The home team talks with Matt Martin, cofounder and CEO of Clockwise, which offers AI-powered time management and scheduling tools.
Clockwise is a time orchestration platform that optimizes schedules to create more time in your day. Clockwise AI, their new GPT-powered scheduling assistant, is launching in beta. Join the waitlist here to get early access. (They’re also hiring!)
Ryan wrote a recent article about whether meetings are making developers less productive.
Cal Newport’s instant classic Deep Work is about learning to tune out distractions and focus on cognitively demanding tasks.
Speaking of classics, Paul Graham of Y Combinator wrote about maker’s vs. manager’s schedules back in 2009.
Connect with Matt on LinkedIn.
Kudos to Stack Overflow user Joe Caruso, who won a Great Question badge with Get current time in hours and minutes.
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BP Hello, everybody. Welcome back to the Stack Overflow Podcast, a place to talk all things software and technology. I am your host, Ben Popper, Director of Content here at Stack Overflow, joined by the wonderful members of my content crew: Eira May and Ryan Donovan. What's going on, y'all?
Ryan Donovan Oh, not much. How’re you doing?
BP Not much. I don't know if you know about this, but there's a new AI feature. I could be reading off of a script but it makes my eyes look as if I'm looking at you. So I'm actually reading. I'm not even looking at you or thinking about you, but my face says I'm paying attention.
RD Smoothing out the indifference, I love it.
Eira May Awesome, good to know. Thank you, Ben.
BP Exactly. That also works for our one-on-ones, just FYI.
EM Yeah, I was assuming.
BP I didn't want to rub it in or anything. Our guest today is Matt Martin from Clockwise. We are going to be chatting about productivity, developer productivity, AI, software, and his experience in the tech world and also building things at a company. So Matt, welcome to the Stack Overflow Podcast.
Matt Martin Thanks so much for having me. I'm pumped to be here.
BP Tell folks a little bit about yourself, just a quick fly over, and then what it is Clockwise does and what you do there. It's like a watch, it's a Swatch competitor?
MM That's right. We're very, very, very big in Switzerland. No– so a little bit about myself, I'm Matt Martin, I'm the CEO and one of the co-founders of Clockwise. I do have a technical background, I'm a self-taught software engineer. I mostly did front end, so I spent much of my life on Stack Overflow. And Clockwise, which we founded about six years ago, is an AI-enabled calendar automation tool that coordinates the way individuals, teams, and companies prefer to work. So it helps take the pain out of scheduling and helps create time on your schedule for your most productive work. And we do that largely by coordinating meeting times. So, over the companies that we work with, we've rescheduled 12 million meetings, we've created 5 million hours of focus time. And we tend to work with other stuff for technology companies like Netflix, Uber, Atlassian, et cetera, but we can work anywhere.
BP Okay, you reschedule. How many meetings have you just canceled? How many meetings can you just take off? Could have been an email, just don't even bother with this meeting. Do you do that as well?
MM So I have to let the audience down. We have canceled no meetings.
BP Bummer.
MM I know, I know. Huge bummer. We encourage that philosophically. If it shouldn't be a meeting, take it off the schedule. But the last thing that we want to be responsible for as an automated technology is for you to wake up in the morning and go, “Hey, did Clockwise just delete this meeting?” So we shy away from full deletes.
BP Sounds pretty good to me, but okay.
RD So I wrote a piece about meetings a little while back about how they're kind of overall terrible for productivity if they're done badly. How do you feel about meetings in general, and then how do you think changing the schedule makes them a little better?
