Ask a Manager

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

1. My boss won’t stop complaining about my maternity leave

I’m four months pregnant and I had to (chose to) tell my boss when I was eight weeks due to my nausea and sickness. When I told him, his first reaction was, “How much maternity leave are you taking?” I replied, “All of it.” We get FMLA 12 weeks — nothing special.

Since that point, at least once a week/once every other week, he talks in front of others about how we’re going to have to handle my “situation,” to which I say, “It’s only 12 weeks and it’s a standard leave.” He most often rebuts, “It’s a very important 12 weeks for us.” Obviously I’m going to set up my team for success and do everything I can to make sure people have what they need.

But at this point, the constant put down about how I’m leaving for 12 weeks and that will leave the team in a lurch is really getting to me. What do I do about it?

Are you comfortable talking to HR and letting them know that your boss is constantly complaining about your upcoming maternity leave and making you worry you’re going to be professionally penalized for taking it? This doesn’t sound quite bad enough to count as pregnant harrassment, but competent HR still usually prefers that employees not be hassled for taking legally protected leave.

Alternately, an option is to address it with your boss directly: “Do you want to have a conversation about plans for my leave? I’m taking a pretty standard amount of leave, but you’ve sounded so concerned that I’m wondering if there’s something I’m missing.” If he repeats that it’s a very important time for your team, then say, “Is there something you want me to do differently? Obviously I can’t change the timing of the leave, so is there something else you’re looking for?” At some point in that conversation, you might also want to say, “I’d appreciate it if you’d treat this like any other medically necessary leave that’s protected by law.”

2. Communicating with a team that doesn’t read email

I am one of several managers in my building and I manage a team of about a dozen people who all have different schedules, with two people manning the floor at once. They all overlap with me at some point, at different times, throughout the week. All the jobs are part-time and most people have a second job. Because I can’t get everyone into the same room together to have regular meetings, I’ve been trying to use email to communicate. But people don’t read their email, or they skim and forget, because when I ask to make a change it just … doesn’t get made. As an example, I recently sent an email asking everyone to please put out X in the morning and bring it in at night, and it hasn’t been moving.

These are work email addresses, and the staff in question are stationed at computers at service desks; the bulk of their job is helping customers, but there’s downtime that could be spent checking email.

Higher management and I have repeated “can you PLEASE read your email” ad nauseam, and for really important issues have started sending out emails with PLEASE REPLY in the title, insisting that everyone reply with some detail from the email. Nothing has helped and I’m at a point where I feel like I need to accept that email is not going to work here as a way to communicate.

But what will? I can talk to everyone individually about every tiny issue that comes up, but it would be prohibitively hard to remember to do that, and to remember who I’ve already talked to, every time a shift change happens all week, and then it would also take much longer to get information out. I could print out reminders and leave them on counters, but 1) those would also get ignored and 2) there isn’t a lot of counter space. Maybe you have another creative idea?

Since these emails sound mostly like one-way announcements that they just need to read and be aware of (as opposed to something with back-and-forth), you need an announcement binder. Print out announcements, put them in the binder, and ask people to initial them once they’ve read them. Hell, have a standard list of everyone’s names that get pasted onto the bottom of each announcement so that it’s easy to see who’s initialed it and who hasn’t. And then make checking the announcement binder a requirement at the start of every shift.

If they don’t have jobs that use email a lot (and it sounds like they don’t?), it’s easy for people to not even think to check for messages. You’ll probably haven an easier time making “check the announcement binder at the start of every shift” a routine part of people’s work. That said, there will be a learning curve! You should expect to have to remind people a lot at first, you should stick a “check the announcement binder!” sign at the service desks, and you should make a point of quickly following up with people who haven’t initialed things. If you’re diligent about that, it should stick in time. (And as new people are hired, make that part of how they’re trained from the start. It’s easier when it’s part of people’s routine from the beginning.)

To be clear, if these were email-heavy jobs, this wouldn’t be a reasonable solution; in some jobs people just have to be responsive to emails, period. But I think the problem you’re running into here is that email isn’t a central part of their work.

3. People keep commenting on my rosacea

I have rosacea, and my face is red most of the time. I am currently exploring treatments with a dermatologist. The cream I’m using makes it so I can’t really wear foundation to cover it. On an almost daily basis, someone I work with makes a comment about it. I get asked if I’ve been out in the sun or they just comment on how red I am. What would be a way to politely tell them it’s a medical condition and to stop commenting? I feel unattractive and embarrassed when people point it out so often.

