People Leading People: Katie Womersley, VP of Engineering at Buffer, on managing an entirely remote team

Season 2 of People Leading People is here and for our second episode, we sat down with Katie Womersley, VP of Engineering at Buffer, to learn how she leads and manages an entirely remote team of engineers.

If you were to go back in time and give yourself one piece of advice to be a better remote employee, what would you tell yourself?

‘I think I would tell myself that the work I did to keep my team informed and to be very communicative was my job and was my work. That was something that would often stress me out a lot because I had this idea of, well I need to code for 8 hours. And then all of the time that it takes to keep my team informed, to keep Jira tickets up to date, to send screen shots of my work, put things on dev service, I would then do that like in the after hours. I didn’t realize that was sort of part of the job. So, it was incredibly stressful.

I didn’t realize like, when were you supposed to do this communicating? So, I think if I were to go back in time, I would say, “That is the job, if you’re a remote employee, communicating really well with your team.” They should never wonder what’s going on with you.’

“That is the job, if you're a remote employee, communicating really well with your team.” @katie_womers Click To Tweet

What’s one thing you’ve done that has 10x’d your productivity?

‘Battering my calendar and carving out time for specific things, especially big projects that need to be done. And I am highly organized about my time. If it’s not on the calendar, it’s not going to happen. I don’t have like these long to-do lists with, “I’ll do it at some point.” And I colour-code my calendar into when I am operating like as an exec at the company level with other executives, when I’m operating as a line manager to my manager direct reports, and when I’m doing like other kinds of work that is sort of overall within engineering but it’s my own deep work.

And I have different needs for those sort of things. For the deep work, I need 3-4 hours blocked out in a coffee shop, to create a new manager career framework. So, I like block that off. It’s happening on Friday. This is exactly what’s happening. That has made me 10 more productive because it solves that problem of I’m spinning my wheels in the whirlwind trying to keep everything running smoothly and I have super busy long days that are not productive. Yeah and just not believing in, “busy.” If you’re feeling super busy and there’s a ton of things and you’re running around. Busy is an anti-pattern.’

Listen to the full episode below and if you’re inspired by what you hear, give us ⭐️⭐️⭐️⭐️⭐️ on Apple Podcasts or your favorite podcast network.

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People Leading People: Season 2, episode 2 | Katie Womersley of Buffer (transcript)

Jillian Gora:  People leading people is a podcast about the stuff that pops up when you lead people at work. Join Brennan McEachran, CEO of SoapBox and Jillian Gora, Customer Experience at soapbox, as we interview the people leaders that inspire us most. 

Jillian Gora: Being a manager is hard enough when you’re all sitting around the same table, so many things are misunderstood and held back in face to face meetings that it’s hard to imagine that these things don’t just get amplified when your team is remote. Katie Womersley, VP of a completely remote Engineering team at Buffer shares her tips for building a productive and motivated team from afar.

Okay so, hi! Welcome Katie!

Katie Womersley: Hi, thank you so much for having me.

Brennan McEachran: We’re super excited to pick your brain today, I was just sharing with Jill, you know we think management’s hard, obviously that why we put the podcast together to get some insights out of everyone and what has been circling through my head over and over is how does Buffer do it because they don’t even get to you know poke their neighbours or you know ask people how’s it going off the cuff.

Jillian Gora: Because they’re all remote, right? Everyone at buffer is fully remote?

Brennan McEachran: Fully, all remote.

Jillian Gora: Crazy.

Brennan McEachran: Super excited to have you here today we’re gonna pick your brain and go all over the place but maybe before we do that could you fill in the listeners on who you are how you got here, your background?

Katie Womersley: Absolutely, and I think management is hard too but I like a challenge. That’s why I’m here. Yeah so, I’m VP engineering at Buffer and as you know we’re a globally distributed team. We have no offices at all, everyone’s remote. I joined Buffer as a software engineer and worked my way up doing what later transpired to be engineering management. I remember kind of not coding as much, just solving problems trying to help people feel motivated, get things organized, I eventually went to our CTO and just I thought I should tell him that I’m not writing that much code but I was really helping a lot. Because this is the thing, you know we think this might actually be.

