How to work with difficult people?

“Tell me about yourself.”

“I’m always striving to exceed expectations. Mine and everyone else’s.”

Ah. I see. A toxic striver. 

I see you. High achiever. Working your ass off. Always looking for ways to overperform.

Seeking approval. Respect. Safety. Love. The feeling that you are worthy.

Because stillness feels unsafe. Downtime makes you restless. You don’t know what’s hiding in the silence, but it can’t be good. 

Helplessness, maybe. If you don’t keep busy, you might have to face what’s back there.

Maybe it’s because of that one thing you forgot to do back in 2014. That call you missed. That time you slept through your alarm. That time you were underprepared. The world may have forgotten, but it hasn’t forgiven.

So you keep striving. To stay in control. So you won’t be blindsided. 

So that when the octopus revolt happens and they start throwing jellyfish into sunroofs from freeway overpasses, you’ll be the only one who saw it coming. And you’ll have a plan.

If this isn’t you, you’ve worked with this person.

You may see them as a perfectionist. Overbearing. High maintenance. A control freak. Nit picky. 

Difficult.

It’s exhausting. You may avoid them. Or resent them.

Since strivers are often high achievers, they tend to land in positions of power, putting their unrealistic expectations on you.

The best operators I’ve ever worked with recognize striving for what it really is: A sign that someone feels unsafe. 

They identify the source of anxiety and neutralize it. 

If the Difficult Person is riding their ass about deadlines, they give frequent progress updates until the person is reassured that it’s being handled. Then they become human again.

If it’s about image, they ask for frequent feedback. “Did you like the one with the serif or sans serif font? I was thinking blue? No? Yellow? Yellow then.” And then treat it like it’s important. 

Because it is important to build trust. To bring out the Difficult Person’s collaborative side.

Eventually, trust grows. The Difficult Person begins to chill. Becomes more pliant. Can focus on the task at hand rather than waiting for jellyfish to fall from the sky. They can tap back into their creativity. They can reach flow.

Recognizing and neutralizing the pain behind Difficult People's difficulty is one of the most valuable skills I’ve developed in my career. 

Thank you for coming to my Ted Talk.

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👋 I’m Claire. I plan to sell umbrellas in the octopocalypse. ⛱️🪼