Episode 639 | The Secret Sauce to Building Happy, Motivated Teams

Rob Walling:
Welcome back to another episode of Startups For the Rest of Us. I’m Rob Walling, here with the cold that I’m getting over. I caught it last week while in Malta. We had an amazing kickoff for our European TinySeed batch followed by MicroConf Europe in Malta.
I did not leave unscathed though. For the first time ever, more than 30 in-person events, I missed a day of MicroConf. I was so sick I had to stay in bed. It was absolutely devastating to me. I effectively lost my voice, and it wasn’t going to be a good scene if I went and tried to MC it.
So mad props and thanks to producer Xander and the rest of the MicroConf team for stepping up and making it happen. Just goes to show you we can’t do these things alone. These should be lessons that we all know by now. But at some point, you’re going to get sick. At some point, you’re not going to be able to show up. And having amazing people that you work with that have your back is what it takes to do this over the long run.
Today I’m talking with Andrew Berkowitz, the founder of Suggestion Ox. And we dive in to the secret sauce to building happy, motivated teams. We talk a lot about trust. We talk a lot about not having these strict policies that have been in place for a hundred years because the job market and the way we run companies today is and should be different than the way we ran companies 50 or a hundred years ago.
So without further exposition, let’s dive into our conversation. I’d like to welcome Andrew Berkowitz to the show. He’s the co-founder and CEO of Suggestion Ox, which is a feedback platform that helps HR teams build truly candid communication between leadership and employees. And before that, he co-founded TeamSnap, which was a sports management platform that was acquired in 2021. Andrew, welcome to Startups for the Rest of Us.

Andrew Berkowitz:
Thank you, Rob. It’s great to be here.

Rob Walling:
Absolutely. It’s good to have you. Today we’re going to be talking about trust, the secret sauce to building happy, motivated teams. That sounds like a book title and a subtitle. Are you secretly working on a book?

Andrew Berkowitz:
I might be secretly working on a book. Might be at least secretly working on some content to help get more customers.

Rob Walling:
A manifesto? Yeah, great.

Andrew Berkowitz:
Yes.

Rob Walling:
That’s awesome. I’m glad we’re talking about trust in building teams because this is something that I think when I started… When I started as an entrepreneur, it was all four hour work week type. You hire a bunch of freelancers; no loyalty to you. And really, they’re a black box I need a thing done. They’re task-level thinkers, right? And I was the project owner level.
Eventually I realized, if I want to get big, seven, eight figure company, I need to start hiring what I call team members, right? Employees, but team members who are in it. And whether they’re W2, whether they’re 1099 is irrelevant. Because sometimes 1099, someone’s overseas, you just have to do it, right? So that, the designation of how they’re paid is separate in my head from whether they are a core part of your team.
And a big thing that I always leaned into was this concept of loyalty. I’m loyal to you, you’re loyal to me. And what I learned is that’s a byproduct of trust. The trust is actually the core. I thought loyalty was the core because that’s how I was raised. But trust is the core. Trust between the employee and the employer. Tell me why you’re fascinated with this topic; what you’ve seen that basically instigated you reaching out and saying, “Hey, let’s record an episode about this.”

Andrew Berkowitz:
Fundamentally, there’s been a shift in the balance of power between employer and employee over the last 20 years. It started with the internet where people could work from anywhere, so suddenly you could take your skills anywhere; not just to your town, but anywhere around the world. So accelerated by COVID, employees have so much more power now. There’s not just one game in town for where they can work.
So when you think about what people are looking for, they want to be part of something. They no longer want to just feel like they are working for a company, that they’re owned by the company. They want to feel like they are part of it. And I always like to say, about my employees, “I don’t want them to feel like they work for my company. I want them to feel like they are my company.” And that comes from being bought in, from being passionate about what you’re doing. And I think the root of that is really trusting people like you’d trust your family members. We talk about companies being like a family. And companies aren’t really a family because you can’t fire your family members. But when you treat people with that trust, they’re part of your family, they will dive in with you, and they will run through walls for you.

