Ask a Manager

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

1. Manager is always scratching his chest inside his shirt

I am a recent transfer to my current office, 10 years with my company, and I have an issue with a manager. “Mark” wears his shirt with the top three buttons undone and he is rarely seen without his hand inside the shirt, scratching his chest. Am I wrong to be grossed out by this?

Mark is my direct manager, over my immediate supervisor. I have talked to my supervisor about my feelings and I was told that if I felt like this was a serious concern, I should take it up with HR.

What can I do? Short of reporting this to HR or trying to ignore him, which is hard to do since he will stand right in front of you and scratch his chest while he talks to you.

You’re not wrong to be grossed out; someone regularly having their hand inside their clothes is odd, and three unbuttoned buttons is more skin than you see in most offices.

That said, your supervisor is correct that unless you think it’s a big enough deal to take to HR (and I agree that it’s not), there’s nothing you can do about it. Mark’s scratching his chest; he’s not fondling his man parts or otherwise crossing glaring lines. The behavior is uncouth, but it’s not obscene.

At most, the next time he does it you could say, “Are you okay? You keep scratching yourself” — which could make him realize he’s doing something noticeable enough to be remarked on — but if that doesn’t work, then realistically you probably just need to accept the dude is a bit boorish (or very itchy).

2. Is it OK to drink non-alcoholic beer at work?

In your opinion, would it be okay for an employee to drink non-alcoholic beer in the office? Since it contains no alcohol, they wouldn’t be getting drunk and negatively impacting performance. But maybe it falls under the category of “not work appropriate.”

In most offices it would seem pretty weird. It’s an optics issue, not something strictly logical. Partly it’s that people won’t necessarily know it’s non-alcoholic at first glance; a lot of non-alcoholic beers look exactly like regular beer, and it’s not a great move to look like you’re swigging a beer at your desk, whether or not you actually are. Many people won’t stop to check and will just assume they’ve witnessed you drinking at work. But mainly it’s just going to come across as a weird choice in an office — like you’re trying too hard to be provocative, or not sensible enough to know that it will come across strangely, or just too invested in the choice in some way.

If you want to debate whether it should be okay to drink non-alcoholic beer at work, that’s a different question. But realistically, in most offices the optics are going to be bad.

3. My employee won’t take any time off for an injury

I work for a mid-sized city and was recently promoted to the division manager (leading eight staff overall). Our work group is tight and hardworking, and we are all super passionate about our work. As is often the case in the public sector, there is always more work that can be done.

One of my coworkers, Faye, has always worked long hours. She works late and nearly every weekend, and almost never takes time off. Even when she goes on vacation, she usually works part days throughout. She is extremely smart, dedicated, conscientious, and hardworking. Faye is now my direct report, but we worked for years as colleagues running parallel programs. I consider her a work friend, but she is older than me and we are figuring out what our new work relationship is.

When we were peers, how she took time off was none of my business. Now that I am her supervisor, I’m running into an issue because Faye is dealing with a really bad back injury. We are going into the third week of her working through extreme pain. She has been continuing to work through it from home, since she says it doesn’t make a difference if she’s working or not. She’s been working slightly fewer hours, but mostly just pushing through, working through pain and pain-induced insomnia.

I know it’s not appropriate to manage her time off, but I am starting to be concerned because I strongly believe in taking time away from work, unplugged, to heal and recuperate. I also don’t like the expectation it sets for the rest of the team. We get generous time off, with interchangeable vacation and sick time that rolls over into the next year. Faye has about 10 weeks of time saved up, in addition to access to paid medical leave through our state. Our workplace also has a donated leave program.

What is my role here? Is there anything I could/should do, beyond letting her know we can cover if she needs to take time off? I did encourage her to turn on her out-of-office message so she feels she can step away from email, which she did. And I’m covering any in-person duties (which are pretty minimal).

I agree with your philosophy about real time away, unplugged … but I also believe in letting adults make their own choices in that regard until and unless it’s affecting your team.

Reasons to tell Faye she needs to disconnect would be:
* if you’re seeing signs that other team members feel pressured to mirror her behavior
* if “working through pain and pain-induced insomnia” is affecting her work quality or output (hard to think it wouldn’t, but who knows)
* if you have reason to think she’s burning out
* if you need her at her well-rested best for something more important in the near future
* if her never being away means you have no chance to spot weak points or cross-training needs on your team (or fraud, for that matter — there’s a reason many financial jobs require people to fully disconnect for two weeks each year)
* if your sense is that she’s doing this because she truly feels there are no options to cover important work (in which case you’d need to work to find some)

I suspect at least a few of these are in play. But if they’re not, you can urge her to take real time off and emphasize that things will be covered in her absence, but otherwise should leave it to her to decide.

