Welcome back to The Digital Workplace podcast. Today, our guest is Luke Thomas. He is the CEO at Friday. Hey, Luke. How’s it going today?

Hey, Neil. Thanks for the invite and excited to chat with you today.

I’m super excited about this. You have a lot of fun things to talk about. There’s a lot of commonalities we have. But first, we got to make sure that you’re a human because we don’t want to just be talking to a robot today. So your CAPTCHA question is, do you plan your days off or do you just let them flow?

I definitely let them flow. I would say that’s the default.

Yeah, I struggle sometimes, like I love having a very structured day off in terms of if I have a lot of tasks to get done, or if I really want to make sure to hit this one thing to do. But I think I’ve learned to lean into more of the unstructured time, especially we’re just coming off this holiday break, so it’s been nice.

Yeah, I have two kids. So you just never have any idea what’s going to happen. So that’s part of the reason why I just let things roll. Because it’s like, you never know what happens when you have two kids under the age of three.

Yeah. You don’t want to put too many expectations on that time. Excellent. Well, cool. You’re a certified human. So welcome to the show, officially.

Awesome.

So introduce us to Friday. Tell us a bit about how it got started and what it does.

Yeah, so Friday is a home for your company. And the reason why I started working on Friday was because I started working for fully and impartially distributed companies since 2013. In just about every single role I was in, whether it was an individual, contributor, team leader, or an executive, I just always run into the same issues over and over again. Naturally, they’re expressed in different ways, depending on if you’re a leader or you’re not. But I saw the promise of working from anywhere, and it’s like, my goodness, this is amazing. I don’t have to live in a city I don’t want to be in. At the time, I lived in Boston, and I wasn’t really a huge fan. But the reason why I was there was because that’s where the job opportunities were. So my wife and I moved down there. We were just itching to go somewhere else. That’s what that promise of people are chattering about remote work, I was like, okay, this seems really interesting. Growing up, I was homeschooled as well. So I was very used to this very flexible day.

Then it was like, hey, you need to come into the office every day of the week. It’s like, okay, I’m literally working from a laptop. I’m showing up to the office. I’m opening my laptop. I’m putting on headphones. How does this make any sense? It’s not that I don’t like my coworkers here. It’s that it just seems like there’s a better way, especially if somebody works from a computer. So I became very interested in the space but quickly ran into issues. The more I dug into the issues, the more I just felt like, hey, there’s such an opportunity here, but there are very real challenges that need to be overcome. Yeah, during my research, I started building Fridays and nights and weekends project, then started digging more and more into the space and realized that just about every single thoughtful, early leader at remote and more asynchronous work had built their own company home.

So anecdotally, there are a bunch of examples. So Zapier built a tool called async. Automattic built a tool called P2. Gitlab is known for their handbook, but they also do a lot in threaded discussion using their forum or their issues product. The more I dug in, the more I realized that it’s like, why are you hand rolling all of these tools? Why are you doing this all yourself? Why hasn’t someone built this solution? The more I dug in, the more I just realized, hey, there’s a need for a home for your company that glues together your work in one place, helps reduce your dependency on Slack and workplace chat, but still complements it. It’s not necessarily about ditching all the tools that you’re using. Instead, it’s about harmonizing them. And so yeah, that’s the backstory of Friday.

I started this before the pandemic, then the pandemic hit, then it was like, okay, more people want this. But what’s really interesting about our tool in particular, I think, is in the early days of the pandemic, everybody was searching and hunting for a way to replicate the office online. Friday is not that clone of the office. Instead, it’s this solution that you look for after you figure out that cloning the office doesn’t work. So yeah, we continue to see more and more attraction the longer this happens, because people just intuitively understand that spending your entire day in Slack or on Zoom calls just doesn’t work. And so yeah, that’s, I guess, the backstory behind Friday. We’re just trying to make work a bit more flexible. And we think that you need to have a home for your company, like you had a physical office before the pandemic. And so yeah, that’s the thesis behind Friday and what we’re up to.

Awesome. It’s such a great start. Bleeds right into what we talk about at The Digital Workplace. We talk a lot about that level two organization where you are just trying to replicate what was there in the office. That is a horrible place to be. Because if you have those expectations out of your digital tools, you’re just going to be upset and dissatisfied and say, we got to get back to the office as soon as possible.

Yeah, there’s so many companies that are still in that state transition. I am going to assume that you pulled that levels off of, I think, Matt Mullenweg.

Matt Mullenweg, yeah.

Such a great framework, such a great framework. Most companies are still in the early days of this process.

