Nervous about Managing Your Former Boss? Ask Madeleine

December 6, 2025 Madeleine Homan Blanchard

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Dear Madeleine,

I was hired into my company a few years ago. I love my company and my job. The person who was my boss when I started had some kind of personal issue and took a leave of absence. He was a great boss and taught me a lot.

There has been a ton of reorganization in the company and my group has had several leaders, none of them particularly invested in us. I have been informed that I am going to be promoted as of January 1 to lead the team, which I find both exciting and scary.

I just learned my original boss will be joining my team. Now I am terrified. How is that going to work? How do I lead the person who was my boss when I knew nothing at all? It feels so weird.

Any tips for me as I go into uncharted territory?

Weirded Out

________________________________________________________________________________

Dear Weirded Out

Oh, this is indeed an uncomfortable situation. But if your former boss is okay with it, there is no reason for you to be overly concerned. You may want to address the weirdness head-on instead of trying to pretend it isn’t awkward.

My experience working with managers in organizations is that more and more hierarchies are being dismantled in terms of one person having a lot of power over others. But someone needs to have oversight to make sure

    • the right work is getting done by the right people in the right time frame,
    • people have what they need to get the work done, and
    • everyone has a direct connection to the organization as a whole.

Often a boss is more of an air traffic controller than anything else, making sure everyone knows exactly what is expected of them and what a good job looks like—and ensuring that people stagger their holidays!

Your former boss may actually want to be an individual contributor again. Having the conversation about how the two of you will work together would be a good first step; one you will want to take with each of your direct reports. It isn’t that unusual for managers to have less experience and subject matter expertise than those who report to them. You don’t have to know more than your people, but you do need to know your people.

In terms of other tips on leading the team, you might break down what your former boss did that made him a great boss, and attempt to replicate those things. The point of view at Blanchard is that the best thing you can do as a boss is to “catch people doing things right,” leverage strengths, help people mitigate their weaknesses, and redirect when necessary without blame or judgement. The thing you want most is for your people to feel like you have your finger on the pulse of the organization so that they feel connected and that you have their backs. You might want to check out our *free* Leadify app, which is a treasure trove of content for emerging leaders.

It is appropriate to be nervous. Leading others is a big responsibility that will force you to grow as a leader and a person. You will make mistakes because everyone does. Simply admit it when you do, and learn from each one to avoid repeating it.

Good luck!

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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