The Remote Manager’s Manual with Katie Womersley | DistantJob - Remote Recruitment Agency

The Remote Manager’s Manual with Katie Womersley

Luis Magalhaes

Today’s guest is Katie Womersley, a champion of remote work from Buffer, where she works as VP of Engineering. Her writing about management and tech leadership has been featured in The Next Web, Inc Magazine and Fast Company, to name but a few.

Katie Womersley

Read the transcript

Luis Magalhaes: Greetings, ladies and gentlemen. Welcome to another episode of the DistantJob Podcast. I am your host Luis, head of marketing at DistantJob, and DistantJob is, as always, a podcast about how to build and lead incredible remote teams.

Luis Magalhaes: And with me today, my guest is Katie Womersley, and Katie is a champion of remote work from Buffer, where she works as VP of engineering and she’s been featured in several outlets as The Next Web, Inc. Magazine, and Fast Company, but she is also very prolific in her writing, and there’s quite a bit of writing if you want to check it out later. I will include it in the show notes, of course, but welcome Katie.

Katie Womersley: Thank you so much, Luis. It’s really great to be here.

Luis Magalhaes: Yeah, well, it’s great to have you. Now, just for our listeners’ benefit, I’m going to tell them a bit about DistantJob and what DistantJob does very briefly. DistantJob basically is here to help you build awesome remote teams. If you’re starting out, you have a lot of things to worry about, you’re trying to build your MVP, and trying to hire the best talent from all over the world might be a bit overwhelming. So we handle search, we handle scheduling interviews, and we even handle payment, HR, and whatever perks you want to give your employees. Basically, you get your great, awesome employee to create awesome stuff with you, and we handle all the red tape.

Luis Magalhaes: We work with starting companies, but we also work with companies that are already established but haven’t given the jump to remote yet and are having some questions about how to handle their usual processes, how to change their usual processes. So we help you with all of that. This is what DistantJob does.

Katie Womersley: Amazing.

Luis Magalhaes: Thank you for writing so much about management. Some stuff is super interesting. You write mostly on Medium if I’m not mistaken.

Katie Womersley: That’s right, yes. I try to write on Medium, and I’m glad you think that I write a lot because I often feel quite embarrassed at not having written nearly as many vlog posts as I intend to.

Luis Magalhaes: No. Life gets in the way, right? Okay. There are so many things that I want to talk with you about, but I really want to … I guess that we should start with Voltron.

Katie Womersley: Yes. Building a manager Voltron.

Luis Magalhaes: Yes, exactly. It was a very funny analogy. You talked about building your Voltron when you were talking about something resembling building a peer group in an interview. Can you elaborate a bit about that? How important is it for a manager managing remote teams to have a peer group and what does that peer group look like and how did you come to get to the Voltron reference?

Katie Womersley: Absolutely. I think building a peer group as a manager is very important because management can be a fairly lonely job. You’re not the friend or the direct teammate of the people you manage. You’re on the team, but also you’re separate, and you need to maintain that presence but separation to be an effective manager. A failure mode for many managers is when they don’t successfully that sense of separation. What can happen there is you could end up being overly helpful which your teammates might call micromanaging. You might call it helping them a lot. Another thing that can happen is when managers don’t have sufficient support from their managers or their within-company peer group, and then start trying to meet whatever want or hope of support with their direct report.

Katie Womersley: So you get the, what I sometimes call the reverse one-to-one where the manager goes into a one-to-one with the teammate and ends up talking about their problems half the time, not in a way that’s useful for sharing context, in a way that’s really downloading on that direct report which is very unhelpful. That person then leaves the one-to-one, their problems aren’t solved, but even worse than that, they’re now taking on their manager’s problems and they’re feeling a lack of confidence in the organization because they think, “Wow. My manager’s not really coping.”

Katie Womersley: The manager’s support from peers is really important to prevent this, and with a remote management job, you’re looking at this in extra hard mode because you’re not getting the consistent social reinforcements and social recognition and support from being around people in the office. You’re at home by yourself a lot of the time or in a coworking space, and you’re quite physically isolated. And when you combine that physical isolation of being a remote manager with the general sense of leadership being often a lonely and isolating job, remote managers can be more likely than co-located managers to fall into these negative patterns of being overly helpful or micromanaging because they’re trying to connect because at the end of the day they’re lonely and they’re not sure of their value or of not having their need for support met so they’re downloading on a direct report.

Katie Womersley: If you’re a remote manager, it’s important that you are getting the support that you need to make sure that whatever’s going on for you is being addressed before you go to support your teammates. And this is where having other managers that are also remote managers maybe at your company, but for me it’s more typically being people at other companies. In Slack communities, the Rands Leadership Slack community is great, and there’s dedicated channels for remote work. And there’s also a Slack group called Engineering Managers Slack aimed at newer engineering managers, and we’ll put these in the show notes, and they have remote work focus there as well. And there’s a lot of remote work communities. Twitter can also be a good source, I found, for making friends with people.

Katie Womersley: And it’s very, very helpful as a remote manager to understand that the battles that you have are not unique to you. If you are struggling with how to get your team to be more collaborative, that’s a normal remote leadership problem. Everyone else is struggling with the same thing. Nobody has it all figured out and shiny. Some people might have it more figured out and they can share lessons. Other people, you’re going to find, are struggling with something that is actually going really well on your time, and I have often found that it’s when I talk to leaders of other remote teams, I’ll often end up feeling a lot more confident, a lot more positive because I’ll hear about problems that I don’t have at that point in time and I’ll remember all of the things that my team is doing really well and all of the things that are going great.

Luis Magalhaes: Yeah. I really like that point because sometimes we’re listening to podcasts or reading interviews or something like that or TED Talks and it looks like everyone has got their stuff together so well. It’s nice to know that everyone is struggling with a part of the process or with something.

