Simple (Remote) Leadership with Christian McCarrick | DistantJob - Remote Recruitment Agency

Simple (Remote) Leadership with Christian McCarrick

Luis Magalhaes

Todays’ guest is Christian McCarrick, VP of Engineering at Auth0 and host of the SimpleLeadership Podcast. Christian has been a technology leader for almost two decades, and through his Simple Leadership Podcast, has learned from dozens of the best in the industry.

Christian McCarrick

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Luis Magalhaes: Welcome, ladies and gentlemen to the DistantJob podcast. I am your host, Luis. And in this podcast, in the DistantJob podcast, what I do is I interview the leaders, the managers, the builders of incredible remote teams and try to figure out what makes them tick, what do they do differently that helps them build such wonderful and successful teams? The commonality of which is that the people work remote.

Luis Magalhaes: And today I have a very special guest because it’s the first time I’m interviewing a fellow podcast host. I almost shudder at saying that because Christian McCarrick, the VP of Engineering at Auth zero, some may call Auth0 hosts the SimpleLeadership podcast, which is, in my view … His work as a host is miles away from mine. But, I do try to improve, and hopefully I will get there some day, Christian.

Luis Magalhaes: But it was a wonderful conversation. Christian is not only a great podcast host, but he is also clearly someone who has given a lot of thought to how to properly build and manage remote teams. He’s been a technology leader for almost two decades, and in the following interview, we talked about a wide breadth, a wide variety of subjects. We talked about our remote work, it can really help introverts shine and participate in the debate. We talked about how to make sure that brainstorming sessions work in remote, how to promote conversation equity, meaning that everyone actually gets to have their own say regardless of their charisma or conversation techniques. We talked about hiring and testing people for remote teams. We talked about Christian’s favorite books from lately.

Luis Magalhaes: So, there’s definitely a lot here, and I had a blast. Christian really knows his stuff. It was incredible. Thank you, Christian. And hey, I hope you will enjoy it, as well. Ladies and gentlemen, I bring you Christian McCarrick.

Luis Magalhaes: Welcome, ladies and gentlemen to the DistantJob podcast. I’m your host, as usual, Luis. And this is a podcast about building and leading remote teams that win. And with me today, tonight … It’s evening. Is the VP of Engineering at Auth0 and the host of the SimpleLeadership podcast, Christian McCarrick. Christian, welcome.

“Kristian”: Thank you, Luis. Thank you very much. I appreciate being on the show. It’s always interesting to get on the other side of the mic, so to speak, and be the one answering questions instead of asking the questions.

Luis Magalhaes: Yeah. But well, we’ll get into that. But so … You’ve been a technology leader for a while. Is it two decades now?

“Kristian”: Yes, but I like to downplay that a little bit. I’ve been in technology since college. I think I started my first company, my tech company, at my senior year in college and I’ve been doing that ever since.

Luis Magalhaes: Okay, so obviously I want to get to Auth0 and the remote teams, but since it’s so rare for me to actually have someone that hosts a podcast, I do want you to tell me the story of how you came to the decision of building your podcast. That’s about tech leadership, right? It’s the simple … I’ll admit I haven’t gone through your whole corpus of work. I did listen to some episodes that I’d like to bring up. But it seems that the focus is that, right?

“Kristian”: That’s correct. I think the focus for the podcast itself, again as you mentioned, SimpleLeadership podcast is about improving the craft of software engineering technology leadership. I think that there’s a couple … Your question is how did I get into that? I think, like anything else, it was a little bit by accident, a little bit of evolution. I found myself not … I love to write, and I found myself not having enough time to write. So, I figured, “Oh, this podcast thing seems to be pretty easy. I’ll just talk for a half an hour and that’ll be awesome.” And –

Luis Magalhaes: Yeah. It didn’t go quite as you expected, did it?

“Kristian”: No. I had a first few episodes, where it was just me talking. And I was like, “I don’t wanna listen to myself for half an hour, why would anyone else wanna listen to just me talking for a half an hour by myself?” And then I started … Well, I would … How about I get, you know, popular format is the guest interview format and why don’t I do that? I was always been interested in the leadership aspects, the management aspects of running software engineering teams. So, that I kinda navigated to that as a topic. And I have to say, though, that in retrospect, and you know from doing a podcast, that I probably should’ve just spent … I probably should’ve just stuck with blogging. It would’ve taken about ten percent of the time.

“Kristian”: Because for now, as you know, coming up with finding guests and taking the time to actually prepare and write questions, and do the research, and then do the editing and the post production. It actually takes up quite a lot of time. But you know it’s –

Luis Magalhaes: I know. Yeah. Yeah. Definitely. Definitely. Much more than … So, that’s why I find it fun because I kinda thought the same thing. But it’s like I’m a writer and I enjoy writing. And it kinda helped, as well, to be like, “Oh, so I just have to talk now. Cool.” But actually it takes a lot more. But it’s also different because instead of you just being stuck in your head, you actually get to learn with people. Which is, to me, the best. The high point. The high point of it.

