Sometimes Alison at Ask A Manager and I like to answer questions about workplace awkwardness together. It’s always fun to have an actual coworker for this strange, wonderful job, especially when that coworker is Alison.
Here is the current batch of questions, which is crossposted at her site today as well.
1. My boss keeps me on the phone for hours.
My whole company and I have been working from home since last March. I recently became the lead on a new project and am working with a boss I’ve known for years but this is my first time working directly under her, although it is not my first time leading a project.
She wants me to check in with her over the phone every few days, which I’d have no problem with if we could keep it short to go over what I’m working on and what I plan to do next. But unless I strategically plan calling her before scheduled meetings we have with other people, she’ll keep me on the line for hours. She wants to talk not only about our work, but also wants to narrate what she’s doing while she also tells me about everything in her life and every job she’s ever had. I try to redirect these conversations to “how can I help you with this right now” and “I’ll work on that, thank you for your help,” but she’s undeterred. One time this went on from 3pm until 7:30pm, until she finally told me she didn’t know how to hang up her phone.
I understand that she may sometimes want to work on something together, which would necessitate longer contact, but I can’t handle the hours-long conversations. I’m unproductive trying to keep up with my work, following her work, and listening to her stories. It’s exhausting. It doesn’t help that she often does this later in the afternoon and stretching into the evening, long after I normally log off for the day. How do I tell her that I’d rather keep our conversations shorter and more focused on work?
Jennifer: It sounds like your boss is very lonely and not functioning well in isolation. That’s awful, and very real for many people, but it’s not fair for her to pressure you to fill her social and emotional tank.
I have had several versions of this coworker, and in my experience, the professional, “we’re all adults here” conversation you hope to have, where you explain that you need to keep phone calls shorter and more focused on work from now on, is a necessary first step to remove her plausible deniability that what she is doing is normal and okay with you. But it’s only the first step; there is rarely only One Awkward Conversation To Rule Them All. Even if she agrees to be more conscious of time, next time she’s in the grip of whatever is making her “not know how to hang up her phone,” that professional, reasonable conversation you had is unlikely to translate into stronger impulse control in the moment.
You are going to have to run the meetings, interrupt her, and end the conversations. You have ample evidence that someone who will keep you on the line for four and a half hours (!!!!!!!!) will never do this on her own and will not take any hints.
Your strategy of scheduling calls with her right before other commitments so there is an external out point is a solid one, keep doing it. In addition, try this:
- Schedule “other commitments” even if that means “you, alone, quietly working on things” so that you mentally have “Oh, sorry, that’s all the time I have, I blocked out the rest of the day to ______” in mind before you even pick up the phone.
- Or, have you got a solid, trustworthy, team member or direct report who knows what’s up? Schedule or “schedule” update meetings with them right after your Boss calls. You’re not avoiding your boss, just, Englebert promised you a draft this afternoon and you need to check in with him.
- Try to schedule a set weekly 30-minute status meeting (vs. “every few days”) at a time that is good for you (your workflow, your patience level, your known “out”).
- Email your boss a very brief agenda before any status update call. “According to my list we should cover x, y, z on the call today. Sound good?” Do this even if she’s technically the one calling the meeting and should make the agenda. After each call, send a brief email with what the agreed next steps are. These are your anchors that show that you’re not being “difficult” if she reacts badly to limitations.
- At the beginning of a call, set a timer for 25 minutes.
- During the call, keep politely referring back to the agenda. She goes into tangent-land? “Interesting! Okay, next on my list is ____.”
- Own “not being much of a phone person” as a personal quirk and let on when you become distracted. “Sorry, what were we talking about again? I lose track during long conversations.” “Well that’s everything from my list, any chance we can wrap this up?” “Can this wait? I confess, I’m fading.” It is okay if she gets the impression that you are annoyed, tuning out, bored, not really here for whatever this is – it’s the truth!
- When the timer goes off? Set the timer for 5 more minutes, and interrupt her, if necessary. “I’m going to have to wrap this up in a minute. According to my list we’re good to go on x, y, and z.” After the ding, use zero question marks if you can possibly help it.
- When the second timer goes off, if she’s not wrapping up on her own or covering anything useful for work, interrupt her again. Get. Off. The. Phone. Use whatever you need to get it done: Upcoming meeting you need to prepare for. Deadline you need to meet. Bathroom break. Vagueness is a-okay: “So sorry, I have to excuse myself, I’ll email you the details.” GO.