Yeah, there’s still a long way to go. Speaking of that, I want to get into you talk about a home for your work. I feel like what I want the meat of our conversation to be is where does that start? What was the first thing that’s going to compel someone to want something like this? And where does it stop? Because people are just going to keep wanting to say, hey, add this, add this, I want this in here. I want this in here. But eventually, it’s like, that’s not your home anymore. You need to keep separate places. So how do you manage that? First off, what was the first module that you wanted to build in Friday to make sure it was there? And do you have any, I guess, walls or boundary to say, I’m not going this far?

Yeah, so how we think about it at the highest level is that we’re trying to be a home for the most important stuff at work. What that means is that you have to have an opinion about this stuff. The issue that I see that’s pretty prevalent in the marketplace is that there’s a lot of productivity and workplace tools, but they’re heavily unstructured, and they treat everything the same way. So a message in Slack is a message in Slack. Sure, it can be grouped into a channel. But it’s like, if we think about work in the workplace, not everything should be treated the same way. So they’re like objects at work. A goal is an object. An update or a status update is an object. Saying thanks to a coworker, that’s an object. There are these building blocks for building out the interactions and the behavior that happened at the office. And so right now, it’s just being jammed into all these different tools and there’s no real structure and order.

When I first started Friday, I started off the core wedge or the core experience for a team was this idea of a check in. A check in is basically just systematizing your communication. The way that I think about the problem is Slack and other tools are filled with lots of ad hoc communication. That’s fine if you’re in collaboration mode, because you have no idea what could come up. But when it comes to you maintaining this visibility and this awareness into what people are working on, you actually need to create systems to the way that you communicate. And so that could be expressed in a variety of ways. It could be a team every morning sharing what they’re working on. Or at the end of the week, it could be a team leader sharing, hey, here’s what my team accomplished this week. It could be a monthly or biweekly update from the CEO, oftentimes, that’s an all hands meeting. But sometimes it could be a weekly email from the CEO outlining what’s on their mind or like some KPIs or something.

So I saw it as I’m getting all this communication, but it tends to be low value. How can I create more systematic communication? So check ins is just a way in Friday of automating any routine update you can think of. And so when you create systems to the way that you communicate, information flows on a predictable, repeatable basis. And so that’s the first wedge that we started with. We still integrate with Slack. So you share what you’re working on, and that can be pushed into a channel, but it can also be rolled up into like a feed in Friday. So if I want to see all the daily stand ups for my team, I can click and see that. I don’t need to hold a meeting to understand what people are working on. If I want to understand how people felt about their week, I don’t need to hold a meeting and ask people and go around in a circle. Instead, I can just ask them a series of questions in Friday. Some of that can be shared out into Slack, some of it doesn’t need to be.

And so that’s how we originally started. But yeah, maybe to get back to the original question, we very much try to think about things as what are the most important objects or units of work? And how can we centralize the stuff that is currently being just scattered and tossed? And how do we pull in the stuff that lives in a different system? A project is a unit of work, but that wasn’t a project management tool. And there are plenty of tools that do a really great job of that. So, we don’t really feel like we need to be a home for projects. Instead, yeah, we should talk to them. But instead, it’s like, what are these disparate units of work that are just flowing in other tools that are not heavily unstructured and easily forgotten? That’s where we see our opportunity. So yeah, it requires having an opinion. I wish I had a more well thought out plan, but oftentimes, it’s just influenced by our customers and users.

I love the framework of thinking about how structured those units of works are, because some of them are extremely ad hoc, like you said. A Slack message can just be without any context, just throwing it out there to talk about, as opposed to checking in on an automated process that’s running in the background, and wanting to know how that specific thing is working and creating that thing, which is highly structured, and going back and forth across that spectrum. You have projects to be talked about. So projects are in the middle. I find that a lot of, just talking to industry talk for a while, when we look at companies that are trying to own the digital workplace, or not own, but like say, hey, we’re a solution for everything. A lot of them are coming from that project management space. I feel like, as we’ve done our reviews to say like, they say everything at work is a project. And we can push that narrative. And you see other companies that specialize in workflows or other companies that specialize in chat, they’ll say, hey, you can use chat and then do everything else off of that. One thing that’s unique about Friday, I feel like, is that you’re saying, no, it’s not all one thing, that there are different types of things that come through. So talk about that perspective you brought in.

Yeah, so the first thing I’ll mention is, there’s so much more than projects. Because if you think about it, if you were to go into the office and walk around, and talk with coworkers, and collaborate with coworkers, how much of that discussion, how much of your work day would be spent around projects? And make no mistake. A meaningful amount of your day is spent talking about that type of stuff. But there’s so much else that happens at the office that so many people are missing out on right now. To be even more specific, so many of these project management tools out there are adding in goals. Well, goals is another unit of work. Task rolls up to projects. Project rolls up to goals and strategic initiatives. But there are so many other things. As I mentioned earlier, like saying thanks to a coworker, that could be a unit of work. Learning more about a coworker, like we call them icebreakers. But it’s just basically, help me learn about the people that I work with.