Brennan McEachran: And you did that as well at Buffer, for a while you had no managers? Is that right?

Katie Womersley: Yes, we absolutely did. We didn’t have any managers at all for a period, so we experimented with the entire like holacracy self-management thing. It didn’t work for us. I probably couldn’t say it can’t work, but for us it didn’t. And yeah fun fact about me, is I have never not worked remotely. So, I have worked with a lot of people who are new to remote work and managers who are new to remote managing, but my entire career has been remote. I never understood going to a location in order to do my job, so I just never did.

Brennan McEachran: Yeah. That’s awesome.

Jillian Gora: So awesome.

Brennan McEachran: That’s like the perfect opposite viewpoint. We always think, like you know how do we keep the podcast short so that people can listen to them on the commute to work.

Katie Womersley: Right, which is important.

Jillian Gora: But maybe it’s, maybe it’s so that they can listen to it while they’re making themselves breakfast in their own kitchen before they go and sit at their desk.

Katie Womersley: Well it’s a funny thing, people actually miss commutes when they go remote for the first time. A lot of people, they love not having a commute, but some people do have that thing of well I don’t know when to fit in my podcasts you know that was my time for me to just listen to.

Brennan McEachran: Decompress and get ready.

Jillian Gora: Exactly, or read a book, like I do all of my, well not all of my reading, but a lot of my reading on the subway

Brennan McEachran: Yeah, okay so you’ve never experienced the other side of it, management you’ve only experienced both being an employee, with a remote manager and being a manager of remote employees. What do you think, now that you’re a manager or I guess VP of engineering, what do you think if you were to go back and give yourself one piece of advice to be a better remote employee, what would you tell yourself?

Katie Womersley: I think I would tell myself that the work I did to keep my team informed and to be very communicative was my job and was my work. That was something that would often stress me out a lot because I had this idea of, well I need to code for 8 hours. And then all of the time that it takes to keep my team informed, to keep Jira tickets up to date, to send screen shots of my work, put things on dev service, I would then do that like in the after hours. I didn’t realize that was sort of part of the job. So, it was incredibly stressful.

I didn’t realize like, when were you supposed to do this communicating? So, I think if I were to go back in time, I would say, “That is the job, if you’re a remote employee, communicating really well with your team.” They should never wonder what’s going on with you.

Like if they ever get that inkling, like, “Hey, I wonder what’s up with Katie? What is she working on? What’s Happening?” You’ve got a communication breakdown.

Brennan McEachran: You’ve something wrong.

Jillian Gora: And so as a manager of a fully remote team then, what are the things that, or like, I guess it’s the processes or whatever that you have in place with your team to make sure that communication is happening, but also to make them feel comfortable that part of their day is communicating and it’s not all about coding all day?

Katie Womersley: Right. Well, the obvious thing is you talk about it. So, just tell people part of your job is communicating that’s okay. A lot of people don’t say the obvious thing, just say it. And then of course it is the manager’s job to set up processes that so their team. So it would be different for every different team and we change our processes overtime, but especially with software teams, there’s no reason to have to share status face-to-face talking. Like, we have GitHub. we have Jira. There is email you can use, Idonethis you can use Todoist, like there’s a plethora of apps and tools you can use so there’s, there’s no reason why it needs to be hard to know what your teammate is doing. Basecamp’s another one we’ve tried and liked. Yeah.

Brennan McEachran: And so, that that’s always- it’s funny when I think about that type of communication I imagine it’s always like such a well-oiled machine at a remote company because it kind of has to be. I think the part that makes me scared is how do you do like the “soft skill” stuff? Like how do you check in on, you know, how a member of a team feels about, you know, the other members of the team. Or, or you know, how they’re you know doing when you know, you’re not around or you’re not on the video call or something like that. Are there ways that you sneak that in or is it very formal?

Katie Womersley: So, the soft skills thing takes time. So we don’t sneak it in the sense that we do one-to-ones with each manager to teammate for one full hour every single week, which is, it’s a fair amount of time and I’ll also do skip level one-to-ones. So, engineers that report to managers who report to me I’ll speak to them every six weeks for about half an hour and I’ll ask them things like, “Right is there anything that I can do at Buffer to make working here more fun? Who on your team is doing really well?” And then listen to who’s doing really well, but also listen for the people that don’t come up. And then you know, okay, maybe there’s something there, maybe not. But like, listening to the silences is a really helpful way to get a bit of a deeper sense of like, is there a slight problem here that’s brewing?