Katie Womersley: But you know, nobody writes the blog post which is, “I have this problem, and I don’t have the solution.” People only write the blog post once they’ve figured out, right? So if you’re looking at the [crosstalk 00:07:26]-

Luis Magalhaes: I’m going to start doing that. Maybe some people might-

Katie Womersley: Maybe we should do that. Yeah.

Luis Magalhaes: Maybe I can just outsource people solving my problems, and that’ll be [inaudible 00:07:34]. I’ll just write [inaudible 00:07:36] my questions.

Katie Womersley: Just all the things I don’t know how to-

Luis Magalhaes: [inaudible 00:07:39] Go internet. Attack this.

Katie Womersley: That would probably work. I’ve done that with Twitter sometimes. Hey Twitter, what do you think about this? Yeah.

Luis Magalhaes: This is probably the most positive use of Twitter that I’ve heard in a long time. So cool. Okay. One thing that you wrote about that I found very interesting and I actually started doing, it’s not finished yet but I’ve started to work on it is actually you built your own operating manual.

Katie Womersley: I did.

Luis Magalhaes: Yeah. I wish everyone that I would interview would do that. It makes my work so much easier. But anyway, there are a couple of things that you mentioned that, and I wonder, you say that you want overcommunication from your direct reports. You want them to communicate with you in excess, better to communicate in excess than too little.

Katie Womersley: Not at all.

Luis Magalhaes: But you wrote about the story where you realized you were being unfair to one of your employees because you were not focused, you were scattered, and that wasn’t really helping him or her. I don’t recall who the employee was. But anyway, the employee called you out on being unfocused, and [crosstalk 00:08:56] made you realize that it was also important to have a purposeful focus and to do deep work. What are some tips and tactics that you found to keep the balance? To on one hand ask for overcommunication, but then on the other hand, you do need time for deep work which is, it’s kind of not possible when Slack is buzzing constantly.

Katie Womersley: Well, Luis, I have a blog post about this.

Luis Magalhaes: Cool. I missed that one. [crosstalk 00:09:23]-

Katie Womersley: I’ll send it to you for the show notes. Yes, I ask my direct reports to overcommunicate with me because in a remote setting, what I want is communication and most people think that they are communicating outwards enough information, but the person on the other side often feels like they aren’t receiving enough information. So I ask people to try and overcommunicate. I’ve actually never had the experience where I felt they really are overcommunicating. Typically when people make the effort to overcommunicate, the balance we end up with is I have an idea of what’s going on with them and it feels about healthy.

Katie Womersley: That’s why I specifically ask them to try to strive for overcommunicate, almost overcorrect because in a remote setting, the main breakdown that you see is a lack of casual communication. You don’t walk past somebody on your way into the building and say, “Oh, I forgot. I wanted to ask you, did you give me access to that admin panel I asked for yesterday?” “Oh, sorry. It slipped my mind.” That kind of thing will happen in a building. Remote work, those little opportunities don’t happen, so there’s a huge amount of communication that just gets completely knocked out there. That’s why I ask for overcommunication.

Katie Womersley: How do I then balance that with getting anything done, being really present in one-to-ones, and yeah, I have been called out on being unfocused in one-to-ones. My face is quite expressive. If I have a Slack notification pop up on my screen, you will see my eyes read that. You will see me start think about the Slack notification, and it is very obvious that I am not focused on the direct report who I am having the one-to-one with or the one-to-one with my boss, whatever it is. What I do about that, I have do not disturb on my computer enabled at the operating system level at all times, so I never have notifications pop up on my screen.

Katie Womersley: When I’m doing a podcast, right now, all I am doing is this podcast. When I’m in a one-to-one, all I’m doing is that one-to-one. I also have my Slack permanently set to offline. It’s a gray dot all of the time. People still Slack me a lot, but I don’t have the Slack icon jumping up, making sounds, pushing notifications onto my screen because I found that that made me less effective at whatever it was that I am doing. What I do do is people will communicate as much as they want. You can send me 28 Slack messages, that is not a problem whatsoever.

Katie Womersley: I’m not going to be reading them while I’m in the podcast, but the minute I hang up this call at 10:00 a.m., I have half an hour blocked out on my calendar and I’m going to go into Slack and what I am doing then is communicating back. I’ll reply to all of these messages. I will make sure to close that loop. I will get back to you. If somebody is ending up in quite an involved back and forth Slack conversation where the way I’m working a little bit asynchronous, I’ll jump in the Slack for half an hour, but then I’ll have another meeting and I’m not going to be on Slack in a meeting, right? I’m going to be in the meeting. I will ask them to move it to a one-to-one agenda.

Katie Womersley: If it feels urgent, I will say to them, “Look. At 3:00 p.m. my time, 6:00 p.m. your time, I know it’s a bit late, but this seems urgent for you. Let’s have a quick call.” And I’ll pop that 15-minute call on the calendar. I’ll move it into a time. That’s what I do to make sure the communication stays flowing, but that I am having that deep workflow and that focused time. And why that’s important especially as I manage managers is I want every manager at Buffer to be fully present for the task they’re doing. If you’re in a one-to-one with a teammate, that teammate for that hour is your whole world. You are not looking at your Slack notifications. If you’re replying to Slack while you’re in a meeting with somebody else, you are wasting the time off the person that you’re in a meeting with, right?

Katie Womersley: And similarly for ever engineer, I want every engineer on my team to feel like when you’re coding and you’re solving a bug or you’re in the flow, that is your full focus. That problem is all that matters in the world for you right then. It’s not only okay, but it’s encouraged to have that focused time. I do expect you to come back for Slack. Don’t go and have focused time for three days straight and we don’t know if you’re alive or dead. I expect that you will, at some point, you’ll come back after lunch or at the end of your day, you will return and answer those messages.

