Lessons

Lessons

The Management Pretzel đŸ„š

The cost of trying too hard to make someone successful or happy

Molly Graham
Aug 14, 2026
∙ Paid

I was talking to a leader recently who was doing everything in her power to keep someone on her team. She was considering a re-org, creating a vertical for this person to own, changing titles, and more.

At some point, I had to ask her, “Would you do any of this if this person wasn’t here?”

The answer was no.

“Do you want to do this stuff regardless? Is it the right thing for the business?”

The answer was unclear.

“Do you sort of feel yourself contorting—turning yourself into a pretzel—for this person?”

Yes. That’s exactly what it feels like.

Welcome to the management pretzel đŸ„š.

There are these moments in management when you are trying really hard to make something work. Trying to boost up a low performer. Trying to make the right space for a high performer. And somewhere along the way, you stop asking, “What’s the right thing for the business?” or “What would I do if this person quit tomorrow or wasn’t here?” Instead, you’re asking and answering a very person-specific question: How do I make


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