Managing Remote Product People and Product Teams w/ Michael Sacca, VP of Product at Dribbble

Hello everybody, welcome to another edition of Industry Product Reviews. This is really exciting. I don't normally fill in for Mike, but this is a once-in-a-blue-moon opportunity that I get to do these sessions. Mike Belsito, your usual host, is happy in Disney World at the moment. With his family, having, having a great time. He deserves the break, I think you should all agree. So today we've got an awesome session with Michael Sack, and we'll get to Michael in just a moment. You can see him there smiling. We'll get to him in a moment, but I just want to give you a little idea of how this works. So this is a collaborative interview, so I have some questions here, but it'll be cool to share to allow you to ask questions too. So if you look down the bottom, there's a feature called Ask a Question, and believe it or not, you can ask a question there. And so please do ask questions. If you don't have a question, you can open it up and you can vote on people's questions that have already been submitted. On the right, and I've noticed somebody has— doesn't have audio. If you're having technical difficulties, which sometimes happens, just let us know in the chat box We really encourage you to use Google Chrome for this. Hopefully there won't be too many problems with technical stuff. So please do introduce yourself. Let us know who you are, what you're working on, where you are. And people from all over the world join these sessions, so it's really cool to see where you are, what you're doing. This session will be recorded, so if you miss something, don't fret. You can come back and open up the same URL, and it will be there. Alright, so let's get started. Michael, thank you for taking part in this.

Yeah, no, I'm excited to be here. This is great.

Great. And Michael, you're VP of Product at Dribbble. So Dribbble is a web app that I've used on many occasions. I'm sure many of our guests have used too. How long have you been with the company?

I've been with Dribbble almost 3 years, and we came over with the Crew acquisition. I was at Crew for about 3, 3 and a half years before that. And both of those teams were remote in some capacity. And so I know that's a lot of what we'll be talking about today. So yeah, so I've been remote for about the last 6 years. Dribbble is one of the largest sources for design inspiration and places where designers, digital designers post their work daily. So yeah, so I'm excited to get into it.

Awesome. And it kind of was shocked to hear how big your product team is in Dribbble. Can you tell us a little bit about the size and where, where they're located.

Yeah, so, um, we have a 22-person product team that spans everything from data support through engineering, um, and we are all over North America. Um, so we, we generally hire from Pacific to Eastern time zone in the US and Canada, and, uh, we're fairly spread out, right? Where we've, we've got people in Montreal, we've got people in San Francisco, um, and then we've got people in Atlanta. So we, we have a wide, uh, team, and none of the actually works physically together day to day.

That's crazy. So that's a pretty big team with nobody working together in the same physical location. Well, yeah, mostly. And so what's the best thing about being managing, or let's start kind of more in a more personal point of view rather than a leadership point of view. What's the best thing for you when it comes to working remotely?

Yeah, so I find that I have more time. And I think I can put some of that time back into my work. I can also put it back into my, to my family. So we all get up, we get dressed, we drive, you know, 30 minutes to an hour to work, and then we come back. We lose a couple hours every day just getting ready and commuting. And so what I found is, at least for my quality of life, is I get to spend more time with my children, with my family, And then if I need to put a little extra time in work, I don't have to worry that I also have another hour till I get home for dinner. And so I like the flexibility there. I can also work from anywhere. So, you know, today I'm at home, sometimes I'm out at a coffee shop, but even if I travel and go on trips, I can still connect in in the exact same way that everyone else on my team is. And so we lose a lot less time and productivity when people are kind of out of pocket, because it's really easy to open up your laptop and put in a couple hours of work no matter where you are in the world.

And for somebody who is not the leader of the team, it seems like working remotely would be immensely easier than if you had a team. As you say, you can go to a cafe, open up your laptop, and kind of work away. But you're the leader of 22 product people. So what's the best thing about managing a remote product team as opposed to you're just yourself.

