Dear Joseph,
Our owner and her twin sister seem to think that yelling, threatening, and showing no empathy for employees will get people to reduce errors and work harder. How can I help them know the opposite is actually happening?
Signed,
Coaching Upward
Dear Coaching Upward,
The best first step is to find out if they want to know. If you’re trying to coach a boss, you must first gain permission. Here are some tips I suggest you use to help that conversation go well.
Master Your Story
You’ve used words like “yelling” and “threatening” and “showing no empathy” in describing what the owner and her sister are doing. Those words are pejorative. It sounds like you have a story about the owner that might be generating feelings of judgment and disgust in you. You’re unlikely to have healthy dialogue with her until you challenge that story. For example, can you come to see them as frustrated and disappointed rather than threatening and lacking empathy? Your story creates your emotions. And if you’re carrying emotions of disgust, they’ll cloud your conversation.
Get Your Motives Right
The only motive that will work is a genuine desire to help your owner get better results. If your true motive is to criticize them for what you see as abusive behavior, it will come through in your approach. If you have a track record of empathizing with them and genuinely helping them achieve their goals, you’ll likely have enough trust to make this conversation work.
Start with Safety
Before you can offer feedback, you’ll first have to ensure they feel safe. That only happens when they truly believe you care about their interests and that you respect them—even if you don’t respect some of their behaviors. Create safety as you begin by sharing any genuine feelings you have about them and about your intentions. For example, “I’ve been here long enough to know that this company is your life. You take our work personally and want it to be of the highest quality. I respect that. I see some things that I think are compromising our ability to do that.”
Ask for Permission
One of the best ways to create safety with someone with more power than you is to ask for permission to share. This honors their position and gives them a feeling of control over the conversation. People are willing to take more emotional risk when they are given the opportunity to choose it. Continue by saying, “Some of this has to do with how you handle problems here. I’m willing to describe that dynamic if you’d like. I also care about our ability to do our best work and think having this conversation might help. And I will honor your preference if this is something you don’t think is worth going into.”
From there, if all went well, you’ll have a chance to make your argument. Be sure you’re prepared to make it based on more than just your disdain for their behavior. If you believe their behavior is undermining your boss’s own interests, present robust evidence to support your claim.
With that said, I add a caution: When people in positions of authority act abusively toward others, it’s often as much about how they handle emotions as about some theory they hold about how to improve performance. If that’s the case with your owner, change will require more than compelling logic about improving results. People rarely make deep change until they see both potential gain and feel some threat of loss. If there is no one with the power to coerce attention to this concern, you’ll have to hope that any business, social, or ethical arguments you can make will motivate growth. I’ve coached dozens of executives over the years who needed to find more humane ways to lead, and none succeeded unless a CEO or board chair held them accountable.
I wish you all the best as you influence where you can.
Joseph
I’ve utilized Crucial Conversations for years and have been challenged with a leadership style/personality that all tools from the toolbox have been used and will not change.
I work in the utility sector and two major factors is the leader doesn’t fully understand implications of our business and our work, plus a leadership style where he manages up and never receives feedback from his teams. In fact, we’ve conducted three years of Engagement Surveys and nothing subs that’s ever been implemented.
As someone who lived for years under an oppressive personality, we need to hold space for the fact that there are people who believe in their core that treating people badly is their right. They will just become more covert when confronted by their superiors. Living in this environment actually can make you sick – autoimmune diseases, IBS, anxiety, migraines are all documented effects. If you don’t see a pattern of changed behavior over time, plan your exit quietly.
While it may or may not be true, I just want to point out that “there are people who believe in their core that treating people badly is their right” is not a fact, it is a story.
I was once in a new role as an assistant manager. My boss had two teams and told me several times that I would be responsible for the success of my team. He would say, I only have two staff members, while you have a dozen.
The organization I worked for was big on weekly team meetings in addition to 10 minute “stand-ups” a few times a week.
During one of the stand-ups, while talking with my team, I was leaning against my desk. My boss looked at me and waved his hand in a motion to suggest I should stand up and not lean against my desk. Fortunately, no one on my team saw this.
Once I was done with my team, I followed my boss into his office. I stated that if this was truly my team, and their success falls on my shoulders, I can’t have him undermine me like that in front of them. That it was inappropriate for him to have done that where my team may have seen it, and that I can’t be a leader for the team if he is going to do things like that (I was more diplomatic than I am framing it here).
He took a moment to reflect on the conversation. He apologized, said I was right, and that it would not happen again.
I often look back on that conversation and realize that it could have gone much differently had he been a different person. He was one of those people who was willing and able to take accountability and showed it often.
In this article you wrote, “People rarely make deep change until they see both potential gain and feel some threat of loss.” This is such an insightful and powerful observation. I wrote this quote down and will use it as a guide in 2026 to evaluate the deep changes that I need to make in my life and to identify the potential gains and threats of loss that will motivate me to take action. This is a simple, yet profound, insight.
You continued, “I’ve coached dozens of executives over the years who needed to find more humane ways to lead, and none succeeded unless a CEO or board chair held them accountable.” Your honesty that, even with the best coaching, these executives would not take positive action until they experienced the threat of negative consequences is an important observation. It, also, supports Janet Kimball Kelly’s comment, “there are people who believe in their core that treating people badly is their right.” It is not a story. It is a reality.
Thank you for your valuable insights and observations.