Thinking About Bailing on a Losing Company? Ask Madeleine

September 23, 2023 Madeleine Homan Blanchard

Dear Madeleine,

My boss is the Chief Revenue Officer for a billion-dollar, publicly traded company, and I am watching her melt down in real time. She has been in the job for two years and has made one spectacularly bad decision after another.

Sales have tanked to an all-time low. I know for a fact that the earnings reporting is…not accurate. The stock price is slipping.

On Zoom calls she is manic, erratic, often making bizarre proclamations. I watch the faces of my peers and to a person the eyes are wide, lips tight. But no one is saying anything.

I can’t understand why our CEO, whom everyone acknowledges is a genius, put her in the job to begin with or has tolerated performance that has gone steadily downhill. It makes no sense.

Things have just gotten so weird; I don’t know who I can get a reality check with. It feels like I am losing my mind. I have been with the company a long time, and it has always been on a healthy upward trajectory. The CEO never would have tolerated such poor performance in the past.

I have a lot of stock options as part of my comp, and I am thinking now would be a good time to vest, with the stock price so low. I get calls from headhunters all the time, and I am beginning to think I should take them. I would feel bad abandoning my team, all of whom I love and care for. I am so conflicted.

Should I Bail?


Dear Should I Bail?

It sounds like a topsy-turvy world. I think when people start behaving strangely, especially when the CEO is asleep at the wheeleither actively ignoring an obvious problem or, as you imply, is somehow misrepresenting the numbers—you must assume something shady is going on. If no one is pointing out that the proverbial Empress Has No Clothes but you see it clearly, I would say you should trust your own judgment.

I can’t tell you to leave your job but I can ask you this: If your best friend told you all of what you have told me, and you trusted his judgment, what advice would you give him? If your immediate answer is “are you kidding, get the heck out of there!” —well, there is your answer.

There is no harm in taking the calls from recruiters, exploring your options, and getting a sense of what opportunities are available out there. You can brush off your resume and update your LinkedIn profile to be poised and ready to exit if your instincts prove correct. The only person who is going to care about your career and financial stability at this point is you, so preparing is smart. I applaud your concern about your team; it would be painful to feel like you are letting people down. If you do bail, you must trust that they will take your lead, start looking for options, and all land on their feet.

I often ask successful people what their biggest mistake was, and fascinatingly, almost to a person, it is a variation on “I didn’t pay attention to my gut and went along when I knew I shouldn’t.” You have been with the company for long enough that you can tell when you are seeing things that don’t add up. If you are not habitually negative and think something is going terribly wrong, then you are probably right.

Good luck to you.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’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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