transcript for “I’m the Boss and I Messed Up”

This is a transcript of the Ask a Manager podcast episode “I’m the Boss and I Messed Up.”

Alison: Hi, and welcome to the show! You might have noticed the show didn’t come out on Monday – we’re switching back to Wednesdays only, but we’re keeping both formats – so we’ll still have the format where I have a guest come on the show and spend the whole show talking through their problem, and we’ll also still have the format where I answer a bunch of shorter questions from different people. People seemed to like both formats, so we’ll stick with both. Today’s show is a bunch of shorter questions from people. And the first question today is from a manager who messed up at work, and is wondering how to handle it.

Caller 1: I supervise a small team of four at a software company. My team is amazing: reliable, fast, accurate, amiable, etc. I couldn’t ask for better people to manage, and I’m proud of the work we accomplish each day.

That’s why I’m particularly embarrassed that I made a noticeable mistake at work today. We have a task that requires each team member to show up to work early, rotating through all members of the team, including me. I didn’t arrive to complete this task, which means a few of my subordinates covered for me when they arrived at their normal start time. While this didn’t ultimately affect our software’s stability, it certainly could have. I immediately notified our work chat that I’m mortified about the oversight and plan to make up for it by taking someone else’s early start this week. I also plan to directly verbally address it during our team meeting, reasserting that I am held to the same to the same expectations and standards as everyone on the team. And of course, moving forward, I will do everything in my power to ensure this doesn’t happen again.

But my question more generally is: how do managers hold themselves accountable to their subordinates when they make a mistake? And I was wondering if you thought my response sufficient, or is there something more I should do to ensure my team can trust me.

What makes this stickier is that I have a chronic mental health issue that contributed to me failing at this task. And I discussed the health issue with my own supervisor, but it seemed inappropriate to bring it up with my direct reports. Do you agree? If I continue to struggle despite my best efforts, what would be the best way to address that matter professionally?

Alison: Well, first, as far as how you handled this, it sounds like you did everything right! You immediately acknowledged the mistake, apologized for it, you took someone else’s early start, and you’ve been explicit that you believe in holding yourself accountable to the same expectations as everyone else. So if you were my boss, I would be pretty delighted with the way you were handling this. Really, if anything, it’s possible that you erred just a little bit on the side of going a little overboard – I don’t know that you even needed to do that last piece about addressing it in a team meeting, since you had already addressed it in the group chat. There’s nothing wrong with doing that, but I want to make sure you’re not flagellating yourself over this, because – at least based on what you shared here – this doesn’t sound like it deserves flagellation. I mean, yes, you messed up. But you’re human, and humans do sometimes mess up sometimes, that’s what we do.

I’m curious how you would react if one of your employees did the exact same thing, immediately acknowledged it and made it clear that they knew it was a mistake and that it wouldn’t happen again. I don’t know all the details about what happened of course, or what the ramifications were of you not being there on time, but my hunch is that if one of your employees did the same thing and had the same reaction toward it that you had, you would tell them that it was okay, you know of course don’t let it happen again, but people are human. So when you talk about holding yourself to the same standards that you hold your staff to, make sure you’re not being harderon yourself that you would be on your staff. Because when you talk about worrying that they won’t trust you just because you made one mistake, one that you quickly took responsibility for, I think you’re probably being a little bit too hard on yourself – and harder than you would be on an employee who did the same thing.

You asked more broadly, how should managers handle it when they make a mistake? And the first thing to know is, you will make mistakes. This isn’t something that, oh my gosh, you did this and you’re a terrible manager for doing it, and other managers are out there working flawlessly every day and never messing. Managers mess all the time because again, we’re human and that is what humans do. What’s important is that when you get it wrong, you acknowledge that. It doesn’t have to be a huge thing – it can be as simple as “hey, I realized that I made the wrong call there. I apologize about that. Going forward, let’s do X instead.” Sometimes it doesn’t even require that. If it’s a pretty routine mistake that doesn’t have a huge impact on other people, it can just be, “Agh, I messed this up – can you help me do X to fix it?” It’s true that because you’re a manager, your actions do carry more weight and sometimes your mistakes can be ones that have more impact on other people, and it’s good to factor that into how you handle mistakes, but I don’t want you to feel like just because you’re the boss, the very act of making a mistake, no matter how big or small, is somehow worse, because you’re not expected to be perfect just because you’re the boss. If that were the expectation, no manager could be successfully. And I do hear a little of that running through the language you’re using, so watch out for that.