Brennan McEachran: Yeah

Katie Womersley: And we put a lot of effort into our one-to-ones. We try to make them not about status, not about a project, about who are you as a person. What do you value right now? Why are you here at work, like what is motivating you? What is challenging you?

Brennan McEachran: Yeah.

Katie Womersley: So I tend to try to have quite, sort of, deep one-to-ones. Like, tell me about a really happy childhood memory and they’ll be like, oh you were surrounded by all of your family. Does that mean you’re really extroverted? Like is it challenging that you’re by yourself at work now? You know, so we’ll, we’ll do that kind of thing.

Brennan McEachran: So you’re doing an hour every week with all of your direct reports.  How many direct reports do you have?

Katie Womersley: Well, I have managers reporting to me. Right so, yeah a good number is around like 7 plus/minus 3. A manager can sustain up to about 10. I certainly had more than ten engineer director reports before, at like times when we were growing quickly and you haven’t sort of build out-

Brennan McEachran: You don’t have time.

Katie Womersley:  You don’t have time. But yeah, you get more practice at it. I think up to about 10 is doable 7 is probably like a healthier number because it does take a bunch of time.

Brennan McEachran: But you’re spending, you’re spending about like one full working day per week just in one-on-ones.

Katie Womersley: Oh, yeah. Easily. Yeah. Yeah.

Brennan McEachran: Easily. And then what do you do- like, how much time do you think you spend, and I get- I think this is like interesting. You were saying communication is part of the role. What do you, you know, if you’re just spending that one full day communicating about the people things, how much time do you think of your work changes when you come out of those meetings? Do you, do try to cram them in all in one day? Do you go, you know a couple a day? How much like, how much does your day get shifted based on those conversations or is it pretty stock in standard every week?

Katie Womersley: So they typically scheduled ahead of time so I’ll have you know, I one-to-one with this person and it will be on Tuesday at 2:00 p.m all the time unless we need to move it. So, they’re pretty scheduled. We put a really high priority on not moving around those meetings. Both parties really respect them. They think about them beforehand. But when it comes to how do you schedule your calendar that varies a lot by person some people like to have, some managers, like to have all their one-to-ones in one day because they get into a certain mind space and works. Others find it really challenging especially if you have a couple direct reports and they’re going through a hard time and then you have one once one and there’s somebody suffering and they’re struggling and you’re feeling drained and then the next one-to-one and it happens again, then that can be tough.

So, my- my personal threshold on that is I can do four hours of back-to-back video calls fine. I can knock through four and a half hours. I am done.

Brennan McEachran: Right.

Katie Womersley: Yeah, so you need to know your own limits and kind of learn those. So, some people like to scatter around and change things up; a one-to-one, then a team sync, then they’ll have some hands-on time. Other people like to keep their calendar very defragmented and it’s just about knowing what works for your type of energy.

Like does was one-to-ones give you energy or lose your energy. Plan accordingly.

Jillian Gora: So, in terms of, because I’m imagining you have been remote this whole this whole time so for your whole career, but have you if you know of people kind of in your circle who have maybe made the transition to being a remote manager, what are the things that sort of they’re anxious about or what are the mistakes that you see or see the making or hear them talking about?

Katie Womersley: Right. So a big anxiety is overthinking all communication because there’s not a lot of natural just seeing a person’s full body and all their body language. So, new managers that have, used to work non-remotely and are now working remotely, that’s a big thing. It’s like, do they like me? Is everything okay? Every single Slack message, it’s like agonizing over that emoji choice. Like that’s really common that kind of anxiety around, you know wanting to be likeable and professional and relatable, but it’s suddenly remote for the first time. And that’s completely normal. I always tell people that if you feel that way and you’re overthinking your communication a lot it doesn’t mean that it’s the wrong company or that remote’s not going to be the right fit for you, it just means that you’re learning a completely new way of communicating. You’re in a different medium. And yeah, it’s going to feel weird for a little bit.