Hopefully she will adjust to having a predictable routine and appreciate being kept gently on task. If not, track how many work hours these phone calls are eating up, and throw your Project Lead weight behind it. How are these chats with her accounted for in the project’s time sheets and scheduled deliverables? “Brenda, we were on the phone for ‘status reports’ for 7 hours last week, and only 2 of those were billable. That is not sustainable given our deadlines. Can we agree to keep phone meetings to 30 minutes once a week unless there is an emergency?” “As project lead, I need to keep a tighter grip on the team’s time, including my own, so I’m not going to schedule calls longer than 30 minutes. Appreciate your help in keeping us all on track!” (Bestowing unearned praise for something you hope someone will do is an Ask A Manager special, I steal it all the time).
Alison: Yes, yes, yes! I second all this advice. Jennifer has covered the logistics of the how so well. What I’ll add is that you should give yourself mental permission for this. So often, I think people get into a mental mode where they feel like they can’t interrupt their boss or assert boundaries with their boss — because it would be rude or insubordinate or something in that neighborhood — and that if their boss wants to have 4.5-hour-long phone conversations (!), that must be the boss’s prerogative. And there are some bosses who would be outraged or deeply affronted if you tried to set this sort of boundary but, truly, those are outliers. Most managers are going to be okay with it. They might be a little surprised the first time, maybe even be a little hurt. But even if so, the vast majority of the time it will be fine. The vast majority of the time, it will not ruin the relationship or get you fired or ostracized. (If you have real cause to think it will, then the problems are much deeper, and likely unsalvageable.)
That assumes, of course, that you’re warm and matter-of-fact about it, and that you ensure you do cover the work-related stuff that needs to be covered. You’ll get the best outcome if you’re cheerfully efficient and then breezily bring the call to an end, using a tone that signals that of course it’s reasonable for you to need to move on to other things and of course your boss will see it that way too. (In fact, I think this technique is the cousin to what Jennifer said about bestowing unearned praise for something you hope someone will do. Often if you act as if of course everyone in the conversation will agree that Reasonable Thing X is reasonable, because it is so clearly obvious to all people of sense, you will find that they don’t object.)
2. I love my job but it makes me incredibly anxious.
I’m hoping you can help me, because I’m not quite sure where to go from here. I work at a non-profit doing policy analysis and legislative strategy. I really love what I do and am passionate about the work, tiring as it is. I also say specifically what my industry is to show that mistakes, even small ones, have a large impact on our work.
The problem is, my work environment has made me incredibly anxious. We’re a small organization (less than 15 employees including leadership), and my specific team is me and my boss, a senior staffer. Because we’re so small, my boss manages most of the rest of the employees, and doesn’t have a lot of leftover time between his management duties and the work that he himself has to do, making him really hard to reach on any given day.
A second layer to this, is that my boss is a micromanager. I don’t think he ever intended his management style to be this way (in that, he just really enjoys the work that we do, so he wants to be involved in every decision to maximize our reach), but it has led me to second guess myself constantly, and never want to take initiative because I’m nervous that it’s going to end up being incorrect. I would say that a lot of this is just my inherent need to people please, but when I try to push that aside and take initiative anyway (at things I’ve done before!) I’m reprimanded for it.
But the final layer is that since we’re such a small team, my boss needs to rely on me to get things done and manage small projects. I’m also in my mid-late 20s and would like to begin taking on some additional responsibilities, and learn how to lead/manage, but my anxiety over the potential of being wrong (and then having that confirmed) is overwhelming. For example, I want to throw up as I’m writing this, because I need to send an important email about an event next week ASAP, but a decision has to be made about the time of the event, and I’ve already called my boss once this morning and haven’t heard back, and I’m terrified of making the wrong decision and inconveniencing folks.
I really like my boss as a person, and he’s very good about making sure we’re using our benefits, etc, but I don’t know how to keep this up. I’m in therapy, and overall get good reviews (even as I’m corrected on a day-to-day basis), but I’m wondering if you have any suggestions.
Jennifer: I’m going to build off the previous advice for the Constant Contact boss. If your boss insists on having final say on anything that you do, he needs a structure. It doesn’t sound like he has an assistant managing his comms and calendar, and asking him to create a structure isn’t really going to get you anywhere except more confused about how you are supposed to simultaneously “just take initiative” and “wait for his say-so.” Ergo, you’re going to have to make a structured workflow for yourself and communications flow for both of you.
I’m going to use event planning as an example, even though your upcoming event will be over by the time you read this, and the overall method applies to any project.
Imagine you are 100% in charge of planning the next event your company hosts.
- First step, grab a calendar and build a spreadsheet that lays out all the details: date, time, venue options, invitation list, graphics, speakers, a/v needs, catering, budget, notes, etc.