“It’s rosacea.”
“It’s rosacea, you don’t need to let me know.”
“That’s just my skin.”
“Yes.”

Most people will understand the subtext is “stop commenting.” But if anyone continues: “It’s a medical condition and I’d rather not get into it.”

4. Telling a rejected candidate I wish they had been hired

I’m a consultant working part-time for a global nonprofit with a very small staff (three in total). As the workload is increasing and I can’t do more than part-time, we just made an offer to a more junior person who will take on part of my workload so I can focus on specific projects. I think they were the weakest candidate by far and I supported another candidate. I was overruled by the two other members of the hiring committee, both more senior than me but with no direct experience in my field. We’re very transparent as a team; I know their reasons for choosing that person and they know I strongly disagree.

Anyway, I know this battle is lost so I’ll obviously make the new hire feel welcome and I’ll work with them as well as possible. However, I’m really disappointed for my favorite candidate who ticked all the boxes – experience, technical skills, soft skills, background, work culture, you name it.

I know I can’t email them to say, “Hey, I’m so sorry, you should have gotten the job because you were the best.” But is there a professional way to let them know, directly or indirectly, that they’re awesome and that I wish they had been hired? The standard rejection emails have been sent and they replied very courteously and professionally. I’ve been on the receiving end of rejection emails as many of us have and I know how disheartening it can be when you know you were a good candidate.

You definitely shouldn’t imply they were the best and should have been hired (that could cause problems for your organization, as well as just being out of sync with the kind of united front you’re generally expect to put on once a decision is made). But you could say something like, “I wanted to contact you personally to let you know how much I enjoyed talking with you and how impressed I was by (details).” You can include specifics about why you thought they were great, as long as you do it without comparing them to the person who was ultimately hired. And you could conclude by saying you’d love to stay in touch and hope there might be opportunities to work together in the future. (I’m slightly torn on that last part because I don’t want to raise false hopes that your org might hire them in the future, given how small it is, but you could finesse the wording to whatever makes sense.)

5. Deescalation techniques for poll workers

After hearing about the nationwide poll worker shortage, I volunteered as a poll worker for the spring presidential primary and will be working again for a state level primary next month and then the November election. I just attended a more in-depth training, which had very specific instructions for how to handle ballots when various issues arise. The early voting process was brand new in the spring and is more convoluted compared to the traditional election day process (mostly boils down to early voting requiring a voter to be marked off in a physical binder along with a digital check-in) so the majority of the training was spent making sure everyone was clear on what to do. The town registrar emphasized how important it was to get every process right because tensions are expected to be high in November. However, there was no advice or real discussion on de-escalation when a voter gets angry with a poll worker, beyond flagging the person who administers that location’s election.

In the spring election, there was some grumbling about “what was the point of early voting” by voters, which I felt was difficult to redirect without crossing a line into something that could be considered a political statement (by law, we’re not allowed to discuss politics). I didn’t run into any true anger in the spring, even when we had a slowdown in processing people, but in the past as a voter, I’ve definitely seen poll workers get yelled at for things out of their control (like a voter didn’t realize their assigned location had changed and were told they needed to go elsewhere to vote after standing in a long line). The registrar also glossed over questions about more serious security concerns, so they don’t seem to be the best resource on getting a script to direct people to the moderator’s station. The moderator for my location has been doing this for 40+ years and said they’ve seen everything so while we should expect it to be hectic in November, we shouldn’t worry. The only work experience I have with dealing with members of the public who might get angry was limited to phone interactions, so I’m still a bit nervous about getting yelled at in person. Do you have any advice or know of free resources on de-escalation and redirection techniques?

Mostly, I just want to build more confidence, especially as the moderator for my location is hoping that the summer election will be enough additional experience so they can move me into an assistant position in November. While that seems quick to me, the moderators seem very eager to give the younger crowd experience and more responsibility because most of the town’s poll workers are retirees and they’re having issues with retention between elections.

I don’t but I will bet a lot of money that some readers do. Commenters? (I also found a lot when I googled that could be helpful.)