Katie Womersley: And within your workday, I will expect your response. If I Slack message somebody, I’m not going to be waiting there for them to respond right away because they’re probably doing their job and that’s what I want from them. And they want me to do my job too, but at some point they’re going to come back into Slack, when it works for them, and they’re going to reply. And if we need to have a back and forth that feels very synchronous, but I’m in a meeting and they’re in a meeting and our schedules don’t line up, we’ll book a time for it. We’ll be like, “Okay. I can see you. In three house let’s hash this out.”

Luis Magalhaes: Yeah. Yeah. Okay. That’s very interesting. I definitely can feel the similar thing. I actually drove an internal campaign in my company to replace Slack and Trello, which we were using just by Basecamp, simply because Basecamp is much less intrusive when it comes to notifications. But yes, definitely a good Slack hygiene I find is very important.

Luis Magalhaes: I want to move onto some other things. One of the things that you want to do is help others see more clearly than they do. I read this as focusing the talent that they already have, and this is something very interesting and it’s something that I’ve written in the past. I want your opinion on this because there are things that we all know, and especially if we’re experts in our field, but sometimes we just forget. We just get caught up in the moment. It’s a bit like when we’re driving, we’re just driving. We get to the place that we were driving to and then suddenly we think, “What happened on the way here? It’s like I sat in my car and then I arrived. And I don’t recall anything that happened in the way.” This is definitely something that I find super interesting, and what are some mental jiu-jitsu tricks that you use to help people access that knowledge that they have?

Katie Womersley: Luis, just to recap your question so I make sure I answer it right. You’re noticing the way I lead I will tend to prefer to coach people or help them see more clearly the problem that they have rather than tell them exactly what to do to solve their problem, and that is how I try to lead and I believe that that is effective for … I think it’s effective in general, but specifically in software engineering, it’s very important that we are developing people’s critical thinking skills and their judgment. Telling someone what to do actually undermines their critical thinking and undermines their judgment, so it’s just unhelpful to say, “Do X.” That’s why I put it in there.

Katie Womersley: And you’re asking, so what about the how. How is it that you do this? How do you help somebody see a problem more clearly when they might be in a state of unconscious competence, where they’re doing something very well but they don’t know what it is that they’re doing? Yes. This is something that I see quite often if I’m working with, say I’m doing a skip-level one-to-one with a very senior engineer who is trying to get better at teaching other people to be a good mentor. This is a case where often senior engineers are great teachers, but we now want them to scale that and help other engineers become great teachers, but this is a case of unconscious competence where that senior engineer might just naturally know how to pare in a way that works, how to pare code in a way that works.

Katie Womersley: And they’re having a lot of time sharing that skill and telling others, “Here’s what I do when I’m mentoring someone. This is how to be a mentor.” They’re like, “I don’t know how to explain it. You just kind of mentor.” But it’s important that they do explain it because we want mentoring to improve at Buffer and for that individual’s career progression. For them to get promoted to the next stage, they need to start developing the mentor skills of others. So they are now blocked a bit in their career and this is my job to unblock.

Katie Womersley: If we take that example, one of the tactics that I use quite effectively there is to ask a lot of questions because people know the answer, but they’re having trouble accessing it. Asking them questions like, “Tell me about a time where somebody … Do you remember a time where somebody had a concept just click for them for the first time? You were mentoring, and you saw that time click.” And they say, “Yes. I remember recent time.” And then I go, “Okay. Describe everything you were doing before that.” And it’s almost a bit like rubber duck debugging, and they say, “I did this and this and this.” And then I say, “Okay. So you’re describing it as you remember the actions, so which one of those do you feel had impact there? Which one of those actions do you feel … And you know you know the answer, we’re just trying to access the answer.”

Katie Womersley: So I ask these kind of targeted questions, leading the person through their thought process to access the description of the knowledge they already have. I also often do this when somebody comes to me with a problem that I know they can solve. I know that they don’t need me to tell the the answer, but for some reason they’re sort of spinning around in their head, often maybe they’ve lost confidence, they’re overwhelmed by details, they can’t remember what’s important or why they’re trying to solve the problem. And I’ll use a very similar tactic there where I’ll ask a lot of leading questions. I’ll say, “Okay. Why is it that you’re trying to solve this problem? What is the goal here? What matters to you?” And often then starting with the goal is helpful. And sometimes they’ll get there quite fast. They’ll say, “Well, my goal is to have a single source of truth or state management,” and then they’ll go, “Oh, okay. I know exactly … I’m going to go and talk to this one and that one.”

Katie Womersley: So asking what’s the goal, and sometimes you’ll need to ask a lot of questions and keep kind of asking questions, but the important thing here is not to slip into the situation where you think you know what the teammate needs to hear so you just tell them. That is then telling them what to do and you’re not helping them develop their judgment and develop their critical thinking. So keeping asking those questions when you’re helping them develop their judgment is important. There are cases, though, where I will just give direct advice. Sometimes people are, they’re stuck in a bad state and they literally they do not know how to solve the problem. There are cases where you actually, as a manager, you do need to step in and say, “Look, I think you should do X,” or even, “You need to do X now.” You need to give that employee feedback, and it needs to be written feedback, “This needs to happen.”

Katie Womersley: So there are cases, you know, you can’t coach forever, and as the manager it’s important there that you are aware of when is it that you’re helping somebody develop their judgment and their critical thinking, so you’re coaching by asking questions, and when is it that this person’s actually in a critical position and the most important thing for you to do as a manager is help them get the task done. So what are the consequences here of this going badly? Is it okay for it to be a learning opportunity? 90% of the time, it’s better for it to be a learning opportunity, but there is that 10% of the time, especially when the stakes are high, when actually a business critical project might just fail or somebody might end up unfairly getting fired. Don’t then coach. That’s when you should step in with, “Here’s what to do.”