“Kristian”: Absolutely.

Luis Magalhaes: But that was part of the reason why I wanted you here because I was listening to your interview with Liam Martin from Time Doctor, I think that’s his company. And you really got Liam’s story. And I was listening to it and it struck me that Liam is giving us some really good advice. But it felt like you were playing down your remote team management experience. So, I felt that this was a good time for me to find out what you know and not just what Liam knows.

“Kristian”: Sure. Yeah. And for reference, yeah … If you go to iTunes or SimpleLeadership dot o, you can find the podcast episode that was discussing. And Liam, he’s … I think the one thing I wanna point out is in the … In podcasts, or in dealing with software engineering leadership, a lot of us are doing these things just because in some cases we truly believe in it, we’re passionate about it, and we wanna give back. So, it’s a shout out to yourself, to Liam, to a lot of the other guests that I’ve had on my podcasts, because we’re not getting paid for this, for [inaudible 00:07:19]. We’re just doing this because we truly wanna help. We wanna open source … For me, instead of open source tech leadership and help other people not make the same mistakes that we’ve made along the way.

Luis Magalhaes: So, since you’re on the topic of tech leadership, tell me how do you feel tech leadership most differs, if at all, from leadership in non-tech companies?

“Kristian”: That’s a good question. It’s something we often talk about. There’s very … When people ask me … I wanna be an engineering manager, what should I read? What kind of books? What should I go? And obviously, as people have mentioned on my podcast, sometimes there’s a few tech leadership books out there. Camille Fournier has the one right now, which is The Manager’s Path, that’s really one of the more popular ones. And actually really good, as well.

“Kristian”: But there are so many pieces of just leadership and management that are common throughout whether you’re in marketing, whether you’re running a brick and mortar store. I think ultimately there are so many things that come down to focusing on the people. And I think that’s where it really becomes important.

“Kristian”: Now, there are some very specific things that I would call out that are specific to tech leaderships. I think there are some stereotypes, too, of people in technology and software engineers, and as a rule … Not as a rule. But I think as what I’ve found is our industry also tends to attract more people that are more introverted than extroverted.

“Kristian”: So, if I was to say is it specifically to software engineers? I would say no. But I would certainly say honing your skills on managing groups of people who tend to be a little bit more introverted versus extroverted is probably one of the important skills to try to learn, and to understand.

“Kristian”: There’s a great book out there, I think it’s called Quiet. And it’s basically about the power of introverts. So, I think I also recommended it if you’re an engineering leader, to read that book, too. To sort of get a good understanding of kind of how … And myself, too, I’m primarily an introvert, as well. But I can be more extroverted in situations. But ultimately, yeah.

Luis Magalhaes: That’s a great recommendation and I actually read that book recently. It’s especially good to advocate for introverts. It’s not that it outlines a plan for you to manage introverts, though it does a bit of that, too. But it mostly explains how people tend to dismiss, be a bit dismissive of introverts. And actually they can contribute as much as extroverts, only in a different way. So, I will second that recommendation. It’s a very good one.

Luis Magalhaes: I will have links to it in the show notes, just I will after your podcast, and to everything else we mention in this interview.

“Kristian”: Sure.

Luis Magalhaes: So, going from technology and into remote specifically, tell me about the remote situation, the split at Auth0.

“Kristian”: Yeah, Auth0 was interesting. There are a couple of companies out there, which are remote only companies. I say Envision, or Buffer. A couple of ones like that. Automatic, from Word Press. And then there’s the other extreme, which is, well, you might allow remote workers. If you’re maybe a big company, someone can work from home one day a week. And Auth0 is a lot closer to the almost entirely remote than it is only allowing a few remotes.

“Kristian”: I think to say, we’re sort of remote first and definitely remote friendly. Our co-founders of our company, they both came from, originally from, Argentina and Buenos Aires. Our CTO and co-founder still lives in Buenos Aires. Our CEO and co-founder lives in Bellevue. So kind of, naturally, the company was, I would say, distributed, sort of to start. At least kind of, in those locations, and being a start up, kind of in the beginning, very scrappy. It wasn’t a lot of the funding, or the decision was made not to use a lot of that funding to build out offices, and to kind of build a thing.

“Kristian”: So, although right now we do have three locations where we have an office in Buenos Aires, we have an office in Bellevue, and a new office in London. But, I like to call those our private we work spaces. Versus it’s an office that’s optimized for the number of people we can fit in chairs. Although we are a distributing company, I would say from an engineering perspective, 85% of my engineers are fully distributed. They do not work in an office.

“Kristian”: But, although our company is very distributed, we also understand the importance of face to face interactions. Not only for productivity, but also from the social/emotional, sort of well-being standpoint. So, we’ve built these sort of three hubs, and built them as more of collaboration spaces. Where, we do have off sights. Each of our teams has an off sight in one or two times a year. And, those off sights tend to happen in one of our three locations, so that where there is some of that collaboration, there’s mixing. Sometimes we’ll try to get different teams together at the same time. So, we do have that kind of interaction.