4. My manager won’t take any responsibility for us dropping a ball

Last week, my boss messaged me, “So, how’s project A going?” and I had no answer because I had done … nothing! This is a project that usually requires over a month of preparation and coordination between multiple teams at the company. However, I never knew it was my responsibility! I replied that I didn’t know it was my responsibility and I thought another team had it handled. He mentioned a meeting we had with the other team a few months ago where we had apparently agreed to handle the entire thing. But it didn’t come up in any documentation, meeting notes, my monthly goals, our yearly goals, and he hadn’t checked in until today, a week before the project was supposed to be completed!

In my work life (eight years) and under this manager (1.5 years), this has never happened to me before, and certainly not on an assignment that requires so much preparation. I have always gotten really good feedback on my ability to juggle multiple projects, prioritize, and communicate effectively, so this really rocked me. I feel like my manager dropped the ball on this, but he refuses to take any responsibility for it.

I did work like crazy to get everything figured out in less than one week so we are still on schedule, but it was one of the worst weeks I have ever had at work. We had a follow-up conversation where I mentioned the lack of communication or documentation, but he seemed completely nonplussed at the situation (and definitely not apologetic). I apologized for any miscommunication and really tried to give him the benefit of the doubt … but I can’t help feeling that I shouldered the entire situation and he has walked away oblivious to how big of a problem it was. How do I get across to him how much this affected me? And how do I prevent this kind of thing in the future?

If he’s normally a good manager who communicates well, one option is to leave it where it is now, since you’ve already had a follow-up conversation where you mentioned your concerns. I see why you’re thrown by his response to that (or lack of response, really) but if it’s not part of a pattern, you could just figure it’s been addressed, you see it differently for whatever reason, and it’s now settled enough — as long as it doesn’t keep happening.

But the other option is to go back and say something like, “I know we talked about it a bit, but I’m pretty rattled that I was unaware of such a major project for so long, and I hoped we could figure out where we miscommunicated so I can make sure it doesn’t happen again. If your sense is that I dropped the ball somewhere, can we dig into what happened so I’m better prepared next time? Or if your sense is that something else caused it, can we figure that out too?” There is a danger here that if your boss feels it’s already been discussed and handled, it could be annoying to reopen it, so you should factor in your sense of that, and also how open he’s historically been to acknowledging when he has messed up. If he’s not one to admit fault, there may be no point in revisiting it — not because he doesn’t necessarily need to hear it, but because in that case his previous non-response is probably as good as it’s going to get.

Also: he mentioned a meeting you were a few months ago where your team agreed to handle the project. Unless you have reason to doubt that’s correct, one takeaway might be that you need to be more proactive about following up with your boss on those types of commitments yourself, rather than assuming he’ll check in with you about them.

5. Submitting a reference from a job not listed on your resume (because you were fired from it)

My partner, Linda, was recently fired without cause after a month at a new job. She was still within her probationary period, the job was not a good fit, and the training was extremely lacking, which is why her performance suffered.

At this job, Linda worked closely with Tracy. Tracy was in a tenured position but not in Linda’s chain of command. Tracy was very pleased with Linda’s performance and was definitely one of her cheerleaders during her time there. Now that Linda is back in job-search mode, Tracy reached out and offered to be a reference.

However, Linda was only at this job for a month and, due to the nature of her departure, she is not including this position on her resume. Is it appropriate for her to list Tracy as a reference? If so, how would she note that Tracy is a reference from a job not listed, and with such a short length of employment? I’m concerned that a hiring manager will see yellow flags at best if Linda includes Tracy as a reference. Linda has other options for references, but they are from a position that ended in June.

I wouldn’t use Tracy as a reference, unfortunately. It’s more likely to cause concerns than it is to strengthen her candidacy (because of the firing, but also because one month of working with someone generally isn’t enough to produce sufficiently strong and nuanced feedback to outweigh the firing, or even to count for all that much on its own).

The exception would be if Tracy is personally connected to someone Linda is applying with; in that case, it could change that calculus (in part because Tracy would be able to talk more candidly about what happened and her assessment of Linda would carry additional weight).

