities.

This is not just a style preference. It’s a scale error. A way of working that can be useful when the system is small becomes dangerous when the system is too large for any one person, or any small circle, to understand. Jobs proved that an operator can only scale if they aggressively constrain the organization’s scope and selectively orchestrate the domains they don’t understand. This administration is doing the opposite: applying operator logic to an unconstrained organization, while replacing people with domain depth with people whose main qualification is trust.

Operator logic doesn’t build depth. It builds loyalty. And an organization run on loyalty rather than expertise is one that devalues what it doesn’t understand.

The irony is that this is the same trap that catches founders. They don’t fail because they’re not smart or not hardworking. They fail because they’re applying a model that was right for one stage to a context it was never designed for.

The question worth asking

So back to the opening question: does your company know things you don’t?

If you’re a founder, a few years in, and the honest answer is still no, that’s worth sitting with. Either your company hasn’t grown yet, or you’ve built an organization still only as capable as you. That’s a ceiling, not a strategy.

The goal is not to become an orchestrator because orchestration is morally superior. Some businesses can and should remain tightly founder-led. But that should be a conscious choice, not a reflex. If the company is only as capable as the founder, then the founder has not built an organization. They have built a dependency.

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PS

One reason this transition is so hard: some leaders come out of apprenticeship cultures (like medicine, banking, or family businesses) where leadership mostly means being better at the same work. If your whole career taught you that seniority means doing the same craft at a higher level, it’s easy to assume the people below you are just less-developed versions of you. Then you enter a genuinely complex organization, where specialized teams do work that is entirely invisible to you, and the old model breaks. You don’t just struggle to orchestrate. You may not even realize orchestration is the job.

I used to think I could get by on six hours of sleep. Most of us do. We grab a coffee at 2 PM, push through the afternoon slump, and figure it’s just the baseline cost of being a busy adult. But a US Navy study wrecked that delusion for me, and it holds the real thesis for how we need to think about rest.

For decades, the Navy used an 18-hour watch cycle for submariners. This schedule meant sailors regularly got much less than the recommended 7 to 8 hours of rest in a 24-hour period. When researchers finally tested the cumulative effects of this schedule, they found that sleeping 6 hours a night for two weeks straight causes the exact same level of cognitive impairment as staying awake for two full days. Those restricted to 4 hours of sleep reached this same level of impairment much faster (showing severe declines by about day 6).

The most terrifying part of the study was the invisible decline of the sleep-deprived brain. The sailors actually felt fine, and their subjective feeling of sleepiness leveled off, but their objective reaction times plummeted to legally drunk levels. They genuinely believed they had adapted, even as their test scores collapsed. Like the sailors, I was lying to myself.

That’s the true danger of sleep deprivation, and it’s the core argument of this guide. Your judgment is the first casualty of exhaustion. As your cognitive bandwidth narrows, you lose the self-awareness required to realize how tired you actually are. It creates a brutal feedback loop: the less you sleep, the less able you are to make the rational decision to go to bed.

TikTok and Reddit are currently fixated on wringing an extra 2% of efficiency out of our sleep cycles with expensive tracking rings and complicated routines. But if you’re a normal person navigating work, friends, family, and the friction of modern life, you don’t need that noise. We just need to systematically reduce the friction around a few boring, highly effective basics.

Before we dive in: this is straightforward, but not easy. Sometimes life just gets in the way. If you have crying babies or toddlers waking up at 3 AM (or, ahem, a teen out with the car on a Saturday), you probably aren’t going to get enough sleep. There should be a different article on how to survive acute sleep deprivation (checklists, single-tasking, letting folks know what’s going on, and cutting yourself slack). But that’s not what this guide is for. This one is about fixing your baseline when you actually have the agency to do so.

Why sleep actually matters

We tend to treat sleep like passive downtime, but your brain’s actually doing the heavy lifting while you’re out. The American Academy of Sleep Medicine and the Sleep Research Society both say that adults need seven or more hours of sleep each night. Right now, nearly 36% of adults get six hours or less.

When we consistently sleep less than seven hours, things start to break. Short-term memory doesn’t get filed into long-term storage. Your glymphatic system acts as your brain’s plumbing network, and it absolutely requires deep sleep to function. Cerebrospinal fluid physically washes through the brain while you sleep to clear out metabolic waste (specifically amyloid-beta proteins). Failing to get enough restorative rest ruins your sleep architecture, and that disruption is strongly linked to the buildup of these proteins and the development of Alzheimer’s disease.

Lack of sleep also disrupts your hunger hormones, leptin and ghrelin. This shift drives intense hunger and cravings, making you significantly more prone to weight gain, insulin resistance, and type 2 diabetes. Combined with weakened immunity and cardiovascular stress, you can’t just power through these realities. We can, however, fix the underlying habits.

The ordered steps

Ignore the expensive gadgets and tackle these foundational steps. The first few are the absolute backbone of good sleep, while the latter ones are more conditional depending on your lifestyle. They’re ranked roughly by how much ROI you get for your effort.

1. Anchor your wake-up time and ignore the sleep bank

Stabilize your biological clock before you worry about anything else. Waking up at the exact same time every day, including weekends, is the single highest-yield habit for better rest. We have to abandon the myth of the sleep bank. You can’t accrue a sleep debt during the workweek and pay it off by binge-sleeping on Saturday. Studies show that weekend catch-up sleep causes metabolic dysregulation and social jet lag, giving your body a hangover every single Monday.

A 2024 study in the journal Sleep actually found that sleep regularity predicts mortality risk better than total sleep duration. Waking up at the same time keeps your brain’s master clock perfectly in sync, ensuring your evening melatonin release happens predictably. Of course, there’s some flexibility. Sleeping in by a half hour on a weekend is fine and won’t derail your rhythm.

2. Seek morning light

Your brain needs bright light to know the day has started. Getting 10 to 15 minutes of outdoor sunlight within an hour of waking up sends a massive biological signal to your brain. Indoor lighting usually isn’t bright enough to fully trigger this mechanism on its own. If you wake up before sunrise, turn on as many bright overhead lights as possible to start the wake-up process, and then get natural sunlight later when the sun is up.

If wrangling kids prevents you from stepping outside immediately, just get the light as soon as you realistically can. Any morning sunlight is vastly better than none. Your commute can be highly effective, as the natural light you receive while driving to work is often enough to trigger these biological signals. When bright natural light hits specialized cells in your eyes, it sends a direct signal to immediately halt melatonin production and start a countdown timer for when you’ll feel tired that evening.

3. Respect the caffeine half-life

I quit caffeine a few years ago. I did it mostly so I wouldn’t have to manage the chemical clock in my head, but the self-righteousness is nice, too. If you still drink coffee, you need to respect its caffeine half-life (roughly 6 hours).

If you drink a large coffee at 3 PM to survive a meeting, half of that caffeine is still actively circulating in your brain at 9 PM. A chemical called adenosine builds up in your brain throughout the day to create sleep pressure. Caffeine physically blocks the receptors that detect this pressure, hiding your exhaustion from your own brain. Try to set a strict caffeine cutoff time of 12 PM or 1 PM to ensure the drug clears your system before bed.

You might know someone who drinks an espresso after dinner and falls right asleep. But passing out isn’t the same thing as getting restorative rest. A landmark meta-analysis in the Journal of Clinical Sleep Medicine showed that consuming caffeine even six hours before bed disrupts objective sleep architecture. When monitored in a lab, even people who claim to be immune to caffeine and can fall asleep still show degraded sleep quality, reduced deep sleep, and frequent micro-awakenings.

4. Eliminate the alcohol trap

Alcohol’s the most misunderstood sleep aid in the world. A glass of wine might act as a sedative and help you conk out faster, but sedation isn’t quality sleep.

Alcohol initially acts as a central nervous system depressant, but its metabolism later in the night triggers a sympathetic nervous system arousal. This rebound effect suppresses highly restorative REM sleep early in the night and drives fragmented, low-quality rest in the second half (why you might wake up with a racing heart).

Social drinking is a very real part of adult life. If you choose to drink occasionally, lessen the blow to your sleep architecture by drinking smarter. Opt for a happy hour instead of a late nightcap, and aim to stop drinking at least 3 to 4 hours before your head hits the pillow. Drink a full glass of water for every alcoholic beverage and eat a solid meal to slow the absorption of alcohol into your bloodstream. Expect an elevated resting heart rate and poor sleep quality, accept it as the cost of a fun night out, and get back on your regular schedule the next day.

5. Control your environment and your stimuli

Remember that feedback loop of sleep deprivation? Your judgment degrades first as you get tired. Staying up late to watch another episode is usually an issue of competing goals and environmental friction, combined with that impaired judgment. Revenge bedtime procrastination (like bingeing Netflix when you know it’s time for bed) is a desperate bid to reclaim a sliver of your day when you lack the cognitive bandwidth to make a better choice. Make the right choice the default choice by moving your phone charger into the bathroom and buying a cheap alarm clock.

You also have to protect your brain’s association with the bed itself. The human brain is an associative machine. If you regularly answer work emails, watch television, or scroll through social media while lying under the covers, you train your nervous system to associate your mattress with alertness and stress. Use your bed exclusively for sleep and intimacy. If you want to read or watch a movie before bed, do it on the couch.

If you can’t fall asleep within 20 minutes, get out of bed and do a quiet activity in dim light until you feel sleepy. Staying in bed while frustrated teaches your nervous system to associate the mattress with anxiety. Break that friction by resetting in another room.

6. Cool and darken your shared cave

Aim for a bedroom temperature between 60 and 67 degrees. Your body must drop its core temperature by one to two degrees Fahrenheit to initiate and maintain sleep. If the ambient room temperature is too warm, your brain will struggle to cross the threshold into deep sleep. Combine this cooling with absolute darkness. Even small amounts of ambient light from streetlamps or electronics penetrate your eyelids and suppress pineal melatonin production. Blackout curtains or a simple eye mask are incredibly high-yield investments.

Clinical sleep guidelines often assume we sleep in isolated vacuum chambers. The reality is that most of us sleep in shared, messy ecosystems. You might know a cool room is best, but you still have to negotiate the thermostat with a partner who runs cold. Good sleep hygiene requires pragmatic compromises. Maybe suggest changes as temporary experiments rather than absolute rules. Agree to try a cooler thermostat setting for just two weeks to see how it impacts energy levels. If your partner runs cold, heat the person, not the room. Invest in separate blankets with different warmth levels rather than fighting over the duvet (my wife and I did this last year, and it’s been life-changing).

7. Time your meals and exercise

Late-night digestion competes with your body’s attempt to lower its core temperature and rest. Try to avoid heavy meals within three hours of your target bedtime. But going to bed hungry can also disrupt sleep by causing your blood sugar to drop, triggering the release of stress hormones like cortisol to wake you up. If you’re genuinely hungry before bed, opt for a small, easily digested snack rather than suffering through the hunger.

Aim to finish strenuous exercise at least two hours before you plan to sleep. A major meta-analysis in Sports Medicine found that evening exercise is generally beneficial for sleep, with one major exception. Vigorous, heart-pumping workouts completed within an hour of bedtime significantly delay sleep onset and reduce total sleep time because they heavily elevate cortisol, heart rate, and core body temperature.

8. Optimize the mattress within reason

The right environment’s crucial, but don’t fall into the trap of thinking a luxury mattress will cure your sleep problems. Most studies suggest we should use a medium-firm mattress to alleviate back pain, but your preferences may differ, and spending lots of money is unlikely to produce measurably better sleep. Treat finding the right mattress as another experiment. Take advantage of generous trial periods and return policies offered by many companies to test out different options. Get something comfortable and supportive that isolates motion if you share a bed, and then focus your effort on behavioral habits.

The noise: supplements and biohacking

Once you master the basics, you might be tempted by the world of sleep supplements and trends. These interventions usually offer marginal gains at best for people who are already doing everything right. Some are easy and safe enough to try, while others are potentially harmful and should be avoided entirely.

Melatonin is a clock, not a hammer

Melatonin is the most widely misused sleep supplement on the market. People treat it like a sleeping pill because large doses right before bed act as a mild sedative. Biologically, melatonin is a darkness signal that tells your brain it’s time to begin the wind-down process. Taking massive doses is counterproductive and usually leaves you groggy the next day. Clinical data show melatonin is most effective in micro-doses (0.3mg to 0.5mg, which is way below most of what is sold but is within the range of what your body produces naturally) taken several hours before your target bedtime to gently shift your circadian clock.

Blue-light glasses and night modes

Consumer blue-light blocking glasses are incredibly popular, but the clinical data don’t strongly support their use. Standard consumer lenses don’t actually filter out enough light to prevent the suppression of melatonin. Software features like night mode or warm color shifts on your phone and computer are also mostly a matter of personal preference. The raw brightness of the screen and the cognitive stimulation of whatever you’re looking at matter far more than the color tint. Turn down the overall brightness of your screens or, ideally, put devices away entirely.