“Kristian”: But I think the … We can get into some of the specifics, obviously there’s challenges in not being 100% fully distributed and not being … But, where I think we’re much further along with being more fully distributed than we are having a few people that are token working from-

Luis Magalhaes: Oh, of course. Of course. And that’s something that I wanted to discuss. So, obviously it’s very nice to get that face time. And that’s why I see that it’s very interesting and very healthy for the company to have those get aways, where the company flies a team or all the teams, depending on how the company operates to a place. Because that really increases the empathy and the relationships between the team.

Luis Magalhaes: So, recently, and forgive me if this is something from your podcast, but I don’t remember where I heard this. But, I heard an interesting data point, that the half life of empathy is like 18 months. If you do that gathering once a year, you reap the optimal benefits. So, was this one of your recent guests, or … Because I’m … Every day I’m consuming more and more of this material, and sometimes it just all mashes in my mind.

“Kristian”: Sure. I don’t believe that that’s … It might’ve been from one of my guests but I don’t remember. I don’t think it’s from … Certainly not from myself, and I’m not sure if it’s from my podcast. But no, you’re right. And we always feel … So, to take a step back. Our company also does an all company meeting off sight once a year. And for anyone listening, we’re hiring. So, if you’d like to participate in our one at the end of May, which is going to be in Cabo San Lucas, feel free to apply. And if you get in, in time, you can join us there. Have to put in those plugs, of course. I wouldn’t be a good-

Luis Magalhaes: Feel free. Yeah, you’re my guest. Plug away. Plug away. I will also include that in the show notes. So …

“Kristian”: But we also … I think though, that we definitely get a … I don’t wanna call it a burst of enthusiasm, or a little bit more energy. There’s certainly, after our off sights, for at least three to six months post, there’s certainly, I feel, kind of an uptake of some of that energy. And certainly, especially for those people I’ve never met face to face before, a lot more comradery that can happen and a little bit more bonding. And, as you say, empathy for the other individuals.

Luis Magalhaes: Yeah, because they become 3D. We’re talking about Zoom, to me, it’s the pinnacle of remote work technology is Zoom. I am not paid for Zoom to say this, but I certainly would like to be. So, if you want, call me. Call me, if anyone from Zoom is listening. Look, this is the pinnacle of remote connection technology, but it’s still not 3D. Wearing a virtual reality headset is still a bit weird. So, the best way is really to meet someone. Suddenly when I’m talking … When I meet someone from my team, from DistantJob’s team in person. The next time I meet them online, it’s the person that I drank coffee with. It’s, you know, the person who we shook hands. There’s a different interaction.

Luis Magalhaes: So, that said, since you have mixed team, more on the remote side, but still mixed team. How do you avoid a common pitfall, which is the people who are co-located. They tend to have more say or be more up to speed on decisions because they’re just close. They see each other, it’s easier to talk between themselves. I bring this up because it’s something that the previous guest, [inaudible 00:17:05] from MailChimp, we talked about it a bit. It was a problem for him and he instituted a one remote, all remote rule. Which means that even if people are working co-locatedly, they still work as if they were remote. Have you felt that there is this kind of power dynamic when you have part of a team co-located and part of the team remote?

“Kristian”: Yeah. For us, I would say, again, because we skew so heavily towards being mostly remote. That we don’t really run into that too much. I would say it’s not so much a power dynamic. There is certainly some benefits of … You know, you can tell that maybe there was some information that gets passed between two people in an ad hoc conversation that might not be distributed widely, right. There has been some of that. Again, not so much power dynamic, but more maybe some information that happens between a couple of people that might be in a similar location that isn’t necessarily shared throughout the rest of the orb.

“Kristian”: I think there is a great article, and I’ll try to find it for the show notes for you, to send you. As an engineering manager, it says you’re leading engineering managers, but you’re really leading a team of writers. I have to find that because … And it really resinated with me because from a remote company, communication and explicit communication, meaning writing is so important as part of the culture and functioning. That it’s actually all the things we should do even if you’re all co-located in the same place. It’s actually best practice, but people get lazy when they’re together. Being a remote team, it actually forces you to document everything.

“Kristian”: I think we’ve sort of made it a social faux pa in the company to have conversations and not document them if you happen to be one on one or face to face. Even in one on one meetings, we have one on ones with groups. We make sure that we have documented. We happen to use Confluence, but you can use everything and I think documentation is great. Now, there’s a flip side to that which is now managing that and keeping it updated and correct becomes another headache. Especially as you grow in scale. But, yeah.

Luis Magalhaes: No, no. Go ahead. I didn’t realize you weren’t done.

“Kristian”: Yeah and … But, to your point, the one all remote. We do try to especially … you mentioned Zoom. I spend my days on Zoom. You know, just for the listeners too, I am not in one of the offices. So, I am remote myself. I think that as a majorly distributed engineering team, that it is important for me as the leader of that team to also be remote. I think it would be very hypocritical to be in an office while everyone else is remote. That brings some extra challenges for me, but I think it allows me, as you mentioned before, to have that same empathy for my managers and all the other engineers in my company. To help understand the challenges that they face.

