You have someone on your team who was a perfect hire two years ago. Lately, something feels a little off, and you can’t quite put your finger on why. Their work is fine. Their effort is there. But the fit isn’t what it used to be.

Here’s the thing: it’s probably not them. The work changed.

That’s a quieter kind of challenge, and a more hopeful one than it first appears. It’s not about performance problems or bad hires. The work itself has shifted. Someone who was exactly right 18 months ago is now operating in a role that has quietly changed shape, and the gap between what the job used to demand and what it demands now is widening faster than anyone updated the job description.

This is the real story underneath a lot of the anxiety in product orgs today. The pressure isn’t that product management is going away. It’s that the skills that make a product manager valuable are evolving, and the people who stay in demand will be the ones whose skills keep pace. The good news, and the reason this matters for how you lead, is that most of those skills can be developed. The first job of a product leader right now isn’t to sort the team. It’s to grow it.

So the question worth sitting with isn’t “did I hire well?” It’s “what does this person need to grow into the work ahead, and am I giving it to them?”

A question that points toward growth

Here’s the question I use to surface all of this:

“If this person applied to the company we’re becoming today, would I hire them?”

Not the company you were. Not the company you are right now. The company you’re becoming.

That framing matters, because it moves the evaluation off the past and onto the future. You’re not grading anyone on the job they were hired into. You’re asking whether the skills the work now rewards are present, emerging, or worth investing in.

And here’s the part that keeps this developmental rather than punitive: a “no” or an “I’m not sure” is not a verdict. It’s the start of a better question. The moment you land on “I’m not sure I’d hire them for where we’re going,” the next thing out of your mouth should be: “What would have to be true for that to become a yes, and what would I need to invest to help them get there?”

That single move changes everything. It turns an assessment into a development plan. Most of the time, the honest answer is that the person is closer than it felt, and the gap is nameable, specific, and coachable.

What happened when four co-founders asked it

I was working with a founding team recently. Four people, different functions, different vantage points on the business. I asked each of them, separately and with no conferring, to run through their team using this question.

They came back with near-identical conclusions.

Not because they’d talked. Not because one person anchored the group. When you strip away politeness and seniority and the social cost of being the one who raises it, leaders often already sense where the growth needs to happen. They just haven’t had a clean, low-stakes way to name it.

That convergence matters. When different people, reasoning from completely different angles, land on the same read, the signal is real. It isn’t bias or a bad day. It’s a shared picture of where the work is heading, which is exactly what you need before you can help anyone grow toward it.

And where they diverged? That was useful too. Divergence didn’t mean one person was wrong. It meant either the role wasn’t defined clearly enough for everyone to evaluate it the same way, or the team didn’t yet share a picture of what the role now requires. Both are worth resolving, because you can’t develop people against a target that keeps moving in everyone’s head.

How to run the exercise, development first

Here’s the sequence I’d walk a leadership team through. Notice that developing the team comes first, and stays first.

Step 1: Name what the work now demands

Before you assess a single person, get clear on what the role is becoming. What skills does the work reward now that it didn’t two years ago? What does great look like for this role in the company you’re building? You can’t fairly evaluate or coach anyone against a target you haven’t defined.

Step 2: Ask the question separately

Then ask each member of your leadership team, or just yourself to start, to go through each person and answer: “If they applied today, for the company we are becoming, would I hire them, and if not yet, what would it take?” Write it down. The “what would it take” half is the point.

Step 3: Compare the reasoning, not just the verdict

When you bring the group together, talk about why. Two people can pause on the same person for completely different reasons. One because a specific skill needs to grow, one because the role itself needs redefining. Those lead to very different, and usually very fixable, next steps.

Step 4: Build the growth plan

For each gap you’ve named, decide the investment. What does closing it actually take? Often it’s concrete: a stretch assignment, pairing with someone stronger in that area, focused coaching on a specific skill, clearer expectations, or simply the time and feedback to build a new muscle. Set a checkpoint to reassess. This is where most of the value lives, and it’s the part leaders most often skip.

The skills worth developing

If you’re wondering where to invest, the throughline is adaptability. The product managers who stay in demand are the ones who treat changing requirements as the job rather than an interruption to it, who can learn a new tool or way of working without being dragged to it, and who get genuinely energized by the work changing under them. That orientation is more coachable than people assume. You develop it by giving people exposure, naming the new skills explicitly, celebrating the stretch rather than only the polish, and making it safe to be a learner again. A leader who builds that kind of environment grows people faster than any single training ever will.

And yes, sometimes the harder call

Be honest with yourself, too. Sometimes, after you’ve named the gap, made the investment, and given a real runway, the answer is still that the work has moved somewhere a person isn’t able or willing to follow. When that’s genuinely true, naming it isn’t disloyal, and it isn’t the goal of this exercise. It’s the rare exception you reach only after development has had a fair chance, and it’s often kinder than leaving someone in a role where their strengths no longer fit.

But that’s the last page of the story, not the first. The first pages, the ones you’ll spend most of your time on, are about clarity and growth.

This is hard to do alone

If this resonates, here’s the honest part: the question is simple, but doing it well is not. Defining what the work now demands, having generous and specific growth conversations, staying objective about people you’re close to, and holding the line between developing someone and avoiding a needed change, all of that is genuinely hard to do from inside your own org. It’s exactly the kind of work that benefits from an outside partner who has helped other product teams through the same shift.

That’s the work I do with product leaders and their teams: getting clear on what the role is becoming, building real development plans for the people you already have, and making the honest calls with care when you need to. If you’re looking at your team and feeling the gap between who you have and what the work now needs, I’d love to talk it through with you. Book a call and let’s have a conversation.

You might be surprised how much of this is an invitation to grow your people, not replace them, and how much further they can go with the right support behind them.