Brennan McEachran: Is the advice just a power through that until it’s not awkward? Is there is there a right level of agony that you should just always have? What do you thinks like the appropriate? Like for me, Iwould go insane. I know I would go insane. Only because oh I think maybe because like my background is just more in face-to-face human, you know visual and so I’d be on the hunt for those subtle body language cues. And if I don’t have them, I don’t know what I would do. Is there, is there an appropriate amount of like, especially as you’re new getting up to speed, that is is right or too much or not enough?

Katie Womersley:  That’s a good question. I would say it depends a lot on your company culture. But what you will need to do as a remote manager is make the switch from relying on a person’s full body language, to being able to read somebody over a video call and interpret what their text-based communication means for them.

Brennan McEachran: Okay.

Katie Womersley: So that’s going to take a lot of focus up front. If after 90 days, you’re still feeling like you’re in the terror zone, it’s a great idea to seek help.

Brennan McEachran: Right.

Katie Womersley: Ask other managers like that, that are working remotely like there’s there’s a lot of us. You can find me on Twitter.

Brennan McEachran: We’re tweeting about it.

Katie Womersley: Yeah, so should it take focus? Yes. It will take focus. Should it be continuously terrifying past your first 90 days? That…maybe you’re under too much stress. Like yeah, I’ll ask for help.

Brennan McEachran: What what’s like subtle text-based body language clues that most people learn? What are like the common ones that if someone sends you a slack message like this: It means they’re happy or upset or.. Are there any common ones or is everyone unique?

Katie Womersley: Everyone’s very different. So you kind of need to figure out how to learn your direct reports communication style fairly quickly and that’s why our one-to-ones have a lot of very specific questions. Like, “What makes you grumpy? How will I know if you’re feeling upset? What are your tells if you’re starting to burn out?” For example, really common engineer burner tells: Losing your sense of humor, any change in your dream state. If you don’t usually dream and you’re now dreaming a lot, that’s like an early warning thing. Or if you, if you used to dream a lot and you’re just like blacking out each night, like no dreams that can be a warning sign as well. Yeah, so we talk about these things very explicitly because it does vary by person to person.

Jillian Gora: That’s so interesting. I don’t think I’ve ever heard a manager like say, “Oh in my one-on-ones I ask my people about their dream state. What did you dream about last night? Did you dream last night? Are you good on Dreams?

Katie Womersley: Yeah. Well, I wouldn’t say what did you dream about. Like are you noticing any dramatic changes in your sleep patterns or dream state. And if they’re like, “Yeah, it’s been really different.” I’m like, “Oh, interesting.”

Brennan McEachran: You’re like ut-oh. Mental note.

Katie Womersley: Yeah, then I’ll like ask other questions. I’ll be like how about your sense of humor? Are you like attaching a huge amount of importance to lots of little things?

Brennan McEachran:  Yeah, how’s your giphy usage.

Katie Womersley: Yes as well, then I’m like, okay, like are you babbling?

Brennan McEachran: So you mentioned you’re- that the questions you asked in a one-on-one are really structured. Do you, you know, when you’re managing your managers kind of promote, “Hey, here’s- here’s the template. Here’s the thing.” Yeah.

Katie Womersley: Yeah, yeah, I’ll share like these are these are helpful questions that I have found helpful. But I also encourage them to find their own voice and maybe they want to ask different questions or add on the questions and we all kind of share all the questions around with each other.

So a manager will read some blog article and say, “Oh apparently it was great to ask, you know, is there anything you’re afraid of it work?” And everyone’s like, oh gee that’s ask that in the next one-to-ones.

Brennan McEachran: That’s awesome.

Katie Womersley: Yeah.

Jillian Gora: And what about when you have to have a difficult conversation with someone that isn’t necessarily going to be prompted by a question of like, “What do you find difficult at work?” When, when you Katie as the manager, are like, “Okay, we need to really sit down and talk about something.” How do you approach that?