Yeah, so, so I will say that remote, I think, is a huge advantage for ICs, right? So our design team, our engineering team, I think they drastically benefit from being able to get that heads-down time, create the environment that they need. I know when I worked in an office, there was always complaints about the music. It was too loud, the type of music, right? We could never as a team agree on what the vibe was in that office. With remote, we don't have to worry about it, and everyone can actually create that ideal situation for themselves. And work at the ideal time. Some people work better at night. Some people wake up at 5 in the morning and get their work in before the sunrise. That's all fine, right? And then, but what I like about the leadership side is the focus on communication. So the hardest part of remote is communication. And when you're leading a remote team, you have to overcommunicate. And that's been a fun challenge to take on, right? I, you, As a CEO, you know, they often say you have to repeat yourself 100 times until the team actually understands. And it's kind of the same when you're leading a product team, especially of this size, is you end up saying the same thing over and over and over again. But that helps you refine your message. And I think in the end, it forces me to be a better leader and a better communicator because I don't have those advantages of just being in the office, tapping someone on the shoulder and asking what they're doing. The other part that I enjoy about it is the element of trust. And so it makes it very conscious when you're hiring who you're going to hire, because you have to be able to trust that, that person. I don't know what the 22 people on my team are doing every day. We can see it through the results, but I can't actually walk behind their desk and see them working, right? We can't pull into a meeting and, and, and run through what everyone's working on because it would just be disruptive, right? And so you have to hire really good people and you have to hire people that you can trust. And I think it all starts at that stage. 'Cause if you don't have people that you can trust on your team, it's really hard to train for that. And, but what I've enjoyed is that you build a very mature team, you build a team that it can be a bit autonomous and they're all self-starters and you've got a winning recipe for a remote team. And those are generally the people that I relate to.

Excellent. And kind of ripping off that a little bit, why would you think twice about doing this? So we've talked a lot about the advantages and the positive aspects of working and managing remote product teams, but what would really kind of make you think twice? What have been the biggest challenges for you as you've done this?

Yeah, so one of the things that's really hard in remote is training. And so the ability to bring on more junior folk is something that I think is a bigger struggle in remote than it is in, in an office, right? Where you can have a lot more of that hands-on time. So that, that's definitely something that we've been working on. I don't know if we've perfected it yet, but it's something that we've had to really consciously concentrate on. I know in the past when I've been in an office, it's a lot easier to have a junior person come in and you, you work directly with them. You could be very collaborative throughout the day. With remote, you're scheduling a lot of these calls. You're scheduling your time. And so the opportunity for training is difficult. So we ended up hiring more senior and mid-level people. But I would like to kind of figure out that how do we bring on people and then train them a bit better? I think the other really tough part is people tend to silo when they're remote. And we constantly have to be very conscious of people working alone for too long. Because then we're not actually solving problems. And too often we get into kind of these, these silos where we are running down a path that's really not relevant or important. And so we have to catch people quickly, but it's very natural when you're alone in your office to try to solve the problem alone. But we always solve problems better collaboratively. So that's why we actually prioritize hiring from Pacific to East Coast time so that we have that 5-hour overlap as a team because we are very collaborative. And so we do a lot of Zoom calls, a lot of planning meetings, and that's how we've kind of bridged that gap of remote and still make people feel connected to the work that they're doing.

And so if you've been in in-person situations, in-person companies as opposed to remote companies, and so you've said these challenges, but what's kind of most surprised you? What's kind of taken you out of yourself a little bit and shocked you so much that you've maybe kind of had to take a step back and question your whole approach to managing remote teams?