MM So I think that as a software engineer and as somebody who is a software engineering manager, I enjoy as much as everybody else bashing on meetings. They get in the way, they can be extremely unproductive, they tend to capture way more attendees than they need, often you sit around and wonder why you're there. But you do need them, and especially as we've all become more remote, more hybrid, they become a critical piece of connectivity. Sometimes you just need to hop on a call. So I think that it's about asking, “A– does this need to be a meeting? Do we have the right set of attendees?” but then also asking, “Does this work for everybody's schedule for what they need to get done?” And Ryan, I'm glad to hear that you were writing about this. There's so much good behavioral science on the cost of meetings, and normally when people think about the cost of meetings, they're doing back of the head math of what's everybody's salaries in the room multiplied by the number of hours this is. And sure, that's fun math to do, but there's kind of a blast radius around every meeting. And there's this term called attention residue, and I love it because it's so descriptive. I think we've all had that experience of you coming out of a meeting and you're still thinking about some of the tasks and stuff that came out of it. You fully switched into meeting mode, and getting back into work mode actually takes some time. It takes some time for you to switch context to get back into flow, to get back up and running. That seems intuitive. One of the things that surprised me is that it also exists at the front end of the meeting, because as you're approaching that meeting you're going, “Ehh, I have 5-10 minutes left until this meeting. I'm not going to take on the rewrite of this function. I'm just going to go check Twitter, I'm going to go do something else,” and so you pop out early too. Unless you're like me sometimes and you're really in flow, and then you arrive at the meeting 5-10 minutes late because you forgot. So the timing and placement of it can really be pretty damaging because it's not just that 30 minutes you're in it, it might be 15 minutes on both sides. And if you only have 30 minutes between the meeting, you're just not going to switch contexts into something meaningful and substantive.
BP I like to think of my day as broken up between the chunks of answering emails, snoozing emails, waiting for meetings, just finishing meetings, then the day is over. I think the day is almost over.
MM So there's this author that your audience might be familiar with. His name is Cal Newport, he's a professor who studies productivity a lot. His most famous book is Deep Work, and his core thesis is that it actually takes work and practice to get in the flow and also to regularly pop into deep, meaningful, sustained work. And Ben, that schedule that you just described, I think it's not just that you're flailing around through the course of the day. You're actually retraining your brain to kind of seek that dopamine hit of “I'm going to snooze this. I'm going to take action on this meeting.” When your flow becomes batting away distractions and other things that you don't actually have that heads down time to go into a flow state, it actually reprograms how you approach your day.
BP Right. For me, you're talking about the middle manager sweet spot. I just get that sweet, sweet dopamine all day. I do the meeting, I send the email, I snooze the email, and seems like it's working for me.
EM Yeah, I was just going to say, I very much relate to your complaints about your meeting flow schedule, Ben. Maybe it's a millennial cliche, but I feel like I spend the first 20 minutes before every call sort of dreading the beginning of the call, and then I'm in the call and then I have to recover emotionally from the call. But I did want to ask you, obviously something that we think about and talk a lot about at Stack Overflow is developer experience and the quality of developers lives and not just at work. And it sounds like you see Clockwise and tools like it as having a role to play in companies’ efforts to make developers' lives at work better to prevent burnout. Would you say that that's something that you've been thinking about from the beginning with that tool?
MM 100%. So I'll take you back a click here, which is I was at Salesforce as an engineering manager, and this was after the company that I was at got acquired by Salesforce so that was kind of a cultural upheaval in and of itself. And we spent so much time, rightfully. I am the type of engineer who can totally geek out on a build process and get into the details on how we're going to make the startup time, the cold start time for a front end build faster and how we're going to make the iterative cycles faster, because you can see the yield immediately on those results. If everybody is able to make a change and see it in the browser faster, it's less likely that you get pulled out of flow. And we all know what that's like where you have a build that takes way too long and so you go start on something else and then by the time you come back, you're forgetting. And so I love that sort of stuff and we spend a lot of time as developers, engineers, as a community, looking at how we can make those better. I fall prey just like everybody else to seeing a new JavaScript build tool that’s a bit faster and being like, “Oh shit, we’ve got to use that.” But meetings are such a bigger offender in a lot of ways and we don't address those and so that was really one of the insights that led me to jump on this problem space. I think everything we do in terms of developer velocity and developer productivity in terms of the tooling is so critical, but there's this huge missing component, which is, “I don't have enough hours in the day because everybody keeps interrupting me, or I don't have enough hours in the day because a recruiter, well intentioned as they are, put an interview in the middle of my afternoon when I was supposed to go after this big project.” And that sort of stuff happens all the time in organizations. I think it's so much more disruptive to flow state and productivity than some of the other minor offenders. So long-winded answer to say yes.