Katie Womersley: So, in the first one-to-one I do with people I ask them, “How do you like to get feedback? Do you like it to be routine, like in a weekly one-to-one? Do you like it to be as soon as possible as it happens? And do you like it to be over email or over Slack, or over a video call?” And then I will try to follow the format that they find easiest. So if they like to get written communication first, I’ll send them an email that will say, “Here is the difficult conversation kind of laid out. Let’s talk about it in our next one-to-one.” If somebody prefers it to be- it’s difficult when people prefer it to be ad hoc and on video calls. It means you do need to do that thing of like, “Hey, can we talk?”

Brennan McEachran: Yeah, which is terrifying. That’s what I’m always so worried about. Yeah.  

Katie Womersley: Most people that think they like that preference of feedback, like the first time they try it, I’ll ask them like, “How did that really feel for you doing that?” So, a lot of the time they’ll walk it back like, “No, let’s do something different.”

Brennan McEachran: The anxiety getting a message that says like, “Hey, we have to talk immediately right now. I have feedback to give you.” It’s like whoa.

Katie Womersley: I mean some people do legitimately prefer that but yeah, it’s it’s a bit stressful. And with giving feedback, what’s very helpful is the nonviolent communication approach where you don’t say, “I’m disappointed in your selfish actions at working on a conference talk while the team was busy hitting a really aggressive deadline.” I would say, “I noticed that you were working on a conference talk and also that the team was struggling to meet this aggressive deadline and that made me feel concerned for your relationships with your teammates and that you might be eroding trust there. Would you be willing to..” And then like ask the specific requires. So like I asked for the exact, like behavior change that I need. So it’s very much about I noticed this behavior. This is the impact very specifically and would you be willing to change it to this behavior? It’s not about- it’s not emotional.

It’s not about who they are as a person. It’s not that I’m upset. I’m generally not upset. It’s just like I noticed this behavior, it’s not effective for this reason. Would you be up for this behavior? If yes, I’m like great, solved. Like that’s the behavior. If they don’t understand the behavior we’ll work through like, “Okay do you not understand why that would be helpful or is it that you understand why but you’re struggling to do it?” And I’ll be sure to ask, “What can I do to support you in making this behavioral change?” And often people will ask for like ongoing kind of, “Well, every time I do that, can you nudge me? Can you add a specific emoji reaction to any slack message that you think is passive-aggressive?” And just add a little emoji between you and me like we’ll know. And it actually folds, it can build a really really strong relationship going through that with somebody. I mean it can also just not end well. You can keep trying and they’re just not getting it and you have to end up letting someone go like…

Jillian Gora: Or like, everybody else also clicks on the emoji reaction and you’re like, oh God.

Katie Womersley: Yeah, that would be, that would be interesting.

Jillian Gora: That’s awesome.

Katie Womersley: Yeah.

Brennan McEachran: Very cool.

Jillian Gora: Great. Well, it’s that time of our episode when we like to ask a secret question, put you on the spot. So if you could pick a number between 1 and 3?

Katie Womersley: Great, I pick one.

Jillian Gora: You pick one. All right doop doop doop do doop. Okay. What’s the one thing you’ve done as a leader that has made you 10 times more productive?

Katie Womersley: Battering my calendar and carving out time for specific things, especially big projects that need to be done. And I am highly organized about my time. If it’s not on the calendar, it’s not going to happen. I don’t have like these long to-do lists with, “I’ll do it at some point.” And I color code my calendar into when I am operating like as an exec at the company level with other executives, when I’m operating as a line manager to my manager direct reports, and when I’m doing like other kinds of work that is sort of overall within engineering but it’s my own deep work. And I have like different needs for those sort of things. For the deep work, I need 3-4 hours blocked out in a coffee shop, to create a new manager career framework. So, I like block that off. It’s happening on Friday. This is exactly what’s happening. That has made me 10 more productive because it solves that problem of I’m spinning my wheels in the whirlwind trying to keep everything running smoothly and I have super busy long days that are not productive. Yeah and just not believing in, “busy.” If you’re feeling super busy and there’s a ton of things and you’re running around. Busy is an anti-pattern.

Brennan McEachran: Yeah, it’s not a good thing.

Jillian Gora: And do you, do you carve out time, to carve out that time? Because, I feel like that would also be an exercise in just sitting back and saying, “Well, okay, how am I going to accomplish all these things? When’s it going to get done?”