Luis Magalhaes: Oh, yeah. Yeah. Absolutely. It also sends a message that this is what the top brass does. So people don’t get that feeling. That my colleague is remote and I’m co-located so we’re different. Now, if the top brass does it, it’s an example. It’s leading by example, right? That’s the thing.

“Kristian”: And it’s important for … People sometimes ask me, well, if they’re applying for a job, how do I know you really support remote culture. I’m like, well, I’m remote and then that stop the conversation, right? Because if the VP of engineering is remote, then you know, we’re eating our own dog food. We’re living what we’re saying.

Luis Magalhaes: There you go. That’s a nice way to … I wouldn’t call remote dog food. I would say it’s [crosstalk 00:21:20] But, sure. Whatever. No, but, I do think that, obviously, that remote work is the future. The company I work for is built around that and that’s why I joined them. Because I believe that, but it definitely comes with it’s own challenges. It kinda segues me into a very cliché question, but I have to ask it. Because I wouldn’t be doing my job properly if I didn’t. What was the biggest challenge that you’ve found with working with remote teams?

“Kristian”: I could break that into two, right? So, there’s certainly-

Luis Magalhaes: Give me the top if you want.

“Kristian”: Yeah. Well, there’s two, sort of, categories. I think there’s … Managing remote teams and working with remote teams is one category. And then the second is also being remote, right. So, there is certainly [inaudible 00:22:14] right. If the challenges of being a remote leader and being remote myself, have its own set of unique issues as it is then just about, okay, the challenges logistically of running, I think, remote teams. I think there’s certainly … One of the things is around … We’re fairly distributed. So, time zones, you know. There are pros and cons to having our team so widely spread. I think as a culture becoming a little more used to asynchronous work and the concept of, you can put questions, you can put a pull request, you can put something in Slack and not necessarily getting the answer in five minutes.

“Kristian”: You might have to wait for a person who’s maybe ahead or behind of you from a time zone perspective to answer that question. I think for teams, one of the challenges is certainly getting used to that more asynchronous type of working style and communication verus the synchronous. I think that is certainly one of the challenges that we have for most teams.

Luis Magalhaes: A big part of that is trust, right? I mean, just today I had to deal with a colleague who was more or less, not saying names to protect the innocent, but more or less freaking out because there’s a deadline coming. He had asked the person responsible for an update and it was like one hour, one hour at best. He’s like, “Luis, I’m not getting my update! What should I do?” I’m like, “Chill, trust.” The person knows that she needs to do this. Has a history of delivering on time we work asynchronously, trust. Sometimes that line is looming and it can be challenging for people that are still not that used to it.

“Kristian”: Yeah. I mean, exactly. Another piece is hiring. Hiring is challenging in general and although, again, pros and cons of each. Having an opportunity to hire anywhere in the world opens up the door for us to so many more opportunities. So many more people who aren’t living in the top six cities in the world where tech talent tends to cluster around. I think it’s a phenomenal ability for companies to help with diversity and inclusion. I think there’s a lot of ways for us to be able to work on allowing and hiring people from underrepresented groups who might not have had the same background, be necessarily able to afford to live in say, the San Francisco Bay area or other. Whether it’s working moms or other people in other areas, I think.

“Kristian”: So, all the things are fantastic. The downside is how do you find the appropriate signal when you’re hiring, when you’re not going to have the sort of face to face, right. We make a very conscious effort to, except for the very, very top execs, to not have onsite interviews even though we have some offices. Because we want to evaluate people in the setting that they will be working in, which is remote. Now, it’s hard to get that signal and we have some … Like other companies, Zapier and some other ones out there that are fully remote, we’ve had to optimize our hiring and interview process for remote to get the most signal we can.

“Kristian”: It tends to then sub-optimize, sometimes, hiring in some of the bigger areas where people want to move quickly and there’s a lot of competition.

Luis Magalhaes: Yeah. It’s so right that you brought this up because … First, this is my playing field. This [inaudible 00:26:18] is all about is the remote recruitment team, a remote recruitment company. We help people build their remote teams and you just listed all my USPs. All my company’s USPs. So, hey, great. Ladies and gentlemen, I promise you that no money has changed hands. But, I don’t need to run my usually advertisement at the end of the show because Christian is a pro and he’s done it for me. So, thank you very much.

Luis Magalhaes: I want to dig a bit deeper into that.

“Kristian”: Sure.

Luis Magalhaes: First of all, I saw that you wrote a beautiful post, which I dramatically recommend all my clients to read. Because you wrote the post where you list ten things about building a hiring plan. Thank you for doing that. We make part of our business helping people build hiring plans because so few people do it and even fewer know how to do it. Just thank you for putting that information out there in such a nice way. It really is essential for good recruitment practices. I want to dig a bit deeper into the specifics of, besides interviewing them remotely, what other aspects of wanting people to preform well in remote do you factor in when you’re building that hiring plan? What are the three key things that you’re looking for when you are interviewing or even putting the description out there for remote people?