Luis Magalhaes: That would be an instance where it would be preferable to give the direct answer, but I absolutely agree 100% with that because certainly … And this ties into another thing that I wanted to talk about which is something that I read your article, and I felt that we had a common experience because you talked about you being a manager. You were a manager while you weren’t as good at the technical work as some of the people reporting to you, and I had that same experience because when I became head of marketing, I certainly wasn’t the person who knew the more about ads or the more about social media marketing or the more about this, but I did have the knowledge to tie all the things together and to help people find their best at forward, and I think this is something that most people that get promoted to managerial positions don’t get. They feel a bit of an imposter syndrome, so if you can tell a bit of when …

Luis Magalhaes: Tell me about the day you realized that having the benefit of the bird’s eyes view, you could really lead your people to doing best what they were already the best at doing?

Katie Womersley: Right. Well, it kind of came, funnily enough, from talking with engineers and realizing as a software engineer myself and talking to my teammates about where do you see your career going, what is it that you want to do, and a lot of them wanted to remain software engineers for the foreseeable future or even their whole careers. And they would say things like, “I want to be the best possible engineer I can be,” or “I aspire to be like this famous engineer.” And they wanted to be at the top of their game specializing and being experts, and I realize that relatively few people wanted to get promoted out of software engineering where they abandon it entirely and were mostly doing a different job.

Katie Womersley: And management is a different job to software engineering, right? Of course they’re related, but different. And that sort of got me thinking like, well, if my teammates are going to become the best in the game at a specific expert skill, there’s a very different role where the manager can’t then be aiming to be better than them at every possible skill. You’re not going to have a manager who is a better front-end developer than the most senior front-end developer and also a better site reliability engineer if you’re managing cross-functional teams, and it might be the case that the manager happens to have the deepest technical expertise. But as an organization if you optimize for the manager always being the best, two things happen there that hurt your time. The first-

Luis Magalhaes: They can’t manage.

Katie Womersley: Well, the first is they’ll need to spend a lot of time keeping their skills at the top of their game. Yeah, they can’t actually do the people management side of it, but if your managers need to remain technically better and stronger than their direct reports, they have an incentive to not grow their direct reports. In fact, they have an incentive to keep their direct reports back because if the manager needs to be technically the best, then that manager … If a senior engineer says, is doing really great and is growing and becoming stronger and stronger and stronger and they’re coding eight hours a day and that manager needs to remain better than this engineer, there’ll come a time where the manager’s incentive is going to be almost to sabotage their direct report, right? Which is entirely dysfunctional.

Katie Womersley: And the second thing which you don’t really see that happen too often, luckily managers generally don’t, but the second thing you’ll see there is you’ll end up losing your best engineers and end up creating unhappy mediocre managers where instead of having a team of really strong expert engineers that are doing a very specialized job incredibly well, you end up having a team of unhappy and not very good managers because they don’t want to do the management job doing management poorly. And the engineering team is being impoverished as the best engineers get harvested out into management. And the management team is looking very weak because if you go over and sit in in a meeting of managers, everybody is like, “I just … Get me out of here. I can’t even face the day.”

Luis Magalhaes: That sounds terrible.

Katie Womersley: That’s a low-performing team.

Luis Magalhaes: Seriously? I wouldn’t-

Katie Womersley: Yeah.

Luis Magalhaes: I don’t see why. I don’t see why, but … Yeah. Yeah. You touched on something interesting which is career progression. Something that I usually say to people on my team which is the opposite of sabotaging them, at least I hope it is, it’s like, “You know, the best thing you can do for me is get me out of a job. If you can do whatever I do better than me, then I’m the happiest person in the world.” But that said, it’s not always that direct because, again, what I’m doing is management and that person, they might want to improve, but not necessarily into a management role. So how do you try to incentivize the kind of upward mobility in your team?

Katie Womersley: Well, I do think that the manager’s job, as you say, there’s often a lot of overlap between other types of roles, and there’s a reason why everybody dreads the micromanager who gets overly involved in the details. It’s because managers often are close enough to the details that there is some overlap in that job, especially when it comes to the priorities, visions, strategy, that side of the work. That’s often work that’s typically manager work that a direct report that’s doing a specialized individual contributor role could take on, would take on very, very well, and might even do better than the manager themselves. There might well be things that, as a manager, you’re doing that you don’t have to be getting the context of all of the individuals on the team.

Katie Womersley: What that is varies completely depending on your work as a manager, but in general this is something where one-to-ones are really important where you want to know what are the strengths of your teammates. Don’t delegate a task that you know that they’ll be terrible at because at the end of the day you do need to deliver results, right? So know your teammates’ strengths, that’s the first thing to know. And then secondly, know your teammates’ interests. And then thirdly, look at what you are doing as a manager and see is there anything you’re doing that could possibly be a good fit for your teammates’ strengths and interests.

Katie Womersley: They’re interested in doing more project management, and you feel like they’d be competent at it. Are you currently doing quite a bit of project management yourself as a manager? If so, think about how that can be delegated to your teammates to help them grow. And often managers don’t do this because the teammate is not going to do that new task as well as the manager was doing it because the manager’s practiced at it, so my rule there is if your direct report is going to do that task 70% as well as you would have done it, delegate it. If it’s going to be less than 70%, you need to train them before you can delegate. If they’re going to be doing it more than 70% as good or even better than you, that’s a growth moment for you as a manager to reflect on you should have delegated that task a long time ago and you’re probably micromanaging if you’re at that point.

Katie Womersley: Yeah. So look at the skills and the interests of the direct report, look at your own workload, and see are there tasks here that I can delegate where a direct report is going to do it 70% as well as I do. Delegate that. Managers often then don’t want to delegate because they are afraid of, “What am I going to do if I give away my work? I just sit here. If all the work’s getting done, what’s the point in me? And then the organization might realize and fire all the managers, and I’m out of a job.” People are scared rationally of getting out of a job, right? You need the job.

