transcript of “Do You Have to be a Jerk to Succeed at Work?”

This is a transcript of the Ask a Manager podcast episode “Do You Have to be a Jerk to Succeed at Work?

Alison: Today I’m going to answer a bunch of shorter questions from people. Our first question is from someone who is managing people for the first time and wondering what the hell she’s supposed to talk about with them when she does one-on-one meetings.

Caller 1: I am a new department director, promoted to my position a little over a year ago. I manage a team of around 15 — eight of whom are direct report staff. When I took over this department, it was a train wreck (and even our company president would agree with that assessment). I’ve spent my time trying to get everything back on track, meeting deadlines, and getting some more in-depth regulatory training for all of us. And now I’m pleased to say the department is significantly improved. We’re moving in the same direction, deadlines are being met. I feel like I can take a step back and the entire department can take a breath.

In one of your podcasts (The Talkative Intern from July 18, 2018), you talked about the importance of regular one-on-one meetings with employees. And it was like someone turned the lights on for me.  I haven’t been doing that. You see, my background is project management and this is the first time I’ve managed humans. So I had to do an internet search about what these meetings should look like, and of course, I started with Ask a Manager. I literally have no idea!  So I went ahead and started these meetings this week, even though I’m still fumbling in the dark some. But I would love your thoughts on what a typical check-in meeting would like like. About how long it should last? Is there a standard length of time that we should spend in these meetings? Is there anything that should be covered in every single meeting with each employee? Is there a good standard on frequency or does that totally depend on your staff and your business and what everyone does and what projects you have going on, etc. etc. I’ve learned so much about managing employees since I started listening to the podcast and reading your blog, so I’m really looking forward to your input on these very important meetings. Thanks!

Alison: I’m really excited to get this question, because doing check-in meetings – well, doing them well –  can make a huge difference in how effectively you’re managing your team and how much your employees themselves feel like they’re on track. I know it might not sound like the most exciting topic to people listening, but I think it kind of is, because doing these right can be like the entire backbone of management! It’s really, really key. And so many people don’t really do them effectively, if they do it at all.

The idea with is that having a regular time to touch base one-on-one with each of your employees about their work keeps both of you focused on the results that they’re getting and creates a place for you to check on how projects are coming, serve as a resource to them, agree on priorities, and give feedback.  They’re really your core forum for management – they’re the primary place where you do the work of managing.

You asked how often to have them. For most people, meeting weekly works well – but if you have more experienced staffers or if you have people whose work just doesn’t require weekly conversation, you could do every other week. Most of the time, though, I wouldn’t do less frequently than every other week. And usually they’re going to be 30-60 minutes. I would start in the beginning scheduling them for an hour in the beginning and see how they go. If you keeping finding that you don’t need that much time, you can always cut them down.

And something that’s really key is, always use an agenda, so that you’re both clear ahead of time on how you’ll use the time. You can ask the staff person to prepare that agenda and send it to you ahead of time, and you can ask that it includes specific sections each week – so things like a section for key project updates, a section for priorities for the coming week, a section for items that need your feedback, a section for anything the person is waiting on you for. And then, don’t just use their agenda – I mean use it, but add your own things to it. Jot down your own items that you want to raise. And actually, before the meeting, it’s a really good idea to just take a few minutes and reflect. Ask yourself, what are you the most worried about as it relates to this person or their work? What do you really want to use the time to focus on? It sounds obvious, but making yourself do that every time can make sure you’re focusing on the right things. For example, you might realize one day, “Oh, the thing I’m most worried about in Jane’s realm is the question of what more we need to do to generate tickets sales for our upcoming event, so I want to spend some time with her brainstorming other approaches we could use.” Or you might realize, “Huh, Jane has seemed kind of off her normally very good game lately, so I want to ask her if she’s doing okay and if there’s anything going on that I can support her with.” So the stuff that you’re most worried about, that you most want to talk about, might be the day-to-day work, or it might be something a little bit more big-picture when you step back and really think about it.

It’s also helpful for you to keep a running list throughout the week of things that you want to raise at the check-in – which could be a piece of feedback you want to give, or a reminder to yourself that the staff person was supposed to check into topic X but you haven’t heard any update and so you want to follow up on it, or so forth. By keeping a running list all week long, that way you won’t forget anything, and you won’t be bugging people throughout the week about things that can wait for your time together. And that can be helpful in making sure that people don’t feel you’re hovering.

I would also consider having a section on the agenda for reflecting on what’s gone well recently and what could have gone better. And you can ask the employee to bring their own thoughts on that, you can make it part of the agenda you’re using every week, you can ask them to come prepared to share their thoughts on that and you can offer your own. That’s going to make feedback a normal, regular part of your meetings, and it’s super helpful when you normalize feedback like that, it doesn’t feel so scary to people, and you ensure there’s this constant flow of both positive and development feedback, which is a really awesome thing to have.