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

1. How can I help an awkward new employee connect better with coworkers?

I am a senior team member. Reporting to me are Bill (mid-level — seven years of experience), and three people at the junior level (one to three years of experience). Bill is the newest hire on my team, hired because we really needed someone to take some stuff off my plate and also hopefully act as a resource and mentor to the more junior staff.

Bill’s work is good and I am happy with the hire, but without fail, he says the perfectly wrong thing. It is harmless, socially awkward stuff: trying to join a joke but the delivery is loud and the reference is obscure, or unknowingly suggesting something that is a pain point. Think of Michael Scott’s cringiest social moments and you will have an idea.

This is compounded by the fact that two of my junior level staff applied for this role when I announced we were hiring. I discussed with each of them that the move just was not right, they were too junior for the responsibilities, and they understood, I think … but it for sure makes interacting with Bill extra grating. Bill has noted to me that it is hard to join a new team where there are established relationships so I know he is picking up on it. The two staff members will text and grab coffee together sometimes, though they are certainly cordial to everyone. I have organized a weekly lunch, but it winds up just adding to the awkwardness because Bill kills the conversation with a disconnected statement about a topic we all finished talking about 10 minutes ago.

I think Bill’s attempts to make social strides, especially with everyone but especially with these two is just adding to the pressure and awkwardness of it all. It is painful to watch! Any suggestions of how to coach someone on connecting with coworkers, but to just the right degree? Should I be taking any other action to make everyone like each other more?

It’s not really your role to coach Bill socially. And he may just be an awkward guy, which is okay — people are allowed to be awkward! There are probably some places where you can coach around the edges (“when you made that reference to X, people were confused because X is pretty obscure and most people don’t know what it is”), but I wouldn’t count on it making a significant difference. I’d also lay off the weekly team lunches, or at least do them much less frequently — they don’t sound like they’re working and might be making things worse, and either way that’s a lot of organized togetherness.

What I do think is your role, though, is looking for ways to set up Bill where he can do better. What’s he good at? Can you look for opportunities where it would be logical to pair him with one of your junior people to collaborate, in an area where he has expertise and is comfortable? Can you keep an eye out for times where a junior employee is struggling with something and you can genuinely suggest Bill as a resource? And then set Bill up for success there as much as you can — for example, letting him know that he’s great at X specific nuance of Y and asking him to collaborate with Jane on that specific element of it. You’ll need to keep an eye on how those interactions go — you don’t want to increase everyone’s aggravation if he doesn’t handle those well — but the hope would be that if people have more positive interactions with him, it might change their comfort with him and he might start feeling less awkward too.

The goal should be less about revamping Bill’s personality — some awkwardness and quirkiness is totally okay in most roles — and more about getting everyone more familiar with each other through the work itself and helping the rest of your team see Bill’s value.

2. My boss asked me to talk to a coworker about her cleavage

I am the office coordinator for the school where I work, and my boss asked me to talk to a coworker/friend of mine about showing cleavage at work. My boss has been approached my parents as well as other staff members about this coworker’s clothing. I don’t know how to approach this. She’s an educational assistant and most of the EA’s here are fairly dressed down, as it can be a pretty physical job. She does have a large chest and I know that that can be an issue when buying clothing, as I have the same issue.

I just feel uncomfortable speaking to her. I think the reason my boss asked me to speak to her is because I am friends with her and so that it’s not an “official” reprimand and could be dealt with discreetly.

Her direct supervisor is a man, but the principal (the one who asked me) is a woman. I do have some authority within the school but it’s mostly organizational; I have some administrative responsibilities and have been asked to sit in on these types of meetings in the past with other employees, but I am in no way a supervisor of anyone and I am not in HR.

You should decline to do this. It’s not your job to give dress code feedback, and it sounds like you’re being asked to do it so someone else can avoid an awkward conversation, which is not a good enough reason. And if it’s really true that they want to avoid it being an official reprimand, they can easily accomplish that by … not making it an official reprimand. Managers can give feedback without it being memorialized as formal discipline; it can simply be a conversation/reminder about the dress code.

If your coworker isn’t in compliance with the dress code, that needs to be handled the same way your employer would handle any other dress code problem — which presumably means a reminder by someone with the authority to issue that kind of reminder, not asking a friend to pass along a message.

I’d go back to your boss and say this: “I thought more about your request that I talk to Jane about her clothing, and I don’t feel comfortable doing that. It should come from someone with the authority to discuss the dress code and answer questions if she has any. I think she’d feel very awkward hearing that from a peer, and I’m not comfortable delivering that feedback to a peer.”