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

1. My interviewer mocked my speech impediment

I recently had a job interview that was extremely unpleasant. I won’t go into the details, but suffice it to say, there were so many red flags that the conference room was practically shrouded in a crimson miasma. I’m writing to share what was, to me, the most egregious moment. When I introduced myself to the hiring manager, she promptly blurted out: “Where are you from, Rhode Island? (imitating (me?)) Look at Missusth Daffy Ducky speakth through her teef.”

I’ve never been to Rhode Island, for the record. I don’t sound remotely like I’m from Rhode Island. I have no idea how Rhode Island plays into all this. Was she conflating “Looney Tunes” with “Family Guy?” The mind boggles. Anyway…

My speech is pretty unusual and distinctive. I had a severe speech impediment when I was a kid. Speech therapy tamed the worst of it, but I still have a mild lisp and probably will for the rest of my life. It is definitely noticeable, but nothing that prevents me from speaking clearly and coherently. I’ve actually done very well in roles that required a lot of public speaking, possibly because I’m so used to putting in conscious effort to enunciate clearly and carefully! I certainly don’t sound like Daffy Duck.

Complicating things further, I had a very transient upbringing — I grew up not only in numerous states but also in several foreign countries (think military). As a result, I have a bizarre patchwork accent that people can’t place easily.

So, yeah, I sound weird. I KNOW I sound weird. It’s my biggest insecurity. Not coincidentally, I’ve always felt most comfortable in diverse, multinational workplaces where there are all kinds of accents and English-speaking abilities. About half of my coworkers at my last workplace were immigrants, mostly from India and China. So nobody cared that I had an accent, or that I sometimes struggled with pronouncing English words perfectly — I was in good company!

Obviously, I have no intention in pursuing this position further. But should I report this interaction to the company? If it was just me, I would shrug it off. But I know it can’t just be me! For one, I can’t imagine this hiring manager treats immigrants or even American-born POC decently, let alone fairly. If that’s how she treats people who don’t have a generic, bog-standard Midwestern accent, I wonder now if she would have even interviewed me if it weren’t for my white-sounding name. Moreover, I feel like singling out my speech impediment with that ugly little Daffy Duck impersonation must be an ADA violation of some kind … right? I sure don’t feel like I was treated fairly.

Could you clarify this for me? Typing it all out, the answer feels like an obvious “yes, report it” to me. But I there’s a very loud and mean part of me saying “shit happens, so get over it, ya weird lisping-hybrid-mutant-accent-having freak.”

Yes, please report it; this is awful. Not only was she cavalierly cruel for no reason, but it (a) raises a ton of questions about how she treats candidates who are different in other ways too, as you point out and (b) opens the company to legal liability under the Americans with Disabilities Act (because if you wanted to argue that she didn’t hire you because of your speech impediment, she handed you a lot of ammunition). She’s also apparently profoundly ignorant about how to treat people, which is a problem in anyone but particularly a problem in a manager, interviewer, and person representing the company.

You could frame it as, “I want to share with you why I’m withdrawing from this hiring process and hope this is not how you want your interviewers treating people with disabilities.”

2. I’m having a baby unconventionally — how do I talk about it at work?

I’m coming up at the point of wanting children, some time in the next 2/3 years. However, I do not have a partner and don’t anticipate getting one in that time frame. I have prepared to go it alone and have made financial and housing plans accordingly. My intention is to have a baby using a sperm donor, through the clinic that I choose, so I won’t know them. In addition, I do not plan to use my own eggs. There are many very generous couples who donate eggs or even embryos so that other people can have children, too.

I have chosen this for a specific reason: I am neurodivergent — specifically, autism and ADHD. The genes in my family for these are strong and in hindsight many members of my immediate family could very well have been diagnosed had it been accessible to them. The blunt truth is, I do not want to pass this onto my child. I know it is partly selfish — I was a difficult child, despite being academically gifted — and partly because it would not be fair to have a child knowing that they are likely to continue our family tree with all the difficult “quirks” we possess. I am an adult who has learned to live with these conditions — I have a job, I am successful in it, etc. so I am not incapable — but I want to break this genetic legacy.

How do I explain to the people I work with that a) this child will not be genetically mine and b) I don’t want to have a child of my own? It will not be likely that I can conceal the first part — as embryos are donated, the child may not match my ethnicity and appearance. And I don’t want to spend time justifying why I chose this. Oh, and c) how do I explain to people that yes, autistic people want to be parents, and they may do it unconventionally but it doesn’t make them less of a parent or mean their child is worse off?

