Struggling to Salvage a Relationship with a Direct Report? Ask Madeleine

November 1, 2025 Madeleine Homan Blanchard
A paper origami bird holding a green leaf with the text: 'Struggling to Salvage a Relationship with a Direct Report?'

Dear Madeleine,

I am an American working overseas. A few years ago I took a break from adventure travel to make some cash by accepting an entry level job in IT operations.

I was surprised to find that I liked it. Never in a million years did I think I would be happy or successful working in a large corporation. I liked it so much that I stayed with the company and moved to a country where I have dual citizenship so I could keep working.

Long story short, I kept getting promoted and now I find myself in the very uncomfortable position of being the boss of someone who was once, briefly, my boss. I’ll refer to him as H.

H was easily the worst boss I had at this company; maybe ever. He knows that I know how he treats his people. He makes no bones about how much he hates me and tries to undermine me with his peers every chance he gets. He hasn’t had much success with that, which is good, but his lack of power only fuels his desire to sabotage me as well as the efforts of his team.

My HR business partner and my boss know about the situation, so I am not afraid for my job. But I am getting tired of the chaos H creates. The HRBP has suggested I document all of his actions, and both she and my boss have made clear that if I have a good case, I can fire him. I already have more than enough.

I just wonder if there is any way I can salvage this situation. I want to “catch him doing things right,” as Ken Blanchard would recommend, but he literally never provides me with an opportunity. If there is a way to take the high road, I have yet to find it. I hope you might have an insight that could help.

Seeking the High Road

_________________________________________________________________________________________

Dear Seeking the High Road,

How wonderful that you were open-minded enough to experience a happy surprise, and congratulations to you on your unexpected success. I appreciate your thoughtfulness and your willingness to make an effort. Your ability to not take H’s actions personally is impressive.

You have some options, all of which I am sure you have considered. The first is to attempt reconciliation or at least negotiate a peace treaty. If you think there is even a sliver of a chance that H would be open to negotiation, it is worth a shot.

I have been soundly mocked in the comments of columns where I suggest to managers that they try having an open and honest conversation with a direct report who is not acting like a team player. But that won’t stop me from doing it.

The issue with negotiation is that you must be prepared with your bargaining chips: what you are willing to give up and what the consequences are for H should he be unwilling to negotiate. And you will need to be ready to follow through on any consequences you state.

I would recommend you not start with trying to get H to acknowledge what he is up to. Simply cut to the chase and ask what it would take for him to cut it out. If he is smart, he won’t pretend he doesn’t understand what you mean. If he tries to act innocent, it is game over.

If H does take ownership of the damage he is doing, you can offer whatever leadership training is available in your organization, potentially even a coach. You might suggest he subscribe to Leadify, Blanchard’s leadership app. It is free and easy to use. Keep in mind that while you can help people who are willing and ready to become more competent, it is a long road to persuade people to look at themselves in the mirror and work on their character defects.

Your other option is to fire H and start looking for his replacement. Based on the little you have told me combined with your boss’s and HRBP’s assessment, I suspect any other efforts you make will just prolong the distraction. You and your teams may be better served by letting him go, since, despite your best efforts, very few people can be saved from their own nasty disposition. Change is hard for everyone, and most people don’t change until the cost of not changing becomes too high. Even then, many are compelled to dig in their heels until they have lost everything.

Have I become cynical? Possibly. But really, what I want for you is to expend your energy on people who have earned it and where it can make an impact for the better of your teams and your organization.

You may need to try option one just so you know you did everything you possibly could. You have to ask yourself if the juice is worth the squeeze.

Love, Madeleine

About Madeleine

A professional headshot of a woman with short blonde hair, smiling, wearing earrings against a blurred neutral background.

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services as well as a key facilitator of Blanchard’s Leadership Coach Certification courseMadeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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