Now what you don’t want to do with these meetings is have them turn into just a big list of project updates, where the person runs down everything they’re working on and where it stands, and then the meeting ends. The point of these meetings is not to make the person document where their time went that week. It’s to see how the person is progressing toward their big goals, ask probing questions, spot any areas of concern, serve as a resource to them, help problem-solve if needed, help balance priorities, debrief projects, and give feedback. So make sure that you’re not letting these just turn into a report on how the person spent their time in the last week – that’s not what you’re doing here. And actually, you can even ask people to include short bulleted updates in the agenda they send you ahead of time, so that you can read the updates before the meeting. And then that way, that’s out of the way and you can spend your face-to-face time on the stuff that really requires conversation.

And then I’m also going to point you to my book on management, because there’s a whole chapter in there on how to do check-in meetings well. So the book is called Managing to Change the World: the Nonprofit Manager’s Guide to Getting Results (paid link). And as you can tell by the title, it’s written for nonprofit managers, but 95% of what’s in there is going to apply in any sector. So hopefully that will be a good resource too.

Caller 2: Hi, Alison. First off, thank you for your great podcast on work questions and the like. I’ve found myself often relating to a lot of the issues that come up in some way or another and it has definitely helped me navigate my office culture, so thank you.

I wanted to email you about an issue that has come up often in my career in regards doing the right thing. I am a late 20s male who has been working in a technical environment for the entirety of my career. I don’t know if it has just been the companies that I’ve worked for, but there seems to be a prevailing issue of image vs. actions in regards to people’s behavior when working in an office environment. When things go wrong, which they inevitably will because nobody is perfect, there tends to be a flurry of finger pointing and claims of innocence with no accountability of the issue. Accountability is brought up a lot, and what I mean by accountability is the person holding themselves accountable for their own quality of work. I find myself to be a person with integrity who does not like throwing people under the bus. I will also readily admit when I have made a mistake. The thing I have an issue with is that if I am the only one who does these things, I end up looking like a screw-up instead of building a reputation as someone who is honest with themselves. Even worse, those with Machiavellian tendencies can achieve a lot before people see the “person behind the curtain,” if at all, and will steamroll over people like me if I wait for the higher-ups to “see through” what is happening. Office environments are full of these types of people who will kick and claw and tear others down to look useful to their boss or others. I want to succeed but I want to do so honestly and I want to earn it. Am I just not cut out for working in an office? Thanks.

Alison: I wish I knew what field you work in, because I don’t actually think that this is typical! There are certainly people everywhere who are just out for themselves and who are willing to step on other people in order to advance, but they usually stand out as pretty unusual. They’re not typically the majority of people in an office – unless you’re in a dysfunctional office or a dysfunctional field. So I’m very curious about what work you do, because some fields are definitely more populated by jerks than others. But so often, this kind of behavior is because the organization’s culture allows it – you don’t find it in offices that prioritize transparency and integrity, and where leaders are modeling those things themselves.

If I were in your shoes, I would try to get a read on, is this just your industry? Or have you worked at particularly bad companies? One way to do that is to seek out a mentor, someone who works in your field but is a bit more experienced than you, and talk to them about what you’re seeing. Ask if they think it’s just the nature of the work you’re doing or if it sounds off to them. Or if you have friends who also work in your field but at different companies, you can bounce this off them as well.

My hunch is that it’s about the companies you’ve been at. You said you’re late 20s, so that’s probably something like one to three companies, I’m guessing. And that’s not a huge sample size to draw conclusions based off of, but certainly by the time you’re seeing it for the third time in a row, you’re naturally going to start to wonder. So talk to someone who’s in the same field who has a more senior vantage point on it, and see what they say.

But to answer your broader question, no, this isn’t just the way offices work. It might be the way your offices have worked so far, but it’s not a normal thing. So the next time you’re job searching, I would really dig into the culture of anywhere that you’re considering taking a job, and really prioritize cultures that do emphasize transparency and learning from mistakes, and try to talk to people who work there before you take a job so you can figure out if it’s just going to be the same thing all over again.

And actually, one other thing that can help with this is having a really good relationship with your manager. I would really lean into developing that, like building trust and credibility with your boss, because that will pay off in two ways – one, you say that you feel like being really up-front about your mistakes is making you look like you’re a screw-up because no one else is doing it. But if you have a good, strong relationship with your boss, that’s less likely to happen because your boss will know you and will know that you’re very up-front about that kind of thing and, if they’re at all a decent boss, they should respect or at least understand that. And then the second way that it can help is, if you develop a good enough rapport with your boss, potentially you can potentially ask her about this too, and she will be really well positioned to talk to you with much more nuance than I can about what you’re seeing and whether you’re reading it right. So I’d really work on building that relationship. Good luck!