BP So you said you don't cancel meetings but you've rescheduled 12 million. What is the sort of protocol you use for deciding when you can reschedule, or what's a more efficient way for multiple people to meet up. And is there a secret sauce there? Is it something very procedural? Is there a Gen AI back there writing a poem that explains when the meeting should be? How does it all happen?
MM Yeah, it's actually just turtles all the way down. A couple of different things here– one is that sometimes I think that I'm truly nuts that I jumped into building a company where time zones and recurrence rules are our bread and butter. There's a lot of complexity in calendars and there's a lot of sensitivity. And so I note that at the start because, for better or worse, we're relatively conservative in a lot of areas, more conservative than I would like to be as a startup founder. Because the worst thing that I can do for one of our customers is mess up their schedule. If I come in and mess up your schedule and make it worse, I burned a bridge and you're never coming back because that's a firing offense. And so where it all starts is we suggest to you a set of meetings that we think are scheduled inefficiently or we think could be improved, and you opt into either rescheduling them or letting us manage those meetings for you. And so a classic example might be a recurring one-on-one that you have with somebody. And there’s some one-on-ones that you really want to happen exactly at 9:30 on Tuesday if that's what works for you, but a lot of times it's just fine if it's every Tuesday. I don't care that it's at 9 AM, that just happens to be what was available when it was first scheduled. And so then when you opt into that, we will then look at your schedule and all other attendees and we take a pass at a couple of different levels in order to look at if we can find a better time. But one of the most meaningful things we look at is, can we kind of de-Swiss cheese this, can we defragment this schedule? So we'll try to make it so that you're in meeting mode and then you're in flow mode instead of jumping between the two. So if we see a 30 minute meeting that could be moved 30 minutes earlier to abut against another meeting or maybe abut against your lunch or maybe abut against another commitment that we've synced over for your personal account, we'll do that. And then of course make sure that it works within time zones, make sure it works within the schedules of the other attendees, make sure that it works with some of the preferences that you set on our end. But the core of it is that we're trying to make your schedule more efficient.
RD Some of the research I saw was about the sort of broken day, but there was also research around, I think it was four or more meetings in a day that kind of ruined a person. Do you do anything around that?
MM So there are a couple of things that we do here. One is that we're a great tool for enabling no-meeting days, so if that's culturally something that you want to enable, and that's pretty popular among a lot of engineering communities, we do one on Wednesdays. And we'll help enforce that, so we'll help to automatically reschedule the meetings off of that day, but then also as you're scheduling into the day, if somebody schedules over it, we will send them an email that says, as politely as we can, “Hey, this is a no-meeting day for the team. Here's some other times that might work better.” And then we do something similar for what we call focus time. So part of what Clockwise does is kind of the offense of moving the meetings to better times, but then a huge part of it is also defense. Once you vote out the time, now it looks like a really great time for somebody else to schedule with you. So again, all under your control, but by default we will automatically schedule focus time blocks where there are 2+ hour blocks of time, because again, according to some of the behavioral literature, you need about two hours or more. That's a good proxy for flow state. So when we see two hours or more, we will put a block up and then we can defend that as well, and we defend it through communicating through your Slack status that you're in focus time, turning on DnD in Slack, but then also we can do the same thing that we do on no-meeting days, which is, if somebody schedules over it, we'll politely send a response that says, “Hey, this has been declined because Ryan's trying to go heads down right now. Here's some better times for you.” One of the other pieces of literature –I think this one that came out of Microsoft's recent studies as everybody went remote– is also how damaging it can be just to be in nonstop meetings, that meeting overload and Zoom fatigue is not just something that we all perceive of it, it's real. And there are a bunch of tricks that you can do, turn off the self view, etc, but one of the best things is just to take a break, get out of it, take a walk. And so also it speaks to the complexity of how people want their days to flow, but also if you're in 2+ hours of meetings back to back, we'll insert a break automatically. And you can reconfigure that however you want, that's just the default. So you can make it every 30 minutes, you can make it every four hours. But it is about that balance of how does your day need to flow, what are the demands of your job, are you just a middle manager who just wants to move paper around? If that's what you want to do, that's great, we'll help you. But if you want to go heads down, we'll also make that happen.