Over-the-counter aids and cannabis

People frequently turn to over-the-counter antihistamines like Benadryl or ZzzQuil when they struggle to sleep. Your body builds a rapid tolerance to them, rendering them ineffective within days. Long-term use of these anticholinergic drugs is also linked to an increased risk of dementia in older adults. Cannabis is often used to initiate sleep, but it actively disrupts your sleep architecture by suppressing REM sleep and often causes rebound insomnia when you try to stop using it.

Magnesium and other supplements

A massive industry has been built around supplements like Magnesium Threonate, Apigenin, and L-Theanine. While some mechanistic evidence suggests these compounds can promote relaxation, the clinical data for their effectiveness in treating actual sleep issues are relatively weak. The American Academy of Sleep Medicine states there’s insufficient clinical evidence to recommend supplements like magnesium for the treatment of chronic insomnia. (I take a low-dose generic magnesium pill before bed because it gives me incredibly vivid dreams - but not for sleep.)

The mouth taping trend

Mouth taping has become a popular social media trend, promising deeper sleep and reduced snoring by forcing nasal breathing. Nasal breathing is physiologically superior, but taping your mouth shut is a potentially dangerous band-aid for an undiagnosed problem. If you breathe through your mouth at night, it’s usually because your nasal airway is obstructed or because you suffer from obstructive sleep apnea. Taping your mouth doesn’t fix the obstruction; it just forces your body to work harder to get oxygen.

What about naps?

While napping is an incredible tool for cognitive performance if you follow a strict playbook (a NASA study found a 26-minute nap improved pilot alertness by 54%), naps are a double-edged sword.

Keep them under 30 minutes and finish them before 3 PM. A brief nap keeps you out of deep sleep, preventing that severe grogginess when you wake up. Keeping it early means you won’t burn off the valuable sleep pressure you need to fall asleep that night. Napping longer or later erodes your nighttime sleep drive and is linked to diabetes and metabolic dysregulation.

And while we’re here, you might have heard of polyphasic sleep (breaking your rest into multiple short chunks around the clock). Don’t worry about it. It’s an extreme optimization trend that you shouldn’t even consider.

Age-specific nuances

The biological rules of sleep change as we age. Teenagers aren’t just being lazy when they want to stay up until 1 AM and sleep until noon. Biology triggers a legitimate delay in the circadian phase during adolescence. Their bodies simply don’t release melatonin until much later in the evening than adults, making early school start times a severe biological mismatch.

Older adults frequently experience an advanced circadian phase, feeling tired very early in the evening and waking up before dawn. The timing shifts, but the biological requirement doesn’t. Older adults still need 7 to 8 hours of sleep for optimal health. Changes in brain architecture often make it much harder for them to consolidate that sleep, leading to frequent nighttime awakenings.

When to stop trying and see a doctor

Sometimes, good habits aren’t enough. If you’ve diligently reduced the friction in your routine for several weeks and you’re still chronically exhausted, it might be time to look for a medical issue. Good sleep hygiene can’t fix structural problems, and attempting to lifestyle-hack a clinical disorder is frustrating and dangerous. Consult a primary care physician or a specialist at a sleep clinic if you regularly experience certain warning signs.

Obstructive sleep apnea

Loud snoring, gasping for air, or waking up feeling like you’re choking are classic symptoms of Obstructive Sleep Apnea. This condition occurs when your airway physically collapses during sleep. If diagnosed, a CPAP machine physically keeps your airway open, immediately restoring oxygen levels and deep sleep. Talk to a doctor - if untreated, this is very dangerous.

Chronic insomnia

You likely need clinical support if you consistently can’t fall asleep or stay asleep despite having a good sleep environment and a strict schedule. Doctors usually prescribe Cognitive Behavioral Therapy for Insomnia (CBT-I) to address the underlying anxieties keeping you awake, as that’s been found to be successful in most people and much more effective than drugs.

Restless legs syndrome

An uncontrollable, uncomfortable urge to move your legs when you’re trying to rest in the evening is the hallmark of Restless Legs Syndrome. A doctor will likely check your iron levels and can prescribe supplements and/or medications - this is fixable.

Hypersomnia and narcolepsy

Severe daytime sleepiness that interferes with your life is a major red flag. If you find yourself falling asleep during normal, active situations (like driving, sitting in meetings, or talking with friends), your brain is experiencing a pathological level of sleep debt. Treatment is highly specialized and prescribed by a sleep specialist.

The truth about consumer sleep trackers

Wearable devices like the Apple Watch, Oura Ring, Garmin, and Fitbit have made tracking your rest incredibly accessible. But doctors rely on an electroencephalogram to directly measure electrical brain wave activity to accurately define sleep stages. Your smartwatch or tracking ring can’t read brain waves. These devices rely on secondary signals (primarily movement and heart rate variability) to estimate what your brain is doing.

Trackers often struggle with wakefulness detection because they rely heavily on movement. If you lie in bed awake but completely still, your device will likely assume you’re asleep. Consumer trackers often overestimate your total sleep time, creating a false sense of security about your rest. The detailed charts showing your light, deep, and REM sleep should be viewed as educated guesses rather than clinical facts - none of these trackers work universally well. Use them to observe broad, multi-week trends in your bedtime routine, but don’t obsess over a single night’s sleep score. If the numbers make you anxious, take them off.

The bottom line

We spend a lot of time obsessing over the perfect evening routine, our nighttime pills, the right mattress, and the exact temperature of our bedrooms. Those things matter; however, they’re entirely secondary to the real battle.

The biggest threat to your sleep isn’t a glowing screen or a late-afternoon cup of coffee. The biggest threat is the invisible decline of your own judgment. When you’re tired, your brain loses the capacity to realize it’s tired. It’s pernicious: you can’t decide to go to bed, which only makes you more exhausted the next day.

You don’t need more willpower to break that cycle. You need to build a system that makes the healthy choices automatic. Anchor your wake-up time, cut off your caffeine at noon, and put your phone charger in another room. Systematically eliminate the friction required to get into bed, and your biology will take care of the rest.

If there’s a shortcut, I’ll take it. If there is a tool that promises to do my work while I nap, I will buy it. When the new wave of “agentic AI” tools started dropping (tools like Claude Code, Devin, or AutoGPT), I was first in line. The pitch was incredible: Don’t just get help writing the code. Get an agent that writes the code, runs the tests, fixes the errors, and deploys it while you watch Netflix.

Trigger warning: this post will have a lot of “grumpy old man” energy.

I remember the last time we were promised a magical solution to software development. It was the early 2000s, and the promise was “outsourcing.” We were told that if we just wrote a detailed enough spec, we could hand it to a team in a different time zone, pay them a fraction of the cost, and wake up to a finished product.

We all know how that ended. We spent big bucks to build products that checked every box in the spec but failed in the market. I recall endlessly revising documents to explain “user delight” to a team that had never used the product, only to get back code that was technically functional but excruciating to use.

The good news is, today’s non-technical founders aren’t dropping $100k on an agency. They are dropping $20/month on Claude. But the bad news is the industry is lying to itself again.

I see founders convincing themselves that the reason outsourcing failed was the people. They think, “If I can write the perfect prompt and include the right context, the right skills, and use enough tokens, I’ll get it right,” and “Well, the offshore team didn’t understand my vision, but Claude Code does! Claude is smart!”

But outsourcing didn’t fail because of the people. It failed because the handoff is a lie.

The return of Waterfall

I recently tried to use Claude Code for a simple task, a Python script to scrape some data (well, a lot of data). I spent 20 minutes crafting the perfect prompt (the modern PRD). I set up the permissions. I hit enter. I leaned back.

Two hours later, I came back to a mess. I had 14 new files, 600 lines of code, and a confident README that described a script that didn’t quite work.

The agent had technically done what I asked. It wrote code. It passed tests. But it had built the wrong feature.

For example, the dataset had missing timestamps. A human partner would have asked, “Should we drop these rows or infer the time based on the sequence?” The agent just dropped them. It was a valid code decision - the script didn’t crash - but it made the time-of-day analysis I wanted to do impossible.

What it built was technically correct, but practically useless.

We’ve confused toil with thought.

We are trying to outsource the hard work of thinking to a machine that is designed to satisfy a prompt, not solve a problem. We are recreating waterfall development.

It feels like speed. It looks like shipped features. But it’s actually just “unplanned work” waiting to explode: the firefighting that destroys your roadmap. Agents are efficient engines for generating unplanned work. They let you ship “planned” code today that requires a forensic investigation to debug tomorrow.

Agents fail when you use them as a batch processor for ambiguous work. You trade the tight feedback loop of a copilot for the blind handoff of an agent.

When you use an agent to do the work for you, you skip the friction. You skip the learning. You get “alibi progress,” a pile of artifacts (code, text, slides) that look like work, but contain no actual understanding.

The “micro-Boeing“ moment

We’ve seen this movie before.

In the early 2000s, after the merger with McDonnell Douglas, Boeing’s culture shifted. The new finance-driven leadership didn’t want to run an engineering company; they wanted to run a “business.” And in a business, you reduce costs.

For the 787 Dreamliner, they decided that “integration” was just another cost center to be slashed.

They didn’t just outsource the parts (Boeing had always bought tires, landing gear, etc), they outsourced the integration (assembly). They told their “Tier 1” suppliers: “Here is the spec. You figure out how to build the entire fuselage section. Just send us the finished product.”

The finance team loved it. It looked efficient on a spreadsheet. But they had made a mistake: They had outsourced the struggle.

In the olden days, Boeing engineers fought with suppliers, argued over tolerances, and battled over how the wiring harness would fit through the bulkhead. That friction wasn’t waste; that friction was where the quality came from.

By handing off the integration, they removed the moment (and the incentive) for the different parts of the process to struggle together.

The result was a mess. It started with 787 sections that arrived at the factory and didn’t fit. It festered into a culture where nobody owned the whole. And it ended, twenty years later, when a cabin door plug blew out of a 737 MAX mid-flight. The door plug failure was symptomatic of the same pattern: when you separate the people doing the work from the people designing the work and from the people bringing it all together, you lose the ability to catch the small things that become big things.

My Python script was a “micro-Boeing” moment.

When I handed off the task to the agent, I created what manufacturing folks call traveled work: the work comes back without the why, and now you’re paying a tax to reconstruct the context.

This is an architectural failure, not just a process one. We forget that software architecture mirrors our org structure. When you hand off a task to an Agent, you are effectively creating a silo of one. You sever the high-bandwidth communication loops required to discover, understand, and solve complex problems. You aren’t just outsourcing the task; you are breaking the architecture.

Polanyi’s Paradox explains why: We know more than we can tell.

I can’t prompt my taste. I can’t prompt my risk tolerance. I can only apply it while I’m watching the work happen. When you pair-program or pair-write with a copilot, you transfer that knowledge in real-time. When you hand off to an agent, that knowledge is lost.

The partner and the associate

So, are agents useless? Absolutely not. I use them every day. But to use them effectively, I’ve found I have to treat them very differently depending on the mode I’m in.

When I use a copilot, it feels like pairing. I’m still driving; it’s just faster to explore options. I type a little, it suggests a little, I accept some, reject most, and the real work is that constant nudging (my judgment is in the loop every few seconds).

The authors of Apprenticeship Patterns call this “Rubbing Elbows.” You learn by sitting next to a master (or just a peer) and watching how they work. When I use a Copilot, I am rubbing elbows with the model. I am learning from its suggestions, and it is constrained by my intent.

An agent is different. An agent is a handoff. You point it at a task, go make coffee, and come back to a finished-looking artifact. That can be amazing, until you realize it made ten “reasonable” choices you never would have made, and now you’re debugging someone else’s mental model.

It’s like delegating to a brilliant first-year associate: they are smart, diligent, and eager to please, but they optimize for “finishing the task,” not “solving the problem.” And because you treat them as an expert, you don’t supervise them. You let them work all night, only to discover they produced the perfect solution to the wrong problem.

The mistake we make is assuming the associate can do the partner’s job just because they work hard and talk smart.

The commodity trap

Lately, I’ve noticed a pattern in myself. If I can build it in Claude Code, it might be cool, and it might solve a problem, but I’m likely not fundamentally adding value in a strategic way. (Check out my site https://goodmon.day to see what I mean.)

In engineering strategy, we distinguish between “Core” (what differentiates you) and “Context” (what you need to exist, like logging or payroll). Agents are incredible at Context. They can scaffold a boilerplate app in seconds. But if you use them for Core - if you let them define your unique value proposition - you are admitting that your Core is generic.

If I can describe the solution so perfectly that an agent can build it without my intervention, then I am building a commodity.

Satisficing vs. differentiation

The heuristic comes down to one question: Is “good enough” actually good enough?

Use agents for satisficing (the toil). There are parts of your job where “perfect” is a waste of time. Formatting a messy JSON blob from a legacy API. Writing unit tests for a stable function. Summarizing a 60-minute meeting transcript. Converting a Jira ticket into a release note. In these cases, the outcome is binary. It works, or it doesn’t. If the agent gets it 90% right, the cost of fixing the last 10% is low. Delegate the toil.

