Wes Winham

How to manage a team remotely

08 Mar 2020   |   Remote Teams

Wes Winham

How to manage a team remotely

08 Mar 2020   |   Remote Teams

What are we talking about?

Managing remote teams.

Why is managing remote teams important for the future of work?

Are you serious?

What did Wes Winham teach us about managing remote teams?

Trust on remote teams. Trust is important on a remote team, but it doesn’t build as quickly. It takes time and often requires creating intentional points of friction throughout the day. A completely frictionless work experience is actually not optimal. You need moments in the day that get interrupted. 

Building in friction. As much as engineers hate it, Wes says, “You must have meetings that don’t have a business purpose.” In fact, there’s a lot of human stuff that happens in a co-located space for free that you have to add back into remote teams. 

Daily standups are great, but there’s a difference between a check-in (“How are you doing?”) and a status meeting (“What did you do?”). Remote teams work best when they are focused on the future. Also, those standups might be better in the middle of the day instead of at the beginning. 

The talent motivation. Wes says that the #2 reason companies look to remote work is about talent (second to global pandemics). Companies often start remote when one key employee needs to move away. While remote hiring can help with bias, “Remote work does not fundamentally solve bias in hiring, but it makes us more aware of bias.”

Taking care of remote workers. Wes encourages his remote team to go to at least one meetup a month to make sure they stay social. He also gets nervous if people respond TOO quickly on Slack. (I feel like I’m interrupting you). Slack can be asynchronous or synchronous, but will go to synch without guardrails.

Time zones. Wes has strong feelings about time zones. Although he feels like you don’t need an HQ for your company, it makes sense to have a time HQ that everyone works with. 

Communication rules. Wes says that being remote forces you to build up your processes and communication for a much bigger organization that you actually are. Woven practices a communication hierarchy of durable communication, Slack messages, and email (yes, Wes still uses email). Wes highly recommends video on for every call that happens. 

Wes says he’s a federalist, meaning that he tries to establish some thin rules for the entire organization, but thinks individual teams should create their own rules. 

Links from Wes Winham

Woven website

Work simulations from Vervoe 

Stripe’s post on a remote HQ hub 


Today, our guest is Wes Winham. He’s the CEO of Woven and this episode is Work Minus Remote Hype. Hi, Wes. How are you doing?

I’m doing great. I’m excited to be here, Neil.


We’re excited to have you as a part of our show. Tell us just briefly a little bit about who you are, what you do, and what is Woven.

So, I’m the founder of Woven. That means I’m herding all the cats and doing all the jobs that we don’t have anyone that’s actually good at it to do right now. We’re about 10 people so it’s very much early stages. At Woven, we help companies hire better fit developers faster, and we do it with less engineering effort. And what’s weird about us is we’re focused on hidden gems. So, those are folks that are really good. But maybe the resume doesn’t show it. We help companies find those folks so they hire faster and they do less headhunter fees, all that nonsense. And really that’s about reducing that credentials bias in the first step.


I think we’re going to get into some of the specifics of what you guys do and a lot of the bias stuff that comes in. But your team is completely remote. But we should say this is not your first venture into remote work. So, you have a 10-person dispersed team, but tell us about your history with remote work.

At my last company, started colocated and then it came time to scale the engineering team. And what I realized is it’s really hard to hire engineers in a given city, doesn’t matter where that city is. So, I opened up remote just as a way to get around my pain. And it was kind of a cheat code for hiring. Just you get so many more candidates. You find candidates that care about your thing that have a personal connection to your admission. We’re both based in Indianapolis. Imagine this podcast, but only in Indianapolis, it’d be pretty good. You could get a good podcast, but you’re unlikely to have people… It’s a big world out there people really excited. I lucked into international remote and then had to deal with time zones and had to deal with building trust and had to build a hybrid team and keeping them connected to the rest of the org. It was super challenging. But I got to work with some really great people, and it made hiring easier. So, I learned a lot of lessons the hard way when it came to managing remote team.


