manager who makes too many assumptions, spending sick leave in Cancun, and more

This post was written by Alison Green and published on Ask a Manager.

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

1. I manage a manager who makes too many assumptions about everything

I manage a manager, Jane, who openly for all to hear assumes motivations for our clients, consumers, and employees on everything. It’s not only unhelpful, but it also is incorrect. For example, we had a project that was having some difficulties and Jane said in a team meeting, “Oh, they’re going to ask us to work the weekend,” when this was never mentioned. It not only put all others in the meeting on their heels and made them nervous, but it also made it seem like our clients were overly demanding. They never asked us to work through the weekend, nor did we need to. Her throwaway comment stressed a lot of employees out and also put our client in a false bad light.

Another example is when an employee Jane manages asked about a glitch she found on a project when she was reviewing it. I had more interaction with the glitch, so I asked her to compile all the feedback she received from different individuals experiencing the glitch, and then we could look at it as a whole. In response, Jane said, “It must have been a one-off situation,” but it wasn’t. There were a lot of people who experienced it, and we needed to come up with a solution – but her comment downplayed the seriousness. I appreciate if she was trying to bring levity, but she is always interjecting assumptions without any basis, and it’s not helpful at all. How do I approach this without knocking the wind out of her sails? Other than this, she does good work – but her additional anecdotes are becoming a lot to piece through.

Name the pattern! And explain that people put a lot of weight on her comments because she’s a manager, and so she needs to be more thoughtful about not making throwaway comments that people are taking seriously or rushing to conclusions without first asking questions. For example: “I’ve noticed a pattern recently that I want to bring up to you. You’ll sometimes make what I think you’re thinking of as a throwaway comment, not one you’ve necessarily thought through or expect people to act right away on. But because you’re a manager, your words carry a lot of weight — and when you haven’t thought through what you’re saying and are working from an assumption that you haven’t taken the time to confirm, it can send people down the wrong path, stress them out unnecessarily, or leave them with the wrong impression. For example (supply examples).”

Obviously, you don’t want the result of this conversation to be that she clams up and never speaks again because she’s afraid of doing what you’ve described, so there’s going to be some art in working with her on this. And it’s unlikely that a single conversation will solve it — but it will flag the issue and provide the framework to make it easier to talk with her about it when you see it happen the next time. It’s likely going to be an ongoing process of coaching (because at its core it’s about judgment), and you’ll need to talk through what she should be doing instead (asking more questions, probably), but this framework should help you name what you’re seeing and why it’s a problem.

2. Was it inappropriate for an employee of a client to invite me for drinks?

When I was 20, I worked at a consulting firm. I worked for a client overseas and worked mainly with a team, but occasionally I had to interact with other employees of our client company. One of those times, a female employee really appreciated some help I gave her and we talked a bit. She mentioned that she would be in my city for a work trip and that we could go out for some drinks if I wanted.

I felt a bit uncomfortable and didn’t answer and then we both pretended nothing had happened. I didn’t want to meet because I thought it would be weird (we really didn’t know each other and I suspect she didn’t know how young I was — she never saw my face) but I also felt it wouldn’t be appropriate. As a man, I didn’t want anyone in my company to think I was trying to hook up with employees of our client (even if this wasn’t the case; I think she was just being friendly). This happened many years ago and while I praise myself for my caution I still wonder if I was right in thinking this was inappropriate.

It doesn’t sound particularly inappropriate; people often meet up for drinks when they’re traveling through the city of someone they work with. I’d assume she was just being friendly and/or networking. If she’d kept pushing you to meet up after you’d declined, that would have been inappropriate — but it sounds like she just suggested it, you didn’t take her up on it, and that was that. Which is also fine! You’re under no obligation to agree to invitations if you don’t feel comfortable or just don’t want to go. Ideally, though, you should decline gracefully — citing other plans is an easy way to do it — so that no one feels awkward about it.

3. Coworker wants to spend sick leave in Cancun

I have a coworker who’s having a medical procedure done and is taking a week to recover. The second week he’s going to Cancun but wants to include that as sick time, not PTO. Can he do that? It seems like if he’s well enough to fly, it should be considered vacation.

It’s possible for someone to be well enough to fly but not well enough to work — depending on the physical and mental demands of the job, and also on what recovery entails (i.e., being laid up in bed is different from just being too mentally fuzzy from painkillers to work). But most employers are going to be awfully skeptical of someone submitting sick time while declaring they’re spending a week in Cancun. Your coworker is pretty much asking for pushback on it.

That said, if you don’t manage him/aren’t in HR and his absence isn’t going to significantly impact you, it’s not really your business and you shouldn’t get involved.

4. My new boss is in my D&D group

I work for a government organization with many departments. During the pandemic, a few semi-official hobby groups were created to allow people across different departments to socialize, including but not limited to a book club and a D&D group. They still exist “post-pandemic” and I’ve been part of the D&D group for about a year. We don’t meet during work hours, and we avoid discussing work during gaming sessions.

Earlier this year I interviewed for a higher position in a different department, and just got the news that I got the job! During the process, after I’d already interviewed, a new person joined the D&D group, and it turns out she’s going to be my supervisor for this new position. She’s fairly new to the position herself.

I know from past letters that you’ve cautioned people about getting too casual with their supervisors and reports, and because of the nature of tabletop RPGs, the group is pretty informal with each other. What’s the best way to avoid any professional missteps or awkwardness when my supervisor and I are pretending to be wizards together in our off hours?

I can’t speak to D&D-specific missteps (although I bet some readers can in the comments) but assuming you’re, you know, a reasonably well-behaved person and not the boor of the group, this is more of a potential landmine for your manager than for you. She’s got to be thoughtful about ensuring that others on the team don’t feel you’re getting special access to her or that work conversations are happening during these get-togethers that they’re not included in. You don’t need to manage that for her, though; that’s hers to navigate.

5. Asking for a raise: a success story

I wanted to share a success story with you! I’ve been at my current job about 18 months now, and am a mid-career nonprofit professional who freelanced a bunch before getting this steady gig because I needed a more stable income. I realized recently that I need a raise as I was taking on new responsibilities, and had already received a new title (budget issues at the time of the title bump meant asking for a raise was not prudent). But the budget has steadied out, and I figured it was time.

I read all the stuff I could on your blog about how to ask for a raise and then sent my boss an email asking for a salary discussion to be put on the agenda for our upcoming 1:1. In my email, I mentioned the accomplishments I’ve had recently and new projects I’m taking on that she’s expressed happiness with, and provided research about the market rate for my position, which my salary was at the low end of. My boss agreed to the discussion, and it turned out: the discussion didn’t need to happen. She showed up with a salary memo from HR in hand, with a 12% bump in my pay.

The hardest part was getting up the confidence to just ask for it! I knew I wasn’t going to leave over it, so I figured it couldn’t hurt to have the conversation. And I’m so glad I did!