Use copilots for differentiation (the strategy). Then there is the work where you are making substantial bets: Defining the product vision, architecting a new system, or writing a difficult email to a churning client. In these cases, “satisficing” is failure - if your strategy is just “average,” you lose.

This doesn’t mean you can’t use agents within strategic work, like drafting copy, summarizing research, or enumerating edge cases. But you have to keep the core judgment loops tight. The agent tries to minimize friction to get to “Done.” The copilot forces you to engage with the friction to get to “Good.”

Shadow competency

The final danger is shadow competency.

When TSB Bank had its massive IT meltdown in 2018, locking millions of customers out of their accounts, the post-mortem was fascinating. They had outsourced so much of their IT that they no longer had the ability to judge if the work was good. They had lost their shadow competency, the ability to inspect the work of others.

The classic book Pragmatic Programmer advises using “Tracer Bullets, “ code that penetrates all layers of the system to test feasibility (I love this model). When you write the code or the email yourself, you’re firing tracer bullets. You feel the friction of the database; you see the latency of the API, you notice the awkward phrasing. To maintain shadow competency, you need to do enough manual reps to know what “good” actually looks like. You need to read the code. You need to rewrite the draft. You need to ask, “What would make this wrong?” before you ship.

Why does this matter? Because if you don’t know what good looks like, you can’t spot what bad looks like.

The tl;dr

If you’re a product manager, tech leader, or founder, your value isn’t your output. Your value is your judgment.

When you hand off a task to an agent, you are trading your judgment for speed. Sometimes, that’s a great trade (fixing Excel errors). But for the work that matters, the work that requires empathy, insight, and strategy, that trade hurts you.

Don’t try to outsource your thinking. Use agents to clear the brush. Use copilots to climb the mountain. And know the difference.

Try this:

Try the Surprise Test. Look at the last piece of AI-generated work you used. If you were surprised by the output and just accepted it, you are likely in the “satisficing” trap. If you argued with the AI, refined the output, and caught a nuance it missed, you’re doing it right.

Then, audit your friction. If you spent longer writing the prompt than you would have spent doing a rough first draft, you tried to waterfall a creative process that only reveals itself while you’re building it. That’s your cue to switch modes.

Finally, define your “associate” tasks. Pick five recurring chores that don’t require judgment, set up an agent workflow for those, and keep the rest close—because that’s where your taste and strategy actually live.

It was Monday, 8:30 AM. My first day. The whole company, all eight of us, crammed into the tiny conference room. The CEO, gesturing towards a half-erased whiteboard sketch, kicked off the “weekly backlog review.” He told me just to listen while I got my bearings, but sitting in the corner didn’t feel right. I’ve been hired into new roles like this a bunch of times. Some transitions went well; many could have gone better. Mapping out a 30-60-90 plan sounds great on paper, but in a startup, it collapses fast. My process is counterintuitive and fueled by late-night Notion pages and endless Slack threads. But it works.

Especially if you're an experienced hire joining a rapidly evolving company, that traditional 90-day roadmap is usually too slow. I tried the usual path at a 2,000-person PE-owned company. My first few weeks were spent interviewing colleagues and stakeholders, reviewing plans. But by my third month? Massive turnover and a new company strategy rendered much of what I’d learned irrelevant. And in the meantime, I still hadn’t done any “real” work. Startups pivot. What looks important on Day 5 might be a forgotten relic by Day 45. Your meticulous plan? Obsolete before you even hit the halfway mark.

People crave structure during transitions; the 30/60/90 tries to set expectations and track progress. But in the startup world, where velocity is king, resources are tight, and change is the only constant, that rigid, lengthy structure often crumbles. Its underlying assumption of stability just doesn't fit.

What’s my alternative? A counterintuitive process I call the 3/6/9 Onboarding Plan: what you should accomplish by your third day, sixth day, and ninth days on the job. The numbers are approximate, but the core idea is: Take on the “physical” work faster than you think you should, and go slower on applying judgment.

The “shadowing trap”

Let’s begin with typical advice when starting a new job: “You’ll just shadow me for a week.” It sounds helpful. In practice, it's often a disaster.

That person you’re shadowing? They’re already drowning; that’s why they hired you. Now, they still have their full workload, plus they have to teach you. In addition, the constant question of whether you’re finally ready to go solo adds to their cognitive load. For a while, every day is a little worse than the one before. Their stress level increases. And when people are stressed? They take shortcuts. Instead of explaining, they just do it themselves. And as the newbie, it’s rough to watch your presence make things worse.

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The 3/6/9 plan: Dive in, document your learning, delay big calls

Instead of passively shadowing, you’ll hit the ground running, learn by taking ownership, and build trust fast.

Phase 1: Grab the work & start logging

Day 1. Don't just shadow. All the meetings, reports, updates, etc., that you’ll ultimately be responsible for? Start doing them right now. For instance, I grabbed Tuesday’s bug-triage call, the one nobody wanted because it always ran 20 minutes long and left everyone grumpy. Take them over. Tell your new colleagues, “As of right now, I'm running. It'll be messy at first, I'll ask a million questions, but I'm taking it.” You’ll feel incompetent, maybe even overwhelmed; that’s okay. Even better, you were likely hired because someone wasn’t able to give the work as much time and attention as it deserved—you may not be as bad as you think!

Key point: while Day 1 is rough, Day 2 is slightly less rough. Every day is a little better than the one before. You’re creating an upward trend. Your colleagues see progress daily, not weeks down the line. Because of recency bias, people tend to weigh recent events more heavily and feel this positive momentum strongly. The faster you can contribute meaningfully, the quicker you build confidence, both your own and the team’s.

And start writing, but for yourself. Start a doc or crack open a new notebook – your Phase 1 Log. Dump everything in: names, terms, workflows you see, questions you have, stray thoughts. Don't organize, just capture. This helps you handle the flood of new information and frees up mental bandwidth.

Phase 2: Do the work & structure the mess

Week 1: Keep running the things you took over. Your questions will naturally get better, less “Where is...?” and more “Why this way?” Build relationships by doing the work alongside people. But resist the urge to critique or change. You don’t have the context. Assume people were smart when they set things up. Avoid the “action imperative,” that urge to “fix” things before you understand them, a trap Michael Watkins warns about in his classic, The First 90 Days:

Falling prey to the “action imperative”: You feel as if you need to take action, and you try too hard, too early to put your own stamp on the organization. You are too busy to learn, and you make bad decisions and catalyze resistance to your initiatives.

Focus on comprehension. You can still deliver small, straightforward wins, like fixing a nagging bug in the checkout flow or drafting that overdue help doc, to build credibility.

Now, structure your notes – Phase 2 Synthesis. Start organizing that log from Phase 1. Focus on the concrete aspects of how work actually happens – the elements you will eventually influence. I think of these as:

• Artifacts: The stuff – product requirements docs (PRDs), designs, internal wikis, reports, dashboards, templates, code.

• Rituals: The meetings – stand-ups, planning sessions, design reviews, and async team communications, too.

• Cadences: The schedule on which work happens – sprints, release cycles, reporting periods.

• Org Structure: The who – teams, roles, reporting lines. Mapping these helps you see how things actually get done clearly, separate from the big-picture strategy (that comes later).

Phase 3: Map the system & test your understanding

Week 2: You should be getting the hang of the day-to-day. Now, dig deeper into why things are the way they are. Ask about historical decisions. Understanding this history isn't about critiquing the past; it's about gaining the context needed for productive conversations about where to go next.

Start Phase 3 Drafting. Crucially, you're writing things to share, but specifically to get corrected. Take your Phase 2 understanding of artifacts, rituals, etc., and map it out: “Here's how I think our release process works. Please review this and tell me where it’s wrong or incomplete.” You’re making it easy for people to edit your understanding. Think of these drafts as conversation starters, not final proposals. Getting things written down helps everyone get on the same page. You’re also starting to form hypotheses about the actual strategy. What game is the company playing? This is vital because misalignment, especially with a founder's vision, is deadly in startups.

What the listening tour is really for

A listening tour matters, partly because you’re expected to do one. But its real value early on is often misunderstood. Research on trust confirms what feels intuitive: connecting with people personally (warmth) builds trust faster than just trying to impress them with your hard work and skills (competence) right away. For instance, Shelly, our usually quiet designer, only really opened up about her frustrations with the handoff process after we’d chatted about our shared love for obscure board games during a coffee break. (Just be aware of participation bias – how these tours can preference the voices of those most comfortable or eager to speak up). Your goal isn’t to collect ‘objective truth’ and form snap opinions. You don’t have enough context yet, so slow down on judgment.

What you’re really doing is demonstrating that you’re the kind of person who will listen. This helps create the psychological safety needed for people to eventually share honest feedback. And, when you do eventually share your hypotheses or question the status quo (using your Phase 3 drafts), your colleagues will already trust that you genuinely want their input because you showed them you listen first.

Finally, listening tours work great early in your tenure because people will still talk to you! The classic questions (from Watkins): What do you think of our existing strategy? What are the biggest challenges we face in the short term? What are the biggest opportunities we face? What resources could we leverage more effectively? How could we improve the way the team works together? They feel natural on your sixth day but awkward in your sixth month.

The peril of premature judgment

Judging slow—even after a solid listening tour—protects both you and the company from rash calls before you've built that essential trust and context. Jumping in with solutions before understanding the landscape can be disastrous, as the following story illustrates.

A friend of mine, VP Engineering at a startup, saw this firsthand. They were acquired, and a new Chief Product Officer was brought in two weeks after the deal closed. The new CPO, despite a successful track record elsewhere, arrived with "high confidence and low context." On day one, he started making sweeping changes and immediately applied his own playbooks for things like customer migration.

Initially, he had the CEO's backing to shake things up. However, this "pinballing between big decisions" without knowing which ones were truly critical or needed more time became a pattern. Five months in, the board fired him. This story is a stark reminder: good judgment is implicitly necessary to know which decisions are big and should be delayed. Good judgment starts with knowing which calls are big and which can wait.

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Getting to the “real work”

This 3/6/9 isn't easy, but it’s effective. Remember that bug-triage call I took over? By the end of week two, we’d tweaked the agenda, clarified roles, and it was finishing on time. Small win, but it unblocked engineering and made Tuesday mornings a little less dreaded. You build trust and authority through collaboration and contribution, not just talk. You learn faster by doing. You give immediate relief to your boss and colleagues. You avoid career-limiting early missteps and finish your first two weeks on an upswing.

The learning never stops. Ramping up is continual, but after you’ve stabilized the day‑to‑day, it’s your cue to start leading where the org should head next.

Michael Watkins notes you earn “the right to play” only after delivering early wins. That’s why the strategic layer comes only after you absorb operational load and bank trust. This order, doing then thinking/judging, stops you from making plans that don’t match reality while positioning you faster for future success.

Next up: Turn that hard-won context into a clear strategy and roadmap to align your org and empower your team.

At the top of everyone's first-time manager checklist should be “set up 1:1s.” When done well, your 1:1s are how you build a productive and rewarding management relationship. But what does it mean to do 1:1s well?

When I was a young manager, I knew 1:1s were valuable, but I didn’t know how to make them work—sometimes we'd run out of things to talk about after ten minutes, other times the meeting devolved into a complaint session. Often, they felt merely performative. That's why in this article, I present a straightforward and structured model for 1:1s, so you have a guide and don't feel like you need to flail like I did. This approach will be productive, easy to manage, and set you up for success.

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One note: this is a long document, there are lots of details, and might be overwhelming. So here’s the tl;dr: Having a mediocre 1:1 is better than not having 1:1s at all. And ultimately you, as the manager, are responsible for your direct reports, even when you’ve given them work.

What are 1:1s, and why are they foundational?

Skip this section if you don’t need to be convinced!

When we talk about 1:1s, we mean the recurring meetings that a manager has with the people who report to them. These aren't status updates; they are dedicated time to benefit your direct reports. I consider them one of the most powerful tools a manager has, and neglecting them or doing them poorly isn't just missing a meeting; it's failing at a fundamental practice that is essential for successful leadership.

Why invest this time? Having and protecting this regular meeting time boosts engagement and reduces regrettable attrition. They build trust and psychological safety; committing to a regular schedule and protecting that time fosters an environment where reports feel secure sharing challenges and aspirations openly. This dedicated time signals the value you place on their individual growth and perspective.

Because the meeting is routine, it lowers the risk of bringing up hard subjects. Frequent check-ins help keep small problems small, allowing you to address issues before they escalate—e.g., weekly meetings offer 4x the opportunities of monthly ones. This regular cadence also provides an affordance for difficult conversations like feedback or career concerns, making them less awkward. Ultimately, 1:1s are the primary venue to drive performance and development through coaching, feedback, and goal alignment, and they make formal performance reviews easier by promoting alignment and addressing issues proactively.

Keep in mind that these regular check-ins aren’t the only kind. You might hear references to a skip-level 1:1 (a meeting with your boss’s boss), 1:1s tied to performance reviews or as part of a PIP (performance improvement plan), an onboarding meeting, a stay interview, an exit interview, or something else. This article focuses on the regular, recurring 1:1 between a manager and their direct report.