Well, let’s all learn from your hard lessons and mistakes then. So, tell us a little bit about that experience of remote working and especially the ideas that are out there about what we can get from remote work. I mean, you’re going to be able to attract a more diverse geographically speaking talent pool that’s out there. But what are the other main benefits you see of remote working?

I think talent is… folks stick around longer, people talk about the tenure being increased, there are some people that use it as a cost arbitrage, you get cheaper folks. That’s fine. The big benefit to me is we have folks hire engineers, we have a customer that hired seven experienced engineers in 45 days with no recruiters, no headhunters. You need a team of three recruiters to get that same result anywhere else. It’s just a superpower. I’m hiring executives right now. I have folks that I’m talking to that there is no way I get to talk to them if I can only look in any given market, whether that’s San Francisco or anywhere else. So, I think talent is really the number one reason and everything else just a trade off. So, as far as the downsides, though. So, talent’s great. What are the downsides? I think there’s a lot of hype right now. There’s a lot of folks that are going to work from home. We’re in the middle of the coronavirus. We’re becoming aware that it’s among us here in the U.S. so stuff is changing. So, one of the challenges with remote work is you don’t build that trust as quickly. So, the trust is I think of it as a trust battery. So, this is I know you, I know you’re a complex human, you’re not just that guy in customer support that throws me the bugs all the time. And I think you get your bugs wrong half the time, and it’s not really my fault. We always have these frictions. So, it’s that human connection of knowing someone is more than just their job and how their job makes your job hard that makes teams work and it’s just much harder to build it accidentally. You don’t get that “we ran into each other at the kitchen.” So, for me, that meant I had to create meetings and space during regular meetings to simulate that kitchen time. So, we would do check ins. This is something I stole from the book “Holacracy” which is crazy book, recommend it for push your thinking on what management is, but one of the things I really loved is they start meetings with check ins. A check in is not status. A check in is what did I do this weekend? How am I feeling? I felt kind of sick. My baby was crying all last night. So, I’m not at my best. I saw this great movie. It’s like that stuff that we tell each other in between meetings time, but we have to make space for it in our meetings. And I found that took a relationship between developers and customer support that was pretty antagonistic, and actually created some understanding where folks would reach out and give people the benefit of the doubt, because we understood each other a little bit. So, trust is a big one.


I do a lot of remote work. We used to start our meetings with a very human moment. We’re always talking about the future of work. So, we don’t see each other a lot. So, we say what’s something we can talk about that’s very human? We use like the captcha test. Like, how do we prove that we’re logging in as a human, not a robot, just asking each other about some memory from childhood or something like that. That was always fun to bring that. So, I like that a lot thinking about these things. When you talk about trust building, obviously that’s essential to having a good functioning team. What’s the advantage, what is being colocated add to that trust factor? Why is it easier to do that in a colocated space than from remote and is that artificial? And how can we overcome that?

I think the colocated trust benefit is because I think we see business is all about business. It’s about the KPIs. It’s about the next project. It’s about status. So, your manager probably makes a lot of space for making sure the business stuff happens and the human stuff, when you’re colocated, it just happens for free. And that human stuff is really important when it’s gone. We don’t know what’s happening if we’re just in an office, it’s just like the fish swimming in water. The older fish says, “How’s the water?” The younger fish says, “What’s water?” It’s what we’re swimming in. Just being human and realizing we’re complex, and we have contexts and we have bad days and good days. So, it’s happening and it’s important, but when go remote, we just lose it. So, if we don’t build it back in on purpose which means, it’s hard with engineers because engineers hate meetings, it means having meetings that don’t have a business purpose and making that okay. And that’s a challenge for folks that are introverts, are meeting averse, because meetings are not getting work done, which is fair. So, I think it’s being deliberate about that stuff that you usually get for free.


When you talked about the two meetings of the customer support with engineering that tend to be you’re just bringing up bugs, you’re making my work harder, you’re bringing up things that I don’t think are valid. Talk about the other side, too, where you have maybe a team that’s all working on the same project that’s there. Where does friction play a role in that side? Or do you need to introduce more friction? Are there ways to remove it in order to help people to interact with each other more? Or can you be too seamless? There’s a lot of issues around this. So, what’s your take on it?