My workplace is generally positive and diverse — I work in a department that attracts the neurodivergence like flies to honey — but people don’t always think before they speak, and there is a lot of criticism for parents who are not … typical in the media which I worry could impact their perspective of me. I’m not sure how to address this with both my managers (during my IVF journey and afterwards) and with my colleagues in a way that is positive but also firm in my decision?

You actually don’t need to share most of that! Not because there’s anything shameful about any of it, but because it’s no one’s business, especially at work. You are simply having a child (and then later, you simply have a child). No one is entitled to know whether your child’s origins were through IVF or sex, or whether you used your own eggs or not, or where the donor sperm came from, or any of it!

You’re simply excited to share that you are having a child. That’s it! If anyone asks about the father, you can say, “I’ll be raising the baby on my own.” Colleagues don’t need to know whether that means IVF, or a relationship that didn’t last, or a father who chose not to be involved. (Obviously if there are specific people who you’re close to who you choose to share details with, that’s different — and you can let your comfort level and the relationship be your guide there.)

If anyone is rude enough to comment on your child not looking like you, you’re under no obligation to answer their questions … and you’d probably find it helpful to delve into the writing of parents from mixed race and adoptive families about how they choose to field intrusive questions about their kids.

3. I’m a remote manager and nervous about a private meeting on my staff members’ calendars

I am a remote manager and my staff is on-site. I am six months into this position and this is the first time using this model.

I have been in my profession for 20 years, but this current job is very different than what I was doing previously so there is a lot to learn. I am not aware of any issues, but today I noticed my only two staff members had a private appointment scheduled at the same time. My boss’s calendar (also on-site) was also busy during that time but I can’t see it so I don’t know exactly what it said.

Of course, in my mind it was them meeting with him and I’m stressed about it. Do I try and get it out of my head and let it go, or what should I do? I don’t want to ask my staff what the appointment was, so I don’t know that there is anything I can do.

There are lots of reasons their calendars could have been blocked off at the same time that don’t portend anything bad for you — anything from collaborating on a mundane project together, to planning a surprise party for the guy in accounting, to simple coincidence that means nothing at all. Your boss also might do a routine check-in with your staff about how things are going, which is a smart thing for bosses to do from time to time, especially when there’s a new manager in the mix  (but even when there’s not).

But to indulge your worry a bit: What’s your sense of how things have been going? How do you think your team members think things have been going? And then … what are you basing that on? If you don’t really know how they think things are going, you could take this as impetus to check in with them more often, talk about what they need and how you can support them, and ensure that you’re cultivating an environment where they can be reasonably candid with you. On the other hand, if you feel you have a good sense of their perspectives and are fairly confident they don’t see significant problems, it makes sense to relax about what the calendar entries,, figure it’s unlikely to be a problem for you (and if is, you’ll presumably know soon enough), and trust that there are a ton of other things that could account for it.

Related:
my boss called a mysterious meeting with me and I’m afraid I’m going to be fired

4. We’re reimbursed less than the federal mileage rate

I work at a nonprofit. We are currently getting $.58 per mile reimbursed. I am one of a handful of employees that travels frequently to other sites to work. I would say I reimburse about 1,200 miles per year.

I recently brought up to our GM that we’re not getting the federal rate ($.67). He said it was probably just outdated, and we would look at aligning with the federal rate. However, our ED says that we’re a nonprofit so we can offer whatever we want for reimbursement. What say you? I know it’s not illegal, but how would the staff counter this?

Your ED is right that they can offer whatever mileage reimbursement rate they want, but it’s not because they’re a nonprofit. Private employers aren’t required to reimburse mileage at all (except in California, Illinois, and Massachusetts) so if they choose to, they can set the mileage rate at whatever they want.

That said, you and your coworkers could point out that the federal mileage rate is calculated to represent your actual costs (not only gas, but the wear and tear to your vehicle) and argue that employees shouldn’t be out money simply for performing their work duties.

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

1. I’m biased toward midwestern candidates

At the east coast company I work at, I’m frequently on hiring committees for competitive positions that typically include a wide range of candidates from all over the U.S. I recently noticed a concerning pattern in the candidates that I have advocated for hire. Essentially, when other qualifications are relatively equal, I nearly always prefer the midwestern candidate. (I am from the midwest and work remotely from the midwest) for their personability and communication style. And generally, my opinion holds a strong sway for who ends up being hired. While I’ve never advocated for a midwest hire who isn’t one of top candidates in terms of objective qualifications and interview responses, I still don’t think this is a great look.

