Why Working with People Is F*cking Hard

Product leadership is a true test of people leadership. Here are 4 hard people problems and how to survive them.

Yes—I said it.

It’s not the roadmap, not the tech, not the data. It’s people.

With egos, ambitions, and messy emotions. And that’s what makes product leadership simultaneously brutal and essential. Especially because in product, you sit at the centre.

You touch every function: engineering, design, marketing, ops, sales. You feel the tension when things aren’t aligned. You’re held accountable for outcomes that rely on people you don’t manage. You’re expected to lead without authority, influence without friction, and somehow stay strategic through it all.

So when the people stuff gets hard, it really gets hard. Here are four reasons why, and how to manage.

1. The ego clash: when your boss is chaos

You step into a new leadership role with every intention of being methodical, strategic, calm. Then your boss comes in like a storm: constantly shifting priorities, expecting you to keep up without missing a beat. And yes, you try. You try to piece together their scraps of logic. But every time you do and get it wrong, you feel… exhausted, failed, frustrated. Like it’s your problem.

That’s ego dynamics in action. You try to meet their needs to prove you belong. But instead you compromise your own needs. And your confidence. You end up chasing their thinking, hoping it’ll all click eventually.

This isn’t a reflection on your skill - it’s a psychological one. And it happens to many of us due to the dynamics we’ve been caught up in our whole lives.

Instead of staying up to 3am to keep up, ask yourself:

What do I need to lead clearly here? What would I do in their position? Create your own clarity, even if theirs is missing, and you can become a real asset.

2. The shifting ground: When structure doesn’t support clarity

You’re being told to drive more value. Get closer to customers. And you’re trying, really trying. But everything around you is shifting. You’ve got pressure to launch new products, new markets and keep your current customers happy. New people and job titles are coming into the org, what seems daily. There’s pressure to move faster, but no clarity on how decisions get made.

I’ve seen this play out multiple times. Smart and committed Head of Products nearing burnout. Not quite experienced enough to know it’s not their fault or influence the fix. When the reality is the product portfolio is too broad and the team is tiny: of course there is no real ownership.

Then the product team gets blamed: not strategic enough, no ownership mentality. But its no one’s fault - it’s a structural issue. If the organisation is stretched too thin, people start to fail in ways that aren’t fair. And when that happens, it gets personal, fast.

Instead of blaming yourself, ask yourself:

What is the right ownership structure for this to thrive? Make it visible. Map the gaps. Understand the incentives at play. Push for focused ownership: it’s the only way to drive results.

(I’ll go deeper into how to build the right product team structure in my first paid post next week, especially with the impact of AI adoption)

3. The talent tension: when you inherit a misfit team

You step into a leadership role and the team’s already in place. You didn’t hire them. Maybe they don’t trust you, maybe they’ve been burned. But now you’re responsible for their results.

This was the case with a SVP client of mine. One Director is a standout - proactive, self-aware, delivering strong work. The other… needs constant support. They’re in the weeds every week: reviewing their comms, helping them prep for stakeholder meetings, clarifying expectations they should already understand.

And yes, this Director is technically doing okay when it comes to business results. But they’re draining their bosses time and energy.

They feel the pressure to make it work. But they also know: something has to shift.

Because here’s the thing no one tells you - performance isn’t just output. It’s fit. Fit for the role, fit for the stage, fit for the direction you’re going.

Instead of powering through the mismatch, ask yourself honestly:

Will they get there - and how long will you give them?
Sometimes that means a reset. A clear conversation. A plan. Sometimes it means a dignified exit. But either way, ignoring it doesn’t help. It just builds resentment, on both sides.

4. The power shift: when peers feel like blockers

You’re not just leading your team, you’re navigating across. Working with peers who have their own priorities, their own histories, their own turf to protect.

And suddenly, product is becoming more central. You’re no longer a support function: you’re critical to scale. That changes things. Because influence is shifting. And not everyone wants to let go of what made them powerful before.

I’ve been in this story myself. The organisation was evolving. Product needed a bigger seat at the table. But that meant sales and ops had to share power - strategic power, not just delivery timelines. And it didn’t happen easily.

Truthfully? It probably only shifted when the leadership changed.

Because you can’t always “align” your way out of a power imbalance. You can try. You can build relationships, share context, make space. And sometimes that works. But sometimes it doesn’t. Because status is sticky. People hold tight to what they know.

Instead of endlessly trying to push uphill, ask yourself:

Where do I need to influence, and where do I need to let go? And do this: pick your battles. And find allies who want what you want.

This is the work

Working with people is hard, for all the reasons above. Ego clashes. Structural mess. Team mismatches. Power struggles.

But this is the work of leadership. Not the job title. Not the strategy offsite. The day-to-day clarity, courage, and emotional labour it takes to get people moving in the same direction, even when it’s messy.

I’ve felt all of this first-hand. Leading in fast-scaling orgs, inheriting teams I didn’t pick, trying to influence across without the power to change what needed changing.

It’s the stuff that used to keep me up at night, because when it wasn’t working, it felt personal. Like I was the problem.

And that’s why I do this work now. Product leadership jobs are hard because you can’t separate product leadership from people leadership. And when the people stuff is off, you need the support to know you’re not the issue, but there is always something more in your control.