So what so many people tell us when they use Friday is, hey, this is more about the people doing the work than it is necessarily about the unit of work or the project. It’s like, yes, that’s literally what we’re trying to do is because that’s what everybody is complaining about when they talk about missing out on the office. It’s not because they missed out on a project status update. It’s because they missed out on this holistic experience at work. We’re just saying, how can we replicate some of the outcomes in a digital first way? But make no mistake. The means to the end will look very different. And it should look very different. Because you can’t just replicate what you were doing at the office in a digital space. People are just going to get burned out. They’re going to say enough with the Zoom calls and the happy hours. Just give me back more of my day. Let me show up, do heads down work, hang out with my coworkers in a meaningful way when appropriate, and then let me just go do something else. That’s what we’re all about is like that. We all have families. We all have friends. We all have hobbies. We all have activities that we like doing outside of work. That is the promise of a flexible work day. So let’s make that a thing instead of requiring people spend their life on Zoom.

Yeah, absolutely. You talk about having an opinion, which I think is very important for product companies to be honest about, because all product companies have an opinion about how work should be done. But a lot of them tend to hide it inside the product somehow or they’re not even aware of the bias they have as they bring it in. As you think about Friday and the opinion that you want to impact, how would you verbalize that in terms of your opinion about how work should be done? You’ve said a lot about it. But if you could just summarize that in a couple sentences.

If I could summarize it, it would be that life is short. And that I believe that people find meaning at work when they are allocating their time as best as they can, whatever that means for the individual. We’re just really into this idea of show up, grind it out, do the work, and then leave. It’s just being about, it’s one of these things that people talk about these days, output over hours. I really think that that’s important. That’s really what I’m all about is because like, I just, before this call, went down and hung out with my kids for like 10 minutes before. It’s like, what is the value of that? The value of that is priceless, I would argue. As long as you’re still doing meaningful work, it shouldn’t matter the number of hours. And so yeah, show up to work, grind it out. I just think about it like a sport game, right? Like a sporting event. I played a lot of soccer growing up. When you step out on the field, you’re going to give it your best. But the minute you step off the field, that’s the end, and then you go do something else. I think the workplace should be about that. So that’s our philosophy is life is short, show up, do great work, and then leave and go do something else.

So take off your product hat for a second and put on your CEO hat. Now you have people around you that’s, I think a lot of companies have moved beyond the, we’re all family here, because of what you talked about. We’re not a family. We’re here to do work, and then get back to our other families or get back to other things. But some people really do find genuine connection with coworkers and build long-term relationships with them and enjoy that part of it. So how, as a leader of a distributed company, how do you plan to allow for both that, for people who just say, hey, I’m just here to do my work, have fun, and then get out of here, and others who say, I need more from this?

Yeah, great, great question. So the first is that, like a lot of things, there’s a bell curve here, right? So there’s some people, they really just want to do the work and then go. And then there are other people that want more interaction. How I think about it, once again, to use a sports analogy, I just think about being a part of a team. Naturally, there’s some people on the team that they really like the social interaction. And for others, they’re there, they want to win games. and then some limited chit chat. And some of that is just personality differences. How we work to really try to support both groups of people is, we try to do a decent amount of this stuff asynchronously. So I think about it in terms of help me learn more about my coworkers and remind me that they’re people and not robots. I think a lot of that, we’ll call it prep work, can be done asynchronously.

For example, on a given day, so first of all, we have three meetings a month, three routine meetings a month that we do. One of three of them is a monthly kickoff meeting. Then two out of three are what we call coffee shop coworking sessions, where basically we just get together, hang out, and play games and show what we’re working on. I’ll get to that here in a second. But when it comes to async, how do we support this culture, even in an asynchronous way, is part one, respecting the fact that people have lives outside of work. But getting more into the nitty gritty of how do you create camaraderie. There’s a few things that we do. The first is that whenever we share an update, I mean, we use Friday to do this, we have just a way at the end where you can say thanks to your coworkers. We know that people want to feel recognized for the work that they do. There’s always an opportunity to do that. For example, there was someone earlier today that sent a kudos to someone else. This typically happens many times a week. This creates this baseline of just camaraderie. It’s so simple, but it actually works.

So that’s part one. Part two is whenever someone new joins. So we have an intern joining today. I’m going to jump on a call with him and going to walk him through the company and how we operate but also get to know them. Now, I’m not his direct manager, but it’s important to get to know people, especially in onboarding. So that’s just another anecdote for you. For this new intern who joins, he will be able to learn more about all the people that he works with asynchronously. So he could visit the directory in Friday. He can visit people profiles, and literally click around and see each person and learn more about them, what they’re working on, and maybe where they’re located, and other fun facts about them without needing to hold a meeting. This is not necessarily to eliminate the meeting, where you can say, hey, I’d love to get to know you. But instead, it’s about giving some context to accelerate better relationship building when you do meet. So it’s about being super thoughtful about how you spend that synchronous or real time conversation.