Okay, here is our next question.

Caller 3: Hi, Alison. Thanks so much for taking my question. I am a teacher who started a new program with another teacher last year. We work together really well and we’re generally thought to be successful by the administrators supervising the program. There is one issue I had though that I’m curious about how you would suggest I approach. Part of this program requires frequent record-keeping about its progress. One agreement that my colleague and I came to was that we would split up the workload of the program to make it easier for grading the students involved and to keep up with all the paperwork. However, my colleague often waited over a month to update his share of the paperwork. At one point, I offered to do it if he was having trouble keeping up with it, but he insisted that he could do it and wanted to handle it and didn’t want to place an unfair burden on me. I also feel a little weird about continuing to make that offer, as I’m worried about gender dynamics. I’m a woman, he’s a man, and I know often in these situations women get stuck with the clerical work. On the other hand, to measure our progress, it’s important that the records are kept up-to-date, and I’d rather do it myself and have access to the information we need than to wait for him.

We’re about to finish our training process with our new set of students and I’m worried about this happening again once the paperwork increases. The hope and goal is that our program is going to expand, which means that the record-keeping will only get more intense. We don’t have hard deadlines for this, which I think maybe makes him feel like it’s fine if he puts it off. However, there is an expectation that we are keeping our records up-to-date in a timely fashion. Am I being a control freak about this? How do you suggest I approach him about it again, since the last time I tried, I wasn’t successful?

Alison: I do not think you’re being a control freak about it. It sounds like the record keeping has to be done. I think it’s good, though, that he did not take you up on your offer to do it for him – because he really should be doing it himself, and because you’re right about the gender dynamics where women often step in and do more than their share of this sort of office housekeeping-type work because we’re socialized to care about it more, and to be more bothered by it when it’s not done, and to be somewhat comfortable with just stepping up and doing it so that it is done, even if we’re annoyed that we have to do it. So, yeah, it’s not good for anyone when you step in and do that because someone else isn’t pulling their weight.

The exception to that can be if you agree up-front to divide the work that way and in exchange he takes on something roughly equivalent in terms of time and energy that you’d prefer not to do. But even then, you have to be careful that you don’t get the short end of the stick there because if the thing he takes on for you is more high-profile or is seen as more valuable, then you’re at a disadvantage, even if you would otherwise be pretty happy with the arrangement. So it’s important to think about that aspect of it too.

Anyway, as far as what to do here. I think you’ve got to get really clear in your own mind about exactly what the impact is on you if he doesn’t do the paperwork in a timely way. If it’s mainly annoying but doesn’t actually have a real impact on you and your ability to do your job, I would try very hard to let that go. And believe me, I am all about being annoyed by things that are just annoying on principle but don’t actually affect me, so I would get it if that was what was happening – but you would be better off forcing your brain to accept that it’s not your problem to solve. But it doesn’t sound like that’s the case, from what you’re saying – it sounds like you need his records kept up-to-date because you need access to that information. If that’s correct, then that’s the piece of this to focus on. Now, when you talked to him last time, it’s not clear to me if you talked through whythis is a problem and how it’s impacting you – or if you just made the offer to take it off his plate for him. My hunch is that you might have focused more on that second piece, just offering to do it, because that’s often what people do. So I would go to him this time and say something like, “You know, last year, I had trouble getting info like X, Y, and Z because you weren’t updating our records very frequently, and I really want to be able to do blank, so can we agree that we’ll both update our records at least every week?” (Or whatever. I’m just making up a time period there, but whatever makes sense.)  The idea is to be very clear about WHY it matters – what the impact is if he doesn’t do it. So that it doesn’t sound like you just care about paperwork for paperwork’s sake.

And I say that because when you’re someone who is really on top of this stuff and you’re nudging someone who isn’t, there can be this dynamic where it starts to feel to both of you like you’re just the nag, you know, you’re just nagging the other person to do some piddly thing that you only care about because you love order and you love paperwork. So the more that you can ground this in the actual impact that it’s having on you or on your students, the better.

And then, if he agrees to that but ends up not doing it, then you can approach him about it again at that point, and again ground it in the impact – so you could say something like, “Hey, I was looking for X piece of information yesterday and I couldn’t find it. Could you get your records up-to-date sometime this week so I’ve got access to that stuff?” So again, it’s not “do this because you’re supposed to be on top of it” – even though that’s true. It’s “do this because it’s causing this specific work-related issue that we need to take care of.”

Alison: This next caller is someone who wanted to respond to a previous episode of the show, the episode called “My boss is a jerk to me,” where the caller on that show had a boss who was really snippy with her and constantly seemed frustrated with her. The person we’re about to hear from is a manager who feels like she’s in that situation but from the boss’s side – she is the boss is annoyed with her employee.