Related:
my employee’s clothes accentuate her chest — how do I talk to her about it?

3. Left out of a group chat

I work in an office of eight (one manager, me, and my six coworkers), which is then part of a larger division. For the past week or so, my coworkers have all been discussing different New York Times games. I normally play Wordle myself, so I jump into these conversations too. It’s been a fun thing to chat about in the mornings.

However, my coworkers will also discuss these games in a Teams chat that I’m not a part of. I was out sick one day earlier this month, and I’m thinking that might have been the day they started it. I guess I’m just confused by the fact that I’m part of these regular conversations, and for some reason all six of my coworkers (even the guy who started three weeks ago!) have not thought to add me? My coworkers are all very nice people who treat me well, respect my time, etc. — my point being that I have no reason to think they’re purposely excluding me as some sort of schoolyard bullying tactic.

Do I bring this up to them? Do I bring it up to my manager? Thinking about it, I don’t think I care, but it does seem a little hurtful. I mean, what would my manager even do? Wag his finger and tell them to add me?

It sounds like there’s every reason to believe it was unintentional — it’s likely they did start it on the day you were out and then haven’t thought very deeply about it since. You can just say, “Hey, can I get in on the games chat on Teams?” and that shouldn’t be weird (particularly if they’ve talked about it in front of you) and should take care of it. The only way this would be weird is if your coworkers were a bunch of exclusionary asses and it doesn’t sound like that’s the case.

Note: the New York Times tech union is currently on strike and asking people to honor their picket line by not playing Wordle and other NYT games during the strike.

4. My organization doesn’t post job openings until the old person has already left

My organization seems to have a policy of not posting a staff member’s position until that person has left. Is there any way that this makes sense? I don’t know why they want four weeks notice if they don’t use that time to find the replacement. Hiring is slow anyway, so this routinely means that positions are open for months, which I cynically think maybe they like because they are saving money while everyone scrambles to cover the workload. Anything I’m missing here?

I’m curious whether this is actually their policy, or whether it’s just what happens in practice because they’re slow and/or disorganized. If it’s their policy, it’s a bizarre one! Generally a notice period (even a four-week one) isn’t long enough to hire a replacement and have them start while the departing person is still there to train them, but there’s no reason to squander that time; generally you want to move forward on filling soon-to-be vacancies with some sense of urgency. (There are some exceptions to this, of course, like if questions need to be worked out about the position before you post it, but typically you’d want to begin recruiting pretty quickly.)

By the way, four weeks notice is two weeks longer than the standard in most industries, and you might consider whether you really need to stick to that:

can I give 2 weeks notice when my employer says they “expect” 4 weeks?

5. I’m ready to retire young but don’t want to burn bridges

I’m a mid-career manager of a small team of experienced individual contributors involved with fairly high-profile projects for my organization. The organization consistently struggles to prioritize work and provide the appropriate resources; we often are trying to do too much, all at once, with too little. Despite this, my team is well-respected and gets things done. However, I’m tired and have been vacillating in and out of burnout for years. Vacations offer only a short-term fix. I suspect that I have undiagnosed neurodivergence that makes my set working conditions especially challenging.

My company does not offer sabbaticals. I have been focused on FIRE (Financial Independence, Retire Early) for years and I’m finally at a point where I feel like I’ve accumulated enough that I can take an indefinite break and am planning on resigning within the next six months. I’ve worked for this organization for a long time and, as I’m still relatively young, I’m sure my resignation will come as something of a surprise. I don’t want to leave my small team and my manager in a bind, but for the sake of my own best interests, I’m not comfortable giving more than a couple of weeks notice.

I have not yet determined if my mini-retirement will turn into full-blown retirement and mark the end of my corporate career. How do I frame my resignation and deal with questions from colleagues during my notice period when I’m not leaving for another job? I want to leave on good terms, but I’m not open to being convinced to stay with the organization while they figure things out. I want a clean break on my terms.

You’re overthinking it! You’re allowed to resign any time you want. It’s true that people might be surprised to hear that you’re not going to another job but you can say, “I’m taking some time off before deciding what I want to do next.” That’s true! “What I want to do next” doesn’t need to mean a job, necessarily. Or if you’re up for sharing more, you could say, “I’ve worked for a while to be able to take a long break from work, and now I’m able to do that.”