What can I (and the company in general) do to reduce this type of bias during hiring? Should I just hold my opinion if we are between a handful of candidates and I prefer the midwestern one?

A quick caveat: I am, unfortunately, amazing at recognizing midwestern accents, especially in people from the Great Lakes regions (or from the city of Chicago).

Yeah, “like me” bias is really common in hiring, and it’s good that you’re recognizing it! We (often) naturally prefer people who remind us of ourselves and feel comfortable/familiar to us. It’s especially telling that you noted your preference is based on their “personability” and communication style, because those are two things that are really subjective and can be big sources of bias.

So how do you mitigate it? First and foremost, make sure that you’re assessing all candidates on the same list of must-have and nice-to-have traits, and that you’re clearly defining what each of those looks like and not just “I know it when I see it.” For example, you might assess communication style and personability through metrics like: enthusiasm for engaging with people; conveying points clearly; listening carefully and asking questions to understand others’ perspectives; and being able to put people at ease, especially people different from themselves (that last part is key). Also, involve diverse voices in your hiring process (and make sure you get aligned with them about the must-have’s and how to assess those so that everyone is measuring against the same bar; otherwise people will default to their own criteria). Ask people to fill out written assessments independently, so they’re not overly influenced by what you or others think, and ask them to peg their ratings to observable behaviors, not gut feelings.

Those two things won’t solve it entirely — bias is a huge and complicated thing that takes significant work to mitigate — but they should help significantly, and should also surface places where earlier you might have been influenced by bias without even realizing it.

2. The right way to clean up after a reply-all email storm

My inbox was victimized by an external email storm yesterday, and it made me curious about how you’d advise the organization at the center to proceed in the aftermath. A university career center recently launched a new hiring platform to connect students and employers, and they sent a webinar invitation to recruiters across the region — corporate, public sector, school districts, etc. Something went wrong in the system and an automatically generated reply went to everyone, which then generated a service ticket email that also went to everyone. Enter Corporate Recruiter A, who responded, “I’m not sure why I’m on this service ticket.” For some reason this email also generated a subsequent service ticket email. Enter Corporate Recruiter B, who responded, “Same here.” (HELPFUL. Are both of you new to email? And technological systems in general?) City Employee chimed in, “I am getting multiple emails from this. Is there something you need from me?” And then Corporate Recruiter C opened the floodgates with, “Please remove me from your mailing list.” Cue hundreds of recruiters from the region asking to be removed from the list, followed by a handful of well-intentioned folks with the “STOP REPLYING” directives. Every one of these emails generated a separate service ticket email, so it was like the BOGO of email storms.

800 emails later, it has finally stopped. If you were the university, would you ignore all those requests from recruiters to be removed, since you need them to be recruiting your students and they were most unwittingly responding to one specific event? Or are you obligated to honor their request? Do you dare send a follow-up email to explain and apologize? Do you do personal outreach to the recruiters who participated in the melee to mend relations? Just to recruiters from high-value contacts, e.g. Fortune 500 companies and major local employers? Cut the registration fee for your next career fair as a mea culpa?

The emails were annoying, of course, but I mainly felt sorry and frustrated for the university employees. If I were them and I were instructed to send an apology email, I’m not sure I could stop myself from including some “electronic mail guidance for noobs” on how to disengage from an email storm…

Eh, people asking to be removed in that context usually mean “remove me from this shitstorm,” not necessarily “never contact me again.” I don’t think you’d need to unsubscribe all of them, as long as you’re very, very sure that the problem has been solved. You could send an email a day or so later apologizing and assuring people the problem has been fixed and won’t recur (make sure that’s true! the last thing you need is for that email to set up a whole new flood) and offering an unsubscribe link for people who want it. (That said, you’d want to look at CAN-SPAM and any other applicable laws to make sure you’re in compliance.)

I don’t think anyone would expect you to cut the registration fee or call people personally to apologize. (I’d actually be more annoyed by a phone call about it, in an “I still can’t get away from this?” kind of way.)

Related:
the burnt bagel, the excessive candor, and other reply-all email catastrophes

3. How open should I be about family stress that may affect me at work?

I’m tangentially connected to an ongoing family issue which is apparently on the verge of boiling over and causing some irrevocable damage to the extended family. There’s a high likelihood of my brother and his wife divorcing, and they have two kids under 10. There was a deliberate attempt to conceal the issues from me, up to and including lying to my face about how things are with them.