Luis Magalhaes: Yeah. I never understood that. I always figured that-

Katie Womersley: Yeah, let’s talk about that.

Luis Magalhaes: I always figured that if the people under me do a better job than I do, I figure I can probably find something else to do. [crosstalk 00:29:36] better. There’s plenty of work to go around always, and I think there’s always room for people that can groom other people to take their place because [crosstalk 00:29:47]-

Katie Womersley: Absolutely.

Luis Magalhaes: Because mobility is upwards, right?

Katie Womersley: Absolutely. And on that note, two things that come to mind there are Andy Grove’s famous saying from High Output Management which is, “The manager’s productivity is their own productivity plus the productivity of everybody else reporting to them.” So if one of your directs becomes more effective because they’ve leveled up, you as a manager are more effective. That is the job. And the second thing there that comes to mind is that busy is an [inaudible 00:30:19] for managers. If as a manager you’re rushing around and you’re busy, busy, busy and you’re doing lots of things, that is not a good place to be because it means that you’re probably not stepping back and seeing the bird’s eye view. It also means that you don’t have the energy and the time to actually help solve problems with your direct reports when they come to you. If you’re rushing around like a headless chicken because your to-do list is exploding and your email and your probably way in the weeds, and that busyness is not a good sign.

Luis Magalhaes: No, no. Not at all.

Katie Womersley: Yeah. Yeah.

Luis Magalhaes: I love your rule of thumb of 70/30 because that’s a number that for another kind of thing. And, again, it bring to the how important it is to talk about these things because I totally have that mentality on another aspect of management and I didn’t think about this in this context. The context where I usually use is when someone comes with me with an idea and I might disagree with them but, again, if it’s not something that’s going to put their job in jeopardy, if it’s not something that’s going to cause a huge mess of problem for the company, if I think that there’s 70% chance that it won’t work but there’s 30% chance that it will work, I tend to let them do it simply because I think that if I tell them, “No, that’s not going to work, and it’s not going to work because this, this, and that,” that person will probably not be very happy whereas if I give them the chance either they’ll fail and they’ll get part of my experience, they’ll know why I didn’t think it would work instead of me telling them. But, hey, if this succeeds, then it turns out that I was wrong. And I learned something [crosstalk 00:32:05]-

Katie Womersley: Right.

Luis Magalhaes: And I learned something. I want to ask you about how do you feel about this. When do you feel it’s okay to let people make their mistakes and learn from them?

Katie Womersley: I think making mistakes is so important and at Buffer we have a Slack channel called culture and mistakes where we share and celebrate mistakes. And the way I like to talk to my team about making mistakes is when you’re doing anything, say you’re making a decision, the rule of thumb is if you can reverse it, do it. Don’t optimize for getting it right if you can walk it back, if you can undo it, just go ahead. Just do it. If you can’t reverse it, then you might want to think a bit more about that, talk to your manager, but there’s relatively few decisions when it comes down to it that are actually irreversible. Most times you can fix whatever it is. And the ones that really are irreversible, we tend to know what they are. They’re a little more obvious.

Katie Womersley: I say that often to my team. If you can reverse it, do it. Just go ahead, default to action. Don’t default to asking for permission. And when people do make mistakes, we like to share and celebrate what was learned and again here you get mistakes that are healthy to make because they are learning opportunities. And then you get mistakes that are going to put you out of business. So we don’t want those, and that’s why we talk about it in this way. If you can reverse it, do it. Because the mistakes we don’t want to make are the irreversible mistakes. We’ve made a mistake and we can’t really recover from it.

Luis Magalhaes: You know that’s so funny-

Katie Womersley: Those are rare, but if you’re facing that situation, that’s the time when you don’t want to optimize for learning in that case. Everything else, optimize.

Luis Magalhaes: That’s so funny because what I always tell the president of DistantJob is that I’d rather ask for forgiveness than for permission. Definitely and same there. I also read some things that you wrote and interviews that you did about conflict resolution, and I’m pretty sure that you’ve already been in a position where you had someone who was just a superstar. They just carried the team and they did incredible work, but they were just very hard to deal with and they were making everyone else on the team miserable. I think that every manager has had this person in their lives at some point. And sometimes these people are below the chain of command, so you can try to coach them, but other times which I find harder to deal with is when they’re above the chain of command. How would you deal with each one of these situations, with someone that is a direct report or maybe the person that’s causing the trouble is actually, you were one of those people’s reports? How do you deal with the two different situations?

Katie Womersley: Right. So you’re asking me what do you do about the brilliant jerk, as we call them in the industry. This is the person that they’re brilliant, they’re so talented, but they make life miserable for everyone else. And what do you do about that situation? When A, this person is your direct report, what do you do? And B, what happens when you are their direct report, when your boss is a brilliant jerk? And this is the question, right?

Luis Magalhaes: Yeah.

Katie Womersley: Yeah, great. Okay. When your direct report is a brilliant jerk, I have a very simple rule for that. I don’t care how brilliant you are if you’re a jerk. You’re not going to be on my team. I will fire that person. I won’t suddenly fire them out the blue. I’m going to talk to them about the impact that they’re having on the team overall, but if I have one person who is doing great work themselves, but they’re making this not a good place for everybody else, what they’re doing is they are having a negative impact on everybody else’s productivity. Every other team member that they come into contact with is less effective and less happy at work because of this person’s presence, and if you add up that negative impact on every other person of this brilliant jerk’s jerkiness, I think you generally find that the costs of the jerkiness far outweigh the benefits of the brilliance.

Luis Magalhaes: Yeah, that’s true.

Katie Womersley: The other thing that I have found is that the teammates that are traumatized by the brilliant jerk’s behavior, often they are brilliant non-jerks themselves, but they’re not being so brilliant right now because nobody wants to go to work and give their best and be creative and share ideas in a meeting when there’s somebody there that’s going to make them feel awful about themselves and shoot them down and make it a horrible place to work.