- For each of these tasks, what’s the deadline? When must they be done in order to stay on schedule & budget? If there is no outside deadline, what is your deadline for staying sane and getting it all done?
- Now take the actual deadlines and add a cushion of at least 1-3 days before it. That new date is your Boss Buffer Day, the deadline you tell your boss that you need a final decision by, the day you start chasing him down for one.
- This is a confidential tool for you, to put all the details in one place so you don’t lose them but aren’t carrying them anxiously at all times, not a thing to share with your boss or coworkers. Do not reveal the secret of Boss Buffer Day to your actual boss!
- As you move forward with the plan, for things where there are multiple options, prioritize them and try to narrow it down to the two best ones. Which option do you think is best, and why? If you really don’t know the answer or have an opinion, who else in the office is reliable with this topic?
Once you have your list, schedule, and secret buffer schedule, you can build emails to your boss like so:
“Hello, I’m ready to finalize [task].
Our best options are [A] and [B]. My recommendation is that we do [A] because of [reason].
Please let me know if I can move forward with [A] or if you would like another option by [Boss Buffer Day/Time] so we can stay on schedule, thank you.”
If, on the eve or early morning of Boss Buffer Day, you haven’t heard an answer, you can fashion a reminder like so:
“I need to lock in [Option A, recommended because ________, to stay on schedule and avoid [rush fees][losing the venue][presenter conflicts][some other consequence].
If I don’t hear different from you by [time], I’ll assume it’s a green light and get moving. Copying [Team Member] and [Team Member] on this so they can get going on [next task]. Thank you!”
I’m sure you already know how to send business emails, but here is why this specific way of breaking it down might work:
- You are taking initiative, no air quotes.You are researching options, narrowing them down, building a timeline, and making informed recommendations. Limitations reduce anxiety.
- You’re keeping your boss in the loop but reducing how much thought he has to devote to whatever this is by presenting concrete choices and timeframes.
- Making recommendations and sharing your opinions is useful, even if he rejects them. It’s very easy to reply to emails like this with “Sounds good, let’s do it” or “Hold off – B is actually better” or tell you if he wants something entirely different, whereas, “What should we do about X?” takes up way more boss-brain.
- You’re creating – and documenting – a path that lets you actually get things done.
- If your boss gets testy that you are moving forward sometimes without his express go-ahead, it gives you a basis to ask, well, if you don’t answer your emails or phone even to say “Yes” and “No” to time-sensitive stuff, how exactly do you envision this working?
Alison: Yes! Making it really easy for him to give quick answers (yes or no, or A or B) will often vastly increase your chances of getting faster replies. Not always, but often. And “if I don’t hear from you by Thursday, I’ll plan to do X” can be highly effective. Just make sure you’re leaving a reasonable amount of time for him to reply. Don’t say at 9 am on Thursday that you’ll move forward if you haven’t heard from him by noon (unless it’s truly urgent and waiting is not an option, and in that case make sure you’re calling him too).
Also, if you don’t currently have a standing weekly meeting with him, try to arrange for one. It won’t help if you have something time-sensitive that needs to be answered before your next scheduled meeting, but you’ll be able to save up a lot of things for those conversations.
If none of that works, I would recommend having a big-picture conversation with him where you lay it out: “You’re really busy, so it’s often hard for me to reach you when I need decisions on time-sensitive things like X and Y. When I’ve tried to move them forward on my own, it’s turned out later that I made decisions you didn’t want me to make. But if I don’t do that and let things go undone until you have time in your schedule to meet, that would mean we’d miss opportunities like ____, end up paying rush fees, and (fill in other consequences here). Is there a different way to handle this stuff?”
But also, I think this is a very tough situation to be in with anxiety. Some people can just roll with this kind of work environment. They don’t let themselves get all that invested and they decide that if their boss doesn’t move things forward, well, that’s their boss’s choice. With that approach, you can sometimes work reasonably happily in a situation like this. But the combination of anxiety and a difficult-to-reach micromanager is a really hard one and can keep you on edge all the time. It’s okay to just decide this set-up is not for you.
One last random thought: if you want to learn to lead or manage, I’d be cautious about doing it in this environment! The lessons this guy will be teaching probably will not be the ones you want to learn.