Caller 4: Hi Alison, I want to start by saying I just discovered this podcast and I love it!! I have many questions that I will get to emailing to you but I wanted to start with some feedback from the “My Boss is a Jerk to Me” episode.

While I don’t condone being snappy or short with someone, I have to share that I’m sharing a sort of similar experience from the boss’s side. I am sort of a manager/supervisor to the person who filled my last position. I have explained many times since she started and during the interview process that the site has not done a good job of documenting job processes but I tried documenting as much as I can while I was doing the position (which was a lot). I am pointing her in the direction of those to learn but also explaining things that are not documented and encouraging her to edit the script or create a new one. Take as many notes as possible so that it makes sense to you the next time you do it. Review the notes you took a day or two after you completed the task. Refer to them when something similar happens. 

No matter what though, I am getting the same exact questions about things that are simple and that I would have expected her to learn by now. One interaction that stands out to me is that after her return from a vacation day she stopped in my office when she got in and asked me what I wanted her to do. It wasn’t the end of the month or anything where we would need to prioritize those activities. I said she can carry on with her normal day. When she left my office, I wanted to scream, it’s been four months that she’s been here, I expect that you have work you know that you should be doing and that you as a working professional have structured your day around. Anyway, this was a moment where I could have been short with her like the caller’s boss.

I just wanted to share this feedback and I look forward to asking more questions!

Alison: I really appreciate this caller sharing this, because I think we don’t hear enough from the manager’s side of these types of interactions. And managers aren’t always self-aware enough to realize when they are being short with someone, so it’s good that this person is spotting it.

I know this caller isn’t asking for advice, she’s just sharing her perspective, but I want to offer some anyway! I think as a manager, when you’re at the point where you’re really frustrated with an employee, and definitely when you’re at the point where you can tell that you’re on the verge of snapping at someone, that’s a flag to you that there’s a problem that you have to address. You’re the boss, after all – you say what goes and what doesn’t. And in this case, it sounds like it’s time to sit down with her and have a hard conversation. Tell her you’re concerned that she’s not retaining the training you’ve given her, that she’s asking the same questions over and over, and that she’s not picking up the job as quickly as need her to. And ask her what’s going on – because who knows, there may be something she can share with you that will give you some context she didn’t have. But either way, the important thing is to start talking about it. Let her know what you need to see her doing differently, and let her know that the issues are serious ones. See if you can come up with a plan together for how she’ll approach the work differently. And that might help. But if it doesn’t help – and sometimes it won’t – then you will know that you have been very  up-front and straightforward with her and given her clear feedback and that she wasn’t able to make the improvements you need. And at that point you’ll have enough information to conclude that she’s not the right person for the job and you can make a change and get someone in who is, and know that you were up-front and candid with her and gave her the chance to meet those expectations.

But it sounds like you’re at a point where you’re really frustrated, and understandably so, but that you haven’t yet done the step of having the serious conversation and moving toward resolving it one way or the other. And always, when you’re this frustrated, it’s a sign that you’ve got to sit down and address it, whatever it is that’s going on.

Sometimes managers get stuck in the part of the process where they’re seeing the problems, and they’re frustrated by them, but they haven’t moved on to the part where they talk about them. You don’t want to forget that you’re the manager here and you have the authority – and really, I would argue the obligation – to say, “Hey, this isn’t going the way that it needs to. Let’s sit down and talk about what’s happening and what I need to see you doing differently.” And then if you don’t see those changes, you have the ability to decide that you need to make a change. And I know that’s hard to do! But it’s definitely no kindness to the person – or to you or to your other employees – to stay mired in this place where you’re really frustrated with, with good reason for that frustration, but not address it or speak openly about it.

Anyway, I know that’s a lot in response to a call that was just intended as a comment on a previous episode, but I wanted to get into that a little bit because I think that type of frustration is so common as a manager, and it doesn’t need to be.

Before we wrap up, I want to put out a call for office holiday stories. I’m working on an upcoming holiday-themed episode, and I want to include your stories about holidays at work – gift exchanges gone terribly wrong, holiday party disasters, the time your boss got drunk at the Christmas potluck and passed out on the copier – whatever funny or weird stories you have about holidays at work, I want to hear them. And also, any questions that you have holidays in at work – whether or not to give your boss or your coworkers a gift, how to get out of working New Year’s Eve, whether you really have to attend the office holiday party – whatever you’re wondering about, send it in. There are two different ways to submit your stories and questions. You can record them on the show voicemail by calling(855) 426-WORK. That’s 855-426-9675. Or, you can record a sound file on your phone and just email it to

That’s it for today! Thanks for listening, and I’ll be back next time with more questions.