Luis Magalhaes: This is my business and I’m always eager to listen to new opinions.

“Kristian”: Sure. I mean, right off the bat we’re looking for the right candidates for whatever that role might be. Clearly you’re gonna have some specifics as opposed to in the position you’re trying to fill. I think other than that it goes back, a little bit, to one of the signals we’re trying to solve for, is that ability to work asynchronously. The ability to be okay with not being in an office, not being surrounded by people every single day, and being able to work in that asynchronous environment. One of the things that we do is, as we go through the process, the last step of our process is doing exercise. We have everyone, I as the VP of engineering, joined the company and went through an exercise.

“Kristian”: We try to make the exercise something that is really specific to what you’ll be doing at your job. Not some fluff, something that’s totally made up. It may be something that might work on in your first 90 days or some challenges that are happening. We do that over Slack. We create a, sort of, a private external Slack channel with a number of people that are our interview panel and the candidate. We have a sort of a kickoff where we present the exercise that we would like them to do. Part of what we’re looking for in that exercise is not just the output.

“Kristian”: I think if anyone’s going to come … And we give the people the week to do it. Obviously, if you have another job, we can be flexible with time and whatnot. The point is, we’re not looking for you to go disappear and come back in a week. We want to see … We purposely leave out some things from the exercise that would make it necessarily complete. When have you ever gotten, as an engineer, a perfect spec or a perfect set of docs? Never, right?

Luis Magalhaes: Never. Even not as an engineer. My background is in writing and currently I work marketing. I always have to hunt for the pieces.

“Kristian”: That’s right.

Luis Magalhaes: It’s not like the Lego set you got from the shop. It’s like, there are missing pieces all the time. So, absolutely.

“Kristian”: Exactly. We wanna make sure that people, right, can interact well with … We’ve had some people over that who have self selected out just because they just feel this isn’t right for me. And that’s fine, right? We want to make sure that it’s a true partnership, it’s a relationship for all the employees we have bidirectionally. That they feel comfortable, they feel they can be successful, and then we feel that we can also enable them to be successful and be productive.

Luis Magalhaes: Yeah. Quick question. I’m undecided on this. When you give them a project … I assume that you’re looking at several candidates for the same position.

“Kristian”: Yeah.

Luis Magalhaes: So, do you give them all the same project and it’s a bit like a competition even if they’re not aware that it’s a competition? Or do you give them different projects?

“Kristian”: No, we have the same project that … We like to do some level of scientific method. We try to keep some things constant. Now, each role might have a slightly different exercise, but for the specific candidates that are going for that same role, we like to keep them the same. Now, we certainly have evolved that exercise based upon feedback that we get from the candidates. Either ones that we accept or ones that ultimately don’t come to work for Auth0. Frankly, it’s a little bit polarizing, I think. The exercise to some people, they don’t agree with it. They feel we’re getting free work or they don’t have the time for it and it’s silly.

“Kristian”: On the other side, we have people who absolutely love it as a way to showcase their skill and passion and really kind of dive deep into the company and in depth, work with some of the people that they’re going to be working with on their day to day roles and responsibilities. We can’t please everyone. We’re obviously looking for ways to get the most, I guess, acceptance or the most positive experience, but I don’t think we’ve found that yet. We’ll continually take feedback from current and new people, candidates, and employees to try to make that the best experience possible.

Luis Magalhaes: Yeah. What we usually do is, we set a trial period for us, but as well for the employee. Where it’s like, you’re going to be paid as a full employee for three months, but the first month is just to get to know everyone and the processes. We don’t expect you to deliver, really, on anything. You’re still finding your feet. The second month is the month for you to make your mistakes. Then the third month, we expect you to actually deliver. After three months, we get to make a decision. You get to say if you think we’re a good fit for you and we get to say if we think you’re a good fit for us.

“Kristian”: Yeah. We have done that with some candidates, right? Especially ones that are outside of the US. It’s a little easier to do that. Frankly, it’s a little hard for us to do that if we’re trying to win over Aness Sabri from Google or someone, right? [inaudible 00:33:52] their job.

Luis Magalhaes: That’s hard to petition.

“Kristian”: Right, for a three month … right. I think that the important thing is, especially for anyone listening, there’s no one size that fits all. Just be flexible and try to be open to … Because I think the other thing, I think, to point out is, hiring worldwide and globally has just some logistical issues as it relates to payroll, HR type functions, legal, compliance. If you go the straight contracting route, it’s a little easier. If you really kind of dive deep into different countries, it certainly takes some level of effort.

Luis Magalhaes: Yeah, I know. We built a business helping people deal with that so, absolutely. Absolutely. There are definitely barriers, but it’s surmountable. I want to shift from hiring to the actual leading. The point that a lot of my guests do is that the most important aspect, I don’t know if you agree, of managing remote teams, leading remote teams, is really communication.

Luis Magalhaes: You’ve written a really good article. It was about nurturing and managing female talent, but I think that it also applies to just introverts as well. Where you talked about the danger of having certain people dominate conversations. I personally note that remote helps with that because when it’s not everyone in the room, but everyone as their window, I think it’s easier for the quieter people to be heard. Do you think this is a fair assessment? Have you been in any situation where you felt that this was the case?

