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.

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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

Posted by Ask a Manager

https://www.askamanager.org/2025/11/our-board-member-got-scammed-im-the-only-one-who-has-to-wear-a-uniform-and-more.html

https://www.askamanager.org/?p=34203

It’s five answers to five questions. Here we go…

1. What’s our responsibility when a board member gets scammed?

I just joined the board of a nonprofit and at my very first meeting today learned about a mess that we’re in. There are about a dozen members of the board and I’m coming in as an executive member, of which there are four. Apparently, one of the “at large” members of the board received some emails about six weeks ago from the outgoing president about two urgent invoices that needed to be paid, had to happen today, had to be paid online and won’t accept a check, can you please pay it immediately, I’m cc’ing the treasurer who will reimburse you in three business days, etc. The total was just under $3,000.

Apparently this board member went ahead and immediately paid both invoices with personal funds (even though they were a PayPal invoice to a random gmail account!) and is finally speaking up wanting to know why it’s taking so long to get reimbursed, very irritated, this is a hardship for her, etc. When it was explained that the email addresses (“boardpresident9999@gmail”) were obviously spoofed and this was clearly a scam, she was very embarrassed and apologized, and made no further mention of reimbursement.

I do not know why she thought it was appropriate to pay these using her personal funds, as I’m new to the board. It does seem like there’s been a practice of board members covering expenses on a smaller scale and being reimbursed by check within a few weeks (think paying for catering for a meeting, to the tune of a few hundred dollars). There are no written policies or guidelines about reimbursement or payment of expenses. Obviously, that’s the first thing I will be putting on the agenda for our next board meeting!

But now the current incoming president and the treasurer have started a private email conversation with me and the outgoing president saying how bad they feel for her, and that the organization needs to reimburse her as soon as possible. I wrote back immediately saying, “Um, no? She needs to pursue getting the charges reversed by her bank, but the organization is not responsible for paying this.”

I think if she had spent the organization’s funds while being scammed, we wouldn’t be going after her to reimburse the organization, although I would think at the very least we’d need to mandate that she do some training about not falling for scams. But since it was her own personal finances, I do not think we have any obligation to put things right for her personally. The treasurer and the president seem to think we do, since “she was targeted because she’s on the board, so she wouldn’t have been scammed if it weren’t for us” and because they think it’s likely that she won’t be able to recover the money through her bank. The org has just over $20,000 in the bank, and annual budget is mostly focused on a one-day event we put on, which is less than $10,000, so $3,000 is a significant amount for the organization. What do you think?

Yeah, it would be a really big deal to spend 15% of the organization’s finances on this. If the organization had a multimillion dollar budget, it might be different. But you’ve got $20,000 in the bank and want to give a sizable chunk of that away? I don’t see how you can fundraise from donors in good faith after that.

To be clear, this is awful! But the board has a fiduciary duty to protect the organization’s finances, not an individual board member’s. At an absolute minimum, she needs to start by pursuing this with her bank and see what happens there before there’s any discussion of organizational funds being used on it.

(There also need to be immediate policies about spending personal money and what kind of paper trail needs to be in place for expense authorization, as well as some board-wide fraud awareness training.)

2. I’m the only one who has to wear a uniform, and it doesn’t fit

I recently started work as an administration assistant, in a role that provides newly built accommodation for students. We are based at the accommodation complex. There is me, the manager, another administration assistant, and the housekeeper.

As of last week, I have been given two blouses to wear, which show the company logo. They are the largest size. I’ve moved the buttons, but they are still a bit snug. I have to wash and iron these blouses, where before I wore my own tops, with the black trousers that I still wear.

The other administration assistant hasn’t been given any blouses, and when I asked my manager about it, she replied, “Oh , she won’t wear one.” So when she and I are on the reception together, I’m in the uniform blouse, and the other assistant (Sara) is in her own clothes.

The housekeeper commented that my blouse was gaping, and I told her that I’m wearing the largest size. I told my manager of the housekeeper’s comment, but nothing came of this. May I ask your thoughts on this? A uniform was mentioned in my interview, but I assumed that other administration staff would wear it, not just me.

You need to be more direct with your manager! Just passing along the housekeeper’s comment isn’t enough.

Instead, tell your manager that you’ve given it a try but the blouses don’t fit you and are too tight, and you’re not comfortable wearing them so you’ll be returning to your own clothes like Sara does. There’s clearly room to simply decline, based on what Sara is doing.

You might ask Sara ahead of time how she got out of the uniform requirement; it sounds like she might tell you that she simply held firm about it, which might make you feel more confident doing the same thing.

3. People discourage me from taking notes

My memory isn’t great so at work I take a lot of notes. I use a work-provided spiral-bound note pad as it’s small enough to have in my bag/take to face-to-face meetings but has enough pages to last several months. I date them and keep them for a while to refer back to notes if needed.

However, my current manager and a colleague occasionally tell me no note-taking is needed. Normally I’ll say that I take notes as I don’t have a great memory and need to write things down. However, in a past position for the same organization, a manager spread rumors that my past medical treatment had caused cognitive issues (not true). I’m not sure whether this manager has heard this, so I am keen not to say anything that might reinforce that. Perhaps I could say I’m a note-taking person and that’s how I work best. What is your take on this?

Turn it from a negative (“I don’t have a great memory”) into a positive: “I’m super organized and having notes helps me juggle everything.”

That said, sometimes people will say you don’t need to take notes because they’re trying to convey that this is an informal discussion and won’t have action items arising from it — and sometimes they want you more focused on, say, brainstorming than on documenting. I do think you should try to be flexible in those cases — not that you shouldn’t write down any takeaways but that you should recognize when things aren’t at that stage yet and people are looking for a more free-flowing conversation. Obviously if you’re someone who finds it challenging to brainstorm without notes involved, that would be different — but if your real need is to capture details and action items once they’re solidified, it’s helpful to recognize when things are and aren’t at that stage.

(There’s another category of this, where the discussion is something they specifically do not want documented, but it doesn’t sound like that’s what’s happening.)

4. My references are getting checked before final interviews

For most of my career, in the nonprofit sector, I’ve had employers ask for references at the end of the search process, when (it seems) it’s treated like a final confirmation or due diligence. I’ve never been asked for references and then learned I didn’t get the job.

…Until recently. In the past three years I have made it to the last round for five executive director jobs — some handled by search firms, some not — and all five places have asked for references before the final interview. I haven’t gotten any of these jobs and I’ve had to go back to my references again and again to tell them, “Oh, bad news, I didn’t get this one either.” Frankly this has gotten embarrassing.

I’m once again in the last round of a search, #6 in three years, and once again they’ve asked for references before scheduling the last interview. Once again I sent messages to the same set of previous bosses, and I am steeling myself for disappointment.

Is this a common way to handle reference checks for executive jobs? Is there any chance I can push back a little? How can I best maintain my relationships with my former managers when I ask them for references again and again and keep failing to get the jobs?

For high-level, high-stakes jobs like executive director, it’s much better practice not to treat reference checks like a final confirmation, but rather to use them for nuanced information that might influence what topics are discussed in a final interview. At that level, reference checks really shouldn’t just be thumbs-up/thumbs-down, but rather nuanced conversations about things like leadership style, where there aren’t necessarily “right” answers but just information about how this person might operate in the role.

You don’t need to be embarrassed by your references being contacted for jobs you ultimately didn’t get. (You also don’t need to update them every time you don’t get a job, if that makes it easier.) That said, it wouldn’t hurt to check with your references to make sure they feel comfortable giving you a positive recommendation for the types of job you’re applying for, in case something in the reference check is tripping you up. One thing you can do is to ask your references whether they think there are areas you should work on developing in order to be a strong candidate for these positions; that potentially makes it easier for someone to say, “Well, actually, if I were hiring for these roles I’d want to see more X from you” (or whatever), whereas they might not feel comfortable telling you that without you soliciting it.

5. When should a side responsibility become an official part of my job?

I’ve been with my company for five years in my current role. When I changed positions five years ago, my job description was updated, but it hasn’t been touched since.

At that time, I was also asked to take on a small but important side responsibility that fit my skill set, even though it wasn’t connected to my formal job. I had experience with it and it’s a function I enjoy, so I was happy to take it on.

Fast forward five years, and that “side duty” has grown significantly. I now lead a related process across the entire company and coach department leads on execution. When we recently needed broader input from employees on new initiatives, I stepped in again, building and running an employee forum when our original approach stalled. That also went well, and I’m now managing the outcomes.

At this point, this unofficial function has become a significant part of my job and a major need for the company. It’s work I truly enjoy, and I’d like to formalize it by clarifying the role, updating my title, and making it part of my job description in addition to my current formal duties. My boss is hesitant and frames it as “everyone needs to pitch in.” While I agree in principle, this has evolved beyond occasional pitching in.

Does it seem reasonable to push for formalizing this role, since it’s now an important organizational function rather than an “other duty”? Or should I accept that the work will remain unofficial?

Frame it this way: “I’m of course happy to pitch in, which I’ve been doing for the past five years, but at this point it’s become a significant part of my job and an ongoing expectation. I’d like it to be reflected in my job description and title so that those remain accurate.”

If your boss still resists, see if you can find out why. Are there political reasons where it’ll be seen as stepping on someone else’s toes or problematically expanding her own portfolio? Are there compensation implications that she’s trying to avoid? Is she just weak when it comes to advocating for her team? Next steps depend on the nature of her objections, so try to suss those out.

The post our board member got scammed, I’m the only one who has to wear a uniform, and more appeared first on Ask a Manager.

https://www.askamanager.org/2025/11/our-board-member-got-scammed-im-the-only-one-who-has-to-wear-a-uniform-and-more.html

https://www.askamanager.org/?p=34203