Setting up your 1:1s: The logistics

Getting the logistics right demonstrates the value you place on these meetings.

• Frequency: While optimal frequency is debated, I think weekly 1:1s are best for newer or junior employees and new managers. While bi-weekly is cited as a viable alternative for more experienced reports or if weekly isn't practical, and they might be tempting if your schedule is already tight, weekly provides more opportunities for both you and your report to practice the skills of giving and receiving feedback, building rapport, and discussing development. Plus, issues are surfaced much faster.

• Duration: I like starting with 30 minutes because it forces me to be better focused and because I hate saying, “Let me give these 20 minutes back” when we run out of things to say. However, some argue it’s insufficient for deep conversations, so pay close attention: if you consistently run out of time or feel rushed covering topics like career development, consider extending to 45 or 60 minutes. But don’t let the 1:1 devolve into a tactical working session – it should retain its focus on the employee's needs, feedback, and growth.

• Scheduling: Look for a spot on your weekly calendar using a recurring invite. I like to schedule my 1:1s early in the week because those time slots seem easier to protect and to start the week off well. Be careful not to set the meeting too early or too late, as that makes it more likely to be bumped by family or non-work needs, and consistency is non-negotiable. Every time I’ve canceled a 1:1, I could see a bit of our relationship dying. If you must cancel, reschedule immediately, don't just blow it off. This consistency signals reliability and the meeting’s significance more than almost anything else.

• Location (prioritize privacy and preference): As a baseline, find a consistent place where you can both speak freely without being overheard – a conference room, a huddle room, or ensure you both have privacy if remote. Check with your report about their preference; some prefer standard offices/conference rooms, others prefer occasional walks or coffee shops, but not everyone does. Personally, I like walking meetings, either in person or over the phone, as they both feel more emotionally intimate and can reduce tension.

Prework and agenda

I prefer that my reports do the physical pre-work, not just because I’m stretched, stressed, and lazy. This is the first opportunity to illustrate the difference between ownership (theirs) and responsibility (yours). I ask reports to write a “weekly wrap-up email” (template), ideally on Friday, covering three areas: current priorities (for alignment), blockers (where they need help), and what’s on their mind (for broader topics). Critically, you need to read their email before the meeting and come prepared to discuss the details.

Let me say that again: You, the manager, need to read their email before the meeting and come prepared to discuss the details.

Alternatively, many use a shared agenda document (like a running Google Doc) where both manager and report add topics beforehand, with the employee driving the agenda. This enhances transparency. You can search for highly detailed templates (covering OKRs, KPIs, etc.), but these are overkill initially. A potential caution with adding detailed agenda items in writing beforehand is that text lacks tone, and seeing a sensitive topic appear without context causes unnecessary anxiety.

Whether using a wrap-up email, a shared doc, or another method, the key is having some pre-work process so both participants arrive ready for a focused conversation.

Does this feel overwhelming? Start with my suggested structure, pay attention to the quality of the meetings, and adapt as you go.

How to run the 1:1: A recommended flow

While different structures exist (more on that below), here’s a practical flow focusing on the employee's input while making sure key areas are covered. The subtle tension is that even though you’re asking them to “own” the meeting, you’re still the manager and you’re still ultimately responsible for the meeting, the relationship, and their performance.

• Set the tone: Start by being fully present and minimizing distractions (more below). Check your own emotional state and try to set aside any negative energy, as your mood is contagious. Begin with a brief non-work chat, share a win, or express appreciation to build rapport and safety.

• Review priorities and alignment: Start by discussing the priorities your report identified in their pre-work. Is their focus aligned with team and company goals? Is there any new information or context you possess that would change their priorities? If you haven’t shared relevant context earlier that would have impacted their plans, acknowledge that and apologize – it builds trust. The goal here is mutual understanding and alignment.

• Address blockers: Move on to the blockers they’ve identified. Acknowledge each one clearly so they know you've heard it. For each blocker, determine if you can remove it for them (if so, commit to doing it and always follow through) or if it’s something they can solve with guidance. If the latter, coach them through it, asking questions to help them find a solution they ideally control. It’s also good practice to briefly review blockers mentioned in the previous 1:1 to check if they’re resolved or need further action, promoting accountability.

• Discuss “what’s on my mind” (and guide broader topics): This is where your report shares topics beyond immediate tasks. Let them lead. However, your role as a manager is also to teach them the breadth of things they should be thinking about for their role and career. Even if they don’t bring them up, make sure you’re regularly weaving in conversations about:

  • Career development: Their long-term goals and aspirations, as well as promotions and new responsibilities.

  • Skills progression: Where are their growth edges? What opportunities exist to learn?

  • Relationships: How are things going with peers, the cross-functional team, and the broader organization?

  • Ideas and innovation: Solicit their ideas for improving products, processes, or team culture.

  • Feedback: Both giving feedback to them and explicitly asking for feedback on your performance using direct questions (“What can I do better?”) or frameworks like “I like, I wish, What if?”

  • Well-being: Check in on their job satisfaction and work-life balance. Consider using "magic questions" about how they feel (1-5 scale) about work life, personal life, WFH, the company, the team, and working with you. It’s okay for them to drive the specifics each week, but you need to confirm these vital areas aren’t consistently missed. Guide the conversation by asking open-ended questions.

• Quick retrospective check (if needed): Was there a specific event, project milestone, or interaction from the past week that warrants reflection? Decide if a brief retrospective (“How do you think X went?” “What could we learn from Y?”) fits within this meeting or if it warrants a dedicated session. This isn’t a working meeting!

• Wrap up with action items: Before ending, clearly summarize takeaways and define action items for both of you: who does what by when.

A simpler way to think about this: Your 1:1 time is ideal for that work which is important but not urgent.

Other structured frameworks

While the flow above provides a practical approach, being aware of different formal structures is helpful. Flexibility is key; don't let a rigid structure kill a valuable conversation.

• Manager Tools 10/10/10: A simple, popular model for a 30-minute meeting: 10 minutes for the employee's topics, 10 minutes for the manager's topics, 10 minutes for the future (career development, follow-up). Ensures balanced coverage. I love the balance but struggle with the rigid structure.

• Time-based: Icebreaker (5 min), review past actions (5 min), employee-led discussion (15 min), feedback/coaching (10 min), next steps/actions (5 min). Offers a concrete alternative. Same as above, the rigid structure feels like something from an HR handbook rather than a human connection.

• Bill Campbell's structure: Focused on 1) Performance against KPIs/goals, 2) Relationships with peer teams, 3) Leadership/Management development, and 4) Innovation/Ideas. More strategic, suited for longer meetings. While it’s tough for me to disagree with Silicon Valley’s greatest coach, this one never felt right at an early-stage startup.

The manager’s role during the 1:1

• Eliminate distractions: Give your report your undivided attention. This means closing Slack, email, and distracting browser tabs. Turn off notifications on your computer and phone. Make eye contact. Being present signals respect and the value of the conversation.

• Master active listening: Your goal should be to listen far more than you talk. Aim for the report to speak 50-90% of the time. Focus on understanding their perspective, not just waiting for your turn to speak. Feeling heard is fundamental to psychological safety.

• Employ powerful questioning: Use open-ended questions (“What,” “How,” “Tell me about...”) to encourage reflection and deeper discussion. Avoid leading questions or ones that elicit simple yes/no answers. Good questions explore context ("What's challenging about that?"), promote learning ("What did you learn?"), empower ("What does your ideal outcome look like?"), and support growth ("How would you like to develop?").

• Adopt a coaching mindset: Shift from directing and fixing to guiding. Help your report think through problems and develop their own solutions, as they often have more context. Ask questions like “What have you tried so far?” or “What options are you considering?” But, while you should resist the urge to jump in with your answer immediately, making them guess isn’t helpful either.

1:1s in the bigger picture

They aren't the only place where feedback happens. Think of it like a pyramid:

1. Base: A culture of continuous, immediate feedback (both praise and constructive criticism) given in the moment, as things happen. I agree with Radical Candor that feedback should be immediate and not saved for 1:1s.

2. Middle layers: Regular weekly 1:1s (you are here!) and team meetings (for alignment, group problem-solving).

3. Higher layers: Formal performance reviews and quarterly planning (less frequent, more structured assessments and goal setting).

4. Peak: Actual individual and organizational outcomes (company strategy, actual results, OKRs met).

Your weekly 1:1s are a critical middle layer, supporting and being supported by both continuous feedback and more formal processes.

Common challenges & mistakes

Even with good intentions, you face bumps or fall into common traps.

1. Cancellations/unpreparedness: As the manager, model commitment. Avoid cancelling. If your report is unprepared or cancels often, use the 1:1 to discuss why. Is the meeting not valuable? Is trust lacking? Address the root cause.

2. Dominating the conversation: Remember to listen more than you talk. For me, silence feels wildly uncomfortable, so if my report isn’t talking, I’ll tend to fill the gap. Don’t be like me! If you’re staying quiet, you’re giving them space to talk.

3. Using it only for status updates: Handle tactical updates asynchronously or at team meetings. Use 1:1 time for richer conversations.

4. Focusing only on tasks: Employees need feedback on skills and career growth, not just task completion.

5. Different communication styles: Adapt your approach. For quieter reports, focus on building safety, ask open-ended questions about their experience/feelings, and be patient. For talkative reports, use the agenda to gently guide the conversation back on track while ensuring they feel heard.

6. Difficult conversations: Use the private 1:1 setting to address performance concerns or interpersonal issues promptly. Choose your battles wisely, focus on behaviors and solutions you can control. Prepare talking points and use “I feel” statements. If there's been conflict, use the next 1:1 to repair and clarify. When a report is venting or threatening to quit, your role in the moment may be just to listen (but don’t forget to take this promptly to your manager).

7. Absence of difficult conversations: The opposite is also true. Work is hard and stressful, and if you’re not having hard, stressful conversations, your 1:1 is just operating on the surface. There are lots of ways to build psychological safety, but my favorite trick is to change the power imbalance. For example, try scheduling some 1:2 or 1:3 meetings with a few folks on your team (take them for lunch) and see if they open up.

8. Not following up: If you agree on action items, confirm they happen. Dropped balls erode trust.

9. Not asking for feedback on the 1:1s themselves: How can you improve the meetings if you don’t know what’s working? If you do nothing else, do this. It’s a “one weird trick” for being a better manager.

But all that said, remember the tl;dr: Your 1:1s don’t need to be perfect, but you still need to hold them. So, if the only way to get engagement is spending time on updates or tactical work? Start there.

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Are your 1:1s working?

How do you tell if this significant time investment is paying off? Look for these signs:

• Direct report engagement: Are they actively contributing to the agenda? Do they come prepared? Do they seem open and willing to discuss challenges?

• Reduced “surprises”: Are you hearing about problems or roadblocks sooner?

• Improved performance & growth: Are you seeing progress in their skills and contributions? Are they addressing feedback? Are they moving towards their career goals?

• Increased trust and candor: Do they bring difficult topics or constructive criticism to you?

• Action items get done: Are commitments made during the 1:1 followed through on (by both parties)?

• They don't cancel (often): Reschedules happen, but frequent cancellations warrant a conversation.

• Direct feedback: Ask them! Periodically check in: "How are these 1:1s working for you?" or "Is there anything we could change about our 1:1s to make them more helpful?"

As a product manager, good 1:1s feel like good product market fit: Are we excited for the meeting? Is the structure and cadence pulling in increasing value? Would we both be disappointed if we could never have them again

Making your 1:1s even better over time

Your 1:1s shouldn't be static; they should evolve as your relationship with your report grows and their needs change. Periodically review your process. The best way to do this? Ask your team members directly for feedback on the 1:1s themselves. You could ask after a meeting, during a skip-level, or even use an anonymous survey. Ask: What's going well? What's not? What ideas do you have for improvement? Be open to trying new approaches based on their input.

Conclusion: Practice makes progress

Effective 1:1s are more than just meetings; they are a primary arena for practicing and honing essential management skills and for developing the relationship between you and your direct reports. They require consistent effort, but the payoff in trust, engagement, and performance is immense.

1. Commit to consistency: Schedule weekly 30-minute 1:1s and treat that time as sacred. Reschedule immediately if you absolutely must cancel.

2. Prepare and empower: Establish a pre-work routine (like a wrap-up email or shared agenda) that encourages your report to own their part of the conversation.

3. Structure for focus: Use a simple flow – check-in, priorities, blockers, broader topics, action items – to guide the discussion.

4. Be present and coach: Eliminate distractions, listen actively (aim for 80% listening), ask powerful open-ended questions, and guide rather than direct.

5. Follow through: Document and complete action items reliably.

6. Seek feedback: Regularly ask your report how the 1:1s can be improved.

Great 1:1s take ongoing practice. By focusing on these actionable steps, it’s more than just a procedural step; you're actively investing in your people, building stronger relationships, and becoming a more impactful leader, one conversation at a time.