Let’s talk about what you don’t want to do if you make a mistake as the boss. You definitely don’t want to double down and pretend you were right all along. You don’t want to shift the blame to other people. But you also don’t want to seem so mortified by it that you signal to other people that you don’t have any tolerance for mistakes in general – because if you handle your own medium-sized mistakes like they’re giant-sized mistakes, people are going to assume you’ll do the same thing when they’re the one who messed up. So you’re modeling for your staff how you want them handling their mistakes as well. So yes, acknowledge it, work to fix it, work to make sure it doesn’t happen again, but don’t blow it out of proportion either.

Now, let’s talk about the mental health piece of that because frankly, I suspect that the reason you are being so hard on yourself is because you know that it’s tied to this chronic mental health issue. And maybe you are embarrassed about that, because we still are super weird about mental health and there’s still stigma around it in a way there wouldn’t be with a physical health issue. And in fact, I’m curious – if you had missed this task because you were physically sick, would you be beating yourself up as much? I am willing to bet a pretty significant amount of money that you wouldn’t be, and that’s worth thinking about.

You also asked if I agreed that it would be inappropriate to bring up the mental health issue with your staff. I think there’s just no need to. If you continue to struggle with it and you’re concerned that it’s noticeable at work, you can give them some context – but it’s enough to just say that you’re dealing with a medical issue that’s affecting you in X and Y ways. You don’t need to specify that it’s a mental health issue — and in fact, you’ll be modeling good boundaries for your staff if you just keep it to “a medical issue.” Because you don’t want them to feel that they’re obligated to disclose their own personal medical details when they need to ask for time off or when they need a health accommodation. And you’ll be modeling good boundaries by demonstrating, this is what it looks like. It’s okay to just say “I’m dealing with a medical issue that’s making me very tired” or whatever relevant piece of context you want to share.

But go easier on yourself because you are human and that is perfectly okay.

Caller 2: I’m a relatively new grad applying for jobs that are out of state. And I’ve read a lot of advice and listened to podcasts and I’ve recently come across the advice to shoot out a blind email to a company manager or lead asking for either an informational interview or 20 minutes over coffee to “pick their brain” when you’re visiting in their town. And according to their story, it works in their favor each time and they’ve landed the job. I’ve never done this, and I feel a tad awkward asking out of the blue for these kind of things rather than applying for a job on their website. But is this the new and recommended way to find jobs out of state or jobs in general? Thanks for your help.

Alison: This is a piece of advice that keeps getting passed around, and it’s not very effective.

So first of all, managers tend to be busy. And managers who have been managing for a while, and hiring for a while, know that “informational interview” is often code for “I want you to hire me but I am not being up-front about my intentions.” And same thing with “I want to pick your brain.” It’s annoying when people aren’t up-front about what they actually want, and this advice is basically telling you to waste the time of strangers who may not even have a job open that would be appropriate for you. And if they do have job openings and that’s why you’re targeting them, it’s going to be even more obvious what you’re doing. And increasingly, managers are likely to tell you to apply through their normal application process. And definitely when you’re dealing with non-small companies, they’re going to want you to apply that way regardless.

There are some exceptions to this – like very small businesses that are more likely to sort of wing it when it comes to hiring. As a side note, I don’t know that I would encourage you to work for small businesses that wing it when it comes to hiring – they tend to be fraught with dysfunction, but sometimes this approach can work with them. Or if you have a very specialized, very in demand skill set. But for most people, this approach is just not that effective or efficient , definitely not more than actually applying for jobs that are open through the stated application process.

I think people give this advice because they want to be able to sell you on the idea that there’s some trick to job searching, there’s something that will let you get around having to write cover letters and resumes and apply the normal way, because telling you to do it like that is pretty boring advice – but really, this idea of blind emailing strangers for most people just is not very effective. It doesn’t mean that it never works, but it does mean that for most people, it’s not likely to work most of the time. But it’s one of those things where because it occasionally works in rare cases, it gets passed around as some kind of trick to getting a job. But it’s really not the best way to spend your job searching energy.

Now, it’s true that there’s real value in building your network, especially when you’re trying to find work in a another state. But the way you do that is to build genuine relationships, not to ask for coffee for a fake reason that isn’t actually what you’re looking for from the other person.

The things that will really help you find a job in another state are things like making your move sound like a done deal, like putting on your resume and in your cover letter that you’re moving to their area in January or whatever month you pick – not just “I’m hoping to move there in some amorphous point in the future. Or in some cases, using a local address if you’re going to be able to get there quickly for an interview. I wouldn’t recommend doing that if you can’t because if you put down a local address and they’re like great, can you come in in two days and you’re suddenly stuck explaining “uh, actually I live across the country,” it’s going to look deceptive. But if you can be there quickly and there is a local address you can use, that’s an option. Other things like offering to pay your own interview travel expenses, and definitely really leaning on your network to help you develop contacts in the area you’re moving to. And that last one doesn’t mean “blind email” people; it means get the person in your network to introduce you to their old boss who works in the city you’re moving to, or so forth. So that you’re using real connections from your network.

