And she won’t stop telling me what she would do differently. My Employee Keeps Reminding Me She Used to Be the Boss



A reader asks:

I lead a small team at a small company. A few months ago, we hired “Jessica” for an individual contributor role. In her previous job, she had been a manager. We explicitly asked whether she would be happy stepping back into an individual contributor position, and she said she would be thrilled.


Overall, Jessica is a strong performer. She’s reliable, produces consistently good work, brings fresh perspectives, and collaborates well most of the time. However, she frequently brings up her past management experience and comments on what she would do differently if she were in charge.


For example, when we were recently pulled into a high-stakes project with tight (but manageable) timelines, Jessica repeatedly told me I should have refused the deadlines. She said I was setting a bad precedent and that, as a manager, she never would have agreed to it. She also complains about the more routine parts of her role, noting that she’s better suited for high-level planning and supervision.


I’m starting to see this as a potential performance issue, but I’m not sure whether to address it directly, ignore it, or try to give her more responsibility to make better use of her skills. I want her to feel valued, but I also need her to embrace an all-hands-on-deck team mindset.

Alison Green responds:


You need to have a direct, big-picture conversation with her about whether this job is the right fit for what she wants right now.


If the comments were occasional, you could address them in the moment or even let some slide. For instance, when she suggested you should have pushed back on the tight timeline, you could have replied: “This is a priority for us, and I’ve reviewed the team’s workload—we can handle it without overtime.” If she persisted, you might ask, “What specifically concerns you about this? I want to understand.”


When someone repeatedly offers unsolicited management advice, a powerful approach is to treat their input with genuine seriousness. Instead of brushing it off (which can let the behavior continue unchecked), dig in: “You’ve raised this a few times, so let’s talk through it. What exactly are you worried about, and what solution do you see?” This allows you to share context, hear any valid points, and gently reinforce boundaries—without appearing defensive.


Because the comments are frequent, however, a one-off response isn’t enough. Schedule a dedicated conversation. Start on a positive note:


“You’ve been doing strong work—your reliability, quality, and fresh perspectives are making a real difference on the team. However, I want to talk about something that’s been on my mind.”


Then be direct:


“I’ve noticed you’ve mentioned your previous management experience several times and shared what you would do differently here. You’ve also expressed frustration with some of the more routine aspects of the role. I want to be transparent: this is an individual contributor position. Everyone on the team handles both strategic and hands-on work, and that’s not changing. Framing feedback as ‘what I would do if I were running things’ is coming across as dissatisfaction with the current role.”


Reaffirm that you value her input on how the team operates, but make it clear that constantly positioning herself as a former boss is undermining her effectiveness in her current position. Ask her directly whether this job still aligns with what she wants.


**Important:** Do *not* give her more responsibility as a way to address this behavior. That would reward the very issue you’re trying to correct and send the wrong message. You can expand her role later if it makes sense for business reasons and her performance warrants it—but not as a response to her comments.


The goal is clarity and alignment. Either Jessica recommits to the role as it exists and adjusts her communication, or you both acknowledge that the position may no longer be the right fit. A candid conversation now protects your team’s culture and gives her a fair chance to course-correct.

Post a Comment

Previous Post Next Post