What Mark Pincus taught me about turning a roadmap from a checkbox into the heartbeat of a team, right as I’m avoiding building one myself. This week in our Life at the Speed of Play read-along, we hit Chapter 5: Roadmapping Is Your OS. It could not have landed at a more inconvenient time. I recently moved into a new role as Senior Director of Product Growth, I’m building a brand new AI-native product from scratch, and right now, I don’t have a roadmap. Pincus would say that’s exactly when you need one the most. What you’ll learn: * Pincus treats roadmapping as the operating system for an entire company, not a status update. His team ran it through what they called Blue Sheets, one meticulously organized document broken into four quadrants: priorities, OKRs, this month’s objectives, and team health. It’s the difference between a roadmap as an artifact you check a box on versus one that actually holds you accountable week over week. * He names a trap I see constantly in product work: teams without big ideas drown in what he calls “mouse nuts,” small, safe features that feel like progress but don’t move the needle. I’ve watched plenty of product managers (myself included, some weeks) retreat to those because they’re easier and less risky than the big swing. * One rule stuck with me: nobody on his team could change their OKRs mid-quarter, even when the gaps got obvious. That forced them to find a new execution path instead of quietly retreating into small, safe features. My honest struggle right now is that my product is so new I can’t even measure client usage yet, so the only thing I can track is how fast or slow we’re moving. I had to reset expectations with my boss that this is taking longer than we thought, not because we’re failing, but because our original timeline was never realistic. * Pincus’s “altitude” framework (5,000 feet is ground-level execution, 25,000 is strategic, 50,000 is big-picture vision) explains why meetings get dizzying. If you don’t name what altitude you’re operating at, half the room is talking tactics while the other half is talking vision, and nobody feels heard. It’s basically a companion piece to the Working Genius series I did a while back, where I talked about how each genius naturally operates at a different altitude. * I did a retrospective with myself this week (new moon, I’m hippy dippy like that) and landed on a “how might we” of my own: how might I start to feel enough. Not enough at work, not enough with my kids this summer, not enough for my sister or my parents. Part of what I’m taking from this chapter is that avoiding the roadmap because things feel uncertain is backwards. Being transparent about what’s actually happening, even when it’s messy, is the thing that helps. Next week we’re on to Chapter 6, Bold Beats, which Pincus frames as how you actually deliver against a roadmap once you’ve built one. p.s. Here’s me on Friday reading my 3rd Program Review document (600 pages if you include the appendix). It’s painful but massively contributes to the quality of AI features. The insight this week. We often want to share the pretty (that’s social media thinking), but communicating the value of the hard and messy is what helps people learn along with you! Get full access to Confessions of a Creative Leader at creativeleaderconfessions.substack.com/subscribe
