Posted by Ask a Manager

https://www.askamanager.org/2025/11/my-employee-might-be-working-a-second-job-during-our-workday.html

https://www.askamanager.org/?p=34050

A reader writes:

I recently took over managing a team, and have some concerns about one of my employees, John, who was hired by my predecessor. He is pretty good at what he does, but he is super slow at producing finished work. He rarely meets deadlines and if I don’t micromanage him every step of the way on a project, it won’t get done.

At first I assumed he just had too much on his plate, so I’ve taken over a decent chunk of his work and made sure that everyone else on staff keeps me in the loop when they need his help. So now I know exactly what’s on his plate and how long it should take to do it – and he takes much longer than he should on most tasks.

I’ve been trying to figure out why he is so slow, and lately I’ve started wondering if he is working on his side gig during our office hours. We work remotely so I can’t see what he is doing, but I’ve noticed he will send me work first thing in the morning and then later in the evening. I won’t hear from him for hours on end during the 9-5, but the work he sends me in the evening is something that should take an hour or so to finish, not all day.

He does have an agency that he founded and works for on the side, so my theory is that he is working on that and then scrambling to get some of his actual work done before the end of the day. How can I have this conversation with him without accusing him and how can I make sure he is actually doing his work without micromanaging him?

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

The post my employee might be working a second job during our workday appeared first on Ask a Manager.

https://www.askamanager.org/2025/11/my-employee-might-be-working-a-second-job-during-our-workday.html

https://www.askamanager.org/?p=34050

Posted by Ask a Manager

https://www.askamanager.org/2025/11/im-managing-an-employee-through-a-pip-and-its-really-hard.html

https://www.askamanager.org/?p=34255

A reader writes:

For the past several years, I’ve been managing an employee whose work has oscillated between “acceptable but not great” and “does not meet expectations.” In that time, we’ve navigated all the steps HR and I could think of to help her improve (including training, shadowing other employees, more training, developing resources, discussing management and feedback styles that work for her, etc.). We’ve had weekly check-ins throughout her employment where we discuss her work, expectations, and other aspects of her role. Now, we’ve finally put her on a formal Performance Improvement Plan, which will last 60 days.

She is understandably upset and stressed, but has — for the most part — handled the news well. While I think she’s not well-suited to the role, I do generally like working with her, and I’m pretty sad that we’ve come to this point. Based on her performance thus far, I currently expect to have to terminate her employment at the end of the PIP period (though of course that could change).

I don’t want to downplay that this is, I’m sure, much more difficult for her … but so far I am finding this process really hard. While we of course discussed when her work wasn’t meeting expectations in the past, spending every check-in and tons of time in between documenting how she’s failing to meet expectations is depressing both for her and me. Watching her get increasingly stressed and upset about her situation leaves me drained, stressed for her, and concerned about the ways this will impact her life outside of work. We’re in the U.S., so I worry about loss of health care for her and her family.

I would never expect this process to be easy — it shouldn’t be! But I don’t think I was prepared for the emotional turmoil I’d feel as a manager with an employee on a PIP, and it’s starting to impact my own work performance. I spend so much time documenting, brainstorming solutions, and feeling guilty that my productivity has slowed. Do you have any advice for managing someone through the end of their employment without destroying your own mental health? How can I compartmentalize and focus on my own work when I’m not managing her efforts?

It sounds like you have done a lot to try to help her and get her work where you need it to be, but that she’s ultimately just not well-suited for the role. What’s good here is that you’ve really done your part — not just all the energy you’ve put into trying to help her improve, but also being clear with her that she’s not meeting the job requirements and what the potential consequences of that are, so that she won’t be (or at least shouldn’t be) blindsided at the end of the process and has time to look for other work. (At least I assume you have been clear about the potential consequences! If you haven’t, it’s important to spell that out so she knows.) These are all good things; they are you doing everything you can to treat her well.

The flip side of that is … you don’t need to work yourself to the bone in this situation! Yes, you need to coach and document — but you don’t need to exhaust every possible avenue. You do the coaching that’s reasonable to do in the time you have available, relative to other things that also need your attention.

Ultimately, the test of whether she can work out in this job isn’t whether she can do it with intensive support from you; it’s whether she can do it without intensive support from you. It’s okay to do less; in fact, you probably have to do less, both to find out whether she can do the job with a reasonable level of support, and to keep your own job sustainable.

The emotional side of this isn’t as easy to answer. It sucks to watch someone go through this process, especially if you can see that they’re trying hard. But maybe you can take comfort in knowing that you’re uniquely positioned to ensure that she’s treated fairly and with dignity during this process (which includes being kind but honest when it’s not working).

This may help too:

how do you deal with having to fire someone?

The post I’m managing an employee through a PIP — and it’s really hard appeared first on Ask a Manager.

https://www.askamanager.org/2025/11/im-managing-an-employee-through-a-pip-and-its-really-hard.html

https://www.askamanager.org/?p=34255