Yeah, so I think it comes around collaboration. Collaboration for remote took years for us to really figure out, and it was so much harder than I expected. And when you're in an office, you can grab the stakeholders, you can run into a room, you can whiteboard real quick, everyone can grab the marker, and you get that kind of energy. Right? When you're in a video call, the second that there's dead silence, there's immediate this awkwardness, right? You could stick 8 people in an office room thinking about a hard problem, and no one needs to be talking because there's all these visual cues happening around. But when you're just on a video call and everything goes silent, our first instinct is to start to fill that silence. But it's actually counterintuitive to the planning that you're trying to do. People need to think. They need to reflect, right? They need to come up with these solutions. And so you have to really get used to that dead dead air. So we started recently doing these longer Zoom calls where people would kind of pop in, pop out. We just keep the call open for 3 or 4 hours at a time. We'd be working through several issues that we had. And then there was a ton of dead air. And there was a lot of awkward silences. But in the end, we were able to create an environment that was similar to sitting in a conference room solving a hard problem. But it took us a long time to get comfortable enough with each other to get there. And I think in the office, you can build that rapport a lot faster, right? You go out to lunch, you, you do the talk around the, the water cooler or coffee, right? And you can build that rapport so you know the people that you're working with better. Remote, it takes 5 or 6 times longer in order to build up that rapport. And it's a huge challenge. I, I think for anyone that's looking to take on a remote, either a remote role or build a remote company, that's one of the biggest things to consider is How are you going to build a culture and how are you going to get people connected when you don't have the advantage of face-to-face?

Hmm. See what I did there?

That was good.

We all need time to think here. So actually, and related to that, I don't see any questions popping up. Come on, guys, if you've got questions, ask a question on the ask a question feature box and I'll get to it because there's none. There yet, so you're sure to be answered if you ask a question today. So, okay, so you— that's actually, that's an awesome way of doing things, leaving a video conference live over a couple of hours, and that seems to be a kind of a really neat way of bridging that geographical divide. But are there other ways that you can ensure your team stays in close communication throughout the day?

Yeah, we obviously use Slack, right? And so there's constant chatter going on there. We do do other events like a coffee, we do a coffee talk every other week, we do movie club. We try to recreate some of these more informal ways to get together over video that still helps us feel connected. And I think our work, then improves. We do full meetups twice a year where we do get the whole team together. After those meetups, for any of the new people, you can really see the communication gets easier. Once you kind of know someone's mannerisms, you know their personality, the remote communication is instantly easier. So I think it's really important to still keep that notion of getting together. And then we do a lot of planning. So what we, we had a product process where we just kind of built and we built and we built and we said, I don't know, it'll be done in 2 weeks and, and we'll, we'll try to figure it out. What we shifted to, and, and part of this is really based on being remote, is a ton of upfront planning. And so we, we're planning 4 to 6 weeks in detail at a time and then getting in rather than, than just running 2-week sprints, 2-week sprints after 2-week sprints. We also do take a breather similar to Basecamp and their ShapeUp model. Where in between every 4 weeks, we do take a breather and let the— let's do some code cleanup. Let's, you know, kind of get some of the stuff done that's not on our roadmap. But that planning really forces everyone to talk. It forces everyone to have an opinion, and it forces everyone to be in constant communication while we're doing it. 'Cause if we don't do the planning right, we're not gonna do the build right. And so that's something in our process that we've heavily prioritized, and really in order to get people talking. That's the big goal.

Cool. I've got a question here from, I think it's Mia or Maya, I'm not sure. Apologies to Mia or Maya. So a team of over 20 people, do you all get together at the same time or do you schedule smaller groups depending on the project or domain?

Yeah, no, that's a great question. So what we do, we do a team call every week with all close to 40, 50 people on the team. And then we do, team calls. So that'll be the functional product team from engineering to the PM, and they'll do that weekly for about an hour or two, and that's about a 6-person meeting. And beyond that, we do a lot of one-on-ones. We do allow people to kind of grab each other throughout the day as they're working through problems, but we try not to do too many large meetings. Because the communication, we feel like we're wasting a lot of time when we pull even the whole product team together. It's not as productive. So we try to keep those individual and weekly meetings as small as possible so that everyone can participate. If everyone's not participating in the meeting, there's usually a better way to accomplish that communication.