“Kristian”: Yeah, I think that certainly there are benefits to being remote where everyone can be on equal footing, so to speak. I think it’s easy for people, if they’re in physical location, to use your physicality as a tool. But, maybe not in a good way. It’s a way where it can be intimidating if you’re a six foot five male in a room with a booming voice.

Luis Magalhaes: You have a bigger chest capacity, just naturally project your voice more. You don’t do it even intentionally, you just do it, right.

“Kristian”: So, as a leader, I think it’s important to make sure that everyone, there’s equity in conversations. They’ve done some studies about showing the most .. I don’t know what the term was. But, the most satisfied and teams that work well together have almost an equal distribution of sort of input time. Whether that is in written format or in verbal format. I think it’s just important as leaders, whether you’re leading remote teams or not, to make sure that the conversations don’t end if you feel that hasn’t had their chance to have an input. I think that’s a very important thing to do.

Luis Magalhaes: Okay. Yeah. So, absolutely and as you mention again in another of your articles. Part of the role of a good manager is to facilitate the conversations. I’ve found that it’s a bit harder to manage brainstorming sessions through video. I wonder if you have any tips for that. If you’ve figured something out. When you’re with your team in video and you already know that everyone has a more equal voice, how do you keep the idea ball passing around? How do you make sure that everyone is jamming, so to say.

“Kristian”: Yeah. It’s holistic, I think. As you mentioned previous, having some ability to have ever had a face to face interaction with a person, I think can help with that empathy and that connection later. So, whatever you can do to facilitate that is important. Zoom, although as you mentioned, not the 3D experience of being a person I think helps. You can still look at visual cues and people’s faces. It’s still important if I say something to you and I see your face sort of kind of scrunch up or something. I know like, well, I saw you reacted to that. Was that positive? Was that negative? Let’s work on that. I think the video is important.

“Kristian”: We do shared Google Docs for everything so as we’re brainstorming, we’re all in the same docs sometimes and going through. Making sure we’re keeping the thought and ideas that are coming. A lot of us, I don’t have one in this office, a lot of us also sort of have mini whiteboards. We’ll change the camera view which I just did for you. You can’t see it, but I just showed Luis that I changed my camera view. You’ll see that we’ll be writing things on our whiteboard that’s visible to the camera.

“Kristian”: So, people put down ideas on even on a whiteboard so other people can see them. That certainly is kind of helpful as well. We haven’t tried the virtual whiteboard thing. I know a good amount of us do have whiteboards that are visible by the camera. Even at our home offices. So, we’ll be kind of writing and sketching some things down on that. I think it’s important to, and this goes just into general meeting hygiene, is always kind of declaring what the meeting is about. I find that if you declare a meeting as a discussion meeting or decision meeting, right.

“Kristian”: If people know that it’s just a discussion meeting from a brainstorming perspective and no decisions are gonna come out, I’ve also found that people can be a lot more free. Freeing up in their ideas knowing that there isn’t going to be a hard decision, say at the end of it. That opens up some creativity avenues.

Luis Magalhaes: I want to grab your point about empathy because it brings me back to another episode that I really enjoyed in your podcast, the SimpleLeadership podcast. Where you were talking from John Rouda. He has his own podcast, I believe it’s called the Geek Leader or something like that. The emphasis of the podcast was definitely in empathy and he said something, he said one thing that struck me as very true. Which is empathy doesn’t come naturally to him, it’s something that he has to work with. I think that people could use remembering that more often when they’re dealing with remote teams. Empathy is something that you need to work at. It doesn’t come naturally to some of us and it definitely doesn’t come naturally through the computer screens.

“Kristian”: I think that’s a good point. We’ll take empathy as one example. I think the larger concept is that, if you think about the growth mindset, which we may be born a certain way. We may be raise a certain way, but for the most part, if you subscribe to that growth mindset, we’re not locked into that. If you feel that you may not be as empathic as you should be, it’s not an excuse to just say, well, I’m not empathic and that’s it. I think it’s an opportunity for you as a person. As an IC, as a leader, to say, well, I recognize maybe empathy isn’t my strongest point. Now, how can I go about improving my empathy? Especially with being on and running remote teams.

“Kristian”: It is a little harder to get that empathy if all you’re doing is going through Slack or going through a Zoom call. It takes a little bit more of … You know, I think of one example of [inaudible 00:42:34] even from Slack. I’ve found that sometimes using Slack, because it’s so sort of synchronized, just kind of pick up were you left off. We forget some of those social niceties of, “Hey, good morning.” or “Good afternoon.” Or “How are you doing?” It’s just what’s the status of a PR or can you get clarification on this.

“Kristian”: I think it’s important sometimes to take a step back and try to … As someone else mentioned on one of my podcasts too, when you’re working, you bring your whole self to work. Sometimes it’s hard for us to see that whole self when all you are exposed to from an interface is Zoom or Slack. I think you have to over index a little bit not under index on trying to tease out a little bit of the person behind the Slack avatar and behind the Zoom call.