How many times have you been caught in this cycle: write an amazing PRD, hand it off to engineering, but something mediocre ships? We shoot for the “perfect” requirements document, the flawless spec, thinking if we just nail the details, the right product will magically appear. But we’re wrong. Documents like specs and PRDs are terrible ways to communicate and build products.

I’m imagining a canonical product development process: Goal/strategy selection → Problem/opportunity identification → Opportunity selection → Solution identification → Solution selection → Design → Development → Deploy → Release.

I believe we need to prioritize conversations over documentation. What if we used artifacts not as replacements for talking but as springboards for it? Often, the most successful teams aren't the ones with the best docs but the best conversation at every stage.

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Almost 10 years ago, I was brought into a small tech company as their first PM and product leader. That’s right: no formal product management, but somehow, they’d amassed 10 million MAUs. The first time I visited the office, I saw them practicing what I’ve come to call “prairie dog product management.” Someone would have an idea, they’d stand up and just say it out loud. Another head would pop up over the cubicle wall, and they’d talk. Because everyone—engineers, QA, designers, and CSMs—understood the company goals and strategy and all knew the users well, they had a quick conversation. They poked holes in the idea, examined tradeoffs, and tossed around ideas for implementation. Sometimes they decided to build it and sometimes they didn’t but the process was easy and fast. If there was something to talk about, they’d just have a conversation.

While that particular model had plenty of flaws (they struggled to build big things, and when they did make big bets, they often were poorly tested in advance), that image has stuck with me as a model for deep engagement between Product and Engineering.

Let's take a step back and rethink the purpose of documentation, especially if you're a PM in tech. It's way too easy to fall into the trap of viewing our artifacts as the primary deliverables of product management. Common examples include:

• The classic Product Requirements Document (PRD), often trying to cram in everything from Problem/opportunity identification through Solution selection.

• Google Docs stuffed with specs and notes.

• Linear/Jira tickets detailing user stories and tasks.

• Miro/FigJam boards from brainstorming or mapping sessions.

• Clickable prototypes showing flows.

But the real goal shouldn't just be to dump information into these artifacts passively. Good artifacts provide affordances for better, earlier conversations between engineering, design, and other stakeholders. Discussing complex trade-offs during Opportunity selection or Solution selection – like hashing out different login options (username/password vs. 2FA vs. passwordless) – needs an honest back-and-forth, sparked by the PRD or spec, tapping into everyone's expertise. That doc, no matter how detailed, will fail if it’s seen as the final product.

Shooting for “perfect” docs before talking to engineers isn't just flawed, it can blow up in your face, especially at handoffs like between Solution selection and Design. Part of the problem is just the nature of written communication itself. As Jeff Patton frequently points out in his book User Story Mapping, documents stink at creating real shared understanding. Think about it:

• Written words are static; they lack the immediate give-and-take of conversation.

• You lose all the vital tone and body language cues.

• It's incredibly easy to misinterpret things, with different people walking away thinking completely different things.

Do you remember the first time you read Harry Potter? In your head, you pictured Harry, Hermione, Dumbledore, the cubby under the stairs, the sorting hat…all of it. Those books have incredibly vivid, descriptive, evocative writing. But I can guarantee the picture I saw inside of my head differed substantially from the one inside yours.

That spells trouble down the line during Development or Deploy. Writing more doesn't guarantee everyone’s on the same page. You risk falling into the trap of believing the artifact itself ensures alignment across the whole lifecycle, when it often fails to connect the dots between minds. Instead of endlessly polishing that doc in isolation, use it – warts and all – to spark the crucial, high-quality conversations needed to build actual shared understanding early and often, from Goal selection to Release planning.

Who needs to be in these talks? Your engineers, especially as the team dives into Design and Development. They usually have the deepest technical expertise in implementation. Instead of PMs dictating the tech specifics during these later phases, tap into their wisdom and experience. Get them directly involved in figuring out the best way to do it. Some teams might debate feature trade-offs when building a login system (security vs. performance vs. user acceptance) during the Design stage. At Google, I saw teams hiring designers to develop and film evocative product advertisements to clarify product vision before Development kicked off. One of my clients, a graphic designer, made a comic strip. There are countless ways to engage the entire team.

It pays enormous dividends to pull engineers “leftward” in the process, looping them in much earlier – starting from Problem/opportunity identification through Opportunity selection and Solution identification/selection. Looping them into talks about the company's vision (Goal/strategy selection), market needs, and user requirements during these formative stages lets you tap into their diverse experiences. Think about that login options example, but even earlier, during Solution identification, exploring choices like these together surfaces critical trade-offs only engineers might fully grasp before a direction is locked in:

• Username/password

• Two-factor authentication (2FA)

• Passwordless login (like magic links or SMS/email codes)

• Federated login (Apple, Google, Microsoft)

Using narrative tools like story mapping during Solution selection also helps engineers contribute to the “what” by questioning assumptions and shaping the MVP scope.

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Getting engineers involved early means facing a reality they live every day: managing complex trade-offs. And this isn't just one phase; senior devs do this constantly, from weighing different approaches during Solution identification to making tough calls in Development. Figuring out the right balance – maybe between a quick-and-dirty solution versus a 'military-grade' one during Solution selection, or dealing with tight timeline pressures during Design – doesn't happen in a vacuum. It takes real conversation, backed by solid technical understanding, to navigate these choices effectively throughout the middle stages of the lifecycle. Oftentimes, the result is a desperate DM on Slack and the realization that until you answer their question, engineering has slowed to a halt.

Naturally, none of this works, at any stage from Goal selection to Release, if people don't feel safe speaking up. If you're a leader, you've got to be hyper-aware of your impact. Your team reads your cues like kids read their parents' moods. Tiny things can instantly shut down valuable questions or pushback, whether you're brainstorming during Problem identification or debugging during Deploy. Watch out for things like:

• A thoughtless word that dismisses an idea.

• A tone suggesting impatience.

• Negative body language (eye-rolling, checking your watch, checking your email – we see you!).

Making an environment where people feel genuinely safe asking questions, challenging assumptions, and voicing concerns is absolutely non-negotiable for real collaboration across the entire product development process.

With a safe space established, how do you actually drive these discussions, particularly during Solution identification, Solution selection, and Design? My favorite model is user story mapping. Fantastic technique. Imagine your team is building a tool to help with “waking up and going to the office” – breaking down a process invites interaction as the team defines the solution. Consider steps like:

• Alarm goes off

• Stand up

• Shower

• Get dressed

And the clarifying questions that pop up:

• When does shaving happen?

• Breakfast at home or grab something on the way?

• How's coffee getting made?

You can actually represent this with stickies on a wall (or the equivalent online). And when an engineer jumps in with, “Wait, not everyone drives!” it sparks a crucial discussion. Maybe you refine the Ideal Customer Profile (ICP) or simplify the Minimum Viable Product (MVP) during Solution selection or early Design. That's collaboration in action.

Story mapping clicks partly because it leverages the power of stories, which are gold in early stages like Problem/opportunity identification through Solution selection. We're just wired for stories. Instead of dry requirements during Solution identification, framing the work with a narrative – detailing the user (hero), their world (setting), and their struggles (obstacles) – makes the “why” way more relatable. Picturing that person rushing out the door, trying to decide if they’ll get coffee at work or on the way, adds clarity to everyone’s thinking.

Stories are great, but relying only on words can lead to everyone having a different movie playing in their head – think back to the Harry Potter analogy. The moment we all saw the movies, we suddenly shared an identical picture of Voldemort. That's why adding visuals is so crucial, particularly from Solution identification through Design. A visual artifact, like that fake Google ad concept or hand-drawn comic strip, gives everyone a shared picture that:

• Clarifies the product vision during Solution selection.

• Gets everyone on the same page heading into Design.

• Sparks better, more specific questions before Development begins.

How do you bake this conversational approach into your process, especially bridging that critical gap between Design and Development? One powerful shift? Try engineer-led user story creation. Instead of the PM slaving over every detail after Solution selection or Design, the PM provides just a high-level epic (here’s my template):

• A user-centric narrative (Jobs-to-be-Done, hero/goal/obstacles, whatever works for you).

• Key non-functional requirements.

• Placeholders for or links to mockups and prototypes.

Then let the engineers break down that epic into specific user stories as they plan Development. They usually have the best gut feel for how to slice up the work logically, and this process inherently delivers key benefits:

• It forces questions to smoke out ambiguity.

• It creates natural feedback loops for alignment before coding starts.

The job isn’t writing PRDs. You don’t get credit for specs, and your company will never be acquired for its JIRA backlog. But I believe that if you replace written artifacts with better conversations, earlier, you’re much more likely to build a product and company that are truly valuable.

Want to learn more?

The best book on the topic is User Story Mapping, by Jeff Patton. You can find links to the book, presentations, and articles at https://jpattonassociates.com/story-mapping/.

My example product, something to help with getting up and getting to work, was taken from a presentation I give, “User Story Mapping or Partnering with your Devs," which you can find here.

Of course, regular performance reviews should be only one part of your organization’s overall performance feedback system. Ideally, you’d receive continuous feedback from managers, peers, reports, and others. You should have meaningful weekly 1:1s. All of this should be tied to overall business results. 

You may have a manager who can’t provide the comprehensive feedback you need to thrive. They may be juggling too much other work or lack the experience or support to provide you with quality perf. This is why you need to take ownership and consider a personal review process. Whether your goal is a more constructive conversation with your manager, faster advancement, or just personal growth, the goal is self-empowerment. 

How the process works

“Minimum Viable Perf” is a structured approach designed for you to complete independently. Here’s the template (it’ll prompt you to make a copy) and here are the five steps:

1. Review the template:

   • Begin by carefully examining the provided template. The “Attributes” represent the various dimensions of your job that you need to get right to do well. Each attribute has a “heuristic” describing how to tell if you’re doing well. Attributes are organized into “Areas” for convenience.

   • Ensure the template accurately reflects your role and responsibilities. If certain attributes aren't relevant, just remove them. Conversely, if crucial aspects of your role are missing from the template, add them to ensure a comprehensive self-assessment.

   • For instance, you might be a product manager who also handles product marketing. In that case, you should add a new section, along with the appropriate attributes and their heuristics.

2. Refine the heuristics:

   • Scrutinize the "Heuristic" column for each attribute. These heuristics describe how to tell if you're performing well in that specific area.

   • It's essential that these heuristics resonate with you and accurately reflect what constitutes success in your role. If a heuristic seems unclear or doesn't align with your understanding, change it! 

   • Well-defined heuristics are crucial. At least your first time, expect to spend a couple of hours editing them.

3. Self-score and evidence:

   • Now, assign yourself a score for each attribute using the scoring guidelines provided. My scoring is a little different from what you’re used to. Instead of the usual “meets/exceeds” 5-point scale, I have four scores: Does not consistently meet expectations; Meets expectations with support; Meets expectations independently; Consistently exceeds expectations.

   • I’ve found these scores more helpful in describing actual gradations in performance.

   • The most critical part of this step is providing concrete evidence to support your score. Remember: this is supposed to be helpful to you so you can improve.

   • For example, if an attribute is "Specification" with the heuristic "The product released is what was intended," your evidence could include links to well-received PRDs or positive feedback on design documents.

4. Outline edges for improvement:

   • I like the phrase “Edges for improvement” because it’s a reminder that our abilities are constantly expanding. As your skills grow, you’ll always have a fresh edge.

   • For each attribute, identify one or two (no more!) specific actions you can take to enhance your performance in that area.

   • These actions should be concrete and actionable, not vague aspirations.For example, "Attend a presentation skills workshop next quarter" is better than "Improve communication skills." You want to turn your self-review into a tangible plan.

5. Seek external feedback:

   • Finally, request feedback from someone familiar with your work within your organization. This could be your manager, a peer, or another colleague.

   • Share the completed self-review with them and ask them to fill out the "Manager score" and "Manager or peer feedback" columns.

   • External feedback adds another layer of objectivity to your self-assessment and can highlight blind spots or areas for further development.

The pitfalls of the personal review

Self-review is not without its own challenges. It’s hard to objectively assess your own performance. It's easy to fall into patterns of being overly critical or overly lenient with yourself.

That’s why you anchor your self-assessment in concrete evidence instead of just describing your perception. You want a factual record to mitigate recency, similarity, tightrope, or other biases. Additionally, you’ll seek feedback from trusted colleagues for an external perspective. Remember, the goal of a personal review is not just to critique but to gain a well-rounded understanding of your performance.

Seeking external feedback

So, who should you ask, and how, to increase the likelihood of useful feedback?

Your first instinct, to ask your boss, is probably correct. However, many people in startup environments don’t have a manager who understands their job. Similarly, you may be worried your boss is too busy and distracted to take this process seriously. It might then make sense to reach out to trusted colleagues who have worked closely with you and understand your role and responsibilities well. 

When approaching them, be upfront about your goal of seeking feedback to improve your performance. You can say, "I'm conducting my own personal performance review and would value your perspective." Frame your questions to encourage specific examples and suggestions for improvement. You could even share this document! But remember that their perspective and responses will be colored by their own biases. Ultimately, it’s your job to interpret their feedback. 

