CEO Out in the Cold

By Annie Lane

September 26, 2019 4 min read

Dear Annie: Several years ago I became the CEO of a company with employees who work hard and provide excellent service at fair prices every day. I am very proud of what we do. After more than 40 years of working for this same company, I still look forward to going to the office every day. Our prospects, I believe, are bright.

So what's the problem? Before I became CEO, I had good friends at work. But now that I am "the boss," people treat me differently. I hate that. It is especially bad with one person. I always liked working with her. She is bright, energetic, creative and excellent at everything she does. But now that I am CEO she argues with me about everything. I don't think I've made any decision yet that she has liked.

Part of it, I believe, is that she regards herself as the spokesperson for all our women employees. I think she might be afraid she will lose credibility with them if she is ever seen to be in agreement with me on anything. To be clear, she has made some great points and been very helpful to our company in drawing attention to issues of gender equality. And we've been responsive, although never enough to satisfy her. I've accepted the fact that she and I will never entirely agree on all the changes she wants us to make.

But why does she have to be so negative about everything I do? I miss my friend. She has become instead this great thorn in my side. Now instead of seeking her out for her advice like I once did, I find myself avoiding her and dreading her visits to my office.

Is there any hope things can go back to the way they were? — Dealing with a Thorn in My Side

Dear Dealing with a Thorn in My Side: Once you became CEO, you should have known that things would not go back to the way they were. It is lonely at the top. While your former friend made some great suggestions for change at the company, it appears that she cannot accept the fact that you are the CEO now. It's sad that your friendship is not the same as it once was, but because of your promotion, it never will be the same.

Sometimes, when looking back, we see things as better than they actually were. The fact that she has become this argumentative since your promotion is not helpful for anyone — for you, for her, for your employees. You need loyal people at your side. Challenging authority is fine and can often be constructive, but when you dread the person visiting your office, that is not a sign of a valued friend or employee.

Appreciate her good qualities and her well-thought-out suggestions, but insist that if she persists in disagreeing with everything you do, she will no longer be an employee of the company. Successful CEOs are friendly to everyone at work, but they look for true friendships outside the office.

"Ask Me Anything: A Year of Advice From Dear Annie" is out now! Annie Lane's debut book — featuring favorite columns on love, friendship, family and etiquette — is available as a paperback and e-book. Visit for more information. Send your questions for Annie Lane to [email protected]

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