Excellent. Here's another question here. Is there a difficulty respecting vacations with remote times?

So we have an unlimited vacation policy and we, we never deny a vacation, right? It's all about the upfront planning. It all comes back to being prepared. So our methodology is, if you're going to take off, make sure that you're not a blocker during that time. And we do see people take 2 and 3 weeks off at a time, but they have to do all the prep up front to make sure that it doesn't hold back our team. And I think that's relevant whether you're remote or in an office. But that's the philosophy that we've taken is take your time, but make sure that you're not a blocker while you're out.

Awesome. And thanks everybody for asking all the questions at once. We'll try and get to them. We'll try and get to them all. So here's another question from Ali. "It seems like you have to start from strong, trustworthy people to make remote teams work." Yeah, you have to start with strong, trustworthy people. "What do you recommend for on-site teams who just shifted to a remote model across offices? What would be the first step to get everyone, trustworthy or not, to be more involved?" Yeah, so I don't know if this is gonna be a great answer.

I find I think inner office communication is a bit different than remote. And I found that when we have people that are in the same office, when I've worked at like local remote places or places that were half remote and half in office, it never really worked. And the trust, no matter how trustworthy people were, the trust was never really built from the team because there was always the instance where a decision would be made when two people went out to lunch. "Or I was just talking to Joe and we decided this." And as soon as those instances start happening, they're very natural in an office. But when people feel like they don't even have the opportunity to be at that coffee meeting or at that informal walk, the resentment builds up. And so I think it's really hard. You have to be extremely diligent in order to make, to make that work because you're actually building trust between organizations and throughout your organization, I think it's a lot more complicated than just having everyone remote and building trust. My trust is based on are you coming to work every day? That trust is based on are you going to include me in every decision and conversation? At Dribbble, we don't have that issue because everyone is on an even playing field. No one is in— has the advantage of being close to anyone else. But I do find that it's a slightly different issue when you're office-to-office communication. And it takes rigorous enforcement from leadership in order to make sure that your policies don't alienate anyone in the company.

Excellent. Related to that, from, you know, that's from the perspective of an on-site team moving on to being a remote team. But you're in the beneficial situation where you are hiring to be remote.

Yeah.

So how can you tell if a product person is gonna thrive in this kind of remote situation?

So it's difficult, right? So we look at prior experience, we look at personality, right? The biggest thing that we're looking for, especially in our product people, beyond the basics, right? Understanding of data, business knowledge, is their ability to communicate. So in that interview, can they communicate in a manner that is clear and concise. Because that's essentially for a remote company, that's what they're gonna be doing. So if their communication is, comes off as confusing or it's jumbled or they don't have thought clarity, probably as a leader, even as a product manager here, it's not gonna be a great fit. 'Cause essentially what we need is great disseminators of information over channels that aren't ideal. And so, so the trustworthy is, is really a gut instinct. Unfortunately, we can tell within the first 2 months from bringing someone on whether it's going to be a good fit. But the, the other things that we look for on remote are, are communication and then obviously the same skills that you'd be looking for in an office. But can they write and can, can they communicate with the team in a way that's powerful?

And Andrew has asked, when you have a new PM join the team, how do you coach them to build and earn trust with their team?

Lots of one-on-one conversations. I find that with remote, the more that we're talking, and it's awkward, right? 'Cause you have to ask, hey, can I have 30 minutes or 15 minutes of your time? Or build check-ins at the end of the day. But when they, when they first start, the more that they actually talk to the team on a one-on-one basis is the best way for them to build trust. It takes longer than in an office. That's for sure. Right? It takes several weeks in order for everyone to kind of understand how, how we work together. But I find that the more that they can face those conversations head-on early and build that rapport, the more successful they are. I don't think that's that much different than being in an office. It's just a little bit harder.

And moving into the future, somebody's asked, how do you tackle the process of training?

Of, yeah.

