Most senior product people assume they know what the next level requires. David Pereira and Jason Knight both found out the hard way that they didn't. Two blind spots, one invisible ceiling.
You've shipped things that matter. You've led teams. You've been the most senior product person in the room for years. The next role feels like a natural next step, maybe even inevitable.
Then it doesn't happen. And you're not entirely sure why.
That gap between "I'm ready" and "they see me as ready" is what David Pereira and Jason Knight both ran into, in completely different ways. David is a product coach and author of Un-Trapping Product Teams. Jason is a fractional CPO. In Episode 9 of Product Leaders Lab, they each walk through the moment their assumptions about the next level broke down, and what they had to unlearn to get through it.
Two stories. Two blind spots. One ceiling.
Most product leaders don't fail because they lack skill. They fail because they've stopped questioning the assumptions that got them this far.
You build a mental model of what good leadership looks like, usually based on what you wished you'd had as an IC. You learn the craft deeply. You ship. You deliver. And at some point, you start to believe that excellence at the current job earns you automatic consideration for the next one.
It doesn't work that way. And by the time most leaders figure that out, they've already lost the role, or lost months leading a team that needed something they weren't giving.
David stepped into his first head of product role with ten years of experience and a clear picture of what great leadership looked like. He would provide clarity, empower his PMs with goals, trust them to figure it out. That was the leader he always wanted and never had.
Months in, nothing was moving. The PMs weren't asking for help. They were doing research, planning experiments, talking about goals. But nothing was shipping. David started asking questions, checking in, and wondering if he was the problem.
"I started reflecting if I was too dominant on how we worked and teams were afraid. And at some point, of course, I started questioning: am I a good leader? Will I be a good leader?"
That's not the question you expect to be asking six months into the role you've been building toward your whole career.
The realization came from an unexpected place. David reached out to peers who had been heads of product for just a couple of years, people close enough to the transition to remember it clearly. One of them turned his question back on him.
"I asked: what am I getting wrong? And then I received another question. The head of product asked me, what kind of leader are you? And I said, that's an easy one to answer. I am the leader I always wanted to have and didn't have. I provide clarity, I empower teams with objectives, I trust them. And then he looked at me and said very clearly: but is this the leader your team need? How do you know that? I couldn't answer."
He didn't know. He'd never asked.
So David ran a diagnostic. He asked each PM to track every activity over one week: name the task, rate how hard or easy it was, explain why. What came back stopped him cold.
"Decision making was hard for them. Choosing what to do next was hard. Evaluating the result of experiments was hard. What was hard was finding the structure to execute and achieve the goals."
He followed up with one question to each direct report: if you could ask me to solve one problem for you, what would it be? Almost all of them said the same thing: help me structure how to move from goal to value.
Not more autonomy. Not more trust. Structure. A path from here to there.
David had been giving them what he needed as a ten-year IC. They needed something completely different. He built a simple operating rhythm with the team: two days to understand the problem, two weeks maximum to run experiments, everything shippable within four weeks. Not a rigid process. A repeatable container so no one had to start from scratch on "what do we do next."
Six months later, the thing he noticed wasn't the shipping volume:
"The quality of decisions improved when I was not in the room and I didn't have to step in anymore."
That's what leading up actually looks like.
Jason's situation looked different from the outside. His team was performing. He'd been in the business for about a year, shipped a major platform upgrade, built strong relationships across the company. He felt good. He thought the VP of Product moving on meant the path was opening.
He was waiting for the conversation about the CPO role. Instead, a few weeks later, he got asked to help interview external CPO candidates.
"I had simply been passed over effectively. And they had been talking to people externally to come in and interview for that job."
Shock. That word lands differently when you thought the thing was yours.
He eventually raised his hand, got a belated interview, and spent most of it wondering if he was being pity-interviewed. The company ended up restructuring the role under a new CTO. Jason stayed for a while, then moved on.
What's striking is what Jason says looking back. He doesn't blame them.
"I didn't do a good enough job. I don't blame them for not giving me that job because I don't think at the time I was focusing on the right things. It's a different game."
What was he focusing on? He was being a great product person. Helping engineers. Solving problems. Doing the work he knew how to do. But every hour spent there was an hour not spent getting closer to the business, the stakeholders, the strategy.
And there was one more gap, one he frames in a way that hits differently coming from a product person.
"I spent all my time worrying about research we could do with our users. I spent very little time worrying about doing discovery on my stakeholders and colleagues, and what motivated them, and what success really looked like to them. I kind of looked at it all from a very purist lens."
Discovery on your stakeholders. It's such a product way of thinking about a very human problem. You know what your users need. But do you know what your executives actually need from you? What success looks like to them? What they're scared of? What would make them trust you with the next thing?
Jason didn't. And he didn't know he was missing it.
"No one cares about your own career more than you do. So don't sit there and wait for someone to care about it. If you care about something, go and make it clear that you care about it. Don't lose by default."
David's blind spot was internal. He was leading the team he wished he'd had, not the team he actually had. He projected his own needs onto people who needed something completely different. The fix was to stop assuming and start listening: do discovery on your team before you try to lead them.
Jason's blind spot was external. He was excellent at the craft, but the next level wasn't about craft anymore. It was about business, strategy, and stakeholder influence. He never made the case. He never even raised his hand. The fix was to understand what the next game actually requires, and then play it out loud.
Both paths lead to the same underlying lesson: every level up is a different job. Your past success is not a map for the future.
David's blind spot was internal. He was leading the team he wished he'd had, not the team he actually had. He projected his own needs onto people who needed something completely different. The fix was to stop assuming and start listening: do discovery on your team before you try to lead them.
Jason's blind spot was external. He was excellent at the craft, but the next level wasn't about craft anymore. It was about business, strategy, and stakeholder influence. He never made the case. He never even raised his hand. The fix was to understand what the next game actually requires, and then play it out loud.
Both paths lead to the same underlying lesson: every level up is a different job. Your past success is not a map for the future.
There's a diagnostic buried in both stories that most product leaders never run on themselves.
Ask: where am I spending most of my energy right now?
If the answer is solving for your team, being in the details, leading by doing, the question to ask is: what does my team actually need from me? Not what I would have needed. What they need.
If the answer is being excellent at the craft, shipping, building, problem-solving, the question is: who in this organization decides whether I move up? And what do they actually need to see from me?
Both questions require you to stop working from your own assumptions. To do, as Jason puts it, discovery on the thing you're trying to step into.
David said it directly: "Sometimes product leaders forget the difference between being a leader and being a product manager. As a product leader, your team is your product. Your team is responsible for the product. You are responsible for creating the environment where your team can succeed."
And Jason: "You're there to be the executive partner to the business. I didn't really focus on any of that stuff. It was almost a wake-up call for me."
Both of them got one.
You don't have to wait for yours.
What David and Jason are both describing isn't a skills problem. It's a perspective problem.
The transition from IC to leader, or from director to executive, doesn't just require learning new things. It requires unlearning the assumptions you don't even know you're carrying. That your experience translates directly. That the people above you can see what you see. That if you do the work well enough, the next thing will come.
It won't always. But you can close the gap. Not by working harder at what you already know, but by getting genuinely curious about what the next level actually requires, and who in your organization needs to see it from you first.
That's how you stop waiting for a ceiling to lift. And start removing it yourself.
Want to hear the full conversation? Listen to Episode 9 of the Product Leaders Lab wherever you get your podcasts:
