Ask a Manager

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

1. Disgruntled ex-employee keeps contacting current employees

We had an employee, Lark, who served as a director in our business for about eight months. She chose to put in her notice and leave the company this summer. During her tenure, she repeatedly told several members of leadership that she was unhappy, looking for another role, and hoped we would just walk her out. She never said anything like this to me or my husband (the owners of the business).

At the end of the first week of her notice period, we told her that she seemed stressed and was dealing with a lot and she could just take the following week as paid vacation time and not return to the office.

After she left, we found out that she was routinely inserting herself into situations that a director should not have been in (such as sorting out daily tasks for entry-level employees) and was constantly telling people that she was the only one who got anything done and she was their “buddy” or “champion.” She never raised any of the issues she was supposedly advocating for in any management meetings.

Now that she has been gone for six weeks, we are hearing that she is regularly contacting current members of the management team to ask how project X is going or if they completed project Y — work-related issues that she has no business being involved in at this point. It is causing team members to mistrust senior leadership or not be honest with us.

She doesn’t work here, so what can we even do? Everything is hearsay right now because the people she’s contacting won’t show us the evidence (one told us before he quit, which is how we know). We need our team to see how toxic it is for any former leader to be inserting themselves into private business matters and undermining the leadership team. But we also know that if they don’t trust us and we tell them to stop sharing this information with people outside the company, it may give them more reason to mistrust us. What do we do with this toxic behavior?

This is bizarre! Why on earth is someone who no longer works there asking people whether they’ve completed specific tasks? It almost sounds like a continuation of the problems when she was there and wanted to be seen as everyone’s champion, and now that she’s gone she can’t let go of her identity as Extremely Involved … but it’s pretty wild to see that happen when she was only there for eight months, and it’s quite weird that the rest of your staff doesn’t find it odd.

In any case, it’s not strange or suspicious to remind employees that they can’t share internal info outside the company; that’s a very normal policy to have.

The fact that people don’t think it’s weird that a former employee is still inserting herself in this way makes me think that you might have deeper cultural issues than whatever’s up with Lark. The only way to solve this is to lean in hard to good management right now — meaning make sure managers are appropriately engaged with the work their teams are doing, hearing people out and ensuring people have opportunities for meaningful input that you take seriously, being as transparent about possible about decision-making, ensuring people are recognized and rewarded for good work, and otherwise demonstrating through your actions that you’re operating with integrity and openness. That’s the best counter to a toxic former employee like Lark who’s trying to undermine you — but it will take sustained commitment on your end to doing that.

Related:
my toxic former employee is still spreading negativity on my staff

2. When a toxic ex-BFF joins your company

This question is for a very dear friend of mine, Marlie. Marlie works in a very competitive industry. We are both still at the beginning of our careers and are close with a lot of friends from college. Marlie had a close college friend, Amanda, who she bonded with over their shared field and similar backgrounds. After college, they both landed jobs in major cities. They stayed in touch and traveled together, and I joined them on a few of these trips.

They had some personality clashes, but things really started to fall apart about a year ago during a vacation. Some of Amanda’ bad behavior included: not bringing her wallet and making us pay for most things (this happened almost every time we’d go out with her), lying and calling Marlie names behind her back, almost abandoning my friend when she decided to hook up with a guy my friend had expressed interest in (this has happened more than once), calling Marlie desperate and criticizing her taste in men, cursing us both out while drunk, and unfollowing Marlie on social media and leaving her texts on read.

Fast forward, Amanda lost her job a few months ago and has been searching for a new one. Meanwhile, Marlie is thriving in her job and is very happy. A few weeks ago, after a year of no contact, Amanda reached out asking for interview advice, as she’s interviewing for an open position at Marlie’s company. Marlie never responded.

The interview was last week, and there’s a real chance she’ll get the job. Marlie is nervous about the potential of Amanda joining her company and worried she will disrupt the positive work environment. They wouldn’t be on the same team, but she would still see her regularly. Amanda would also likely try to reconnect, especially given the social dynamics at the office. If Amanda gets the job, how should Marlie handle this situation? How can she maintain boundaries with minimal drama and questions from coworkers?

Polite professional distance.

Some behavior is bad enough that it would warrant Marlie talking to the hiring manager and sharing her experience with Amanda, but the stuff on this list doesn’t rise to that level. Amanda sounds like a bad friend and not someone you’d want to hang out with, but it’s all pretty solidly stuff that points to just not renewing the friendship rather than anything more.

If Amanda does get hired, Marlie should be polite but distant. If Amanda makes overtures to grab lunch or otherwise hang out, Marlie should politely decline, saying she’s too busy or so forth. If Amanda pushes the issue, Marlie might need to say, “I want nothing but the best for you, but I don’t think the friendship was good for either of us so I’d rather just be colleagues with different boundaries than we used to have.”

3. Are these interview red flags?

I’ve been interviewing for a new job for the past two months. I thought I had gone through the final round (with the head of HR and the managing director) and then was told last minute that there was one more interview with a senior member of the team, who sits across the country from where this position is based.

As soon as we got through the pleasantries, she proceeded to tell me that they had to fire the last person in the role, their name, the dates of their tenure, and the fact that they failed multiple performance improvement plans before they were let go. We work in a niche and small field. While I don’t happen to know this person who was fired, I very well could.

I’ve never experienced anything like this before, and it is giving me very serious pause about the role. Is this a major red flag? There were other parts of the conversation that were alarming to me, namely, that this person relayed very different information about the annual sales targets (she said they were three times what I had been told by HR), bragged about leaving for the office at 5 am in the morning during the summer months, and gave me conflicting information about the in-office expectations. More seriously, a job can be the wrong fit for any number of reasons, especially at this phase of my career and I would hate to think that if I decided to move on in a year or two, I would be badmouthed all over town about it.

Run. This is going to be a clusterfudge.

If it were just the discrepancy in the sales targets, I wouldn’t be so worried (as long as the numbers sounded reasonable to you) because HR often doesn’t have the nitty-gritty info about a job in the way a manager will. But all the rest of this = huge red flags.

4. My manager gave me her personal money for a work item I bought

My company has a $300 cost limit for a certain type of equipment, but the internal website said the limit could be overruled by higher management approval. My equipment was failing, and the cost for a new one of the exact same brand, specifications, etc. was about $315. My manager approved the purchase, as did her manager, so I purchased the equipment. My reimbursement request was rejected for going over the $300 limit. When my manager and her manager got involved, they were told by the expenses team that despite what the website said, there was in fact no way to go over the cost limit.

In the end, I was reimbursed $300 by the company, and my manager insisted on Venmo’ing the remaining $15 from her personal account, which she was not reimbursed for. I felt really uncomfortable taking her personal money when it was our company that caused the error, but she insisted. The expenses team also promised to update the website to make it more accurate. How should this have been handled?

The company should have covered the full $315 because it had been approved by your management in accordance with their written policies. They can update the policy, sure, but your manager shouldn’t lose her own money because a written policy was inaccurate. (And really, $15? That’s a de minimis amount for your company to eat in the interests of staff morale.)

Don’t feel weird about taking your manager’s $15, though; I’m sure she would have felt far worse if you were the one out the money because of what happened and she probably felt partially responsible. I would have wanted to cover it myself too.

5. Starburst curation

My office has a communal candy dish that includes the little two-packs of Starbursts. A coworker has taken to opening these packets, eating only the Starburst flavors they like (pink and orange), and leaving the remaining Starburst squares (red and yellow) behind for others. On the one hand, this strikes me as absolutely unhinged behavior. On the other hand, this unhinged behavior means I also have a whole slew of red Starbursts (my favorite) at my disposal, without even having to gamble for them. Am I obligated to say anything about this behavior, for the greater good? Or, with two Starburst-happy employees in balance, am I in the clear to continue letting crime pay?

I’m not sure there’s anything unhinged happening here! If your coworker is opening all the packages and removing the pink and orange Starbursts so there are none for anyone else, then yes, this is boorish behavior. But if they’re just taking a reasonable amount of candy and putting back the individually wrapped ones they don’t like so someone else can have them, this is what top minds consider a classic win/win.

Either way, you are under no obligation to speak up and may continue enjoying the red cast-offs without qualms.

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

1. My employee thinks I’m sending “secret messages” about how much time off she has

I’m a new manager with less than a year of experience, and I manage one direct report, Sally. We’re both based in the U.S., while our director is in the UK.

Recently, one of Sally’s collaborators reached out to me, mentioning that Sally has been telling people I’m sending her “secret messages” about having unlimited PTO. This is inaccurate — our team gets 200 hours of PTO per year.

However, our department does have a flexible approach when it comes to things like half days, childcare issues, or doctor’s appointments, partly due to having team members in the UK who follow different guidelines. While I’ve encouraged her to take time off when she’s had childcare or medical issues, I’m beginning to feel that she may be taking advantage of this flexibility. I’ve never suggested anything like unlimited PTO. In fact, I recently made it clear by saying, “That’s what PTO is for. Use it!”

I plan to address this with her this week. While I’m obviously concerned that she may be taking advantage of the flexibility, the idea that I’m sending “secret messages” is more alarming. Could this be a sign of a potential mental health issue?

I wasn’t expecting your last line — that’s a big leap! It’s much more likely that Sally simply misunderstood something. It’s also possible that something got lost in the retelling — like that Sally didn’t actually tell the colleague that you were sending “secret messages” but rather said “Jane doesn’t say it openly, but she’s signaled I can take whatever time I need,” the colleague relayed that to you as “secret messages,” and you thought those were Sally’s literal words when they weren’t. Or maybe Sally did say “secret messages” but meant it as shorthand for something more like this.

Flexibility is a good thing, but it can also lead to people being confused about exactly what is and isn’t okay … and sometimes managers hesitate to spell things out explicitly because they feel that adds rigidity to something intended to be the opposite … but when you have an idea in your head about what is/isn’t okay, it’s a kindness to make sure everyone is on the same page, particularly once you see signs that they’re not. So just talk to her and clarify the expectations, and it will likely be fine.

2. Using a water flosser at work

I have adult braces, so I have to be very diligent about dental hygiene, and your previous answer about teeth-brushing at work assured me that it was not weird. However, sometimes food gets stuck in a way that is not conducive to braces. I have a small travel water flosser — is it weird to use it in a bathroom where other people can see? Something about flossing feels weird!

It’s fine to floss your teeth in the office bathroom. The bathroom is the right place for flossing to happen! Water flossers can be messier than regular floss, so just make sure you’re cleaning up any mess (not leaving water spray all over, etc.). If the area is clean for the next person, you’ve handled it appropriately.

3. Coworker in a different time zone is annoyed I won’t stay late

I’m having an issue with a coworker in another time zone. I work remotely in Eastern Standard and my coworker works in a time zone 2 hours behind me.

Lately, she’s been sending me requests to stay after hours at end of day (4:40-5:15). She consistently waits until my work hours are almost over to ask that I work late. I have classes three times a week at 5:30 and have told the team that I log off by 5:05. So, I’ve been saying no to her a lot.

I also know my coworker has made the request to my higher-ups that I change my working hours to accommodate her working hours, but thankfully they said it wasn’t necessary.

I don’t want to keep saying no, but I do not appreciate being asked to work late last minute so frequently. I would like to confront my coworker about this habit but as a remote worker, I don’t want to rock the boat too much. I feel like I’m expected to get the short end of the stick because I don’t have to commute in.

Is there a way to do this where I don’t come across as rude or a non-team player? Doing it over Teams feels dicey. I’m good at my job, I just want to do it during my actual work hours.

The next time she asks you to work late, address the pattern: “You’ve asked me that a few times lately so I want to make sure you know that I generally need to leave at 5 ET (3 your time). If you’re likely to need something from me same-day, please let me know earlier in the day if you can.” If you’re willing to stay late in very rare emergencies, you can add “except in very rare emergencies.”