Rob Walling:
I always caveat the idea of a company being a family with more of the Netflix approach, which is the company is a high-performing team. And you can think of it as a sports team if that analogy works for you. It could be a chess team. It could be a group of adventurers in a Dungeons and Dragons adventure, whatever analogy. But it’s a team trying to accomplish a goal, and there’s trust there too. I ran track which individual but also team sport ’cause we had relays and no team scores. And also played football. And you had to rely on the person next to you. And frankly, I wanted the best players on the field. And if you were my friend or not, if you weren’t the best right outside tackle, then I didn’t want you because then I was going to get hit because you were going to miss the block.
And I think we’re on the same page with that, right? Whether it’s family or team, there’s a level of trust and a level of wanting to be around other people who are good at their job if you are, so that they don’t drop the ball.

Andrew Berkowitz:
Yeah, and the pushback that you hear on building the trustful organization is essentially, “If I give this trust to people on my team, are they going to perform?” You see it all the time with people asking, “If I’m not tracking the hours that my people work, are they going to goof off? Or if I have a flexible vacation policy, are people just going to take off for six months?” And the answer to that is, if you have high performers on your team, in no way are they going to do that. Because high performers, they want to perform. They want to take pride in the craft of their work, and they want to do great stuff. And so when they feel like they are working for you as a hired gun, and they don’t have your trust, and you don’t have their trust, they’re not going to be interested in doing that.
But when they feel like they are completely bought-in, part of your team, they want to do great work. And think about the great people who have worked for you. They want to do the great work. You don’t have to police them.

Rob Walling:
Yeah, did I ever track the hours of my best engineers, my best whatever, program managers, event…? Nope. Never cared. I want to dig into this so that people understand, a founder or aspiring founder who’s listening to this understands exactly what we’re saying. Perhaps the difference between maybe the old way of doing things and what you’re proposing, which is it’s not like you’re proposing something that should happen in the future. This is happening. Companies are already run in this deep, deep trust fashion. You already mentioned something like not tracking vacation time, not tracking hours, more looking at results.
This is how I run my companies. I have. So I’m saying this for the listener of I’m going to play devil’s advocate during this episode because otherwise I’m going to nod and agree and say, “Yep, that’s pretty much how I do it. Yep, that’s how you should do it. That’s worked for me.” But I want to play the other side of the coin because there are absolutely people listening saying “Yeah, this won’t work, and here’s why not.” And so I need to play that role in this episode. So we named a couple things like some specifics of unlimited vacation policy. That’s something you were saying.

Andrew Berkowitz:
And I wouldn’t say unlimited. Unlimited always gets people freaked out because they’re like, “Okay, Joe’s going to take off for six months to the Himalayas.” So I like to say, “Flexible vacation policy.” And again it’s, do I need to police my people’s vacation, or can I trust them to take the right amount of vacation? Because the old model is essentially you get two weeks or you get three weeks a year, and you basically take that. You ask for permission, and you take that.
The new model is: what do you need to be highly productive? It starts with high productivity. And then it’s going to be different for different people. I have had employees who are, they basically, they’re like a nine to five person, Monday through Friday. And they slow and steady. And they get stuff done that way. And a couple weeks of vacation a year is all they need.
I’ve had other people who, they burn really hard. They’re 12, 14-hour days to push out a feature. And then boy, they need a week off to decompress. And so, one-size-fits-all doesn’t work. And I need them to say what’s going to be right for them. And I need to push down to the team what’s right for the team. There’s a big fear that well, if I have a flexible vacation policy, everybody’s going to disappear at once right before our big release. Well, you put it on the team. You say, “Our vacation policies, you’ve got to coordinate with your team to do the right thing for yourself, the team, and the company. You put company before team. You put team before self. And then you put yourself. And it’s your job to work with your team to figure out what the right thing is.”
I’ve had people come to me and say, “Can I take vacation at this time?” And I’m like, “I don’t know. Talk to your team. I’m the boss. I don’t know what you’re working on. I don’t know what your team is working on. Work it out with your team.” It makes no sense for me to approve your vacation because I don’t know what you’re doing.

