Nov 2025

November 22, 2025

Spent the morning reviewing our Q4 roadmap with the team. We’re at that point where we need to make hard tradeoffs between paying down tech debt and shipping new features.

The temptation is always to push off the debt, but I’ve seen that movie before—it always costs more later. We decided to dedicate 30% of sprint capacity to infrastructure work. Not ideal for velocity metrics, but the right call for team morale and long-term speed.

The best time to pay down tech debt was six months ago. The second best time is now.

Source: Unknown, but feels true

Afternoon call with a founder I’m advising. They’re struggling with pricing—classic early-stage challenge. My advice: charge more than you’re comfortable with, then see what happens. You can always come down, but going up is much harder.

November 20, 2025

Had our quarterly planning session today. These are always exhausting but necessary. The key insight that emerged: we’ve been spreading ourselves too thin across three product lines when we should be going deep on one.

It’s counterintuitive—feels like we’re leaving opportunity on the table—but focus compounds. Every successful product I’ve worked on got there by saying no to good ideas in service of great ones.

Tomorrow we’ll start the hard conversations about what to sunset.

November 18, 2025

Interviewed three PM candidates this week. The bar keeps rising, which is great, but it also means longer hiring cycles.

One thing I’ve changed in my interview approach: I now spend more time on the “tell me about a time you were wrong” question. How someone handles being wrong tells you more about how they’ll work with a team than any case study ever could.

The best answer I heard: “I was so convinced we needed feature X that I pushed it through despite engineering concerns. It shipped, barely worked, and we had to roll it back. I learned that strong opinions need to be held loosely.”

That’s the kind of self-awareness that makes someone great to work with.

On Building Product Intuition

There’s a moment in every product manager’s career when you realize that data alone won’t save you. You have all the metrics, the user research, the competitive analysis—and yet the path forward isn’t clear. This is where intuition comes in.

Product intuition isn’t magic. It’s pattern recognition built from thousands of small observations. It’s the accumulated residue of every customer interview, every feature launch, every failed experiment. The PMs who seem to “just know” what to build have simply been paying attention longer.

The Components of Intuition

I’ve come to believe product intuition has three core components:

Customer empathy at scale. Not just understanding one user’s problem, but sensing the shape of a problem across thousands of users. This comes from doing enough customer interviews that you start hearing the same pain points expressed in different words.

Technical possibility awareness. Knowing what’s easy, what’s hard, and what’s impossible with current technology. This doesn’t mean you need to code, but you need enough conversations with engineers to develop a feel for complexity.

Business model coherence. Understanding how value flows through a system. A feature might delight users but destroy your unit economics. Intuition helps you spot these traps before you walk into them.

How to Develop It

The bad news: there are no shortcuts. The good news: the path is straightforward, even if it’s not fast.

Talk to customers constantly. Not just during formal research phases, but all the time. The PMs with the best intuition are the ones who’ve done hundreds of customer conversations. They can predict objections before customers voice them.

Ship and observe. Every feature you ship is a hypothesis. Watch what happens. Did users behave the way you expected? If not, why not? This feedback loop is where intuition gets calibrated.

Study adjacent products. Your users don’t compare you to your direct competitors—they compare you to the last great experience they had. Study products outside your category. What can you learn from how Notion handles collaboration? How Linear handles speed? How Apple handles polish?

Write down your predictions. Before you look at the data from a launch, write down what you expect to see. Then compare. This practice surfaces the gap between your intuition and reality.

When Intuition Fails

Even well-developed intuition has limits. It’s pattern matching, which means it works best when the future resembles the past. In genuinely novel situations—new markets, new technologies, new user behaviors—intuition can mislead you.

The best PMs know when to trust their gut and when to experiment. They use intuition to generate hypotheses, then test those hypotheses rigorously. They’re confident but not certain. They have strong opinions, loosely held.

The Long Game

Building product intuition is a career-long project. The PMs I admire most are the ones who, after twenty years, are still curious. They’re still doing customer interviews. They’re still shipping and observing. They know that intuition isn’t a destination—it’s a practice.

Start today. Talk to a customer. Ship something small. Write down your prediction. Then pay attention to what happens. That’s all intuition is: attention, compounded over time.

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The Art of Saying No

The most important skill in product management isn’t saying yes to good ideas. It’s saying no to them. Every product I’ve seen fail didn’t fail from lack of ideas—it failed from lack of focus. The team tried to do too much and ended up doing nothing well.

Saying no is hard because good ideas feel precious. When someone brings you a thoughtful proposal backed by data, turning it down feels wasteful. But resources are finite. Every yes is an implicit no to something else. The question isn’t whether an idea is good, but whether it’s better than the alternatives.

Why We Say Yes Too Often

Several forces conspire to make PMs say yes when they should say no:

The stakeholder treadmill. Every team has legitimate needs. Sales needs features to close deals. Support needs tools to help customers. Marketing needs launches to drive awareness. If you try to satisfy everyone, you satisfy no one.

The sunk cost trap. Once work begins on a feature, momentum takes over. Canceling feels like admitting failure. But the cost already spent is gone regardless—the only question is whether to spend more.

The fear of missing out. Competitors ship a feature and suddenly it feels urgent. But copying competitors is usually a mistake. They have different customers, different strengths, different strategies. What works for them may not work for you.

The optimism bias. “We can do both” is the most dangerous phrase in product development. You probably can’t. And even if you can, doing both means doing neither as well as it deserves.

How to Say No Well

Saying no doesn’t mean being dismissive. The best PMs say no in a way that maintains relationships and keeps good ideas flowing.

Explain the tradeoff. Don’t just say no—show what you’d have to give up to say yes. “We could build this, but it would push back the platform migration by two months. Is that a tradeoff we want to make?”

Tie it to strategy. A no feels arbitrary unless it connects to something bigger. “This doesn’t fit our current focus on retention. Once we’ve moved the needle there, we can revisit.”

Offer alternatives. Sometimes you can’t build the full solution, but you can address the underlying need. “We can’t build a custom dashboard, but we can add these three fields to the export.”

Make it temporary. “Not now” is easier to hear than “never.” If an idea genuinely has merit but doesn’t fit current priorities, say so. “I love this idea for Q2. Let’s revisit in January.”

The Freedom of Constraints

Here’s the counterintuitive truth: saying no creates freedom. When you’re not stretched across ten initiatives, you can go deep on two or three. Your team can do their best work. Quality goes up. Speed goes up. Morale goes up.

The products we admire most are opinionated. They do a few things exceptionally well and ignore the rest. That’s not a failure of ambition—it’s a sign of clarity.

The hard part is getting comfortable with the discomfort. Saying no means accepting that good ideas will go unbuilt. Features will ship to competitors first. Some stakeholders will be frustrated. That’s the cost of focus.

A Framework for Decisions

When I’m unsure whether to say yes or no, I ask three questions:

  1. Does this align with our current strategic focus? If not, it’s probably a no, no matter how good the idea.

  2. What’s the opportunity cost? What would we have to stop or delay to do this? Is this more important?

  3. Is this reversible? If we can easily undo this decision later, bias toward action. If it’s a one-way door, be more cautious.

The goal isn’t to say no to everything. It’s to say yes to the right things—the things that compound, that build on each other, that move you toward your vision. Everything else, however good, is a distraction.

Learn to say no. Your product will thank you.

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