Luis Magalhaes: That’s fair enough.

Katie Womersley: So that’s why my tolerance for a brilliant jerk on my team is literally zero. We’ll have a few conversations. If you continue to be a jerk, this person is going to be let go because they’re not making the team effective.

Luis Magalhaes: What does that conversation look like?

Katie Womersley: The conversation around, “Hi, you’re a brilliant jerk. Let’s deal with this?”

Luis Magalhaes: Yes. Yes. [crosstalk 00:36:58], please. I assume it’s not just it. It’s not as easy as just, “Hey, you’re a jerk. Stop it.”

Katie Womersley: No one thinks their being a jerk. People are rational people. Everyone thinks from their perspective they’re being totally rational. So how the conversation goes is I will have very specific examples of behavior, and it’s a very unemotional conversation where you sit down [inaudible 00:37:22] brilliant jerk. I’ll say, “You know, Luis. Yesterday I saw a code review, and here’s the code review I noticed. You made this comment, you said “This is a completely unacceptable way to do things. It should be perfectly obvious that blah blah”. These are the exact words you used. So, Luis, the impact on the other person of these words is they are probably never going to try this kind of approach again. They’re probably not going to be very creative. It wasn’t obvious to them. That’s the impact of the behavior.”

Katie Womersley: So you explain the behavior like you’re a tape recorder. You don’t say, “Luis, you’re a jerk. It’s a problem.” You say, “Luis, when you said “completely unacceptable” and “it should be utterly obvious”, when you use the word “completely unacceptable” and the word “utterly obvious”, the impact of your behavior on the other person was this.” And you explain the impact. You then explain why this is a problem. I’m like, “Luis, if you continue to give code reviews in this way, your teammates are actually going to write worse and worse code, and that is a problem for me because I’m seeing my team get worse and worse over time because of your actions. If your behavior continues to be negative net impact on the team, I want you to understand that it’s a very, very serious situation. Anybody that is a negative net impact, whether it’s because they [inaudible 00:38:37] production ever other day or whether it is because they’re behavior ends up having such a demotivating effect on their team, that person isn’t going to stay on this team. So I want you to understand how serious this feedback is.”

Katie Womersley: But, again, I’m not saying, “Hi, you’re a jerk.” I’m not making any value judgments about this person. I’m not saying they’re a bad person. I’m just saying this is the exact behavior, like a tape recorder, this is the impact of this behavior, and this is why it’s a problem. And then I’m going to tell the person very specifically what they need to do instead. I’m going to say, “Okay, how I want you to do the code review is say, “There was an alternative approach. This is the alternative. It makes sense that you chose to do ABC. I understand why, but this is why it’s not effective.”” And I’ll tell them exactly how to do it right. Most people are not intending to be jerks. If they are unintentionally a jerk, this is going to work. Tell them exactly how to be nice and to be a team player, and if they want to be, they’ll do it. First educate them. If the person actually is some kind of bizarre sadist and just wants to hurt their teammates-

Luis Magalhaes: Yeah, that’s [crosstalk 00:39:43]-

Katie Womersley: It’s probably not the case, but they’re not [crosstalk 00:39:47]. You’re going to end up having three of these conversation, then you have a conversation like, “Look, this is the situation.” And then depending on where you work, you’ll probably need to get HR involved, all the rest, but if somebody says, “Look, I just love making my team members cry. I completely understand the impact of my behavior, but I’m going to keep doing this for fun.”

Luis Magalhaes: That never happened. Is this a conversation [crosstalk 00:40:06]-

Katie Womersley: That has never happened. Yeah, that has never happened.

Luis Magalhaes: Well, you know, points for honesty at least. I do think that in most cases some people just have a mental block that tells them that the way of doing it without being a jerk either takes too much time or I think they see their jerkiness as a bit of matter of practicality. It’s the quickest to [crosstalk 00:40:30]-

Katie Womersley: Right. Well, they have whatever reason for their jerkiness. All I’m interested in is the behavior. And that’s an important thing. As a manager I’m not trying to change someone’s psychology. I’m not going to try and change their world view. I’m only trying to change one thing: their behavior at work on my team. That’s all I’m trying to change about them. They can continue to believe and think whatever they want because their private thoughts and emotions are not something that I own. Their behavior, thought, is something that needs to have a positive effect. And often brilliant jerks end up being and staying brilliant jerks, and it’s career-limiting for them because eventually they get to a manager like me and they get fired, right? But often managers are too scared to lose the brilliant part so they don’t want to upset the brilliant jerk, so they never talk to that person about the jerkiness.

Katie Womersley: And often that person wasn’t intending to be a jerk. They just didn’t understand the impact of their behavior, and because this has gone on for so long it’s literally just a habit. They’re used to treating things badly, and they’re used to getting away with it because they’re used to being that brilliant diva that no manager is brave enough to risk upsetting.

Katie Womersley: I have seen that happen where you sit down and have a conversation and the person says, “Wow. I had no idea. No one has ever told me. I get it. That would be horrible. I would be devastated if someone did it to me, but no manager ever told me it was a problem and this is literally the first time somebody’s being honest with me about my behavior.”

Luis Magalhaes: That sounds like a case well solved, but what about when the jerk is the boss?

Katie Womersley: When the jerk is the boss that is difficult and, honestly, I would say that you can try to give your boss feedback in the same way. You explain, “This is behavior that I noticed, and this is the impact it had on me. And this is how it didn’t help you, the boss. When you did X, the impact it had on me was … When you sent me that two-line email that was very terse, the impact was that I was just really confused about what you want so I ended up not delivering the outcome that you needed to push the project forward because I didn’t understand what you wanted. Would you be willing to write me a longer email?”