Totally. So, when we’re in a team that’s working on the same project, the issues are a little different. We have trust, but let’s assume that we’re doing the basics. We’re having time in our stand ups to meet each other. We’re having some goofy Slack conversation that we post gifs and off topic stuff. So, then it’s about friction. I think you nailed it. A team that has no friction, that has perfect deep work, perfect blocks of uninterrupted time is a team that’s going to struggle. This is counterintuitive, especially in engineers and folks, writers, people that really need deep work. But what you find is if you make that prime, we’re going to have uninterrupted time, you have big wasted blocks of uninterrupted time where you’re going the wrong direction. So, in an office, there’s a bad version of this where you’re interrupting each other all the time and your people are programming and you walk to their desk, and hey, did you get that email. So, that sucks. But the other side is I think more silent and more, at least as bad, which is, you go off for four hours in a direction where someone could have helped you 10 minutes in with a 30-second comment built from experience and saved you four hours. And if you make this blocks of time prime, which I think is common in remote work cultures, you just have a lot of waste and you also feel alone. You feel like this is my thing, I got to figure it out myself. And that’s not a good feeling. That’s not what teams are about.

Teams are about, I have weaknesses, you have weaknesses, maybe our strengths and weaknesses complement each other, we know different things. So, this is back to building in deliberate checkpoints where we can get help asynchronously, where we can sometimes interrupt each other. A tangible tactic here is when I have colocated teams, I like stand up at the beginning of the day because it helps us all get in the office sometimes, which is silly, but developers sometimes it’s a problem. At the same time, get our plan, have hard conversations. For remote teams, I actually prefer, and we’ve switched this a few months ago, I prefer stand ups in the middle of the day because this is at least one check in where you’re not going to go spin off for six hours. Because a stand up where there is no crosstalk where there’s no post stand up meeting, there’s no “I had that problem” is a wasted stand up. So, I think we’re experimenting with other really short check in meetings throughout the day to give people an excuse to be like, “Hey, I’m stuck on this thing,” and all that. I think there’s just a lot of value in seeing someone’s face when they talk to you about a bug. It’s like,”Okay, Wes said he’s okay. But I see his face. I heard the same thing yesterday. He’s not actually okay. He thinks he’s okay. But I know Wes. I’m his teammate. I can jump in and help him get unstuck.”


I like that a lot. When we talk about friction, you’re talking about intentionally building in opportunities for people to rub up against each other almost in this remote environment. That’s really good. You also touched on a topic that I think is really important when we talk about remote work, which is loneliness. People who are in a remote environment, maybe they’re in another country, maybe they’re in some other place where they really don’t get a lot of interaction with other people. How do you counteract that feeling of loneliness that people can feel when they maybe only are talking to people a few times a day?

I think this is very, very personal. So, I’ve worked with folks who are fairly introverted, they love remote work, they feel like video calls are enough connection. That just is the best thing since sliced bread because it solves a problem they have in the office. I’m kind of ambivert, sort of in the middle. So, I feel really good on video calls. I feel like I’m on seven hours of video calls, I feel really good. I don’t really have a big problem that I need to solve as some other teammates who are more extroverted. For them, video calls currently don’t really replace the feeling. So, this is something I’m still working on. What I know is those folks do better in coworking spaces than they do work from home. And for new Wovers, it is not optional but you will find a coworking space during your first couple weeks, unless you’ve worked remote before. If you’ve never worked remote before, you have to work in a coworking space and try it out. So, that you get over that friction of going there the first time. Some people just get energy from that. We also push folks to go to a meet up a month, some kind of community connection. I think it also depends on where you are in your life. If you’re a parent with young kids, maybe you take some time over connection. But it depends. I think getting out in the community is important. And I think work from home is actually really dangerous idea for most extroverted folks.


Yeah, that’s good. I’ve seen other companies that have actually provided some kind of stipend if you want to join a community group like that to make sure that you have the interaction because if you are working from home then you sometimes can be very isolated and that can be lonely. So, making sure as an employer, you are meeting that need that we maybe didn’t realize we were providing with colocated spaces.