BP Can you make me look busier? Could you put meetings on there that don't actually exist?
MM We could do that, Ben. Maybe I'll make a feature for you, the Ben flag, and I'll just use AI to auto generate random titles.
BP It cancels real meetings and puts on fake meetings.
MM So jokes aside, one of my favorite things is you get all sorts of trivia when you focus on meeting culture. At Google, they have an internal forum and there's a long-running thread, it was a very, very popular one about what to name fake meetings so they don't get scheduled over. And so people would take the strategy of scheduling a two-hour product brainstorm session and then actually invite each other, but it was just to protect the time so nobody would schedule with them.
BP I love that, I love that.
RD That's amazing. You mentioned the pandemic and remote work. Do you think meetings are harder because of remote work? I know I've seen some literature around how Zoom meetings or video conference meetings are sort of more taxing because of looking at your own face, things like that.
MM I've seen a lot of data on both sides of the equation and I think it's like a lot of things with remote work, which is that there are big pros and their big cons and so you have to think about the balance of what works for you and your team. So certainly there are things with remote work and meetings that are more difficult. It's easier for me to get distracted. I'm already at my computer, I'm at my keyboard. It's really easy for me to just switch over to that Slack window and start to triage things. People do that all the time. It is more taxing to look at yourself. I think that's been pretty well founded and you can turn off your self view, which helps a little bit, but also there's something human about three dimensionality that seems to be substantiated where it's just a little bit more difficult to look at somebody in flat 2D space and you lose a little bit of something.
BP Zuckerberg was right, bring it to the metaverse. It'll feel more energizing.
MM That’s right. You know what I'm excited for actually– digression– have you all seen that Google experiment? I can't remember what it's called.
BP Where you walk in the holograms, like SuperReal?
MM Yeah. It used to be the size of a booth in a diner.
BP It's like a hyper presence machine. It's one of those X Labs projects. If it ever makes it to the light of day, I'll be very happy.
MM I'll be happy and surprised. But they did get it down to the monitor size and it's still exorbitantly expensive, but man, that sounds great. Just add a little bit of real human interaction. But on the flip side, Ryan, it's also easier to pop in, pop out. So an example is you're working with a colleague on something– and I think people lose sight of this, it's something that gets missed in this because we don't want to bother each other– but if you're on Slack and you're going back and forth, you can flip open a Zoom meeting or you can flip open a Slack, whatever they call them, Huddle or whatever mode you want to use and pop in for five minutes and talk about it face to face and pop out. It’s easier to schedule, easier to get a hold of people, but then the flip side of that, of course, is easier to schedule, easier to get a hold of people. So we saw right at the start of the pandemic the number of meetings shot up because people were trying to accommodate old styles of working in remote. And so I think, again, it's about team culture. It's about what works for the company. There's, unfortunately, I don't think any silver bullet here. It's about being more intentional about how you want to use meetings and when you want to use them.
BP From all the reading you've done on the research, and it sounds like there is a lot of social science here, is there any efficacy to having an EA, a human person who helps you with this? Does that make life better for you or does that mean you have more meetings because more people feel like they can get on your calendar? I think Superhuman and your service obviously seem like they're trying to find a more process-driven software solution to this, but what does having an EA mean for your life of meetings? As someone who will never have an EA and who will never reach that level, I’m curious.