Okay, next question.

Caller 3: Hi Alison. When I listened to your episodes about getting your tone right, it made me think of a question that has plagued me for a while. I am a pretty rational person, I have a masters degree and have worked in scientific research. However,  if I ever do experience any strong emotions, either positive or negative, I tend to react by crying. If an emotional scale was 1-10, if I am below a 3 or above a 7, I tend to cry, and it’s hard to stop myself. This can be very difficult, because I don’t want to seem unprofessional, weak, or unable to handle my workload.

Another factor that compounds this issue is that I am a teacher who works in a middle school that serves very low income kids. This can cause a lot of emotional stress on top of a what one might experience at a normal job.

Is there any wisdom you can share about how to avoid this? Or, alternatively, is there anything I can say in the moment to assure my coworkers that I am not a crazy, over-emotional wreck, but rather a professional, smart, strong… frequent crier?

Alison: I am someone who tears up easily too – I think a lot of us are. It’s true though that while crying once or twice a work will usually be excused, if it’s happening a lot, people are going to worry about what’s going on. They might worry that you can’t handle the stress of the job, or that you’re too sensitive for getting feedback or so forth. And you don’t want that.

So I think the first thing is, if it ishappening a lot, look for ways to get that under control. There are some physical tricks you can try that are supposed to help – people say pinching the bridge of your nose, or pressing your tongue against the roof of your mouth, or even just making yourself think about something totally unrelated, like what time it is, sometimes can cut off the tears. Or if that doesn’t work, you can physically remove yourself from the situation until you’ve regained your composure – like you can say that you need to go get a glass of water or excuse yourself to go to the bathroom. And often that’s going to give you the break you need to get it under control.

But if you do tear up in front of a colleague, most people will take their cues from you. So if you’re really matter of fact about it and you just say something like, “please excuse me – my tear ducts have a mind of their own” or “don’t mind me, I’m an easy crier, but I wanted to hear what you’re saying, so please go on” –something that signals, hey this isn’t a big deal, yeah, there’s water coming from my eyes but it’s not getting in the way of me hearing and processing what you’re saying. So in other words, don’t let it be disruptive, assure the person you’re talking to that you’re hearing them and they don’t need to stop and comfort you, and so forth. And the more matter of fact you can be about it, the better.

Caller 4: I have a complicated situation. I am the manager of a department in a public library. I have an employee who is very kind and helpful, but she doesn’t take feedback very well. This person perceives feedback (and some conversations) to be aggressive towards her and she inflates the way people respond to her, which then leads to her feeling insecure about her relationships with coworkers in a really irrational way. She has also overreacted in the past and has tried to quit because she thought she committed some cardinal work sin, which turned out to be a minor inconvenience. I and my director had to talk her back from the edge in that case.

In the past several months, she has been dealing with difficult matters at home. Her husband found work in the neighboring state (about three hours away) and has been unfaithful during his travels. Rather than leaving him, she decided that she would follow him to his new job and resign from the library. We posted her position and have received more than a dozen applicants, a few of which are very promising.  

As I was about to schedule interviews, she informed me that she is not moving and would like to keep her job. Do I keep her on or push her to resign, as she had planned? She has been in this position for about 18 months and generally does a good job with minor adjustments that need to be made in her performance. What should I do?

Alison: Ooof. You say she generally does a good job, but she sounds exhausting. She takes feedback badly and she gets weird about her relationships with her coworkers, and she’s tried to quit before for strange reasons and you’ve had to talk her down. It all sounds like a lot of drama and distraction. I’m curious – when she resigned this time, did you feel relief? Because if you did, that is a sign that you have probably been accommodating behavior that you should not have been accommodating, and that it might actually be better for your organization to take this opportunity part ways with her.

I don’t know that that’s the right move in this case, but I do want you to know that in theory you’re certainly entitled to say, “You know, you resigned and we accepted that resignation and we’re now moving forward with other applicants, who we recruited in good faith, and we’re going to stick with the path that we’re on and keep your last day as (whatever date was set).” And that is what I’d recommend doing with someone who was a different sort of problem – like if she’d had a terrible attitude and been a jerk to people, I would go with that plan. But you say she’s actually very kind and helpful, so I am betting that won’t feel like the right thing to do, especially when you throw in the situation with her marriage, which sounds pretty awful.