Like having ongoing training programs, which would be pretty standard or easy to implement in on-site teams. Presumably that's a little trickier when people are all over the place.

It is. It's something that we're still actively trying to figure out. So I don't know if I have the best insight here. But what we've, we've have experimented with and what is working is, so we do a couple levels. We do like book conversations, right? Where we're all reading the same book, kind of like an internal book club among the team. That helps us disseminate different ideas that are out there together. We do pair coding for kind of the engineering team, pair designing for the design team. And so we do get kind of our senior members working closely with, with, for us, it's, it's our mid-level engineers in a pair style. So they'll jump on a Zoom call to start working through a problem a couple times a week. I still think there's a lot of progress to be made in this area, at least for us, and it's something that we're actively working on. But those are a couple of things that we've tried recently that we have seen good results from.

Or you could send them to an awesome product management conference called— Yeah, yeah, once or twice a year.

Twice a year.

Twice a year. Hey, so, um, I've— this is kind of, uh, changing the subject a little bit, but you mentioned Slack earlier on, and this is something that's kind of near to my mind a little bit because it's a struggle with too. But, um, this person Jeremiah struggles with Slack over— over— if not overlord, they'll be weird, but overload. Do you use any other collaboration tools to allow more structured asynchronous communication collaboration, for example announcements or brainstorming, that kind of thing?

Yeah, so we are a Jira and Google Docs organization. So we do most of our product planning in Google Docs. We do most, most of our roadmap planning in Jira. And so those are the two tools that we use a bit more asynchronously. Which really help. Slack, we just have to get over the FOMO and start turning off the channels. And so even for me, I've muted most of the channels that are not relevant. While I would, I'd love to talk about dogs or cats or kids all day, I know that getting sucked into those conversations is actually a productivity hit for me. So That's the way that I've approached it. We've tried to structure formal times where we do get together, like the coffees and the movie clubs. And then, you know, for my work, I tend to just shut Slack off except for very important messages, right? And that way I can get that heads-down time. I know at some companies, I love this, I think it was at Wildbit, they actually allow people to just turn off Slack close the program, don't even— and keep it closed for hours at a time. And it's culturally acceptable to do that, knowing that you're not going to be able to get in touch with that person. But that's how they've chosen to give people that heads-down time and kind of get out of that constant ding and notifications. So I'd say turn off as many notifications as you can on Slack. There's really nothing that you're missing that you need to be a part of. And just set those set the parameters so that you get alerted when your CEO hits you up. Yeah. Or your manager, right?

Yeah, so it seems to be something that you need to petition for if you're not the leader. And if you are the leader, it's something that you can set an example for.

Yep.

Yeah, okay, so we were talking about this book, "Remote: How to Work from Home and Be Free" and the Basecamp Boys. It's a famous book, it's a bestseller. It talks about remote working, obviously, but it's not necessarily the way that you work. Can you tell us a little bit difference, the difference between this book and the way you guys operate remote working?

Yeah, so Basecamp takes a very asynchronous model. We have found that for us, at the speed that we wanna move, it doesn't work for us. So we need to be collaborative. And so that's why, you know, again, we're only hiring from Pacific to Eastern time zone. And so we have that 5 hours of overlap. This is where like the long Zoom calls come in. I think that's something that Basecamp probably wouldn't be a fan of, but that's what we do. You know, we've been doing these longer planning meetings. We do follow their methodology of upfront planning, but we do very collaborative planning. So we as a team are constantly talking. That's either in Slack or in Zoom. I probably spend 6 to 7 hours on Zoom a day with the various teams, making sure that everyone's aligned on our initiatives and then working through various problems. We find that video calls are way better than Slack. So as soon as a disagreement comes up, we move it over to a video call, or as soon as an important decision needs to get made, we move it over to a video call. And so we don't expect people to come in and catch up on anything that happened. The day before. Generally, you know, because we're all signing off at the same time or around the same time, people are, no major decisions are being made while they're not there and they don't need to catch up on long conversation threads to understand what's happening. So that's how we've differed from Slack, we've taken, or from Basecamp, where we have taken a very collaborative approach to remote for us. We've— it's working for us. Yeah. I want to address one of the questions around the bottleneck, right, in Slack, just getting back to that real quick. So what I do is I have certain channels where my team will ping me. So we have like urgent requests when we need— when I'm a bottleneck and we need approval. We've got a QA channel when things are going into, into QA, and then we've got like a VPs channel for our vice president team, and obviously like Zach, our CEO, right? I've got those on at all times. But what I mute is kind of some of our general channels, some of our more fun channels, and I go in there when I'm purposely there to chat. But I'm not necessarily distracted by something or a good GIF when that arises. I can always catch up on that stuff later, but I make sure that the important stuff gets through. So it's a bit of curation of your, Slack notifications, it goes a long way.