Need help?

As I continue to revise the template, process, and instructions I’m happy to provide complimentary 1:1 coaching. If you’d like to schedule time, you can do so here: https://zcal.co/jhm/perf.

Since the beginning of the year, I’ve talked to at least 5-10 job seekers weekly. They want feedback on their resumes, want to network, and hope I can point them to new openings.

(This article complements my earlier one: How to get a tech job in 2024.)

But the best advice I can give them is to invest in community. Community is the fastest way to expand your network, increase confidence, and provide emotional support and motivation. Job seeking is hard, but the community can make it easier. But where do you find community?

Key communities:

1) Rands Leadership Slack.

This entirely free community has over 33,000 members spread across the globe and over 600 active channels. While heavy on engineering and leadership, there are channels for industries, professionally focused channels, and many for job searchers. There are also geographically focused channels for networking with people who live nearby and plenty of “lifestyle” channels for whatever your interests are outside of work. The one thing you won’t find is spam: the community is aggressively allergic to commercial content and self-promotion. To join, follow the directions here: https://randsinrepose.com/welcome-to-rands-leadership-slack/. And when you join, let me know!

2) Communities of practice.

Whether you’re interested in product management, sales, design, startups, healthtech, fintech, greentech, edutech, or some other focus, there’s a community for you. While some are free, some are paid, and some require admission. There are also geographically specific groups, sometimes sponsored by VCs. My favorite is the Friends of Lenny’s Newsletter—you get access when you subscribe to Lenny Rachitsky’s paid substack: https://www.lennysnewsletter.com/p/community. It has about 15,000 members, primarily in product management, growth, and founder roles and mostly at startups. You can also search for geographic and alumni communities—for example, I belong to Xooglers, and there are tons of Boston-based tech communities.

3) Cohort-based communities.

I didn’t fully understand the value of these until I started facilitating monthly conversations for several cohorts via Supra. The way it works is that you’re matched up with 7-8 other people with roughly your level of experience and at similar (but non-competitive) companies that meet regularly for structured, supportive conversations. In the case of Supra, for example, the conversations are monthly and facilitated by a professional (that’s me!). The competitor I know best is Sidebar, and while Supra is restricted to mid-senior product leaders, Sidebar accepts a broader range of professionals. If you’re a product leader, you can sign up for Supra here: https://joinsupra.com.

4) Job Search Councils.

In their book Never Search Alone, Phyl Terry recommends that job seekers join “job search councils,” a group of three to five peers at a similar career stage but with diverse backgrounds. The goal is to provide accountability, emotional support, a broader perspective, and an expanded network. For more information about these councils or to read the book (highly recommended!), visit https://www.phyl.org/.

How can I get the most value from communities?

Which communities should I join?

At a minimum, join Rands Leadership Slack and find an appropriate community of practice. Most people will benefit from finding (or creating!) a job search council. If you’re willing to put in the work, a community of practice can be transformative, and a cohort-based community makes sense but can be expensive. I’ll provide a list at the end of this article! 

How do I get the most out of a community?

The biggest mistake I see people make when joining a new community is lurking too long. It’s worthwhile to watch and listen a bit to understand better the norms and unspoken rules of any new community. But don’t spend too long just lurking: you’ll want to start contributing. Join channels where you have something to say, answer questions as they come up, and, as much as possible, speak from your own experience. But surprisingly, one of the best ways to participate in a community is to ask questions. People will appreciate the vulnerability and opportunity to contribute.

How often should I participate?

Think of this like a (small) job: set aside 15-30 minutes daily to post and respond.

What if I have more questions?

Reach out! You can email me at joshua.herzig.marx@gmail.com, schedule a time with me at https://zcal.co/jhm, or DM me in whatever community we share!

List of communities

Rands Leadership Slack, great for everyone: https://randsinrepose.com/welcome-to-rands-leadership-slack/

Communities of practice:

Product management:

• Friends of Lenny’s Newsletter: https://www.lennysnewsletter.com/p/community

• Mind the Product: https://www.mindtheproduct.com/product-management-slack-community/

• Women in Product: https://womenpm.org/join-our-community/

Product marketing:

• Product Marketing Alliance: https://www.productmarketingalliance.com/join-slack/

Design:

• Memorisely: https://www.memorisely.com/

• Designed: https://www.designed.org/

• The Designership: http://thedesignership.com/

Engineering:

• Rands Leadership Slack: https://randsinrepose.com/welcome-to-rands-leadership-slack/

• Engineering Managers: https://engmanagers.github.io/

Data Science:

• Data Science Learning Community: https://dslc.io/

• Data Angels: https://www.dataangels.org/home

Professional writing and documentation:

• Write the Docs: https://www.writethedocs.org/

Sales:

• Modern Sales Pros: https://modernsaleshq.com/

• Pavillion: https://www.joinpavilion.com/ (more generically GTM)

Solution/sales engineering:

• Tech Sales Mastery: https://www.techsalesmastery.com/

Partnerships

• Smarterships: https://www.smarterships.co/

• Partnership Leaders: https://partnershipleaders.com/

Learning and development, tech enablement:

• TechKnowCon: https://techknowcon.io/

Customer success:

• Customer Success Collective: https://www.customersuccesscollective.com/

• Customer Success Leadership Network: https://www.csleadershipnetwork.com/

Documentation and technical writing:

• Write the Docks: https://www.writethedocs.org/slack/

Chiefs of staff:

• Chief of Staff Network: https://www.chiefofstaff.network/

• Ask a Chief of Staff: https://askachiefofstaff.com/

• The Chief of Staff Association: https://www.csa.org/

• Chief of Staff Collective: https://www.chiefofstaffcollective.org/

Research:

• ResearchOps Community: https://researchops.community/

Healthtech:

• Health Tech Nerds: https://www.healthtechnerds.com/c/how-to-join-htn-community

Fintech:

• TWIF/Finnovation: https://thisweekinfintech.com/community

Greentech/climatech:

• Work on Climate: https://workonclimate.org/our-community/

Coaching and fractional work:

• Coaching Corner: https://joincoachingcorner.com/

• Fractional Product People: https://fractionalpeoplepeople.com/

• FRCTNL: https://www.frctnl.xyz/

Nonprofits:

• Social Impact World: https://www.socialimpactworld.com/chat/

• NTEN: https://www.nten.org/

HR:

• PeoplePeople: https://www.getweirdly.com/people-people

• HelloTeam: https://www.helloteam.com/slack-community/

• peoplegeeks: https://www.cultureamp.com/slack-channel-for-people-geeks

• #people: https://hashtagpeople.co.uk/

Investing (for PMs):

• Hustlefund: https://www.hustlefund.vc/product 

Focused on women and NB folks who work in tech:

• Women in Tech: https://witchat.github.io/

• Leopard.FYI: https://leopard.fyi/

Cohort programs

• Supra: https://joinsupra.com (I enthusiastically recommend this one for mid- to senior product leaders)

• Collaborative Gain: https://collaborativegain.com/

• Sidebar: https://sidebar.com

Job search councils

Never Search Alone: https://www.phyl.org/join-jsc

We often need to make decisions with limited data. Sometimes, the information you need simply doesn't exist yet, or collecting it would be too expensive or time-consuming. The “paper model” approach is a powerful tool to make informed decisions in these situations of uncertainty. It allows you to use your best judgment and educated guesses to create a framework for analysis, even when perfect data is out of reach.

Why “paper model?”

In tech companies, we build "paper prototypes" to validate a design or better test user needs. A paper prototype is quick and dirty and isn't expected to survive its primary reason for being created.

Calling this a "paper mode" similarly emphasizes that this is really just a casual, ephemeral tool. Directionality is more important than accuracy, and speed to insight is more important than completeness. It's not about fancy spreadsheets or complex software (though those can be helpful!). Instead, it's about working backward from a desired outcome and getting a clearer picture of how to get there.

Essentially, you sketch out the key variables that influence your success and tweak them until you hit your target metric. The beauty is you then have a chance to step back and “gut-check” whether those numbers are realistically achievable.

A Personal Finance App Example

Imagine you're working on a personal finance app with a million monthly active users. You want to grow your average revenue per user (ARPU), and a board member suggests exploring the idea of an affiliate marketplace. Their definition of success is achieving an ARPU of $3 through this new marketplace.

How does a paper model help you make an informed decision?

1. Break It Down: Map out the user journey within an affiliate marketplace:

>> What percentage of your users log in with enough regularity to even see the offers?

>> Out of those, how many are likely to click through to explore affiliate offers?

>> How many offers, on average, might a user redeem?

>> What's the typical value of an offer redeemed?

1. Plug and Play: Figure out the numbers you know (number of regular users, value of a typical offer). Next, for the remaining variables, adjust them until you’d hit your goal. Even a rough model might quickly reveal that to hit the $3 ARPU target, a staggering 40% of your users would need to redeem at least one affiliate offer a month! Congrats: your simple paper model just uncovered the key metric to watch.

2. The Benchmark Test: This is where things get interesting. Compare your numbers to industry standards. If similar companies see 3-10% redemption rates, that's a red flag. Could your company outperform everyone else by that much? Maybe, but it forces you to question the underlying assumptions.

Why Paper Models Are So Powerful

Paper models aren't a replacement for detailed analysis, but they offer something unique:

• Focus on What Matters: They force you to pinpoint the levers that will have the most significant impact on your goal.

• Uncover Hidden Constraints: Sometimes, a simple model reveals how unlikely a particular scenario is.

• A Kickstart for Informed Decisions: Even a back-of-the-napkin model can prevent you from sinking time and resources into a lost cause. It can also help refine your goals or strategies based on clearer insight.

Limitations

While paper models are an excellent tool for initial planning, it's important to acknowledge their limitations. Here are a few dangers to consider:

• Oversimplification: Paper models can paint an unrealistic picture by neglecting complexities. Real-world factors and unforeseen challenges often arise, throwing your initial calculations out of whack.

• Data Dependence: Even a paper model relies on educated guesses. If your starting assumptions are significantly off, the entire model becomes unreliable.

• Misplaced Trust: A paper model can create a false sense of security. It's crucial to remember it's a starting point, not a crystal ball. Don't get so fixated on the model that you miss the need for further research or data collection.

Put It Into Practice

The next time you face a big decision, try sketching out a paper model. It's great for team discussions, too! You might be amazed at how a fast, simple exercise can illuminate complex problems.

Have you used a similar approach? How did it work for you? Let me know!

Was this article helpful? I provide coaching, mentorship, and advisory support to founders, solo PMs, and first-time Heads of Product. I also have a collection of my favorite tools and templates available for free here. If you want to talk, grab some time!

"Does anyone actually attend their exit interview?"

This casual remark, recently encountered in a tech community, struck a chord. It wasn't just the cynicism that caught my attention, but what it said about the gap between employees and managers. But I can’t blame them because most exit interviews suck.

Exit interviews are not administrative checkpoints to be ticked off. Instead, they are a critical feedback mechanism designed to offer both the departing employee and the organization a moment of candid reflection, honest assessment, and mutual growth. Unfortunately, this ideal is far from reality for many, as evidenced by the apparent apathy towards such interviews. Why, then, does this disengagement exist, and what does it reveal about the broader organizational culture and the employee experience?

1. Time constraints. As employees prepare to leave an organization, their final days are often a whirlwind of activity—finalizing projects, transitioning responsibilities, and the emotional labor of farewells. Carving out time for an exit interview can feel like an unnecessary burden, a box to tick in a long list of last-minute obligations. 

2. Fear of retaliation. In an ideal world, exit interviews would be safe spaces for honest feedback. However, the reality is that the professional world is interconnected and, at times, unforgiving. Concerns about burning bridges or casting a shadow on one's professional reputation can muzzle departing employees, encouraging them to offer platitudes rather than the unvarnished truth. 

3. Lack of trust. If employees feel that their feedback will disappear into the void, unacknowledged and unacted upon, their motivation to participate dwindles. The ritual becomes empty, the potential for change, stagnant.

4. Poor execution. When exit interviews are reduced to a series of rote questions, lacking genuine engagement or the intent to understand and improve, they lose all value. (“What was your primary reason for leaving?” “How do you feel about management or leadership?”) Employees can sense when a process is performative rather than purposeful. 

The good news is, I don’t think it’s hard to do better. 

• Incorporate better, more thought-provoking questions. 

• Listen without the impulse to argue or persuade and acknowledge the validity of the departing employee's perspective. 

• Conclude with a sincere thank you and recognize the value of their feedback.

Here are ten questions I’ve collected and developed over the years that have worked great for me:

1. Anything you want to ask before we start? Is there anything you want to make sure we cover?

2. What was your favorite part of working here? What is your proudest accomplishment?

3. What should we have told you in the interview process? What would have been helpful to know in advance to help you be as successful as possible?

4. Who would you take with you if you could, and why? (Remind them you’re not trying to trip them up and get them to break a non-solicitation agreement.)