This affects my work only slightly: My work is pure physical labor. I deliberately made more work for myself when counting new stock as a healthy way to vent my frustrations and distract myself, and I explained my reasoning for doing that. At what point am I giving too much information, or at what point is giving specific details that there is an issue ongoing necessary?

Hmmm, it really depends on the details. If no one will even notice that you’re doing something differently to get more of a physical outlet, you don’t need to say anything at all. If it’s going to be noticeable, sure, say, “I”m working out some family stress on these boxes right now!” But there’s a fairly narrow window for how much of that is okay at work — tackling boxes extra vigorously is fine, but if it comes close to looking like hostile aggression (even though it’s directed toward inanimate objects, not another person), it’s inappropriate for work. If someone would be nervous about coming near you, you’ve crossed a line. Regardless, though, people don’t really need to know the details of what’s going on with your family.

(For what it’s worth, and I realize I’m saying this knowing almost nothing about the situation: avoid judging other people’s marriages and divorces as much as you can. Divorce is sad, especially when kids are involved — but lots of grown children, including me, will tell you firsthand that the damage to kids when their parents don’t divorce but should can be harder on them than a split would have been. Your brother also didn’t owe you a full account of what was happening within his marriage before he was ready to share. Again, I don’t know the details and certainly there are situations that would enrage any reasonable bystander — but when your feelings about someone else’s marriage are looming this large, it’s worth questioning.)

4. Do I owe a previous employer help with their questions now?

I gave two weeks notice at my job. My manager, the owner of the company, sent a message to all the team leads that I would be leaving and I sent the team leads and the other person on my team a message that I had cleared my calendar and would be happy to meet with them to facilitate my departure. I also created a document outlining several tasks that remained and where I was with each of them.

The other person on my team, Sara, set up a meeting with our accounting firm and participated in several meetings in which the managing owner and she were present but I was excluded. Which is fine, but I did not have any insight into what decisions were reached, so I assumed they had everything in hand. I had one meeting with the two owners and Sara, where they said they felt my procedures were excessive and overdone and instead of learning them, they said there was a better way to do my job. (That was fine with me — I was leaving anyway.) I also asked Sara if she wanted to set a time to go over procedures and how to do tasks, as most would fall on her plate, but she insisted she already knew. No one got in touch, no one asked questions, no one showed any interest in anything I had to share. I completed the document, wished everyone the best, and went on my way. No hard feelings, just excitement for my new role.

A couple weeks after I left, I received a message from Sara with questions — where things were, if I had finished a report, etc. etc. I did not feel like I had any responsibility to answer. I don’t have hard feelings, but I feel like no one wanted my help while I was leaving and now I don’t owe them anything further. I don’t think of myself as bitter or angry, just happy to move on. Am I wrong? Should I have answered all the questions?

You’re right on the principle of it: you tried repeatedly to help with the transition while you were still there and they made it clear that they didn’t want your help and felt they knew better. So it’s particularly irritating that they’re coming back to you now.

That said, it generally makes sense to be willing to answer one or two simple questions after you’re gone if you can do so very quickly, simply for the purpose of maintaining good will. But I’m talking about things like “do you remember where the X report is?” not “can you walk me through the history of this client and all the strategies we’ve tried with them in the past” — and also only one or two, not endless or ongoing contact. So if it would have taken only a minute or two to respond to Sara, I’d advise just doing it. You don’t have to, though; it also would have been fine to let the message sit for a week and then reply with, “Hmmm, I don’t know off the top of my head, but check the documentation I left.” (Or even not reply at all.)

5. I have no idea who to give my resignation to

I’ve decided to quit my job! However, I’m not sure who to give my notice to. My boss has left, and her boss is a C-suite executive I’ve never met. I’m sure I’m overthinking this, but I’m in a very senior role with no clear redundancy / transition plan for my responsibilities, and want to make sure I’m setting my team up for continued success after I’m gone. So who do I talk to about all of this? What are the appropriate protocols here?

Who are you going to for other management things right now? If there were a crisis in your department, who would you talk to? That’s probably the right person to resign to. If there’s no clear answer to that, then default to your ex-boss’s boss. If that’s impractical, head to HR, explain the situation, and let them straighten it out.

Read an update to this letter.