You mentioned the water cooler a little earlier on. I guess it's debatable whether the water cooler is a place where serendipitous stuff happens that is of positive benefit to the company or not.

Yeah.

But you might argue that being remote removes that element of serendipity from a company. How do you make up for that? What's the challenges and solutions there?

Yeah, no, I, I think it's hard, right? And, and I think those style conversations happen much more free-flowing, right? You could be having a cup of coffee, you're talking about your kids, you jump over to your product, you jump into, you know, today's news, you jump back into your product. With remote, you can't do that, right? And, and so you're, you're scheduling 30-minute meetings to talk about something very specific, but you don't get those organic answers. I don't have a great solution other than getting more comfortable having long conversations on video. And so, again, you know, letting our— I do let meetings go a bit longer than 30 minutes if needed. We do have one-on-one conversations with everyone on the team every week. And so those are a bit more informal. They're more about their career growth, but they're also about the product and what they're working on and any ideas. And I think the more the more trust that you can build and the, the more fun that you can make those conversations, the better results. And we can get closer to that. But honestly, I still haven't found anything that really beats that taking a walk with someone and just letting the conversation run for an hour.

Right, right. All right. One more question for you, Michael. How do you know, or how do you deal with people just who are just underworking, underperforming? Skiving off. Yep. Surely that happens.

Yeah, yeah, it does all the time. And remote can be a huge distraction for people. So what we do is there's a different style of measurement. I think every company has their own way that they measure an employee's performance. So we have to set our expectations based on, not based on like your daily performance, but based on what you've achieved and what you've accomplished. And so if someone's slacking off, It's easy to tell in the output, right? And so if, if we see low output, if we see low results from their team, if they're not hitting kind of the, the KPIs that we've set up for the product they're working on, or more specifically for ICs, if they're just not moving fast enough, then that's a conversation that we have. But ours has to be based on output, not just showing up. And I think it's a big shift in the way that you manage a team when you're on site, where you have these other signals. Do they show up on time? Do they participate in meetings? You know, are they culturally liked? For remote, we have to weigh a lot heavier on, do they actually get results? And is their work fruitful? Because we don't actually know if they're working 8 hours, 6 hours, 2 hours a day. And oftentimes it doesn't matter, right? If their work is producing the results that we expect from that position, Not to say that we want people working 2 hours a week, but that's generally how we measure.

Awesome. Michael, thank you so much for being a part of this. I really, really, really appreciate it. It's been a delight.

Always, always happy to be here.

Yeah, so guys, we are— this is not it for product interviews for a long time. We're jumping back into it in a couple of weeks with the Pragmatic Marketing folks. We're going to talk about how to deal with maturing products. And on November 20th, we'll learn how to position our product right from April Dunford from the Ambient Strategy Group. So please do go to— go back to Crowdcast and sign up for those. It'd be cool to see you there. So thank you again, Michael, and thank you again to everybody from around the world for taking part in this. I do, and we'll see you soon.

Thank you.

Take care. Bye-bye.