Rob Walling:
Right. Okay, so that that’s vacation policy. Let’s talk about there’s hours, right? Flexibility of work hours.

Andrew Berkowitz:
Yeah. That’s the big one. I mean people really want to be able to set their own schedules right now. And it’s partly because they’re trying to find that work/life balance. But it’s also because everybody is productive in a different way. And we all know you can have somebody sitting at their desk from nine to five. Maybe they’re getting something done, maybe they’re on Facebook. If they’re a developer, they might be working on their side project because every developer’s got a side project. Hours as a proxy for getting work done is totally meaningless. So what people want to be able to do is set their own schedule.
And again, the fear is, if you let people set their own schedule, they won’t work. Or they won’t be there for that client call, or they won’t be there for their team meeting. Well, that’s not how you manage trust. You say, “You’re in charge of your schedule with your team and with our customers and with the company. Set the schedules that’s going to work best for all of those.” And it’s going to be different for different people. But somebody can’t say, “Well, I don’t work at nine, so I’m not going to do the team meeting at nine.” That doesn’t work. Trust is saying, “Within the parameters of being highly productive with your team, what is your schedule going to be?”
And the magic of this is when you stop saying, “These are these specific hours that you must work,” people will give you a lot more flexibility in terms of what they are willing to work on. So I’ve seen a lot of founders say, “I can’t get my people to work on weekends, or I can’t get my people to work evenings when the servers go down.” And that’s because you’ve told people, “Well, your hours are nine to five. And boy, it sure would be nice if you gave some extra time.” Instead, just say to people, “Your hours are you make your hours. You figure out what we need.” And highly motivated people will figure out, “Oh yeah, we need to do this release at 10:00 PM on a Saturday night, not at 2:00 PM on a Monday. I’m going to work those hours because I have the flexibility to figure it out.”

Rob Walling:
Do people want some type of idea of how much they should work in a week? Like, “Hey, you can work when you want, but our standard work week is a 40-hour week. And if you need a day off, take a day off because we have that flexible policy.” So it’s like, “If this week needs to be 32, that’s fine. And some weeks it will need to be 48 because we have a deployment, because for whatever, because we’re working an event. Some weeks, it will be 60.”
I was in Malta last week with the TinySeed MicroConf team, and I can’t even count. I don’t know if we worked 60, 70-hour week. It was crazy if you count all the stuff we were doing. And then immediately I tell everyone, “The moment you can take one or two days off, when we’re back, in addition to Thanksgiving,” because Thanksgiving is sometimes fun and sometimes stressful, depending on your family. I was like, “We need to take some time off. Everyone try to carve that out.”
But all that said, I’ve always thought of it as, “You’re flexible. Get your stuff done. Let’s collaborate in essence and be a team that’s driving it forward.” But personally, I’m not saying right or wrong, but this is how I do it. I like to say, “Our work week is a standard 40. In general, try to get 40 hours of work done a week.” Do you think that’s helpful or harmful? Do you think that that is more of a butts in seats attitude of hours worked?

Andrew Berkowitz:
I think guidelines are helpful for people. I think if you have nothing there, it’s hard. So I do like to say… I think a policy I wrote before was essentially, “Yeah, we work an average of 40 hours a week. But there’s going to be some weeks where you put in 50 or 60 hours; there’s going to be some weeks where you put in 20. And the key is, we’re not counting, you’re not counting, none of us are counting. We’re just trying to do the best we can.”
And it’s the same with vacation policy. On a flexible vacation policy, I think people want some guardrails. And so I think the policy I wrote before was, “Most people take about three weeks of unplugged vacation a year. But maybe your daughter’s getting married, you got a special opportunity to go to Indonesia for a two-week wedding. This year, you’re probably going to take a little bit more than that. Another year, you might take a little bit less than that. And again, we’re going to be flexible on it. We’re going to figure out what you need.”
Because really, if you are trying to hire really great people, and you should be trying to hire the best people, you should be thinking about the long game. It’s not how much vacation somebody took this week or this month or this year. It’s how productive are they over their career with the company? And I want somebody to be thinking on multiple-year horizons. I want my employees to be thinking about, I’m going to be here for many years, so what I do this month or this year is not as important as what I do over my career at the company.