3. How to be sick in a workplace that doesn’t allow it
The lockdowns have taken away some of the things I like best about my job. I (pronouns: she/her) find myself more anxious, stressed and sometimes depressed than usual. I’ve been using my self-care routines: eating well, exercise, yoga, meditation, online socializing and seeing a therapist. But I keep getting sick. Not really sick. “Just” colds and flu-like things—but ones bad enough that I’m working at about half-capacity most of the time. Doctors have checked me out and there seems to be nothing physically wrong with me—the best guess is that the stress, etc. is bringing my body down.
I’d like to be able to take time off to recover when I get sick. But even though the university I work for (yes, I’m in academia) has a reasonable sick leave policy, there’s no culture for actually taking it. The assumption is that unless you can’t physically do the thing, you should do the thing. Particularly while we’re working entirely online, there are very few occasions where you physically can’t do the thing. I’ve dragged myself through numerous online events from the couch. But I don’t want to be a martyr. I want the chance to recover when I’m unwell.
I’ve raised the issue with my manager (the head of department). His response seems to be that it’s up to each individual to figure out what they can manage and they should do just that—rather than taking official sick leave. He also noted that some of the work I do is “irreplaceable”—such as teaching. What this effectively amounts to is that if I can’t do the work one day, I just have to catch up the next day—which is hard when I’m already struggling with the workload. I think the idea of the unofficial sick leave system is that I would ask, for specific tasks, could someone else do this, citing reason: illness. But we’re a small department. I know that if I don’t do any work that immediately needs doing, I have to lay it on my colleagues, who are also having a tough time. It’s also very hard to find a specific task that I literally cannot do. I can do it. I’ll just stay sick longer or get sick again more quickly.
Am I being unreasonable in wanting to be able to call in sick when I’m sick? Is there a way to have a conversation with my manager that makes it clear that it’s a reasonable request? Or is there some way to mentally reconceptualize the situation so that the workload and sickness policy don’t feel stacked against me? How do freelancers manage these things?
(In case it’s relevant, I’m in a tenure-track position, but the review system isn’t cutthroat. The department and head are both supportive—so I don’t think raising the issue would be a problem per se. So far my teaching and admin performance haven’t suffered. Research has, but we’re anticipating research expectations will be adjusted, given the pandemic.)
Alison: I’m going to defer to Jennifer to talk about the academia-specific part of this, because academia is very much its own weird thing. But no, you are not being unreasonable in wanting to call in sick when you’re sick, and it’s awful that your workplace culture has made you question that.
I would take your manager at face value when he says that it’s up to each person to figure out what they can manage and they should do just that. Great, that is what you will do! When you need time off to recover from being sick, take that time. I would also take your official benefits package at face value as well; if it says you get X amount of sick time, assume you get X amount of sick time.
And then with your manager, when you call in sick I would proceed as if of course what you’re doing is reasonable. I wouldn’t have a big “look, I will probably need to use some sick days throughout the year” conversation with him … just like you also wouldn’t have a preemptive “I will probably need to use some of my salary throughout the year” conversation either. Going back to that “of course you’re reasonable” tactic we talked about with Constant Contact boss in letter #1, proceed as if of course you will occasionally use a sick day and of course that will be fine and normal. Because truly, both those things should be taken as obvious realities.
I know this can be hard to do when it feels like you’re being pressured not to, and especially when it means there will be a pile of work waiting for you when you get back. But you should not compromise your health for a job.
As for how freelancers handle this … well, it sucks. In practice freelancers don’t have sick pay or (usually) anyone to cover for them if they need time off. Ideally they handle that by creating enough of a monetary buffer for themselves so that it’s not a disaster if/when they need time off to be sick, but that can be easier said than done, especially when someone is just starting out. But I also think it’s interesting that you’re asking about freelancers when you aren’t one — because if you’re feeling like you’re that much on your own despite having a salaried job with a reasonable-on-paper sick leave policy, that is a sign of how sick the system you’re in is.
Jennifer, why is academia so messed up?
Jennifer: Alison, institutions of higher learning have figured out how to charge learners astronomical sums while paying much of their teaching workforce with an idea (“If you just keep working here, eventually you might be good enough to work here!”) instead of money and benefits.“Irreplaceable” teaching activities are carried out by highly-trained but increasingly disposable humans, who are the products of the same educational institutions that exploit them. Basically, take the common toxic non-profit mindset that treats workers who expect livable wages, regular raises, and sustainable working hours as if they’re being disloyal to “the mission,” but make it Snowpiercer.
Letter Writer, you’ve got more job security than some, but tenure track isn’t tenured, and the pressure to never actually be sick in academia is real at every level. My last semester as an adjunct, two years pre-pandemic, I was reprimanded for using my union-mandated sick day, singular, to go to urgent care, unable to breathe or stop coughing, because while I had created an online lesson plan to cover all planned material and notified students, I hadn’t notified the department 24 hours in advance or found a substitute myself. I was told that if I was “truly ill,” I should “of course” take time off to recover, but also, more missed days would not be paid.