If you’re pushed to stay longer since you don’t have the deadline of a start date somewhere else, just hold firm: “I do need to stick with X as my last day because I have some immovable plans for right after that.”

This isn’t bridge-burning! You’re not an indentured servant; you get to decide when you’re ready to leave a job. And leaving a job for any reason nearly always creates some inconvenience for the team you’re leaving; that’s just part of the deal with resigning, not a reason not to do it.

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

1. How can I ask out our general manager?

How do I get ahold of someone who works in the offices where I work to ask them out? Her position is GM. I’m intending to ask her if she’d like to go for a coffee or walk on the beach one day after work just to get to know each other. I’d also like to invite her out for lunch for my birthday, which falls on a Sunday in December.

I work in the warehouse downstairs. She works in the offices upstairs when office protocol and company policy won’t let me ask her these questions. I do see her now and then in the carpark when I’m unloading trucks, but she goes straight upstairs through the main building entrance while I’m unloading trucks at the loading area, which is away from the office carparking area.

I’d also like to ask her if there’s a chance of adding her on messenger and Facebook.

What should I do? I’m thinking wait until I see her next in the carport and talk to her before she goes upstairs to the office. I shall never forget the smile on her face when I met her when she was introduced to each worker in the warehouse.

Please do not ask this woman out. She’s there to do her job, it doesn’t sound like you have any reason to believe she has romantic feelings toward you (or even anything more than professional acquaintance feelings), and your office policy prohibits it. She can’t date someone in her chain of command and, even if you’re not in her chain of command (although if she’s the GM, you probably are), she’s there to do her job, not to be hit on by coworkers. It would be different if you didn’t have the chain of command issues and she was sending active signals that she returned your interest.

Active signals that the person returns your interest are an absolute prerequisite for asking out anyone at work. (Smiling at you doesn’t meet that bar; that’s normal professional warmth when being introduced.)

2. My coworker sucks at his job and I rely on him for support

I have been struggling with my coworker, “John,” for over a year. He provides targeted support for a project that I manage and I communicate with him directly regarding associated tasks. I do not manage him, but am senior to him.

Issues include:
• Poor email management. While he occasionally responds immediately, he most often doesn’t acknowledge or reply to my emails at all. When reminded (repeatedly) of outstanding items, he often cannot locate the information sent or only partially responds
• Failure to take responsibility for tasks I have handed off. This includes me having to chase him for weeks for basic requests, having to routinely resend “lost” information, and requiring extensive editing of sloppy work due to poor attention to detail and failure to incorporate all communicated information.
• Refusal to allow for sufficient review time, despite repeated requests. For example, I asked for three business days to review a biannual report. The distribution date is set months in advance so it is a matter of time management on his part. He provided five business hours for review, failed to incorporate any of the information I sent three weeks prior, and the overall quality was poor.

I initially thought there might be a mismatch in communication styles so I have tried other approaches — instant messaging, phone calls, and stopping by his office. I have also offered to use other platforms, like Teams, and even mild shaming by asking about outstanding items in small group meetings. After the biannual report, I scheduled a one-on-one meeting and had a candid and direct conversation about the issues outlined here (all of which had been previously addressed). I also invited him to give me feedback. It was a professional and respectful conversation. He responded cheerfully and acknowledged the issues. Nothing changed in a meaningful way.

John and I are both managed by Jane. Jane has been my manager for five years and I have a lot of respect for her. She has confirmed that everything I have asked from John is reasonable and within his responsibilities. She acknowledges that other team members have given her similar feedback, though she seems pleased with his performance in other areas of his work. She has spoken to John more than once about these issues and is aware that performance has not improved.

I have successfully worked with a variety of personality types and varying levels of competence but I’m frankly baffled by this situation. I would love to take a huge step back but do not know how to do so without failing the client by allowing late, incomplete, incorrect, and sloppy work to go out. It is exhausting to have to fight for the smallest thing and I find myself stewing over this dynamic. Despite how this letter sounds, a relatively small amount of my day-to-day work should involve John and I am spending a disproportionate amount of time and energy managing this situation.

You need to go back to Jane and pose this question to her, because it’s her job to handle it. You were right to try what you’ve tried, but at this point you’ve exhausted your options and if it’s going to get resolved, it’s going to require Jane’s involvement.

Lay out for her everything you’ve tried and use the words you ended your letter with — “I am spending a disproportionate amount of time and energy managing this situation.” Then say, “I’m at the limits of what I can do on my own to resolve this, and I’m at the point where I need your help. How do you want me to handle this?”