One caveat: are other people on your team remote or are you the only one? When you’re the only remote person and especially if you’re in a different time zone, sometimes you do need to be more aware of the impact that has on their work. In many situations it won’t matter, particularly if you’re good at your job. But there are some circumstances where, for your own job security, you’d want to get ahead of any grumbling about it. I don’t have any reason to believe that’s happening here, especially since your boss shut your coworker down, but if you’re the only remote person it’s smart to stay alert for signs of it.

4. Contact doesn’t use reply-all when she should

I am running into a problem with someone I have to email regularly, Kaitlyn, who should reply-all so that everyone cc’d on emails can see her reply, but consistently forgets to do it. One other person, Mike, and I are Kaitlyn’s clients. For a variety of reasons I am usually the person who contacts Kaitlyn, but I always cc Mike since he also needs to see Kaitlyn’s response. Kaitlyn almost always replies only to me, meaning I have to add Mike back in my replies to keep him current on what is going on. We asked her once before a while back to “please reply-all so Mike can see,” but it doesn’t seem to have stuck.

My impression of Kaitlyn is that she is young and relatively new to the workplace. We have other frustrations with her (usually we are contacting her because something has gone wrong). Mike and I have not said anything else to her about the cc problem after the first time because we’re more focused on getting our problems fixed and we’re both worried about piling a complaint on a complaint and on getting snippy with our tone. But this is genuinely frustrating and annoying. What’s a polite way to ask/remind Kaitlyn to remember she has to keep us both in the thread?

You’re getting excessively worried about piling on or sounding snippy — probably because you’re feeling snippy because you’re frustrated. But letting that deter you from being direct about it just means that by whatever point you finally do say something, you’ll be even more likely to sound irritated because your frustration will have built up. It’s much kinder — and easier — to just be direct about this kind of thing as soon as you realize it’s a pattern.

So: “Kaitlyn, we’ve mentioned it before but it hasn’t stuck: we really need you to reply-all when you respond so we both see your responses.”

And then if it still keeps happening, it’s fine to get more terse: “Please include Mike on this response and others in the future.”

You’re her clients. It’s completely normal to let her know what your work needs are!

5. What’s the definition of “three business days”?

Last week, I was directed by a company’s customer service representative to contact their case manager. I sent the case manager an email early Tuesday afternoon and received a response later that afternoon saying that she had received the information, was in the process of reviewing it, and would respond back with a decision within three business days. Which in my opinion would be Friday at the latest.

After going most of the day on Friday without any response, I called the number provided with the email and asked to speak to the case manager, explaining that I was supposed to receive a decision within three business days and today was the third day. The receptionist told me that the case manager takes Fridays off so her third business day wouldn’t be until the following Monday. Is this normal? Isn’t “business days” based on a five-day work week excluding holidays? If the roles were reversed and they needed a response in three business days, could I claim I was on an extended vacation so it could be two weeks before I worked three “business days”?

It wasn’t a life-or-death situation but who gets to decide what is deemed a business day? Several business I deal with are now closed on Friday so this may happen in the future with bill paying/payments, filing/returning paperwork, etc.

Business days are understood to mean Monday through Friday, excluding holidays, unless something else is clear from the context. If someone means “three of my own workdays, which are different than the typical schedule,” then the onus is on them to spell that out — ideally by just saying something like “by Monday” rather than expecting you to do any contorted calculations.

What you encountered was just one weird practice, not something you’re likely to run into repeatedly.

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

1. Writing group member won’t stop talking and we can’t get any work done

I work at an academic institution, and am a member of a writing group that includes people across different departments. We meet every few weeks to write as a way of carving out time for this work, and to hold each other accountable. We usually talk a bit right at the beginning of each session, take a break in the middle, and then chat briefly before leaving.

One member, however, loves to monologue, mostly about their own work, which is in a fairly arcane field, and which the rest of us do not fully understand. This member will often come in late, when the rest of us have started working, and start talking. This is fine, but they will not. Stop. Talking. They talk at everyone else, with little in the way of response, often for 30-45 minutes at a time. Aside from it being extremely draining having to be at the receiving end of this, my time is limited, and I really look forward to being able to write during these sessions, not listen to the nuances of the other person’s work. Any time they reach what I think is the end of what they want to say, I try to turn back to my writing or say, “Okay, time to write now,” but they continue talking. This person has a strong personality, which is why I think other members have neglected to try to stop them as well. It has gotten to the point where, as much as I enjoy the group otherwise, I would rather plan some time to work myself then lose so much to this rambling.

