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A story from my TEDxWilmington talk

Meet Bob

Bob is the kind of boss many people instantly recognize. Controlling. Frustrating. Hard to work with. But Bob’s story is not really about a bad boss. It is about what happens when a good person is promoted without the support, training, or emotional tools needed to lead well.

He’s not the problem. And neither are you.

“It’s not their fault.”

That does not excuse harmful behavior. It creates a better place to start. Curiosity. Clarity. Accountability. And the chance to respond in a way that actually improves the relationship.

Bob Stuffed Toy – Symbol of Difficult Boss in Leadership

This is the central shift of Bob’s story. Instead of starting with blame, start with understanding. That is where better leadership begins.

Bob looked like the problem

I coached Bob many years ago. He came across as demanding, arrogant, insensitive, and controlling. The kind of boss people describe as difficult. But the deeper story was not about cruelty. It was about fear, pressure, and a leadership gap no one had helped him close.

What people saw

Micromanagement

He made too many decisions himself and struggled to let go.

Control

 

He solved problems for everyone instead of developing others.

Emotional friction

 

He came across as demanding and hard to work with.

What was really happening

Bob had been promoted because of strong technical and problem-solving skills. Then he was expected to lead people, motivate them, hold them accountable, and develop them without training or support. He felt incompetent, hid it, and fell back on what had always made him successful: solving everything himself.

That is how good people can fall into bad leadership patterns. And that is why dealing with a difficult boss requires more than judgment. It requires skill.

A Different Approach

Bob’s story is not only about understanding difficult behavior. It is also about responding differently. What if instead of blaming, you led with heart? Leading with heart does not mean being soft. It means being intentional. These small shifts change everything: conversations improve, trust builds, influence grows. And sometimes, even Bob begins to change.

01

Ask for what you need instead of making others wrong.

Instead of leading with blame, name the impact and make a clear request. The gap between intent and impact is where most conflict lives.

02

Get curious instead of judging.

We give ourselves grace and deny it to others. Curiosity helps you uncover what is really driving behavior before you react to it.

03

Assume good intent instead of taking things personally.

Assuming good intent does not excuse bad behavior. It helps you begin from a steadier place so you can respond with more clarity and less reactivity.

Start Here (Free Resource)

If you are dealing with a Bob right now, this is the best place to begin.

Download our free tool, the Co-Create an Effective Working Alliance: A guide for managers and employees

This is a simple, practical tool to help you set expectations, improve communication, reduce friction, and build a stronger working relationship with the people you work with most.

Sign up to receive the free tool and enter for a chance to win a Bob mascot.

GET YOUR FREE COPY HERE

Bob Stuffed Toy – Symbol of Difficult Boss in Leadership
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