Also, start cc’ing Jane on messages to John, especially anything reminding him that you haven’t heard from him, a deadline has been missed, or his work is missing key elements, so that she’s seeing exactly how often it’s happening and is pulled into it each time, which should make it harder for her to ignore.

3. Saying no to a job opening because of moral concerns

I am in the throes of an expansive job search and thus am networking quite broadly. Several times now, I’ve avoided conversations about the reason I was uninterested in a particular job so as not to offend or create a negative interaction.

What is the proper way to politely decline these suggestions without a long explanation of “why” while maintaining the positive relationship?

For example, it has been suggested that I work for the Department of Corrections or become a police officer and I have many reasons those aren’t the right job for me. I’ve also been introduced to people who work for a marketing agency that produces provocative political ads. Even if I was on the same “side” as that agency, I would still not want those jobs. These examples have been suggested by neighbors who I see regularly and I want to keep a friendly relationship.

A few options, depending on what you feel like:

• “Thanks, I’ll check them out.” (That doesn’t obligate you to do anything more with it and if they follow up, you can say, “That kind of work isn’t a great match for me, but thanks for thinking about me.”)
• “That’s not a path I’m interested in, but thank you!”
• “I don’t think that’s the right match for me, but thank you.”
• “Interesting, I’m not sure that’s for me but I’ll think about it.”

Ideally, follow any of these with a quick topic change.

4. Can a referral “save” my application after I’ve been rejected?

I was the victim of a layoff about a year ago, and I’ve been job searching since then in a tough market. Whenever I see an opportunity that I think would be a good fit, I first apply through the company’s official portal, then I reach out to anyone in my network who may be connected with that company/team. However, it can take a little time to pull the connection levers, between reaching out to someone I may not have spoken with in years and asking them, in turn, to connect me with someone in that company who they may not know very well.

Several times now, I’ve been in the process of trying to leverage connections when I received an automated rejection email for that position. Can an internal endorsement or referral that arrives after the ATS may have already rejected me “save” my application and put me back into contention?

Potentially. It’s unlikely to save your application if you’re not a strong candidate, but it’s more likely if you’re clearly very qualified and someone looks at the application with new eyes and realizes that (for example, if HR is rejecting people they shouldn’t reject because they don’t have a nuanced understanding of what the hiring manager is looking for) or if one of the people in that chain of contacts has a lot of influence.

5. How to apply for a job (internally) that I am not sure is even open

I am an office clerk at a law firm and heard from one of the legal assistants that they’ll be moving to a different internal position early next year. (They mentioned they were taking training and I asked what it was for, and then they told me they’re getting the position because the current person is retiring.)

I am not sure if the firm is even going to hire for their assistant position, but I’d love to throw my hat in the ring. I’d love the pay bump and hybrid options, and I have an MLIS degree that I’d love to put to good use.

Problem is, I don’t know if this assistant moving is even public knowledge beyond the people in the department they are moving to. I was told (literally) quietly, so I get the vibe most people don’t know. And again, I’m not even sure if they’re looking to replace this assistant at all, or if I have a shot at it. I also have not been here that long (less than a year), but when I had my three-month check-in several months ago, my boss told me I could let her know if I was interested in any positions at the firm, because she assumed I didn’t want to be a clerk here forever. And I know a few people have moved to other jobs in this firm, so I at least know internal transfers are A Thing here.

But I need to know how to ask, and who to ask. And I’d also not like a courtesy interview — so if they don’t think I’d have a chance, I want to know right away, not just get an interview because I work here. I’ve been burned by courtesy interviews in the past, not knowing they were a courtesy, and honestly that hurt worse than not getting the position.

Go back to the assistant who told you they’re moving and ask if they know whether the firm plans to fill the job they’re leaving because you’d be interested in applying if they do. They will probably know but if they don’t, ask them whether it’s okay for you to ask their manager about it (it almost certainly will be since their manager surely knows they’re transferring, but you can ask to be sure).

And then you’d talk to the manager for that position and say you understand Jane is transferring and you’d love to be considered as a replacement, and ask what the next steps are. As part of that conversation you can ask about the profile of candidates they’re looking for, and you can describe a little about your background and ask if it makes sense to throw your hat in the ring. But beyond that, you can’t really prevent the possibility of a courtesy interview; there’s always a chance of that when you apply internally and it’s better to find a way to be okay with that than to search for a way to preclude it altogether.