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Home Leadership

When You’re Left Cleaning up After Their Mistakes

August 11, 2025
in Leadership
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When You’re Left Cleaning up After Their Mistakes
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Dear Dr. Jo,

I’m in a situation at work that has never happened to me before and I was hoping you might have some advice. I work as Chief of Staff at a local company. I was hired relatively early on, but even so, I don’t feel that I know my boss that well or understand her motivations.

About 6 months ago she made some new hires that to me seem underqualified. I believe she knew some of them from a previous role she held in her last company. However, she never discussed the hires with me, and I try not to give my opinions unless asked. What’s frustrating is that since these new hires have come onboard, I’ve had to clean up several of their mistakes that I thought put the company in jeopardy. Of course, I would do anything to keep this company successful, but I feel more and more resentful that these folks are on board, that I was never consulted about their hiring, and that now I have to work harder just to keep things staying on course because of their incompetence and careless work habits.

I’m wondering if I should say something to the CEO, or wait them out and hope she sees that they are a liability. Or take more drastic steps and  start looking for another job. I really loved this job before but it’s becoming harder and harder to tolerate the behaviors I’m seeing at work. I often end up mulling about work on the weekends and not even enjoying my time off.

~ Torn and Frustrated

Dear Torn and Frustrated,

Man, I hear you! There’s nothing more frustrating than watching something that you’ve helped build, change shape in ways that you don’t feel are heading in the right direction. First though, let’s take a moment and acknowledge all the amazing work that you’ve clearly done up until now to have such a key role to the CEO; clearly she has appreciated your role in her company’s growth and has faith in your abilities. So now that we’ve established all you’ve been able to accomplish in the past, the next question to consider is whether this is where your future lies.

Here’s what I see. The CEO has hired some people she seems to trust, and you have reasons not to. So the question that comes to the forefront for me is this, “Do you think the CEO is blind to their errors, or does she believe that they bring something important to the company that is worth overlooking their flaws for the meanwhile?” Ask yourself this question and look at the evidence you can compile.

If she sees them as they are, then what does she value about their contribution? If the CEO is seeing a future that aligns with these newcomers, do you believe in that vision too? Does that vision align with where you can see the company being successful too? If you can’t imagine that vision being successful, then it would definitely be wise to start looking at the external job market. Especially as Chief of Staff, if you don’t see a successful future on the horizon where you’re headed, you might not be the best person positioned to usher in that next stage. If you’re not sure yet, I’d recommend polishing your resume and LinkedIn, so that as things become clearer you will be in a better position to act.

If you believe that your CEO has closed her eyes to the true realities of these new hires, then your job as Chief of Staff should first be to check that she is seeing the truth of the situation she has created. A good first step might be taking one of the current issues you are fixing and having a direct evidence-based conversation with the CEO. Bring her the facts of what this new hire did and then tell her the steps you are planning to take to rectify this situation. Say you wanted to confirm that she’s comfortable with your proposed plan of action. If she concurs without asking any more questions, there’s a good bet her loyalty to these new hires extends to their mistakes as well and the situation is unlikely to change anytime soon. If she seems surprised, upset and/or asks follow-up questions to fully understand the situation, you might have done such a good job repairing their wrongs that she wasn’t even aware how problematic they were. If that’s the case, you might need to continue to bring your CEO the slipups you’re resolving until either she acts of her volition, or it becomes clear this situation will not get better for you anytime soon.

No matter what you decide, know that it is always your prerogative to leave a job that is no longer fulfilling your goals. When someone takes a risk on us, or gives us outsize opportunities, we should be giving them our best while we’re in the role we’re in. But we never owe a boss the sacrifice of our own happiness or peace of mind. I once heard this quote by Jon Taffer that resonates with me, “The greatest gift of leadership is a boss who wants you to be successful.” Even if it doesn’t feel true, assume that the biggest compliment you can give a manager is to learn from what they’ve taught and take it forward so that you can be even more successful in your future roles.



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