The members would all like to meet again in a few weeks, and I am struggling with how to say that I am happy to meet again, but I really need to buckle down and work. Such a statement would clearly be directed at one person, and I don’t want to start any drama. Beyond that, this person and I had a minor argument over an unrelated manner the last time we met, and I don’t want them to think I am trying to isolate them because of that instance. I don’t have any problem with this person otherwise, I just want my writing group to function as a writing group!

In the discussion about setting up the next meeting, why not say, “I’d love to set up the next meeting, but I really need quiet time to write. We’ve had lots of talking at the last meetings, which makes it tough for me to focus. If some of the group wants to talk and some wants quiet writing time, could we split into two groups so everyone gets what they need from the time?”

And then if the monologuer shows up for the “quiet” group session, you’ll be on solid ground saying, “Like we talked about, I really need quiet writing time. Can we save conversation for the end?”

2. Boss gave me mixed feedback on a task, then framed an interview question for a new hire around that exact task

I have been struggling lately with how my manager, Carrie, communicates with me, and I’m trying to figure out if this is something I should swallow or if it’s worth raising with her, and if so, how best to do that.

A few weeks ago, Carrie asked if I would join her at a meeting with two senior leaders she reports to, to provide an update on a project I’ve been working on but that she is officially responsible for. Later, Carrie decided the meeting agenda was too packed for me to join, so she asked me to prepare two PowerPoint slides to share with them instead.

The project has been to track progress on a high-level organization-wide plan and to document the status of 40 recommendations across four work areas. This is not information that can be meaningfully condensed into two slides. Wondering if she had something specific in mind for how she wanted me to present it, I asked for more guidance on what she wanted me to share. She said, “Just a recap on how things are going – what’s stalled, what’s moving, what hasn’t started, etc.”

I made the call to present the information in five slides – an overall summary, and one each for the four work areas and the recommendations for each. I shared the slides with Carrie and she said over instant message, “Although you went waaaayyyy over 1 to 2 slides, I understand why you did based on the info you provided! Thanks for this — it looks great and I like how you’ve provided the context for each work area diplomatically.”

If Carrie liked what I did and understood why I chose the approach I did, even if it wasn’t within the parameters she initially set out, why belabor the point? It felt unnecessarily petty, and a poor way to give feedback – especially in a written format where any lighthearted tone she may have intended was completely lost.

Then, later in the week, she asked me to review and comment on a draft of interview questions for a new hire for our team. When I reviewed it, I saw one is a scenario-based question framed around exactly the task she asked me to do: “How would you approach creating three slides for a presentation your manager needs to give on a project you’ve been working on but they provided minimal guidance on the content they want?” The qualities the question is intended to explore are “initiative and ability to work with minimal direction, while ensuring the content aligns with project goals. Look for creativity, organization, and proactive communication with their manager.”

Asking this question feels like a dig at me, somehow, given the feedback she gave me on how I handled this exact task. At minimum, she seems wildly unaware of how asking this question in an interview I am participating in would make me feel. How should I handle this? Is it worth talking to her about it? Or should I just let it go?

I think you’re reading too much into it. First, Carrie’s feedback doesn’t sound that mixed; it sounds positive. She noted you produced more than she asked for but also said she realized why, and she said it was great. That’s positive. If anything, though, she might have appreciated an earlier heads-up when you first decided to do additional slides so that she’d have a chance to say, “That won’t work since I already have too many. Can you condense it into three?” It’s always smart to alert your boss in advance when you don’t think you can do something within the constraints they assigned.

The timing of the interview question is, admittedly, a little weird. But I wouldn’t interpret that so negatively either. For all we know, Carrie appreciated what you did and it spurred her to screen for someone who would similar take initiative to problem-solve — or, sure, maybe the mention of “proactive communication” instead is getting at the point above. But it’s also possible that the question has nothing to do with what just happened (especially if she asks for slides a lot).