So there’s a middle ground here. You could say to her, “You know, we took you at your word when you resigned and we put a lot of work into recruiting good candidates, and we have some promising people in the candidate pool now. But we also value you and I don’t want to put you in a difficult spot, but if we short-circuit the search now and you stay, I want to be transparent with you that we’re going to need you to make some changes. You do excellent work, but you also bring a lot of drama into your relationships here, and I need you to rein that in because it can be distracting. I need you to work on not responding defensively when you get feedback and on dealing with colleagues in calm, drama-free way.” (You could give a couple of examples here so that she’s clear about what you’re talking about.) And you could say, “If you can commit to doing that, we can move forward. But if you can’t or don’t want to, we’d want to stick with the ending date you set.” And you should also say, “”You know, you’ve resigned in the past and then rescinded it, so I need you to be really clear that if you tell me again that you’re quitting after this, I am going to take you at your word and we won’t be able to reverse it again.”

You might feel like, oooh that’s kind of harsh for someone who does good work, but what you’re described is actually really disruptive. And you’ve got to think about her coworkers too because if they see her being this disruptive, and then had the relief – I’m betting – of her resigning, and then see her reversing course and coming back, and you being okay with it, the message they will take away is that you’re either fine with all this drama, or you’re not fine with it but you aren’t being a strong leader and addressing it.

So, if you do if let her rescind the resignation, it’s got to be with these conditions on it and a commitment from her to really get that behavior under control.

Let’s take another question.

Caller 5: I wanted to talk to Alison and figure out a way how to ask my boss for a way to go from working 5-8s to 3-12s or 4-10s . When I approached her a few days ago, she told me she’d put me on a list because other employees were going to be asking the same thing because we’re going to be moving from Kansas City, Missouri to Lenexa, Kansas and the drive now is going to be about an hour one way. And that just might not work for me every day. So I need to figure out a way to ask my boss again and kind of make sure she knows that I’m serious and that I want to be taken seriously to have a different schedule coming up in November because Kansas City and Kansas can get very bad with traffic and weather.

Alison: So first, for people who don’t know this lingo, when the caller says she wants to go from working 5-8s to 4-10s, that means that right now she’s working five eight -hour days and she wants to switch to four 10-hour days. So same number of hours each week, but spread out over four days instead of five.

This is potentially tricky because it sounds like your boss is saying that other people have asked for this as well and she doesn’t necessarily want to say yes to it for everyone. And there might be good reasons for that – like maybe it’ll affect coverage in a way that won’t be workable – or maybe there aren’t good reasons for that and she hasn’t fully thought it through, who knows.

I think you need to figure out, is this is a deal breaker for you? If she says no, you definitely can’t make this change, would you leave the job over it? If you would, that’ll affect the way you approach it. You could say to her, “You know, I really love my job and I want to stay in it, but I’m very concerned about my commute after the move. I could make it work if I can switch my schedule to 4-10s, so I’m still working the same number of hours but doing the drive one day less. I want to emphasize that I love the company and I love my work and I want to find a way to make this work if we can, but the drive is not going to be doable for me five days a week.”

And if she resists, you could say, “I really want to see if we can try to make this work because I don’t want to have to leave the job. Would you be open to trying it as a short-term experiment, maybe for one month, and then we can see how it goes and revisit it after one month to see if it’s doable?” Sometimes it’s easier for managers to say yes to something that is just a short-term experiment rather than a permanent change, and then that gives you the chance to show that it is workable.

The other thing is, you’ve probably thought of this, but is it an option for you to work from home at all? Because if it is, you could also propose working from home one day a week, which would also get you that break from commuting.

But ultimately, if she says no, you probably need to decide if you still want the job under these new conditions, with the longer drive. And I know that sucks! But it may end up coming down to that. But have the conversation first, show that you really want to make it work, and see what happens.

I will say that if you have a really short commute now and you’re going up to an hour each way, even just going to 4-10s might not be enough to make that work for you in the long term. I mean, I’m in the D.C. area, a lot of people have one-hour commutes, it’s seen as not that unusual here, but if you’re somewhere where it’s normal to have a 10-minute or a 15-minute commute, this might be a major quality of life compromise that you don’t want to make even if you do get the 4-10s. That still means that you’re spending two hours a day sitting in traffic and you might not want to do that. So give that some thought too. Good luck!

That’s our show for today! If you’d like to hear your question answered on a future episode, you can record it on the show voicemail by calling(855) 426-WORK. That’s 855-426-9675. Or, if you have a longer question where you want to actually come on the show and talk with me, email

That’s it for today! I will be back next time with more questions.