Luis Magalhaes: This is very interesting and very relevant. I was just talking to someone today and I was commenting on that. I personally noticed that I tend to be very … To take, I wouldn’t say offense. When someone communicates with me through text, I tend to their words in a very raw, combative way. Whereas if they would tell me the same thing through video, it would be like, okay, whatever. That’s reasonable feedback. Thank you very much. To me there is a world of difference between written communication and video communication, which goes to your point. You also mentioned that written communication is a very big part of what you do and it’s the same in my company.

Luis Magalhaes: How do you personally, as a leader, deal with this? Do you have any tool, any tacit, any strategy that you use to walk away from what you’re reading. Just stand a bit back from what you’re reading and try to see the whole picture. The more holistic picture, as you say it.

“Kristian”: For me, I think … And I want to break up writing into two categories. One, the short form which is the Slack and the long form which could be Email or a blog post or pinning something. Internal blog post or pinning something in Slack. For me, I spend a lot of my time writing and what I’ve found as a leader in general, it’s not enough to say something once. It’s not enough to just kind of throw something out there without context. It becomes incredibly important, even more so as a remote leader, to one, be consistent. Repeat your message over multiple types of medium. So, have a message in Slack, post something that explicitly goes into it on Confluence. For me, it takes a lot of time, but every two weeks I write a pretty long internal blog post for the engineering teams. Because of our transparency, I share it with the whole company so everyone has a sense of kind of what’s going on.

“Kristian”: Someone might mention something on Slack, like I said, I heard this. Or, if you talk about the rumor mill. Holy cow. The rumor mill can go crazy on a remote team in Slack. It’s that time zone thing, right? Something might pop up and then by the time I hear about it, it’s 24 hours later. The story has gone from … It coulda been the most simple thing or a message that I said on Slack being maybe not as contextually aware as I should have. I might shoot off something and then go to bed. Now, half the world is thinking, oh my god, Christian said this. Or I think he’s upset, or I think he means this. What’s going on.

Luis Magalhaes: Exactly.

“Kristian”: Then it takes a while for me to see respon-

Luis Magalhaes: Are we still going to have a job tomorrow when he wakes up?

“Kristian”: That’s right. You know, he used a weird emoticon he’s never used before. What does that mean?

Luis Magalhaes: Analysis, analysis.

“Kristian”: I think it’s important to not overlook the long form written communication. Slack is good for a lot of acing, but if you really want to go into depth about something, take the time to explicitly write it out. Write it out and say it 100 times.

Luis Magalhaes: We see that there’s a lot of layers of complexity when you want to have good communication with remote teams. This can be a bit daunting when you’re on boarding someone. When you’re bringing … if we go back full circle to the recruitment part. When you’re bringing someone into the team, what’s the conversation like when you communicate these communication expectations? What does that talk sound like when you’re bringing them in?

“Kristian”: I would say just candidly, it’s probably not the best. I talk about how important it is for communications and setting the norms and on boarding. I think, frankly, what they say is one of our internal OKRs for engineering specifically this quarter is actually about improving our on boarding process. I think people still, in general, from a company perspective. People I think, think very highly about our on boarding process and I think it is very good. But, for me, I always think it can be better. I think that there’s a lot of things on the engineering side specifically that I want to improve upon. Being explicit about … I don’t wanna say cut standards, but explaining about what the culture is around communication, around expectations, around all that, I think is frankly really important.

“Kristian”: It’s become a little tribal knowledge instead of really being formalized in an onboarding process. That’s one of the things that we are looking to, I think, codify and help with people on boarding. We’re gonna almost double our engineering team size this year. So, we want to make sure that we deal with that up front so that we can on board people better.

Luis Magalhaes: No, I feel you. I definitely feel you. One of the things that most has occupied my time on the past year, has been coming up with on boarding processed. We’ve come down on a kind of a mentorship solution. Again, there’s always room for improvement. So, it’s interesting to hear how different people deal with it. We’ve been at this for almost an hour. Time flies and I want to be respectful of your time. But, there are a couple of questions that I wanted to finish with before we go. Before we close up with you telling where people can find you.

Luis Magalhaes: If you were, and maybe you’ve done this, if you were going to buy a tool for each person on the team. Spend like 100 bucks. $100 on something and I don’t mean a software program. I mean something physical. What would it be?

“Kristian”: Let’s see, $100. Let me throw out a couple of the maybe finalists in my decision process. I think for remote teams, investing in a good camera and lighting is huge. I’ve been on so many Zoom calls where it’s like the witness protection program. You can’t see their face [inaudible 00:50:26] blacked out.

Luis Magalhaes: They’re like against the window. It’s like those video games character selection screen where you just see the silhouette.

“Kristian”: That’s right. That is sort of my pet peeve, I think. If I could outfit everyone in the company with a light in front of them and a good camera, that would be some of the tops on my list. I think, personally, I’m a huge fan and avid reader. I would probably give people an Amazon Kindle Unlimited subscription or something like that too. I think reading but fiction and nonfiction is really, I think, important for personal growth and empathy. Those are a couple of the things that I certainly would look for, yeah.

