#5 Pleasing vs. Serving

TINY LEADERSHIP STORIES

As a customer experience manager with nine direct reports, Tamsin had built something rare: a team that genuinely loved her. Morale was high, retention was strong, and people felt championed.

But the 360-degree interviews from colleagues revealed a pattern she couldn’t unsee.

“Friend first.” Six of ten people used some version of that phrase. Her boss and peers noticed it. Even her own team members, the ones who benefited most from her warmth, could see it.

The hard conversations weren’t happening. Performance expectations got softened, and feedback got delayed. And when someone dropped a ball, Tamsin picked it up herself rather than holding them accountable.

She was working 55-hour weeks. Not because her workload demanded it, but because she kept absorbing tasks her team should have owned. A project fell behind schedule, and she stayed late rather than have an uncomfortable conversation about deadlines. A team member struggled with a skill gap, and she did the work herself rather than give direct feedback that might sting in the moment.

She knew exactly what she needed to say. She just couldn’t bring herself to say it.

In How Women Rise, Sally Helgesen and Marshall Goldsmith call this “The Disease to Please.” Leaders who have it avoid saying no, take on other people’s burdens, and sacrifice their own advancement to be liked.

In How Women Rise, Sally Helgesen and Marshall Goldsmith call this “The Disease to Please.” Leaders who have it avoid saying no, take on other people’s burdens, and sacrifice their own advancement to be liked.

The painful realization: pleasing wasn’t serving anyone’s best interests. Not the team member who never got the feedback she needed to grow. Not the colleagues who had to compensate for unaddressed performance gaps. Not her boss, who couldn’t trust that problems were being handled. Not the organization. And certainly not Tamsin, who was burning out while her own career stalled.

She finally named it: “I thought I was taking care of my team. I was just protecting myself from hard conversations.”

Pleasing seeks approval. It avoids discomfort in the moment by creating larger problems down the road. Serving creates value. It prioritizes what someone needs over what feels comfortable to give.

Your greatest impact won’t come from who you pleased, but from how you served.

THE QUESTION

What are you carrying that someone else needs the chance to own?

“You cannot escape the responsibility of tomorrow by evading it today.” – Abraham Lincoln

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