Rob Walling:
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And is location and other factor here? ’cause we’ve talked about vacation time and work hours. I realize COVID changed this. But in 2019, if you went to so many companies and said, “Your people can work from anywhere. Would you allow that?” it would’ve just been so many more nos than I think today. But do you factor that in as well as a level of trust of “I don’t care where you are as long as we’re not breaking any state laws.” ’cause if people move to another state, you’re supposed to pay taxes in that state, blah blah blah. Let’s put that stuff aside. But let’s assume they almost become nomads, and they’re kind of moving. Do you factor that in to this flexibility?

Andrew Berkowitz:
I think it’s part of it. I don’t really want to relitigate the work from office, work from home thing again. Because honestly, you can have remote workers with no trust whatsoever. You go on Amazon, you see devices that people can buy that jiggle their mouse every two minutes, so the tracking software that their company has can think that they are sitting at their desk. So companies have any number of ways of tracking their workers who are working at home. So I think they’re kind of separate.
I am obviously a strong believer in remote work. I think it’s great. I think, in general, people can be more productive at home than in an office, over the long haul. But I think that is somewhat separate from trust. And I think for most startup entrepreneurs, you’re not opening an office the first thing you do. Generally speaking, in 2022, you are generally starting remote.

Rob Walling:
Getting an office, in this day and age as a startup, is an antipattern now. I see it when people are like, “So I’m going to raise some money so I can get an office.”And I’m like, “But what? Are you manufacturing hardware device? Warehousing things? Why would you need this?” Yeah, it’s a trip.
So I always hated being in the office. When I was an employee, I hated being in the office five days a week. I hated the nine to five or whatever the numbers were. I hated all this structure. And so when I started companies I said, “We’re not doing that.” So that’s why I started it, was because I wanted to build a company that I wanted to work at. But what you’re saying, I never really factored in. I figured maybe it’ll be more productive, less productive. Maybe I’ll get better people. I don’t know. That’s just the company I want to work at. So that’s why I built it.
You’re coming at it from a different angle though. You’re actually saying, “No, this will allow you to hire and retain better people. You will build a stronger team, and you will have a better company.” Right? Or am I putting words in your mouth?

Andrew Berkowitz:
No, that’s exactly it. Think about what people are looking for right now. Essentially, anybody who works for you can walk out the door and find an equivalent or better job somewhere else because we can all work location-independent now, essentially. So the question is, what are people looking for?
And I think what people are looking for is what we’ve always been looking for as humans, is we want to be part of something. We want to feel like we have a community. We want to feel like we are bought into something. And I think that really comes from the culture you are building and that culture of trust.
So one thing we really haven’t touched on… We’ve talked about the mechanics of how you run, where people work, how they work, what their day looks like. But there’s really a second component to trust, which is the what are you communicating to your company, to your employees, and how are you using transparency to really build that trust?
Because I think there’s also the old school way of doing it is you just tell your employees the minimum that they need to do their job. You don’t tell them what your big company plans are because your fear is that they’re going to run to your competitor and share that information. You don’t tell them the financials because you don’t want them to tell competitors if your numbers look good. Or if your numbers look bad, you don’t want them to immediately go out looking for another job because they see that the company’s in trouble.
But contrast that with what’s a trustful approach? A trustful approach is you share all of that with your employees, so they feel like they are partners in the business. You tell your employees the same thing you would tell your co-founders. And if there’s bad news, if the numbers don’t look good, your employees are going to figure that out eventually. They’re not stupid. But why not tell them that now and let them run through a wall for you to solve that problem.
At my previous company, we had some months that looked pretty bad. The numbers just weren’t adding up. And we didn’t hide that from our employees. We told them. They could see, boy we really need to turn this around or else obviously we’re going to have to lay some people off. And so they immediately dove in, worked harder, looked for ways to save money. They were partners in making things better rather than people who we had to hide things from.

