The conversation that changed how I think about leadership

👋 Hey Friends!

Last week I ended up in a corner at a TechTo event with someone who sits on multiple boards across Toronto.

Too loud to mingle. So we just talked for basically the whole night.

I told him what I was seeing.

The friction PMs are feeling right now between what their customers actually need and what leadership keeps pushing, ship more AI, move faster, be AI-first. And I told him how many of the PMs I talk to are framing that as a strategy problem. Or a leadership problem. Or a "my company just doesn't get it" problem.

He stopped me in about thirty seconds.

"They're not ignoring your customers," he said. "They just haven't heard from them."

And then he explained something I haven't been able to stop thinking about.

Boards talk to investors. Investors talk to other investors. Nobody in that chain has had a real conversation with a customer in months (maybe longer). So the priorities coming down from the top aren't malicious. They're not driven by a lack of care. They're built on a completely different data set than the one you're sitting on every single day.

That's not a values gap. That's a visibility gap.

And the difference matters, because visibility gaps are solvable. Values gaps aren't.

When you feel the disconnect between what leadership is pushing and what your customers are actually saying, your instinct is to push back. To make the case. To pull together data and talk about user needs and prove that you're right.

That's the wrong move, and here's why.

When you position yourself as the person pushing back against leadership's direction, you become the friction. You become the PM who's "resistant to change" or "not aligned with company strategy." And even if you win the argument in the room, you've made it harder to be heard next time.

Your job isn't to win the argument. Your job is to close the information gap.

Because the people above you aren't dismissing the customer. They don't have the signal. You do. That's not a frustration, that's leverage (even though it feels frustrating). And once you start treating it that way, everything changes.

Customer feedback lives in Slack threads, support tickets, call recordings, NPS comments, and your own memory from that customer call last Tuesday. None of that travels up an org chart on its own.

Your first job is to surface it in a format leadership can actually engage with. Not a deck with 40 slides. Not a data dump that takes twenty minutes to parse. One quote. One ticket. One sentence that says: here is what customers are telling us, here is how often we're hearing it, and here is what it's costing us.

If you can't write that sentence right now, that's the gap. Not the leadership gap — your gap. Start there.

This is the one most PMs miss.

Customer frustration framed as feature feedback gets ignored. The exact same frustration framed as churn risk or retention signal gets a meeting. Same data. Different frame.

Boards and senior leaders respond to risk. They think in terms of revenue, retention, and competitive exposure. Ten support tickets saying users can't find a core feature isn't a UX note, it's evidence of a real problem with a real cost attached. Three customers who churned last quarter and cited the same pain in their exit survey isn't anecdotal, it's a pattern with a dollar figure on it.

When you write it that way, it doesn't feel like pushback. It feels like a proof point. And that's exactly what it is.

Don't try to be the PM who heroically brings customer truth directly to the executive team. I've seen this go badly more times than I can count, and it almost always backfires, not because the insight was wrong, but because the move felt like a skip-level ambush.

Bring it to your manager first. Walk them through what you're seeing. Help them understand the gap. Get them to help you carry it one level up. Then work with that person to do the same.

This isn't politics. It's just how information actually moves in organizations. You're not fighting the system, you're using it.

The visibility gap doesn't close because you shared one insight once. It closes because leadership starts to expect customer signal from you.

Pick a cadence. Monthly works for most teams. Every month, something moves up, a quote, a pattern, a number, a short summary of what customers are saying and what it means for the roadmap.

That's when it stops feeling like pushback and starts feeling like a service. That's when you become the person leadership turns to when they want to know what customers actually think.

That's the position you want to be in.

You're closer to the customer than anyone above you in the org. You're sitting on data that changes decisions, if it gets in front of the right people in the right format.

That's not a burden. That's an advantage.

Use it.

— Stef

PS: If you're an early-career PM sitting on customer signal that keeps disappearing into a void - book a free 1:1 with me. We'll figure out exactly how to move it up and make it land.