Katie Womersley: I do actually. I find scheduling things kind of intense and it takes a lot of concentration with all the time zones and I have to like scheduling for the next week or month and I like to schedule like an entire month in advance.

Brennan McEachran: Oh wow.

Katie Womersley: Yeah.

Brennan McEachran: So, batching color coding based on I was thinking as you were saying it like what hat you’re wearing and the particular, like yeah the different hats you’re wearing.

Katie Womersley: Yeah.

Brennan McEachran: Are those the batches? Is it really just like the headspace you want to get into or you batching like task activities and, and..

Katie Womersley: Right, so I’m assigning the so the color of the calendar event is the headspace and then you just group colors. So, skip level one-to-ones, I put them all next to each other because that works for me. And then I’ll ask them all the same kind of things I need to go through and then I can see the patterns and then I go into the next thing. Yeah.

Brennan McEachran: Cool.

Katie Womersley:  Yeah, so you don’t do like one skip level and then a leadership meeting and then work on a career framework and then another skip level, because you’re just all over the place. Well, I’m all over the place.

Jillian Gora: Yeah. No, I feel that too with the stuff I do sometimes it’s just that you’ve got to put yourself in all these different brain spaces and it can be hard to jump from one to one. So the notion of grouping sort of, “Okay. I’m putting this type of brain on or this type of hat on for this chunk of time is-makes a lot of sense.”

Brennan McEachran: Big time.

Katie Womersley: And you’re just in that zone for the day and you just know next Tuesday I’m doing skip level one-to-ones all day. Like I’ll just talk to people all day. That’s why I’m that’s my job.

Brennan McEachran: That’s productive.

Katie Womersley: That’s what productive looks like on Tuesday.

Jillian Gora: Yeah. Oh, yeah.

Brennan McEachran: Make it through. Feel accomplished

Jillian Gora: Because, that’s the other thing too I mean not to just I’m just so curious about this. It’s so interesting, but I know I have some friends who are freelancers and for them the tough part is saying the day is done. My day is done. I have done enough work. I feel accomplished. And I, it’s often because they’re just sitting there alone. They have no feedback on that. They are the masters of their own work and I can imagine that things like that where you can visually see no I added value today, I was productive, would be really helpful in those kinds of situations.

Katie Womersley: Super helpful, and that’s a huge thing with remote work. There’s a great New Yorker cartoon and it’s got somebody in a home office and the caption is, “I can’t remember do I work from home or do I live at work?”

Brennan McEachran: Yeah, that’s exactly it.

Katie Womersley: Yeah, yeah. Boundaries.

Jillian Gora: Boundaries. Awesome.

Brennan McEachran: Awesome. That was super insightful lots of stuff for me to take home and try, but ah that’s all I’ve got.

Jillian Gora: Yeah, thanks so much. It was such a pleasure to chat with you and very enlightening definitely.

Katie Womersley: Thank you so much. This was a lot of fun. And if anyone’s listening to this podcast and wants to talk about being a remote manager, you can find me on Twitter. It’s @katie_womers. Also, I am hiring engineering managers if you’d like to come and work for me.

Jillian Gora: That is a good opportunity.

Brennan McEachran: And try out some of these tactics.

Jillian Gora: Yes exactly. I mean working for a manager as organized as you would be a delight, I’m sure. So, you guys know where to find her: Twitter.

Brennan McEachran: And, and someone who asks about your dreams.

Jillian Gora: Yeah.

Katie Womersley: I promise it’s not creepy.

Jillian Gora: Yeah and in a non-intrusive way.

Katie Womersley: Yeah.

Jillian Gora: Great, okay. Well, thanks so much Katie.

Katie Womersley: Thank you so much.

Jillian Gora: People Leading People is produced by SoapBox, an app that helps managers and employees work better together by giving them a place to manage their one-on-ones, team meetings and company-wide discussions. Download it for free at hypercontext.com/free. Special thanks to our editor, Joel North. If you like what you heard today, do us a favor and give us five stars in the reviews. And if you’re really feeling the love, leave a comment with a secret question you’d like us to ask in an upcoming episode.