So, I did what everybody who can’t afford to both eat and be sick does: I mixed as many cough suppressants, painkillers, and anti-inflammatories as I could legally be prescribed, coughed my way through the rest of the semester in a fog, turned in my final grades, promptly collapsed, and spent most of the summer recovering instead of working on my own projects.
Any workplace that experiences significant setbacks if just one employee is out for a few weeks to recover from an illness is revealing a management problem. What is their plan if someone gets COVID-19 or something else that makes them seriously ill? I mean, I know the real answer is “wing it + everyone else will obviously do even more work,” but that just proves the point: You taking some of your actual sick leave to recover from illness is not causing your workplace to be like this, and it’s grotesque that you are being pushed to second guess whether you’re even “allowed” to care for yourself.
Viruses, or whatever you’ve got going on, don’t care about your work ethic or passion levels, and I agree with Alison.You’ve asked, they’ve given you the “take whatever time you need” (text) “but don’t actually stop working” (subtext) message, so you’ll have to forcibly ignore the subtext, follow the written policies, and decide for yourself when a sick day means logging out of absolutely everything to actually rest.
I think my advice comes down to this: You probably know a lot about excelling at your job, spackling over all the cracks where your institution is stretched too thin is second nature by now. But what would your C+ effort look like, and can you do that for a while? (If your colleagues are as overloaded as you say, your students probably are too, so how long until they even notice that you’re pacing yourself?)
If you really can’t take significant time off to recover, then you’ve got to adjust your expectations. If you knew that you probably have about 20 good work hours in a given week until you’ve really kicked this thing, what’s the best use of those hours? Who do those working hours need to serve? Your students? Your own research, and tenure preparations? Your “service” work within the department, that you’re afraid will just get piled on others? You can’t be true to all three of these endeavors and to your health at the same time, so choose the most important and prioritize those. I vote “health,” followed by “students” (who really won’t get this time back). I think your department head voted for the students, too, when he said that your teaching was “irreplaceable,” so go with it. Make a list of the rock bottom things that need to happen each week to maintain your teaching and do your best with them.The rest of the work will either be so urgent that someone else must step in and do it, or it will still be there in a few months. Objections can be met with “[Chair] told me to really prioritize my students while I’m recovering from illness.”
This also means accepting that some of your work will not get done as it normally would, possibly ever. This is scary because it goes against the culture of constant productivity, but it is also necessary for the project of remaining alive. As long as you keep powering through out of fear that it will all just pile up more later, the department can pretend everything is fine while adding more to the pile. Clearly nobody you work with is ever going to reach in and take things off your plate. Even if any of them had management training of any kind (they don’t), they’re all too busy with their own plates. You must take things off your plate, or you’ll end up plowing through what’s put in front of you until you drop.
If you’re willing, I have a starting baby step for you:
Look at your syllabi. If your students wanted or needed to take their upcoming spring break completely off, could they still keep up with the work in your class? If the answer is no, adjust your assignments until the answer is yes. Then, tell your students that you plan to unplug over spring break and you hope that they will too. Set up an email autoresponder for the entirety of spring break, the most generic, “Hello, I’ll be responding to emails after (date), have a wonderful break.” Don’t tell people where else they can reach you for “urgent” matters, don’t qualify it or give reasons, and definitely don’t tell your colleagues you plan to do this in advance. This is an exercise in taking something that will never be given.
Over break, only you can decide how bad you want to actually rest vs. logging in to read emails that the senders have already been told will have to wait a little while, at least 75% of which can be answered with the words “It’s in the syllabus.”
As I formatted these and got them into WordPress, I noticed the questions all have something in common: They are about conscientious, dedicated employees who must “manage up” and work around systems, constraints, and personalities that are not really the Letter Writers’ responsibility to manage, and where a significant portion might be outside your ability to change. Alison and I can suggest tactics that will hopefully help you regain a sense of control and get you more of what you need from difficult situations. But I hope all of you take away the knowledge that people don’t suddenly forget all sense of time and phone manners, become micromanagers who can’t be pinned down, or fail to make sick leave policies transparent and actionable, because of anything you did or failed to do. Sometimes the win condition you get is “Welp, at least I can be sure I tried my best to make it work and kept it professional.” If that ends up being the case, please don’t turn it all into a story about how you failed somehow in situations that are so obviously failing you.
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