MM So EAs are kind of the power user of calendar. There's a stat that, it's an average, but 80% of EA time is spent on the calendar, which is kind of remarkable when you think about it. Here's a human whose whole day is supporting another human, can add a lot of value in a lot of areas, and they spend all their time on calendar. And so I think there's an element of a matter of necessity. You think about that and you get to the point where the calendar is so busy, so nuts, you need another person that's sitting almost full time to look at it. But if you're in that mode, it is a really nice luxury. Now you have somebody who can translate your intent into the convoluted mess that is calendar. And what we've seen, and I'm very biased here, so I will own that, but I'm pretty stoked about it, is that barrier of access to EA, there's huge room to democratize that if we can get the cost way down on providing that service. And the way to get that cost way down right now is I think generative AI actually does have a lot to offer here. And so Clockwise has been working for the past couple of months on a new breakthrough service that allows you to communicate with your calendar like you would an EA, and you actually see side by side the visual of what the proposal of the actions is. And some of the benefit that we've seen in early results is that you spend way less time managing the complexity of the meeting. Let's say I need to meet with Ben tomorrow, but he's completely jammed. Our service can actually suggest times that maybe Ben has one of those fake meetings, or maybe it just looks like it might be easy to move it and say, “Hey, we found these, but do you want me to ask Ben about it?” and it can automatically facilitate that, But it also allows that person to move at higher velocity. If you have something that's mission critical and it's getting blocked because of either the complexity of trying to find a time for it or just the personal inertia of not picking it up and figuring that out, it can really help. EAs help for that, but I think that there's ample room to help everybody with that.
BP Nice. Can I beta test this, or do you have only company-level services?
MM Yeah, anybody here, anybody on the other side of this podcast, Clockwise.ai, sign up for the alpha. We're letting people in right now and it should be fully available not too long from now. I won't make any promises on dates.
BP Okay, cool. Matt, anything that you feel like you needed to say that we didn't hit on?
MM I find that one of the most difficult transitions is when you're going from individual contributor to manager. And that's when your schedule can really feel awful because now you're living between worlds where you're kind of trying to get some IC level work done but you're kind of in management. It’s the classic Paul Graham article, Maker Schedule Versus Manager Schedule. And I think it's really critical to think with intent about how you're making that transition. I fell prey to this. I've seen so many people that I help out fall prey to it. You kind of try to maintain your IC schedule, but the managerial efforts necessarily exist on a longer time horizon, and so you get less immediate pleasure from the work that you do as a manager than committing code and so then you defer other things and you jump on code things and pretty soon you're really frazzled. So I would say managers need focus time, everybody needs focus time, it's just how you think about incorporating that day in your day and in your week changes, and so you have to think with intent about that.
BP I like that.
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BP All right, everybody. It is that time of the show. I promise I did not plan this. This was awarded two hours ago– a Great Question Badge to Joe Caruso. “How do I get the current time in hours and minutes?” Asked nine years ago, viewed 203,000 times, so appreciate the great question. “I'm trying to collect information from a system. I need to get the current time and hours and minutes.” We have an answer for you. Helps if you're trying to build a calendar app, I promise. I am Ben Popper. I'm the Director of Content here at Stack Overflow. You can always find me on X @BenPopper. DMX. If you want to get in my DMs, let's see, shoot us questions and suggestions, podcast@stackoverflow.com. And if you liked the show, then leave us a rating and review. If you didn't like the show, just don't leave us anything and don't come back. We could care less.
RD Salt, big salt.
BP Big salt day.
RD I'm Ryan Donovan. I edit the blog here at Stack Overflow. It's found at stackoverflow.blog. You can find me on X @RThorDonovan.
EM And my name is Eira May. I'm also on the Content Editorial Team, and you can find me on text-based social media @EiraMaybe.
MM So I'm Matt Martin. You can find me on X or basically any service as @VoxMatt. If you want to tune into my X, it's usually just me laughing about Matt Gaetz being an idiot, but you're welcome to tune in for time management tips as well. And if you want to find out more about Clockwise, hit me in my DMs there for sure. I'm happy to talk about anything, but also the fast path is getclockwise.com.
BP Very cool. All right, everybody. Thanks for listening, and we have a meeting. We'll talk to you soon. We have it set up. We'll talk to you soon. There's a meeting. Put a pin in it. It's on the calendar. It's on the books.
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