We think that it’s a combo, async and sync. Last thing I’ll mention is those meetings I mentioned, the coffee shop coworking sessions, those are fun. Those are just an informal way. It ends up being an hour every two weeks, where we just get together. Hey, do you have anything you’d like to share about what you’re working on? Just more for fun, like, hey, I’m thinking about this and I’m doing this. It aims to scratch the brainstorming and just getting people huddled around a table at a coffee shop just having chit chat. And then the second half we play, it’s called Gartic Phone. It’s just basically Pictionary. And we just chat about like, oh, hey, like, how are things going with you? If someone doesn’t want to show up, or if someone has to go do something else, they can leave. So this is how we try to balance the camaraderie as a fully distributed team. Last thing I’ll quickly mention, and then I’ll stop talking is, if we can meet up in person, we will periodically meet up in person. I’ll offer to buy people lunch. That is really helpful, too. So I think, there’s no one size fits all solution here. But I do think that, yeah, I mean, that’s what we do. It’s a mixture of a variety of things.

Yeah. It’s very important to make sure people understand, when you think about a distributed team, it’s not 100% asynchronous. You need that synchronous time, but you don’t need as much as you had in the office. And in the same way, you think about being apart from each other versus being in the same space. There’s extreme value in being in the same space.

Absolutely.

But do you need it every day?

That’s the question. That’s the question.

Yeah. And then, like you said, too, to train people to say, look, if I only get to be in the same location with some of my coworkers once every four months, what am I going to do with that time? What’s the most valuable thing I can do to get together? Or if we’re only going to be on the same time a couple times a month, then what’s the best value we can get out of that? And how can we push everything else to asynchronous channels, and realize when those are stressing, and you have somebody that is really struggling that needs more time, or you have an intern who really just doesn’t really understand how to work out things, they want more social connection, can you make some allowances for that? I love the flexibility that you have in your model.

Yeah, I mean, it’s worked out pretty well so far. I think that it is, I feel really good about it. Because it’s not meeting heavy, but it still allows for fun and the spontaneous interactions, and I still feel like I know the people that I work with.

All right, Luke. What’s the one question you’re going to ask somebody if they say, hey, look, my home for my meetings, and is this app, let’s say they’re using a messaging app like Slack or they’re using Microsoft Teams or they’re using something like that. What’s a question you could ask them to get them thinking beyond that? Say, maybe you’re missing something here.

It’s a good question. Because I think the honest truth of the matter is that a lot of people intuitively understand that workplace chat tools are being overused. I think our value prop is basically, hey, you’re probably using Slack in one of 100 different ways. It’s best for collaboration, the quick back and forth. What it’s not great for is announcements. So one thing I’ll ask a leader is, hey, so how do you share company wide announcements? They’re like, oh, sometimes they’ll say they use email. Sometimes they’ll be like, oh, I post it in Slack. It’s like, okay, so how many people read that? They won’t be able to say anything. They don’t know. And so that’s a question I ask leaders. For the individual, it could be something along the lines of, like, tell me more about the notifications that you’re getting on an everyday basis. And then for a team leader, it’s, do you know what your team’s working on right now? What I can tell you is most team leaders do not know. They resort to the one on one DMs where they’re like, hey, how’s your day going? Oh, how’s that project going? No manager, no team leader wants to do that. But they have to because the information isn’t flowing to them. Well, how can you get the information flowing without needing to do that?

Luke, this is really exciting. We’re excited about Friday, just as a product. I like what you guys are doing. And especially because you’re not coming from a product that existed, necessarily, in a strong way before the pandemic, but you’re able to take a fresh look, like you said, to say work has these different objects and these different elements to it, and it’s not all the same thing. To elegantly bring us together is a noble task. We wish you the best in it. We are going to be following along and seeing how you update along the way. But this is just going to be a fantastic time for you, I’m sure.

Cool. Thanks, Neil. I really appreciate it. Thanks for having me on. We’re definitely trying to approach things from a fresh lens. Sometimes that means we get things right. Sometimes that means like, it’s a little bit of a scratch, like, why do we do this? But we’re just trying to approach a problem from first principles or just from the ground up.

Yeah, so where can people go to find out more about it?

Yeah, friday.app. And if you have any questions, you can shoot me an email directly, [email protected].

Excellent. Thanks, Luke, for being on the show. We look forward to connecting with you again in the near future.

Thank you, Neil. Really appreciate it.