Dear Reader,

A client said something to me this week that I hear in one form or another all the time:

"I just don't want them to think I'm mean."

She wasn't talking about firing someone.

She wasn't talking about delivering harsh feedback.

She wasn't talking about denying a promotion.

She was talking about setting a perfectly reasonable expectation of one of her team members.

And yet, there it was.

The fear. Not of being wrong or of making a bad decision, but of disappointing someone.

And this is something that I recognize fully, as when I look back on my own career, I struggled with this as well.

And what I now know is that this isn’t a leadership challenge.

It’s a people-pleasing challenge.

➡️ The manager who won't delegate because it's easier to do it themselves.

➡️ The executive who rewrites everyone's work at 11 p.m.

➡️ The leader who avoids giving direct feedback because they don't want to hurt someone's feelings.

➡️ The employee who says yes to every request and then wonders why they're overwhelmed.

Different situations. Same underlying fear:

"What if they stop liking me?"

The irony is that avoiding discomfort rarely creates the outcome we're hoping for.

When expectations aren't clear, people get frustrated.

When feedback isn't delivered, people don't grow.

When boundaries aren't established, resentment builds.

And when leaders try to make everyone happy, they usually end up exhausted (while nobody is particularly happy anyway).

One of the hardest lessons I've learned, both as a leader and as a coach, is that being kind and being liked are not the same thing.

Kindness often requires honesty.

Kindness often requires clarity.

Kindness sometimes requires saying no.

And occasionally, kindness requires disappointing someone in the short term so they can succeed in the long term.

Nobody wants to be the bad guy, but most of the time, that's not actually the choice.

The choice is between temporary discomfort and long-term dysfunction.

What's one conversation you've been avoiding because you're worried about how it will be received? Consider this your gentle nudge to stop rehearsing it and start scheduling it.

With ease, Tracy

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