Absolutely. I think a little bit of budget goes a long way. A budget is a very tangible way of showing support for something.


Yeah, for sure. Talk about timezone. So, like you said, one of the advantages of remote is that you can get talent from all over the world. What’s the best way to handle those things? You talk about meetings at a certain point of the day, but maybe somebody’s beginning and somebody else’s end. So, how do you deal with that?

Personally, I think time zones aren’t worth it. I actually, in most cases, do not recommend someone to have teams across time zones. I think team boundaries are where time zones should be. I am a remote work maximalists. I think people don’t talk about the cons and why it’s hard enough. But I am not excited on asynchronous work. I think there are just very few contexts where it actually does create great output. I think open source projects are one example but that’s not most of our companies and most of our teams. So, when I say all over the world, I’m mostly in my contacts talking about North and South America. We have great team members that are working in the Caribbean right now. I am excited about expanding into South America folks that have the same time zones. I’ve also worked with folks who are in Western Europe but are comfortable with time shifting. I think it’s just really, really hard. I would not, if you are dipping your toes into remote, I would not recommend asynchronous work. There’s a whole other level of deliberate and written and it’s just really hard right now.


I think that’s good advice. I think most people don’t realize how difficult it is to handle the timezone differences when you’re interacting on the work schedule with different people. That’s great advice.

Even three hours is pretty rough, but you go out beyond that, like Envision is an example of a remote company that’s scaled to hundreds of employees. Envision works in U.S. east coast time only. So, they’re not a timezone agnostic group. So, you know this when you’re signing up that this is an east coast company, which I think is reasonable. Those folks are working really early mornings.


Tell us about tools you use, technology tools that are out there. When it comes to communication, when it comes to collaborating on things, what are some things we need to keep in mind? You’ve used the term asynchronous and synchronous communication. So, do you use different tools for those different types of communication? When you’re actually managing projects, is there one tool that you favor over another? What’s your experience?

For me, there’s a hierarchy of communication that I try to keep in mind, which is durable communication. There should be one place for that to live. We’re experimenting with notion. I have not fallen in love with notion like I was hoping I would. Still mostly using Google Docs in a little bit of a folder structure that has a lot of cross linking for durable information. And then the next level up is Slack. Or actually, the next level up is email. So, I do send email sometimes. Those are for slower projects that require a little more thinking. And then Slack. And actually, emails, it’s interesting. Now that Slack is front and center, I get really good interaction on my emails now that I’m one of the only ones sending emails. So, I think there’s still a place.


It takes a lot for someone your age and your position to say you actively send emails. Most people will shy away from that.

I think I send two or three emails a week probably plus my investor updates to internal folks, only about important stuff. And then there’s Slack. Slack is noisy. I think it’s important to accept what are your rules of engagement for responding to Slack. If you do not set them, people will default to being responsive, especially to you as leader, because everybody wants to be fast and respond. I have to have conversations, like, “I noticed every time I say something, you respond to me quickly. That makes me think that maybe I’m interrupting you.” And then I have my manager read me where I say here are my expectations. And if I message you in Slack, I do not have an expectation, fast response. If I do, I’ll text you or call you. So, I’m in that hierarchy. Zoom obviously for video calls. We have a video on every call. And it’s really important when I talk to investors and lawyers and I get a lot of, they’re on Zoom, but it’s a phone call. And it’s just so much worse. It’s just a very different game. The video matters. Video on, very important. And then there’s some specialized tools we could talk about, but those are the really main core collaboration tools.


Tell us a few more of your rules of engagement or digital hygiene. Are there certain company wide rules that you would recommend? Or is it all personal however you want to respond to it?

I’m kind of a federalist when it comes to most company properties. I think it’s good to have a thin layer of rules at the top bullet team that their own rules of engagement. And the team leader’s job is to set those. I think our rules are that there should be rules. For example, the go to market team, sales and marketing mixed, they actually care a little bit more about being responsive and I think that’s a domain where you do get a little bit more advantage from being responsive to customer issues, prospect issues, sometimes things can flow faster on the product development team, that is not the case. So, rules of engagements are things about response time, out working hours, and escalation paths, some of those escalation paths should be I think individual. So, some people like to be escalated to in different ways,


Wes, when you’re working with some of your clients, do you find yourself having to convince them to think about remote possibilities? Or are they already coming to you considering that? Or what’s your stance with that?