Katie Womersley: You can do that kind of feedback with your boss and that might help, but honestly if you’re boss is a brilliant jerk and the jerkiness is really difficult, if you have a good relationship with your boss’ boss, if they do regular skip-level one-to-ones, they should, but many bosses don’t, you can try and talk to your boss’ boss about what you’re struggling with, but you need to know that’s a high-risk situation because it can get back to your direct boss. It could come across as talking around their back or going over their head. It could have consequences for you.

Luis Magalhaes: Yeah, definitely. [crosstalk 00:43:13]-

Katie Womersley: And honestly, it’s very delicate and this may be a case of can you accept working for this brilliant jerk? Are you learning a lot? Is it overall worth it? Can you compartmentalize out the jerkiness and not take it personally? Might be worth it for you to stay in the situation. If you cannot accept it, and truly accept it, not just complain every day about your boss endlessly and be toxic, if you can’t accept it, the best thing might just be to move on, and-

Luis Magalhaes: But even if you can accept it, even if you can accept it and you can prevent it from affecting your performance, but you still notice it, notice that it’s affecting the performance of the other people in the team … Because at some point if you’re really committed to your project and to your company, it’s not just about you, how you feel as an employee, it’s about how the people to your sides are working and being affected. Very rarely a boss is a jerk just to one particular person, it’s usually [crosstalk 00:44:08]-

Katie Womersley: Right, they might be a jerk in general.

Luis Magalhaes: Equal opportunity jerks, right?

Katie Womersley: Right, right. I would say the same thing applies. It’s like you can try to explain to your direct boss the impact of their behavior, “I notice that Maxine was less effective this week because I think she got quite upset when you screamed at her in the meeting and it distracted her a lot. Maybe if you don’t scream … ” You could try that, but you would need a boss that has a low ego and self-awareness to not shoot the messenger. He could end up then just screaming more at Maxine because Maxine got upset. Maxine could get upset that you went behind her back. It is all very delicate. Again, you could try and talk to the boss’ boss if you feel like there’d be a good situation, but that is quite tricky.

Katie Womersley: I personally would default to the same as the direct report situation where it’s a candid conversation, and in that case it’s like, “We are not going to remain on the same team. Either you need to change your behavior or we don’t remain on the same team.” When I’m the boss, it’s the direct report that’s going to leave the team. When I’m the direct report, I’m the one that is going to fire the boss. I’m going to walk out. I’m going to make it very clear. I’m going to sit down and be like, “Listen, manager. This is the impact of your behavior. This is what’s happening. This is what I’m seeing happening on my coworkers. This is not an effective workplace for me to be. I am resigning because of your behavior.” That’s a very extreme situation, but if that is truly how you feel, that is an outcome that one can do.

Katie Womersley: I think it’s important to remember that you’re never trapped with a boss. You can always, in a sense, fire them and get yourself another boss. What that looks like is you quit and you go job hunt. But, realistically-

Luis Magalhaes: It’s intimidating for a lot of people, but it’s absolutely doable. It’s absolutely doable.

Katie Womersley: And I do want to recognize that in tech there’s a lot of privilege. If you’re not working in tech, this might sound like very privileged advice, and it is, and it’s also very easy to hear from somebody who’s VP engineering like, “Oh, well. Just walk out. Quit your job.” I do just want to recognize that is quite an extreme thing, and for many people it might just be get yourself a career coach and work through that specific thing. Make sure you’re getting the support and dealing with a toxic boss is really hard. Take care of yourself and sometimes you can’t change that individual’s behavior as much as you’d like to and all you can change is yourself. You can change how you perceive the situation, how you deal with the situation, and you can change whether or not you’re in the situation.

Luis Magalhaes: Yeah, absolutely. I would also add feel obligated as someone who works in a hiring company that you usually have more mobility than you think.

Katie Womersley: Thank you think, yeah. Yeah, I agree with that.

Luis Magalhaes: You usually have more options than you think, but when you’re inside that box, you can’t see no way out, but most people have more mobility than they think. Since we are on conflict, I also read something that you do. I don’t know if it’s you in particular or if it’s common practice at Buffer is when there’s a conflict inside the team, you organize and moderate the meeting about that conflict. And I’d like to know what’s that conversation like? How do you … Is it like going to see a counselor, something like that?

Katie Womersley: It really depends on the conflict. Some conflicts, yes, we will organize a meeting and we will mediate that conflict. There are conflicts where mediation’s not going to be appropriate. For example, I’m not going to try and mediate a situation with the brilliant jerk we just talked about. I’m just going to give that person feedback, and they must change. But sometimes there’s a situation where there’s conflict, and it’s healthy constructive work conflict. For example, we could use the one technical approach or we could use another technical approach. Both will work, both are valid, but we, as a team, are at disagreement about which approach to take, and right now we need to just choose one and move on. This is a case where mediation can help get in a team meeting, and it’s very important there that the goals are very clearly stated, what are we trying to achieve overall with this project.

Katie Womersley: And then we need to have somebody facilitating that meeting who doesn’t have a clear stance like you as the manager, if you’re facilitating. It doesn’t have to be the manager, but whoever is getting this meeting together to mediate, they’re only role is that we walk out of this meeting with some kind of solution that gets us toward our overall goal. And I’m not invested in which solution is as the mediator. If you are very invested in the particular outcome, you want us to choose React, you’re probably not going to be a good mediator. You need somebody neutral on the solution to mediate, and then you need the parties who have strong opinions on the solutions to come to, “Okay. What is a solution that moves us towards this overall team goal or company goal?” And the goal of that meeting is we walk out unblocked. We walk out with, “Our next step forward is we’re going to do this thing.”

Luis Magalhaes: What’s the conversation with those two? Well, I’m assuming two people, but I guess it can be a multi-layered conflict.

