Crucial Skills | Management & Accountability

What to Do When Your Boss Is a Bully

Crucial Skills | Management & Accountability

Show Notes

What do you do when your boss is a bully?

Emily Gregory, a co-author of Crucial Conversations and a Crucial Learning speaker and consultant, responds to a reader who has this very problem. Emily takes this scenario and uses it to highlight the reality of this situation in many workplaces, and what you can do to navigate workplace bullying.

She breaks down the difference between observation and judgment: what is actually happening with this person vs what our perception of them is. Emily lays out two concrete paths forward and shows how to prepare for that conversation with good intent and fact-based language instead of accusation. Her advice shows that you can do more than just "leave" or " deal with it." Remember, facing a hard situation is the only thing that makes change possible.

Chapters [Start] The Letter: A reader describes a manager whose outbursts and accusatory emails have become normalized, with real health effects on the team. 01:32 Stories vs. Facts: How to unpack our judgment of someone by analyzing the language we use to describe them. 03:33 Two Ways Forward: Looking at two approaches forward when it comes to dealing with a workplace bully. 04:52 Preparing for the Conversation: Three principles to help you prepare for the difficult, but crucial, conversation with a bully. 07:32 A Sample Conversation: An example of a rehearsed conversation showing how to bring up this issue with honesty and specificity.

Links and ResourcesCrucial Learning Crucial Accountability: Proven Skills to Build Trust, Address Disappointment, and Get Results Crucial Conversations ® for Accountability (course) Crucial Learning | What to Do When Your Boss Is a Bully

Learn more about Emily Gregory here.

The Crucial Skills Podcast is brought to you by the authors and experts at Crucial Learning, home of Crucial Conversations for Mastering Dialogue and Crucial Conversations for Accountability training.

More from Crucial Skills | Management & Accountability

Oct 20, 2026

Psychological safety has become a workplace buzzword. But when someone says, “I don't feel safe,” does that always mean there's a problem with psychological safety—or are we confusing safety with comfort?

Oct 13, 2026

Few situations test our communication skills like a teenager who stops listening and starts pulling away.

Oct 6, 2026

What if having too much to do isn't actually the reason you feel overwhelmed?

Sep 29, 2026

Have you ever had a boss who talks about psychological safety but still makes you feel tense when you’re around them?

Sep 22, 2026

Avoiding a Crucial Conversation can come with both a price and a cost. But what’s the difference between the two?

See all episodes →