Everybody’s thinking about it at this point. And most people, if you’re 50 employees, it’s going to be rare that you have zero remote people. Mostly how that happens is you have someone that’s great, and then they have to move, their spouse is moving. They need to move back home. And you’re like, “Do I want to lose this person or do I let them go remote?” Most people choose let them go remote. That’s how it starts. That’s patient zero. So, I think everyone is on the radar. And then the next most common thing I see is we had to hire an executive, or we had to hire this very senior engineer that’s specialized. Those roles are just so hard to hire for. And it’s a cheat code. So, I think a lot of companies will have a remote CEO, and they’ll be against remote work, a CEO that maybe commutes three weeks a year. So, it’s kind of crazy how we see the advantage for some of these hires, but often don’t allow that same flexibility and build the muscle memory and the processes and the skeletons we need to be successful and rope from other teams.


Tell us about that dynamic when there’s one remote employee. I feel like that’s one of the most dangerous situations to get into to say, we’ve never been remote before, we’re always colocated. Let’s just try it with this one person that’s either having to move away or this one hire that we’re going to do. What’s been your experience with that? What are the dangers you see?

My first remote hire at my last company, we have a standing meeting that gets canceled because we realize, oh, half the people are at the office, we go into the conference room, oh, actually, let’s not do this. And then we leave and I go about my day. 15 minutes later, I get a message from our one remote employee, hey, are we still having a meeting? He’d just been sitting there in a meeting, out of sight, out of mind. And at first I was like, well, that’s silly. And then I had a one on one. And this was a guy that was really good at communicating. And he was like, “This can’t keep happening. If you do this, it sends a really strong signal to your remote folks that they’re not as important.” And he was absolutely right. It was easy for me to not think about that as a mistake. But that was a symptom of a wider cause. If you have someone out of sight, out of mind, and everyone else is in the office, it’s so easy for them to not get that update, to not have that hallway conversation, to not know that status change, to not hear that customer story, stuff that is like, most companies, there’s no deliberate channel for this because it just kind of happens. You have that for those remote folks. It’s so dangerous. So, you have to build basically, the processes for a much bigger organization earlier, like your internal comms processes have to be good. And it’s not easy. It’s a superpower if you get it, because whenever you get to 200 people from 50 people, you’ll already be there, you’ll already be ready, you won’t hit that next scaling hurdle because you’ve already built that process. You’ll be able to hire all across the time zone, you’ll be able to find the person that is just really keyed up about network packet switching at enterprise scale, or whatever it is you do. You’ll be able to find that person that has a personal story, but you’re going to have to build one tier ahead on new processes.


Yeah, for sure. I think that’s important to say remote work is not just something you try to do. It’s a culture change. It’s an attitude of saying this is how we communicate, that changes everything about how you work, how you interact, and having that one employee sometimes opens your eyes to what that is and makes you wonder, is this right for us? Do we need to do this? Because to become a remote company is really an entire change on the culture. And again, it can be stressful to the people who are inside it who are used to one way of working, right?

Absolutely. And a story from Stripe, a company I look up to a lot. Everything they write, I’m like, “Oh, that was so good. How do they know that thing?” So, they opened up branch offices over the last few years, and one decision they made is instead of having a headquarters, they have equal nodes. So, their San Francisco office is not their headquarters. They have their Seattle office, and then they have offices in all across Asia. So, that was a deliberate strategy because if you have a headquarters, that has a center of gravity, the other places are less likely to innovate. And what they found is, and this is because they were a remote first company early, they had lots of engineers remote really early and they had a lot of influence. They found that, as a result, the Seattle office has been able to innovate in processes and tools and systems and bring that back to San Francisco, which is not a thing that happens in companies that have headquarters and they have satellite offices. It’s like remote is also very applicable, even if you really are going to have offices.


