Your 30/60/90 is too slow for startups

My 3/6/9 plan: Work fast, judge slow

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.

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.

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.