5. If you could replace or re-assign anyone within the organization, what changes would have the biggest impact?

6. Similarly, what three changes to the org would you suggest we make? These can be personnel moves, changes to organizational structure, policy changes, anything.

7. Tell me about the day you decided to leave.

8. Aside from the work you are directly responsible for, what other work or relationships does your exit put at risk, and how would you suggest we mitigate that risk?

9. What should we know to help the person we hire next be as successful as possible?

10. What else should I have asked you today? Anything you were hoping I would ask or that we would cover?

Don't forget to close out by covering administrative stuff: last day of work, how to return equipment, details around benefits and severance, etc.

So, why do these questions work so well? It's simple: they're designed to get honest, useful feedback and show the departing employee their opinions matter. We offer a mix of questions because not every one will click, but this variety helps us understand what really impacted their experience. By approaching the same topics from different angles, we get a more complete picture.

More than that, these questions set the stage for a positive and productive final conversation. The interviewer's job is to build trust, listen actively, and make sure the employee's last impression is a good one. This not only helps us improve as a company but also ensures the departing employee feels heard and respected and leaves with a sense of appreciation for their contributions.

Want your own copy of these questions in easy template form? https://docs.google.com/document/d/1nMnx7oRSxsB7Q-K_LDcWVL-4y18qFv0CVg19ExQuur8/copy

I hope you don’t need to read this. It’s a checklist for when you’re preparing to let someone go. But between the stories on LinkedIn and the messages in private, a lot of folks are being fired poorly. So why a checklist?

Because firing someone is stressful, and stressful times are terrible times to make plans. You’re rushed for time. Your brain isn’t working right. Checklists are great tools for shifting thinking and planning from stressful times to chill times. I’ve assembled this one over the years to help myself not screw things up. Think of every checkbox and bullet as another time I screwed up my attempt to do better the next time.

Hopefully, this isn’t anything you need. But if you do? Learn from me. Take a few extra minutes to write out a plan, and make sure you don’t skip any steps. The hour or so it’ll take will be an hour well spent.

1. Check with Legal and HR

 As the manager or exec, you need to own the termination process. But your Legal and HR departments are there to protect you from the things you don’t know.

• Consult HR and Legal: Before initiating the termination process, consult with your HR and Legal departments. It’s their job to protect you from potential risks and ensure compliance with labor laws. They have special training, distinct knowledge, and experience you lack. You’ll want to ask, “What risk am I creating for the company and myself?”

• Understand Protected Classes: Pay special attention if the employee belongs to a protected class to avoid potential discrimination claims.

2. Sweat the Details

Good news: you’re already ahead of the game by working a checklist like this. But this is when you want to start writing all the details down. Putting your plan down on paper makes it less likely you’ll forget a critical step, and it means collaboration and assistance from others is much more likely.

• Determine Last Day and Account Access: Decide on the employee's last day and schedule the termination of their access to company accounts and systems. If you don’t have a continually updated list of all company systems, this will be the day to start.

• Practice the Process: If unfamiliar with the process for shutting off access, rehearse the steps to ensure a smooth execution. As in: visit all the correct pages, make sure you have administrative access or know the person who does, and confirm nothing is down.

• Communicate to the Team: You’ll need to let their coworkers know, so plan how and when colleagues will be informed, ensuring the message is respectful and maintaining the individual's privacy. This could be an email, a Slack message, an in-person meeting, or a Zoom call. Be explicit about what you’ll say and won’t say.

• Outline Severance and Benefits: Clearly define any severance package and explain the continuation of benefits, such as health insurance, if applicable. This is another place where you’ll want to work with HR, and if you don’t already have a policy, consider this your first draft.

3. Prepare Communication Scripts

As Mark Twain (may not have) said, “If I’d had twice as long, I would have written half as much.” Write out the words you’ll use to ensure precision, concision, and empathy.

• Craft Two Scripts: Develop one script for the individual being terminated and another for the remaining team members, focusing on clarity and compassion.

• Explain the Reasoning: Whether due to performance, fit, or organizational changes, be transparent about the reasons for the termination in a respectful manner.

• Be brief: No perfect language will make a hard conversation easy. But you sure can screw it up with inappropriate apologies, false promises, sharing private or sensitive information, or any number of ways if you ramble because you’re uncomfortable. 

• Practice Delivery: Practice enough so it sounds genuine. Rehearse delivering these messages out loud and seek feedback from a trusted colleague or advisor to refine your approach. And when you do deliver it? Stick to the script.

4. Engage Key Stakeholders

What arrives faster than an email? Chains of confused DMs between panicking employees.

• Inform Leadership and Peers: Ensure that your manager, the employee's manager, and relevant peers are briefed on the situation and understand the reasons behind the decision. They’re going to get questions.

• Align on Communication: Guarantee that these insiders are prepared to reinforce the official message and provide consistent information to the team. All of your work is for nothing if the remaining colleagues hear differing answers to their questions. And it’s equally important to align on tone. Many companies try to be nice with phrases like: “Not every great person is a great fit for every great company.” Other companies aim for firm, yet fair: “

5. Schedule Critical Meetings

It’s 2024. Everyone knows what the dreaded 15-minute “Quick check-in” means. Don’t be cute, and also don’t be unprofessionally casual.

• Arrange Two Meetings: Set up a meeting with the individual for early in the day and another with the team immediately following to minimize uncertainty. Early in the day minimizes wasted work as well as the awkwardness of everyone knowing about the termination except the person heading out the door. 

• Be professional: For both meetings, make sure you’re someplace private where the critical conversation can have your full attention. Don’t be a LinkedIn horror story of accidentally screen sharing your shopping or revealing your YouTube videos in reflection from your glasses. Everyone deserves respect, and that means attention and professionalism.

• Prepare Email Announcements: If applicable, write an email announcement (or Slack post) about the departure to be sent to the team, focusing on maintaining confidence and proactively addressing potential concerns. For example, if the person is being let go for performance reasons, you can explain that the company has plenty of cash by sharing things like burn rate and bank balances.

6. Importance of Progressive Discipline

This is an issue I see crop up all the time at startups: Surprise at being fired. If this is the case at your company, it’s your wake-up call. Progressive discipline (telling people they’re underperforming long before they’re likely to be fired) is a key part of any organization’s performance management process.  

• Implement Feedback Mechanisms: Ensure the team is aware that the individual received fair feedback and opportunities for improvement, reducing anxiety about their own job security.

• Review your processes: Did someone provide feedback? Was this a known issue? Had it been brought up by peers? Could an earlier intervention have been productive? Should the individual have been let go earlier? If you think Termination was a failure, take the time to do a retro on when and where the failure happened.

7. Handle Reactions with Care

Everyone in your organization is on edge, worried about layoffs, their own performance, and their own job. How you treat the folks who remain is at least as important as how you handle the person leaving.

• Anticipate Questions: Be prepared for inquiries, especially if the individual played a significant role within the company or had been a long-term employee. You need to decide in advance what you’ll say, and you’ll do well to tie what you say to values: both your own and those of the company.

• Be present: Open up some office hours. Make it easy to schedule 1:1s. If you’re in the office, sit in the kitchen or linger by the coffee. If you’re remote, hang out on Slack. And you’ll want to actively check in with key employees to make sure they have a chance to share what’s on their minds. One signal that you’re doing OK as a manager and leader is when people approach you to ask questions. They’re feeling anxious.

That’s it. Seven things to do reflecting at least seven ways I screwed up. This likely won’t be the last time you need to let someone go, so once the dust has settled, turn this into your own learning opportunity: what went well? What was a surprise? What would you like to handle differently? What do you want to add to your own list?

And because this is hard and stressful, feel free to reach out over Linkedin or just book some time during my office hours.

Previously, I talked about what candidates can do differently to help get hired at tech companies in 2024. Now I’d like to talk about something that tech companies can do to hire better candidates: improve the quality of their internal referral programs.

Many on the outside have observed that referral programs don’t have the same prominence they once had: They were seen as expensive, believed not to deliver high-quality candidates, there have been concerns around lack of diversity, they had low participation rates, and (unfortunately) the HR, people ops, and recruiting leaders who administered them may have been let go as part of 2022 and 2023 layoffs. In addition, some execs might have decided that a softening in tech employment meant it was now a “buyer’s market.”

Especially for startups, employee referrals should be the best way to hire. But it doesn’t always work out that way.

Understanding Motivators for Employee Referrals

Before building an effective referral program, it helps to understand why employees participate. Here are three reasons listed in descending order of importance:

• Elevating Network Esteem: When employees refer someone from their network, they're not just recommending a candidate but offering a path to an opportunity where their contacts can thrive. Making a great referral to a great company makes your employee a hero! It elevates their status within their network, as they're seen as a conduit to desirable job opportunities.

• Internal Acknowledgment: When referring in high-caliber talent, your employees should earn admiration from their colleagues and public appreciation from managers and leaders. They're seen as key players in enhancing the company's talent pool, thus contributing directly to the organizational success.

• Financial Incentives: Some companies still pay a fee for referrals who are hired. While monetary rewards are not uncommon, they're often the least impactful motivator. 

Not surprisingly, the strongest motivators are relational, not transactional.

Common Pitfalls in Referral Programs

• Negative Employee Experience: You can’t expect your employees to refer their friends if they’re unhappy at work. This is a fundamental issue, and no referral program will succeed. And if your referral program is failing, you want to rule this out first.

• Candidate Experience Matters: Treating referred candidates indistinguishably from cold inbounds is a mistake. It’s sort of amazing how often internally referred candidates are ghosted, or are screened out at resume review without even having a phone call. It doesn’t take more than a couple of these before your employees will give up on making referrals. 

• Bridging the Skills Gap: Many of your employees, especially those early in their careers, may not even know how to make useful referrals. They may not know how to search their network, may not know how to identify strong candidates, and may not know how to talk about open roles. A skills gap means a lack of comfort and confidence in the referral process and makes it much less likely that a referral will happen.

• Inappropriate Recognition: Monetary rewards are fine, but they can feel impersonal. Again, it’s amazing how infrequently employees are thanked for making a referral, kept up to date on their referred candidate’s progress, or provided feedback on how to improve future referrals.

Crafting a Successful Referral Strategy

In some ways, you can make your internal referral strategy successful by doing the opposite of the section above!

Addressing Employee Morale

• Employee Satisfaction is Key: Before launching a referral program, ensure that your current employees are happy and engaged. This is the bedrock upon which successful referral programs are built. Collect feedback from managers, consider an employee satisfaction survey, and consider keeping an eye on review sites like Glassdoor.

• Preventing Embarrassment: A negative work environment, characterized by issues such as poor leadership behavior, can significantly deter employees from making referrals. And if there are public criticisms of the company (e.g., on Glassdoor), you should expect current employees to get questions from their friends.

Enhancing Candidate Experience

• Personalized Communication: Ensure that all communication with referred candidates is personalized. This could mean emails that acknowledge their referral source and perhaps provide a bit more background about the company or the role they're being considered for. Avoid generic, automated responses. And definitely avoid ghosting them!

• Expedited or Guaranteed Interviews: Offer referred candidates a faster track through the hiring process. This could be in the form of guaranteed interviews or a more streamlined application process. This shows that you value the referral and the time of both the candidate and the employee who made the referral.

• Enhanced Candidate Experience: Make their interview process unique. This could include a tour of your office (virtual or physical), meetings with key team members, or an informal chat with a senior leader. Such experiences can leave a lasting positive impression.

• Feedback Regardless of Outcome: Whether a referred candidate is successful or not, providing feedback is crucial. This should be more personalized and detailed than standard rejection emails. Feedback is unusual, and it will help you stand out.

• Survey for Continuous Improvement: After the hiring process, ask referred candidates for feedback on their experience. This not only provides valuable insights for improving the process but also makes the candidates feel their opinions are valued.

Celebratory and Educational Initiatives

• User-Friendly Referral Platform: Implement a straightforward, accessible referral system. You don’t need a complicated, dedicated portal; just use a simple form. The key is to make it as hassle-free as possible.

1. Clear Guidelines and Communication: Provide clear instructions and information about the types of candidates you're looking for. In addition to great JDs, consider listing the 2-3 differentiating qualities that will separate successful candidates from all the otherwise qualified folks. This reduces confusion and helps employees make more targeted referrals.

2. Referral Parties: This is my absolute favorite. Get interested employees together in a room with the hiring manager and folks from HR and spend a few hours tracking down great referrals. You can provide tools like job descriptions, outreach templates, and even pre-written LinkedIn queries to help identify high-quality candidates in their network. With hiring managers and experienced recruiters in the room, your employees get immediate feedback. Add in some food and music, and it becomes a party. It’ll be fun today, and you’re teaching valuable skills for the future.

Diversifying Recognition Methods

• Public Acknowledgment: Celebrate successful referrals at company meetings, in newsletters, or on internal communication platforms. Public recognition from leaders can be a powerful motivator.

