Five great reads for 6/19/2025
From talent retention to urban planning, success hinges on designing systems that align human incentives.
The Great Talent Drain: Why Your Best People Are Ghosting You (And How to Win Them Back) (Angelo Santinelli)
If you're wondering why your best employees are leaving, this article offers a blunt diagnosis. With a private sector separation rate of 4.4% and over half of employees disengaged, the "Great Talent Drain" is a crisis for startups competing with BigTech salaries. The core issues aren't surprising: poor leadership, scant growth opportunities, and uninspiring company cultures. The key takeaway is that founders can't just wing people management. The piece advocates for concrete actions like structured leadership training, frequent and meaningful feedback (especially for Gen Z), and creating genuine psychological safety. This is the kind of objective feedback leaders need on why their people are quitting; the advantage startups have isn't cash, but the agility to build a culture that truly values its team. (link)
Transmitting user empathy via data (
)Simply presenting data rarely fosters true user empathy within a team. The author argues that quantitative researchers have a crucial role in building this connection by providing the necessary context that makes numbers feel real. A metric like a "2-minute wait time" for a UI operation is just a number until it's framed by the context that users become frustrated after mere seconds. Data is not neutral; researchers must have a viewpoint and deliberately use context to guide stakeholders toward the correct interpretation of user pain. A key goal for leaders is to ensure everyone has a deep, empathic understanding of the user, and that quantitative data, when presented with the right narrative, is a powerful tool to achieve it. (link))
In the face of volatile, project-based AI usage, driving customers to annual plans is a powerful strategy for improving retention and cash flow. This article presents 14 tactical ideas, cautioning against forcing the switch and instead recommending softer nudges. Key strategies include making annual plans the default on pricing pages (a practice used by 88% of Cloud 100 companies), offering more generous discounts based on LTV data, and creating lifecycle triggers that prompt an upgrade early, when customers are most engaged. Hard data trumps intuition, even for people as experienced as the author. While one might think it's best to wait before pushing an upgrade, data shows customers are 3-4 times more likely to upgrade in month two than in month nine. It's a playbook of data-backed nudges over assumptions. (link)
How to redraw a city (Anya Martin)
Japan's evolution into a nation of hyper-functional cities, despite facing immense challenges like fragmented land ownership, offers a profound lesson in urban planning, and planning in general. "Land readjustment" is a process of pooling plots, redrawing boundaries to accommodate infrastructure, and redistributing the new plots. This approach built durable public support for drastic change by sharing the profits of development and requiring supermajority consent from landowners. Does this sound like anything PMs do? The article serves as a powerful reminder of how the planning process can significantly influence the outcome. By designing a system that aligns stakeholder incentives and ensures shared benefits, Japan successfully executed massive infrastructure projects that would be politically impossible in most countries today. (link)
PM Jobs - a podcast playlist (Josh Herzig-Marx)
Here's something I created for anyone navigating a PM job search. It's a custom "podcast" feed that aggregates episodes from several different podcasts into a single, subscribable playlist. You can stream the episodes directly from the page or copy the unique RSS feed link into your preferred podcast player to listen on the go. I built the underlying platform, Podfolio, for anyone who wants to create their own curated collection of podcast episodes. I hope you find it useful! (link)