Katie Womersley: It could be team-wide, yeah. It could be two people or it could be team-wide. Yeah. I would say it varies a lot depending on what the actual topic is, but if you take a technical discussion, I like to take the case of, “What are you optimizing for when you want to do solution X?” And then ask the other person, “What do you think is helpful about their approach?” And get them to see the benefits of each other’s approaches rather than only the benefit of their own approach and the costs of the other one’s approach. Because it’s easy to look at your argument and see everything that’s great, and then you look at what the other one’s opinion is and you see everything bad, so one tactic there that’s helpful is just flip it around, “Tell me everything that you think is going to work about Luis’ approach.” And then mediator asks Luis, “Well, tell me everything that you liked and thought was useful about Katie’s approach.” And that can help people feel a little less attached to their own opinion and a little bit more like, “Okay, so these are just ideas. Ideas are neutral-

Luis Magalhaes: It’s essentially-

Katie Womersley: Which ones are going to get us to the common goal?”

Luis Magalhaes: Strong-manning, strong-manning the opposite opinion, right? Yeah. That’s a good-

Katie Womersley: That can help. Yeah.

Luis Magalhaes: That’s a good process. Okay. I want to be respectful of your time. We’ve been going for almost an hour now. The time flies. Thank you very much.

Katie Womersley: That’s fine.

Luis Magalhaes: Thank you very much for the conversation, but I do need to-

Katie Womersley: Thank you, Luis.

Luis Magalhaes: Give you the final trial which is the Chinese restaurant scenario. I hope you like Chinese food because you are organizing a dinner at the Chinese restaurant where there’s going to be a round table with the technology execs in Silicon Valley where they’re going to discuss the future of remote work. And since you are the host, you get to decide the message that comes inside the fortune cookies. What is that message?

Katie Womersley: Okay. The message inside the fortune cookie to a bunch of Silicon Valley executives leaders and they are discussing the future of remote work, and what’s the message inside the fortune cookie.

Luis Magalhaes: Indeed.

Katie Womersley: That’s such an interesting question. Let’s see. I might need to think about that. If I don’t think about something within about 30 seconds, I’m going to email it to you. It’s a great question.

Luis Magalhaes: It’s going to be a fortune email.

Katie Womersley: Yeah. [inaudible 00:51:59] asynchronous fortune cookie messages. Bunch of technology leaders, and they’re going to discuss the future of remote work …

Luis Magalhaes: I’m not trying to make this an awkward silence. I just don’t want to interrupt your train of thought.

Katie Womersley: No. It’s fascinating. Yeah. I guess I would maybe go for, “If you can dream it, you can build it.”

Luis Magalhaes: That sounds like something that would be inside a fortune cookie, yes.

Katie Womersley: Great.

Luis Magalhaes: Yes.

Katie Womersley: Well, let’s keep that one.

Luis Magalhaes: Okay. Let’s go with that, then. Well, thank you so much.

Katie Womersley: Great. Thank you, Luis.

Luis Magalhaes: Thank you for coming. It’s been a pleasure. And tell people how they can continue the conversation with you online, where they can find you.

Katie Womersley: Absolutely. Well, I do enjoy Twitter, so you can find me @Katie_Womers, that’s K-A-T-I-E-_W-O-M-E-R-S. And they can actually email me too, [email protected]. I am always happy to chat with other people leading or working [inaudible 00:53:06] teams that want to be in touch, and I look forward to carrying on the conversation.

Luis Magalhaes: Well, you know, I hope you get enough emails that you’ll enjoy it and not enough that you’ll be overwhelmed. Again, thank you very much for coming.

Katie Womersley: Absolutely.

Luis Magalhaes: We’ll see each other around. Thank you.

Katie Womersley: Great. Thank you so much for having me, Luis. It was a lot of fun.

Luis Magalhaes: Yeah. Thank you.

Luis Magalhaes: And there you have it, ladies and gentlemen. This was Buffer’s Katie Womersley. It was a pleasure to have Katie on, and don’t hesitate to get in touch with her and to find the links to all of her stuff in the show notes. And in the meantime, if you enjoyed the show, if you would like to support the show, the best way to do it is by sharing the content in social media and also by leaving reviews on iTunes or your podcast listening service of choice. You can also get transcripts of this conversation with Katie and the other conversations by signing up on our blog, DistantJobs/blog and you can find all the previous episodes on DistantJobs/blog/podcast. That is, forgive me if I wasn’t clear before.

Luis Magalhaes: And if you’re still building a team or if you want to increase the team, head to, get in touch, and we’ll get back to you and help you find the best person available in the whole world that fits your culture and your way of work. And you know that from today, the day this podcast goes live, February 22nd, 2019 to the 22nd March, 2019, if you mention the podcast when you give us your job description, we will pay for half of the first month of salary of the employee that you hire with us. So when you need to build your team, think differently, think globally, think remote, think DistantJob. See you next week.


Over the course of our conversation, Katie lays out a masterclass in leadership and management, touching subjects as diverse as: dealing with workplace conflicts, knowing when to delegate and when to educate, how to protect your team from bullies up and down the chain of command,  and how to to focus on deep work while still communicating as much as possible with your team.

Other Resources:

Blog posts on Slack Hygiene:

Rands Leadership Slack:


As always, if you enjoy the podcast, we humbly ask that you leave a review on iTunes or your podcast syndication service of choice – and if you could share it, that would be even better!

Need that one incredible employee to bolster your team?  Get in touch and we’ll find you who you need.

Reduce Development Workload And Time With The Right Developer

When you partner with DistantJob for your next hire, you get the highest quality developers who will deliver expert work on time. We headhunt developers globally; that means you can expect candidates within two weeks or less and at a great value.

Increase your development output within the next 30 days without sacrificing quality.

Book a Discovery Call


Want to meet your top matching candidate?

Find professionals who connect with your mission and company.


    Talk with a senior recruiter.

    Fill the empty positions in your org chart in under a month.