• Feature in Company Communications: Spotlight the employee and their successful referral in the company blog, video interviews, or social media channels. It sounds silly, but employees love being able to show this kind of recognition to their parents, spouses, family, and friends.

• Regular Program Review: You’d be shocked, but asking people how to improve a program–and listening to them–could be the most effective way to show that both the program and the referral are important. Conversely, ignoring your employees is a pretty clear signal that their work to create great referrals doesn’t matter.

• Personal Thank You Notes: Finally, don’t forget the basics. A handwritten note from a senior leader or the CEO can be a simple yet powerful way to express gratitude.

Conclusion

A creative employee referral program is a multifaceted strategy that goes beyond mere financial incentives. It's about fostering a positive work environment, providing a superior candidate experience, educating employees on making quality referrals, and recognizing their efforts in meaningful ways. This not only enriches your talent pool but also strengthens your company culture, making it a win-win for everyone involved.

By implementing these strategies, you can turn your employees into active and enthusiastic ambassadors for your brand, bringing in top talent that aligns with your company's values and vision. Remember, the most successful referral programs are those that are thoughtfully designed, effectively communicated, and sincerely appreciated.

Luckily, there was an incredible television show in the early aughts that teaches us everything we need to know about hitting a tight deadline with audacious objectives and limited resources.

Monster House aired from 2003 to 2006 on the Discovery Channel. Every week, host and foreman Steve Watson would assemble a small and motley crew of builders, plumbers, electricians, painters, and others (who had never worked together before) to transform a boring regular home into something spectacular. The homeowners get to pick the theme (their only involvement); one week, it was space-themed, and they incorporated a crashed spaceship and pneumatic tubes into a single-story California ranch. Other themes included dinosaurs, ancient Egypt, and gangsters.

It’s worth watching a couple of episodes here on YouTube.

How were they able to get such incredible work done within such restrictive constraints?

1. Understanding the 'Who' and 'Why'

The first step in the Monster House method involves ensuring the entire team understands for whom they're building and why. They’d meet the homeowners and hear a bit about why the particular theme was chosen. Each person on the build team got to hear from the family directly and hear their hopes and anxieties. In my experience, this understanding is crucial. We’re not just building a product; we’re crafting a solution for real people with real needs. This empathetic approach fosters a deeper commitment and a stronger sense of purpose, which is indispensable when working against the clock.

2. Crafting a Clear, Shared Vision

Next, the team collectively sketches out what they’re going to build. A week isn’t long enough to truly change every detail of the house. But each of the teammates is an expert in what they do, and they’re called on to visualize (literally - with drawings) what they think can be accomplished in a week to maximize impact. Why do this visually? Because words, no matter how eloquently penned, can be misinterpreted. A shared visual representation – be it sketches, diagrams, or mock-ups – becomes a communal language, transcending individual interpretations. And, combined with getting an empathic understanding of the end users, this is where you create alignment.

3. Locking in Team and Timeline

In Monster House, the timeline (one week) and the team (unless someone storms off in a rage) are fixed. Because “adding people to an already late project only makes it later,” we should think of our fixed deadlines as having fixed teams as well, even if our timeline is longer. After all, anyone who comes in late will lack the context and the alignment previously established. It's also a declaration that the team assembled is the right one and that the timeline set is achievable. We’re fostering confidence and urgency, crucial components for success under tight deadlines.

4. User Stories and Task Lists

This is where the rubber meets the road, and we define scope and commitments. First, as a team, write out the user stories we expect to support when we’re done. And, as a team, make sure this is truly as minimal as possible. The entire project is a stretch goal. No need to make it more of a stretch. Second, turn those user stories into a punch list of tasks. Why a punch list? Builders like those on Monster House use a simple list of things to be completed, nailed up somewhere conspicuous, to ensure everyone knows what they should be working on. Here are some hard-won lessons about how to set tasks:

• Each task has a single person responsible.

• Try and make sure each task is independent, can be completed by one person, and lacks any dependencies. Barring that, make sure there are no dependencies outside the project team.

• If the team, individually and collectively, can’t enthusiastically agree that the tasks are achievable, then they aren’t achievable. Don’t bully your team into failure.

I’ve created a handy template here - feel free to copy, share, and make it your own. And just like a builder’s paper punch list, make sure this one is visible to the team and that everyone is updating it continually.

5. Creative Problem Solving Under Constraints

An unexpected catalyst for creativity lies at the confluence of a fixed deadline and teams. The constraints imposed by such conditions are not hurdles but are, in fact, what ignites your best thinking. You don’t truly understand your challenges, or those of your customers, during the planning stages—this only emerges from the doing. When confined by these boundaries, teams transform constraints into opportunities for creative problem-solving. We see this often on Monster House, where the final product exceeds the expectations of the initial vision. 

6. The Finish Line: Done or Not

As the due date looms, a hard truth emerges: you're either done or you're not. The beauty of Monster House’s method lies in its unapologetic realism. It forces teams to monitor progress closely and descope where necessary. It's about being agile and honest, ensuring that if a scaling back is needed, it's done without surprise or last-minute chaos. And regardless, when you hit the due date, celebrate! You and your team just accomplished something really cool and really out of the ordinary. 🥳

The Allure of the Monster House Method

Why does Monster House have so many great lessons for us, 20 years later, building software products? Because it works and because it’s fun.

The Monster House method is not just a set of steps; it's a philosophy grounded in clarity, commitment, and pragmatism. It speaks to a truth I've seen in all my years of work: the path to achieving great things on tight deadlines is not through chaotic heroics but through disciplined, well-orchestrated teamwork.

Why This Method Works

1. Empathy and Purpose: Understanding the end-user fosters a sense of purpose that can drive teams to exceed expectations.

2. Visual Communication: Eliminates ambiguities, aligning everyone's understanding and vision.

3. Commitment and Urgency: Locking in resources and timelines creates a focused, high-energy environment.

4. Ownership and Expertise: Assigning tasks based on belief in individual expertise encourages accountability and quality.

5. Realism and Agility: Accepting the reality of deadlines and being prepared to adapt ensures progress without panic.

Monster House was a show about transformative results under challenging constraints. It's a testament to what can be achieved when a team is aligned in vision, committed in action, and enthusiastic in execution. In my experience, whether in technology, entrepreneurship, or any field requiring innovation under pressure, this is a framework not just for meeting deadlines but delivering products and solutions that are timely and extraordinary.

Listen to Phyl Terry, author of Never Search Alone and inventor of the Job Search Council, talk with Lenny Rachitsky about how to get a job. It's gratifying to hear so much of what I've been recommending echoed by someone who's truly an expert: https://www.lennysnewsletter.com/p/land-your-dream-job-phyl-terry.

Here are six suggestions that might be helpful for next year, plus a few bonus tips, to give you an edge:

1. Acknowledge the chaotic hiring landscape. It's no secret that companies have always struggled with effective recruiting and hiring. This year, the situation has worsened. Maybe it’s because HR, people ops, and recruiting teams were the first to be laid off. I’ve seen reports of applications going unacknowledged, weeks between interviews (or any communication), and candidates being ghosted after their final round. It's important to recognize this new reality - it's not just you finding it tough; the system is more chaotic and disorganized. This is just as true for big, established companies as for startups.

2. Early application advantage. Timing is crucial. If you're eyeing roles in tech, a useful strategy is to monitor venture capital (VC) job boards. VCs pay to aggregate jobs from across their portfolio, and jobs here often show up days or weeks earlier than on more mainstream sites like LinkedIn. I've listed a couple dozen at the end of this article. Check these sites once or twice a day (I like to keep the tabs open in a separate window). Being among the first to apply can significantly increase your chances of getting noticed and landing an interview. Of course, the moment you apply, you should go into networking mode (see below).

3. Proactive networking is less productive. In the past, especially at startups, you might have been able to connect with a founder or exec, and if you hit it off, they might create a role for you. Or they might have accelerated an open role. But with the end of cheap startup money, you can’t count on the same thing. You should never stop networking, but your next offer will probably come from an open, posted role. Focus your networking for after you've applied. 

4. The power of “cool leads.” In a sea of applicants, standing out is key. If you can't secure a direct referral, consider a “cool lead.” This involves connecting with someone, anyone, within the company as soon as you apply for a job. It doesn't have to be someone in the same department; any internal connection can be valuable. So, apply for the job (do that first!) and then quickly search out anyone you can who works at the company. Have a brief chat, ask insightful questions about the company, and request that they mention your conversation to the hiring manager. You’re not pitching them on yourself as a candidate (they don't know you and probably don't know the role); you just want them to think of you as a cool person and share your name with the hiring manager. This interaction can make your application memorable amidst hundreds.

5. Brace for a longer job hunt: It's likely that securing a job this year will take more time and may feel more frustrating. To cope, consider professional communities (let me know if you need some suggestions) or forming a personal job search council (as suggested in the book Never Search Alone). Preparing mentally for this reality can help you stay resilient and focused during your job search.

6. Invest in Community: Community is the fastest way to expand your network, increase confidence, and provide emotional support and motivation. Job seeking is hard, but community can make it easier. I've written about it here and even included lists of great communities to join.

Bonus evergreen tip: Utilize loose social ties. Don't underestimate the value of your less-close connections when job hunting. These are people you might not talk to often but can be surprisingly helpful (e.g., not family or close friends). Don't hesitate to reach out even if you haven't spoken in years. I spoke with close to 200 tech folks about their professional networking (exploring a startup concept!), and most reported being surprised at who provided the critical introduction.

Bonus tip #2: Recruiters can be your friends. Make a note of who seems to really understand their clients (my favorite question: “What 2-3 differentiating attributes separate the successful candidate for this specific role, at this specific company, from all the other well-qualified applicants you see?”) and be sure to stay in touch. Check-in regularly to see if they have any open roles they’re having a hard time filling. And try to connect them to folks in your network who might be looking.

Bonus tip #3: Are you applying for an exec or leadership role at a startup? Don’t be afraid to help them “manage” their hiring process. This could be as simple as helping them define their hiring rubrics (”What 2-3 differentiating attributes separate the successful candidate? How are you identifying those qualities in the interview process? What questions are you asking and what answers are you listening for?”) or even helping them establish a better process. Make sure you’re talking to the right people, make sure they’re asking the right questions, and if they’ve been struggling to fill a role, even help them think through why. No better way to audition for a leadership role than by showing leadership.

Bonus tip #4: If there’s a book that tells you how to ace the job interview for your profession, read it! I re-read Cracking the PM Interview every time I’m on the market. And if there is no similar book for you, consider reading a guide for the interviewer. I like Hiring Talent and Behavior Based Interviewing.

Bonus tip #5: I don’t know their magic, but Otta.com has been surfacing roles I don’t think I would have seen otherwise. Consider adding it to your rotation, along with LinkedIn alerts and the VC job boards listed above.

Let me know if there’s anything you think I got wrong or missed! And if there’s something I can do to be helpful, please let me know.

UPDATE: There's been a request for a list of VC job boards: here's a nice starting place!

1. https://jobs.500.co/jobs 

2. https://portfoliojobs.a16z.com/jobs

3. https://jobs.accel.com/ 

4. https://careers.antler.co/jobs

5. https://careers.atlasventure.com/opportunities/

6. https://jobs.av.vc/jobs

7. https://jobs.b.capital/companies

8. https://jobs.baincapitalventures.com/jobs

9. https://jobs.battery.com/jobs 

10. https://jobs.bvp.com/jobs

11. https://jobs.coatue.com/jobs 

12. https://jobs.contrary.com/jobs

13. https://jobs.femalefoundersfund.com/jobs

14. https://firstround.com/talent/ 

15. https://www.flagshippioneering.com/join/roles

16. https://jobs.foundationcapital.com/companies

17. https://jobs.fprimecapital.com/jobs

18. https://jobs.generalcatalyst.com/companies

19. https://jobs.ggvc.com/jobs 

20. https://jobs.greycroft.com/companies

21. https://jobs.greylock.com/jobs

22. https://jobs.gv.com/jobs 

23. https://www.indexventures.com/startup-jobs 

24. https://jobs.insightpartners.com/jobs 

25. https://jobs.khoslaventures.com/jobs 

26. https://jobs.kleinerperkins.com/jobs 

27. https://jobs.lightbank.com/jobs

28. https://jobs.lsvp.com/jobs 

29. https://jobs.menlovc.com/jobs 

30. https://careers.nea.com/jobs 

31. https://careers.nvp.com/ 

32. https://careers.redpoint.com/jobs

33. https://jobs.revolution.com/jobs

34. https://jobs.sapphireventures.com/jobs

35. https://jobs.sequoiacap.com/jobs 

36. https://techjobs.sosv.com/jobs 

37. https://jobs.svangel.com/jobs 

38. https://jobs.techstars.com/jobs 

39. https://careers.thirdrockventures.com/ 

40. https://jobs.thrivecap.com/jobs

41. https://jobs.underscore.vc/jobs

42. https://www.ycombinator.com/jobs

UPDATE: If you're interested in PM jobs at big companies (public or valued at > $1B), you can request access to this private list of new roles, updated daily.