Luis Magalhaes: Well, now I have to throw an extra question there because I’m curious, what’s the book that you’ve most given? Given out. Gifted.

“Kristian”: Gifted, you know, I think that there’s a couple ones that are top on the list. I think one of the top ones, it’s probably surpassed right now, is … And they’re both related to communication. One of them is Thanks for the Feedback and it’s a really good book not only about how to give feedback, as a person how to receive it. I think all of us think we’re good at receiving feedback until, as you mention, someone gives you some and you get the [inaudible 00:51:56] right?

Luis Magalhaes: Exactly.

“Kristian”: And Crucial Conversations. I think those are two books that really are important in growing teams. Especially for me, I’m really making an effort to try to build an incredibly diverse team. Especially a diverse leadership team. One of the things about building diverse teams is that you don’t always agree on everything, right? The point is not to be in 100% alignment on everything, right? You want difference of opinion. You want difference of thought and background. The important thing is making sure that your working agreement and your working relationship with each other is built on trust and understanding. And the ability to have those tough conversations and give each other feedback.

Luis Magalhaes: Okay. Well, those sound awesome suggestions. I usually have already read the books that my guests suggest, but this is not the case. So, that’s two new books for me to read. Thank you very much.

“Kristian”: Great.

Luis Magalhaes: The last thing that I wanted to ask you, is the question that I ask everyone. It’s kind of a tradition. Let me setup the scene. Let’s say that your organizing on a Chinese restaurant. You’re organizing your round table dinner where all the top execs of Silicon Valley technology companies are going to go to discuss the future of remote work. Since you’re hosting, you’re the host, you get to decide what goes in the fortune cookies. So, what message are these people going to crack open on their fortune cookies?

“Kristian”: Wow, that’s an interesting one, you know.

Luis Magalhaes: Well, I had to stump you with something.

“Kristian”: Yeah, I mean, that is. Now I’m on the spot. I think if I was to … I think it’d be somewhere on the lines of be prepared, you know, the revolution is coming or something. I think because really, as you mentioned, the future of work, I believe, is not gonna be entirely remote. But, I do strongly believe that the future, a big increase in percentage of how companies work, that remote working, leading remote teams is going to become more of the norm than a side … not a fringe. You know, not quite as mainstream as traditional. I would certainly say be prepared, you know, start putting things in place now if you want to be competitive and if you’re definitely gonna want to invest. That certainly investing in companies and technologies that make remote teams successful is gonna be part of the future.

Luis Magalhaes: Okay. So, that sounds a great message to end on. Hey, tell the listeners, I mean, we’ve already gone through this and everything. It’ll be on the show notes. But, it’s never too much to repeat where people can find more about Auth0. Where people can find more about the SimpleLeadership podcast. And where people can talk to you. Where can people get in touch with Christian McCarrick?

“Kristian”: Sure. Auth0, just go to our website, auth0 dot com or Auth0 on Twitter. Those are, I think, two of the best ways. For me personally, I have DMs open on Twitter and my Twitter is C S McCarrick. So, that’s pretty easy to remember and you can just reach out to me there. To listen to the SimpleLeadership podcast, you can go to SimpleLeadership dot I o or you can search for SimpleLeadership on iTunes or your favorite podcast aggregator and SimpleLeadership is one word.

Luis Magalhaes: Okay. Well, thank you very much. Thank you so much for your time and for your insight. It was a pleasure having you.

“Kristian”: You as well. Thank you very much. I always enjoy talking about leadership and remote working and the challenges about both. So, thank you very much.

Luis Magalhaes: And that, ladies and gentlemen was Christian McCarrick from Auth0. I hope you enjoyed our conversation and I also hope that you realize if I can get guests of this caliber and quality, it’s thanks to you. It’s thanks to your support. You who listen to the podcast, who share it on social media, leave reviews on iTunes and in your podcast services of choice. Number one, thank you. Number two, please keep on doing it. It’s very helpful when it comes to attracting high quality guests and to reaching the ears of other people. Helping them build and manage great remote teams. So, please keep on doing it. You rock and this podcast exists thanks to you.

Luis Magalhaes: On another note, if you want some help building those incredible teams, well, give us a call. Remember, when you look for quality people, you need to think differently. You need to think globally. You need to think remote. You need to think DistantJob. And finally, if you would like to study the podcast in more detail, you can get the transcript for this episode and all others by simply subscribing to our podcast page at DistantJob dot com slash blog slash podcast. There you can subscribe and you get the link to all of our transcripts. So, thank you once more. See you next week.

We dive into topics as varied as how to make sure to hear the opinions of introverts in your team, how to write like a leader and beat the Slack “rumour mill,” what’s the difference between brainstorming for discussion and brainstorming for decision, and much more!

Books Christian recommends:

  • Thanks For The Feedback 
  • Crucial Conversations

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!

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