Monika Lemeshonok for Unsplash+
Working closely with someone changes the way you see the world.
Ever notice that? It starts innocently enough. You begin thinking through problems from their perspective because that's part of the job. Then you catch yourself using the same phrases they do. I'm pretty sure that's how I started saying "y'all" despite being born north of the Mason-Dixon Line.
Proximity is one of the greatest privileges of this role. But lately I've been fascinated by the fact that it's also one of its greatest risks.
The longer you work alongside someone, the more their reasoning starts to make sense. You know what they're optimizing for because you've lived in the patterns with them. You understand the constraints nobody else sees because you see them too. You know everything that happened before everyone else walked into the room. Eventually, the why isn't something you consciously recall anymore. It's just the way you think.
This is exactly what makes many of you successful as a Chief of Staff. Understanding your principal isn't optional—it's the job. Execution depends on it. The faster you understand how they think, the faster you can anticipate decisions, remove friction and move the business forward.
But somewhere along the way we cross an invisible line.
It's quieter than complacency or blind loyalty, and it happens the moment we stop checking whether we're still thinking for ourselves. The danger isn't that you'll eventually agree with your principal on everything, it’s that you'll understand their reasoning so well you stop asking whether the reasoning is any good in the first place.
Understanding has a sneaky way of replacing evaluation.
Context naturally produces empathy, and empathy makes us better partners. But with enough context, empathy quietly becomes identification. You stop interpreting what you're seeing and start inheriting it. And the moment you inherit someone else's thinking, your leverage begins to disappear.
Your principal doesn't need another person who can perfectly explain why they think the way they do. They do that themselves. They need the one person close enough to understand their thinking without surrendering their own. The moment your judgement simply echoes theirs, you've become less valuable, not more.
That's the paradox I've been obsessed with recently. The better you understand your principal, the easier it becomes to stop consulting your own judgement first.
Which is why I don't find much value in the old adage to "speak truth to power." Honestly...barf. By the time you're deciding whether to challenge your principal, the more important work has already happened. The real question comes much earlier.
Am I still evaluating this independently? Or have I become so familiar with someone else's reasoning that I've stopped examining it through my own lens?
Pressure from your principal can absolutely threaten your judgement, but at least you can see that coming. Proximity is different. It doesn't usually change your opinions overnight. It changes the questions you stop asking.
That's why I think this role requires constant recalibration. We have to understand our principal deeply enough to become indispensable without becoming indistinguishable. Your job isn't to mirror your principal's thinking, it's to improve it.
And that only happens if we protect the one thing they can never generate for themselves—our judgement. The closer you become to your principal, the more deliberately you have to return to your own mind.
Your principal already has their own way of thinking. The reason they keep you close is to have access to yours.
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