If it’s bugging you, you can always ask her: “I saw the interview question on X and wondered it stemmed from how I handled the slides the other day. Is that something you’d want me to do differently in the future?”

But I’d bet it’s no big deal at all.

3. Coworkers’ snack bar is in another coworker’s work area

I’ve got a low-stakes question for you. My coworkers have decided to start bringing in different kinds of snacks for people to snack on throughout the day (on their own dollar, which I really don’t think they should be doing on principle, but hey whatever makes them happy). The snacks have been moved around to a couple of different spots, but eventually the snack bar coworkers moved everything next to the mini-fridge in our area. The problem with that is it’s encroaching into someone else’s desk space! (We’re in an open office space. The mini-fridge is in a corner, and someone’s desk is right next to it. They’ve lined up the containers along the windows behind the fridge, but the windows go into this person’s desk space.)

It’s not my desk space, so I don’t really have the grounds to say something. Do I say something to my coworker whose space is being used? She’s relatively new, so she might not want to rock the boat about this. I just feel like this is extremely rude! There are other places to set up these snacks, why are you choosing one that’s already being used?

(Note: the snacks are all either still in their sealed packaging or are in sealable tupperware-type containers. No one’s said anything about any possible issues of just leaving food out and about for weeks at a time, and I don’t think it’s serious enough to raise to anyone.)

Eh. It’s minor enough that it would be completely fine to leave it alone or to say something. If the coworker whose space is being used weren’t new or were known to be reasonably assertive, I’d stay out of it. But since she’s new, it would be considerate to either (a) say, “Hey, can we move these somewhere where they’re not encroaching on Jane’s desk space?” or (b) ask Jane, “Does it bother you that these are being kept here? I can suggest they move them if it does.”

4. What’s up with the term “grandboss”?

I keep seeing the term “grandboss” on your site, and elsewhere. I have an immediate, nearly physical reaction of disgust to this term. The idea that your boss or your workplace is your family makes my skin crawl, and the idea of my boss’s boss specifically being my “granddaddy” somehow crosses the line even more to the point that it feels really yucky.

I’m confused. Why do you use this term? Why do others use it? I genuinely want to understand, because I can’t even begin to fathom accepting this as a normal thing, it just feels beyond gross and creepy to me.

I love your blog and I nearly always agree with your takes and enjoy your responses, so the use of this term and general acceptance of its use from others really throws me.

It’s just because “boss’s boss” or “boss’s boss’s boss” is unwieldy” and “grandboss” captures the hierarchy quickly in a way that’s easy to intuit.

No one actually thinks of their boss’s boss as a grandparent figure; it’s just easy shorthand. (I would fully agree with your disgust if anyone was actually using “granddaddy,” “grandma,” etc., but no one is using those — they’ve just borrowed “grand.”)

5. Can managers ever really get anonymous feedback?

We are a small team (fewer than 10 employees) at a large hi-tech company. There are plenty of avenues for team leaders and managers to give feedback to their reports, but nothing official in place for employees to give feedback to their higher ups.

My relatively new team leader (a little over a year) wants to institute a way for our team to give him feedback anonymously but doesn’t know how to go about it. When he brought it up at a recent meeting, one of my coworkers pointed out that it wouldn’t be truly anonymous as we are a very small team and it would be easy to figure it out, especially as some issues only apply to one person. Is there a way to ask for and receive truly anonymous feedback from your reports?

If you have a very large team, yes. Although even then, a lot of people will worry the feedback isn’t really anonymous (sometimes it’s really not) and won’t be candid. But on a small team, it’s often very easy to figure out who said what (and even more so if the survey includes any sort of job function or demographics).

It’s better for managers to create an environment where people feel safe giving feedback, even if it’s not anonymous (and which ideally would include cultivating good relationships between the team and the manager’s own boss, so there’s another path for feedback if something is really significant).

Related:
why do managers say they want feedback and then get annoyed when they get it?
how to get your staff to be more honest with you