Wes, let’s close this up with one of your favorite topics I know, which is about bias in hiring. What do you feel like what’s the role that remote work plays in trying to correct some of the biases we have? Does it open up our eyes to more bias or what is your take on that?

So, remote work doesn’t fundamentally solve bias, it just makes it easier for us to be aware of our bias. So, for me, I’m hiring a head of customer success right now. And I have a bias towards founders. I love people who start things and that’s just who I am. So, I appreciate it. I can tell you a story why actually, they’re better people and they innovate faster, and they’re more agile, and I don’t know if it’s true, I believe it. So, when you have a remote process, you can just get so many more resumes that you have to build better processes a little early. So, for us, we built a rubric. And I found out once I build a rubric, and a rubric is just you get a point for having hired five plus engineers, you get a point for mentioning an emotional word when you talk about why our mission is meaningful. You get a point for answering this question about an interview funnel to help troubleshoot it for a customer with a correct-ish answer. So, it’s just like there’s a scorecard. And what I found after creating the scorecard after doing an initial pass, is there are like three founders that I was thumbs up on, then I go to the rubric, and thumbs down. And I look at them, they didn’t actually have the experience. They didn’t actually get the questions right. I just passed Wes. Saw that resume and got excited. Like, yeah, they can do it. And that’s just not fair.

So, as a remote company, you have more opportunity to build good processes because most companies are satisficing. It’s like I got three candidates that seem good. I’m going to talk to all three of them and hire one. When remote, you got 100 candidates. If you can really figure out how to get the top 5%, how to be more selective, you can build a fundamentally better company versus just randomly picking among the top half. And there are lots of tools that will help you do skills assessment. We have one for developers. You can also build your own. So, the idea here is give somebody a one-page snapshot of your business, and then ask them to solve a business problem that’s related to their job, and timebox at an hour. And you can even do things, like, you’re in front of a whiteboard, you’re brainstorming this problem with the executive team. What are some of the ideas you write down? Then you count the ideas, you count the breadth and depth, so did they hit ideas across, let’s say, every part of the candidate journey or every part of the customer journey, and then how many ideas they have, and how many of those ideas were creative. And you can see people that have much worse resumes, just they’re okay, they just don’t stand out versus someone that was VP at Adobe. And then you’ll see that this VP at Adobe is just a much worse thinker for your environment. And that’s just magic when you see it over and over. I love work simulations. That’s what we do. There are tools called Verbo is one I like for just generic work simulations. There are sales specific ones that will let you roleplay a sales call. So, these things when you’re remote are just magic because you can find the people that can actually do the job that you need done.


Well, that’s great. I like thinking about it. And I think it opens up the door to saying, if we’re going to bring in a broad, diverse group of people around us, we know that diverse teams perform better, we know that it’s just the right thing to do at this point. If we’re still stuck in, I got to find people who live close to me or in my referral network, you’re not going to scale to that point quickly enough. So, bringing in these things, you’re going to get even more qualified people. And like you said, people you may not have recognized at a first glance, but really focusing on the work, focusing on what needs to be done, I think it’s awesome. Wes, it’s been really fun to talk to you and hear your perspective on all these things. Where can people go if they want to learn more about Woven or you?

We’re at woventeams.com and you can learn about work simulations. We’ll talk about rubrics. If anyone wants to talk to me about rubrics, I could talk about this for 90 minutes. It’s my favorite geeky topic. Talk about bias and numbers, woventeams.com.


Excellent. Wes, thanks so much for being on the show and we look forward to talking with you again soon.

Thanks, Neil.

Wes is a software entrepreneur from Chickasha (Chick-uh-shay), Oklahoma. He moved to Indiana for a software engineering degree at Rose-Hulman and then fell in love with startups. He was the first employee at a SaaS startup called PolicyStat, where he was responsible for product and engineering. He helped grow the company from $0 to more than $5 million ARR and to a May 2017 acquisition.

Wes lives in downtown Indianapolis with his wife and their 3 adorable pet rats, Kaizen, Rebel, and Sisu.

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