In the last post, we talked about what it looks like to show up when something hard is happening. It's about the work of creating space for yourself first, and then for your team. This post goes one step further, into the territory of a difficult person. Or at least, someone who feels that way.
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The Relationship You Keep Putting Off

Every leader I've worked with has at least one.

A team member they quietly dread one-on-ones with. A board member whose comments always seem to land sideways. A peer who pushes back in ways that feel personal, even when they probably aren't. Maybe it's someone whose communication style grates against yours, or someone whose perspective you genuinely struggle to understand.

The natural response is to manage around it. To minimize contact, or steel yourself before interactions, or spend the whole conversation just trying to get through it. Sometimes we move toward resolution too fast, trying to fix something before we've actually understood it.

What all of those moves have in common is that they close the door before we've really looked through it.

What if the relationships that challenge us most are actually the ones with the most to teach us?
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The Relationship You Keep Putting Off

Curiosity, in this context, is not the same as agreement. It's not liking someone, or pretending the difficulty doesn't exist, or being relentlessly positive about a dynamic that genuinely isn't working.

It's a choice to slow down and ask a different set of questions before you react.

What is this person carrying right now? What shaped this perspective? What am I missing about where they're coming from?

Instead of treating a difficult relationship as a problem to solve or a personality to manage, you treat it as something worth genuinely understanding. The question moves from why are they like this to what's driving this. That small change in framing opens up a lot.

One of the hardest versions of this I've seen play out is between cofounders. There's something uniquely charged about that relationship. The stakes are high, the proximity is constant, and there's often an unspoken assumption that shared vision means shared operating style. It rarely does.

I worked with a leader navigating a cofounder relationship that had become really destabilizing. His cofounder struggled to emotionally regulate under pressure. What started as passion and intensity had, over time, started showing up as volatility: sharp reactions in meetings, conversations that escalated quickly, a pattern of behavior that left the rest of the team walking on eggshells.

For a long time, he took it personally. He wondered what he was doing wrong, whether he was triggering it, whether the relationship was simply broken.

What shifted things wasn't a confrontation or a restructuring conversation. It was getting genuinely curious about his cofounder's history: where that intensity came from, what he was most afraid of losing, what he was carrying that he didn't have language for. He didn't get all the answers. But he got enough context to stop taking his cofounder's reactions as a reflection of his own worth or competence.

He stopped trying to fix him. He started working with what was actually true.
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More Honest. More Human. Not Always Easier.

This part is worth naming clearly: getting curious won't always resolve things. You might learn more about someone's context and still disagree. The relationship might still require a hard conversation. Some dynamics genuinely don't improve, even when you approach them with real care.

And sometimes, if we're being fully honest, curiosity isn't even about improving the relationship. It's about self-preservation.

Knowing what someone is afraid of, what they're protecting, what history they're carrying into the room creates a kind of clarity that makes it much harder to take things personally. Their behavior stops feeling like a verdict on you and starts looking more like information about them. That shift matters. It's the difference between leaving a difficult interaction feeling bruised and leaving it feeling grounded.‍

You're not excusing what's hard. You're just refusing to carry what isn't yours.

That said, something else shifts too. When you lead with genuine curiosity, you signal to the other person that they are worth trying to understand. That signal matters more than people expect. It creates the conditions for a more honest conversation, and sometimes a different kind of relationship than either of you thought was possible.

The leaders who navigate challenging relationships well aren't the ones who never find people difficult. They're the ones who stay open long enough to actually understand what they're working with, and clear-eyed enough to know what to do with what they find.
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A Small Practice

Think of a specific challenging relationship you're navigating right now. Not an abstract one. The actual person. Then sit with these:

• What do you actually know about what this person is carrying, in their role, their history in this organization, their life outside of work? And what are you assuming?
• When things get tense between you, what's your default response? What has that pattern cost you in terms of real understanding?
• What's one question you could ask that you haven't asked yet, not to win anything, but just to understand them better?

You don't have to fix the relationship today. Just get a little more curious about it.

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