Working with Impossible People

Bad news: you're the one with the problem.

How do you work with someone you can’t stand? The bad news is they’re not changing, so you’re the one with the problem. The good news is you can change to ease your frustration. These people feel impossible exactly because our usual tools don’t work on them. So try something outside your comfort zone! With a more versatile set of tools, you can make the impossible possible.

One of the impossible people I worked with was my former co-founder. We were longtime friends from grad school, both passionate and stubborn. As friends we could always agree to disagree, but as co-founders that option felt…impossible. So instead we fought, savagely sometimes—right until he fired me from my own company. How could I back down when the stakes were so high? After all, I knew I was right.

That’s the thought I clung to as we sunk the company with our squabbles: he’s wrong, I’m right. Turns out it didn’t matter who was right! Preserving the relationship was what mattered. Sometimes it isn’t, of course: there’s no effective way to work with a bully or an abuser. But mostly, “impossible” is a label we put on people we don’t fully understand. They don’t see themselves as impossible. Their parents, their partner, and their best friend probably don’t either—at least not all the time. If you don’t preserve the relationship, you’ll never get the chance to see past that label.

So let go of being right and blaming them for being wrong. Preserve the relationship by treating them respectfully even when you’re frustrated. Get curious about the sides of them you don’t yet understand. If they’re not impossible, who are they?

Surprise! They’re just like us. My co-founder and I disagreed on a lot, but we were equally stubborn and driven to win. My coaching clients are diverse, but their struggles are universal. CEOs of startup unicorns are quivering bundles of emotion just like the rest of us. So knowing that impossible people are just people, how do you get what you want from them? All you have to do is ask! I’ll write about how to make a great ask next time around.

Whether you get a yes or a no, remember the goal isn’t for them to change—that seldom happens on command. The goal is to ease your frustration. So empower yourself by owning both that emotion and your response to it! Congratulations, you just made the impossible possible.


Got questions on how to handle your own situation? Feel free to comment below or get in touch, happy to help. Subscribe now to get future letters right in your inbox.

Leave a comment