Rob Walling:
But what if you have something that’s maybe a crisis but you believe that it’s temporary? You believe, oh we hit a bump this month, and this happened. Or whoa, we got a big tax bill. Suddenly the company had to pay 300 grand out, and we’re coming real close to not making payroll, but I think we’re going to make it. We’ll be okay. What about that? I realize this is kind of edge-case stuff, but I think, a lot of times, a lot of things in a startup are transient. And they come and go quickly. How do you think about that?

Andrew Berkowitz:
It’s a good question. A CFO I worked with once told me that transparency isn’t necessarily sharing everything. It’s being willing to share everything. So I don’t think you necessarily have to share every potential bump in the road. The problem is, if you don’t share it and then it becomes a thing, then your employee, you’ve essentially busted your trust. Your employees are going to be like, “Oh, you knew about this three months ago. Why didn’t you tell us this?” So you need to be darn sure that it is transient and that you’re going to turn that around. Because if you don’t, then you’ve lost your trust.
And it’s always a challenge to know what should you share and what is too much information that that will get employees spun up unnecessarily? But in general I think share more. You also have to share the context. A lot of employees are not going to have the business context that you do. But being forced to share that context actually creates much more business-literate employees, which is going to be better for your company.
If most employees in most companies don’t know how to make a business case, that manifests in people constantly calling you up and going, “Well, we need to add more head count.” That’s the first thing employees say. “We need to add more head count” because they just see there’s more work that needs to get done, so let’s just add more head count. And so really having them understand the fundamentals of the business and how business works and the levers that you use to make money helps them think through, oh, I see we can’t afford more head count/ we need to be more strategic in terms of what we’re trying to achieve, or something like that. And when employees feel like they’re partners in this, they’ll also push back on you. They’ll turn around and they’ll tell you, “Your roadmap is completely ridiculous. We cannot achieve this with the people we have.” But unless they have the full context, they can’t tell you that.

Rob Walling:
One critique of this that I’ve… I was going to say, “I’ve heard,” but maybe it’s in my own head, is that I do most of this, but I run small companies on purpose. At scale, I really question if this works. This works at 10 people because I’ve done it. I bet it works at 50, maybe at a hundred. At a thousand people, I question. Or 5,000 employees, I question if this level of trust will work because it’s like anything else. The more humans you get involved, the more likely you are to have outliers, both good and bad; the amazing people and then the bad actors who are silent… What is it called? Silent quitting? Quiet quitting that’s happening these days? Which I heard is this big overblown thing and is not happening any more than it used to. But whatever, it’s people just slacking off because they’re remote, and they have the mouse shaker thing you talked about earlier, right?
It’s the same reason that we often hear, “Countries like Denmark have this amazing system, healthcare, whatever it is, and it just works. And why can’t we do that in the US?” And it’s like, “Well, because aren’t there 10 million people in Denmark? And there’s 300 million in the US.” It’s just more complicated. You know what I mean? So I feel like that same, as things scale, (beep) breaks in ways that are really unpredictable.
And any system that I’ve seen scale needs usually more structure. Bigger companies have more structure, I think, because they need it. If I was at a private school with a hundred kids… I was at a public school with 180 kids, growing up. Very little structure. My son goes to a public school now with 2000 kids. And there’s way more structure. And I think it would be absolute chaos if they didn’t. So what do you say to that critique of this idea: this trust works amazing. But yeah, until you grow up?

Andrew Berkowitz:
Well, I think it’s going to look different at every stage. That’s the thing I’ve definitely seen over my career, is every stage of company looks completely different. And so what trust looks like at a two-person company, a 10-person company, a 50-person company is going to be way different than a 5,000-person company. But when you think of a 5,000 person company, it’s really a collection of smaller teams. And each team can still have this same microcosm of trust, even if it doesn’t manifest it the same way for the entire company. So it’s going to be different at whatever size for sure. But think about the team size. And really a lot of building a trustful organization comes down to your managers. And as a startup entrepreneur, it’s you. You’re essentially the manager. And so you’re managing whatever it is: three, ive, 10 people. As you grow and you start getting other managers in, you have to train them in thinking this way too.
And it’s tough because most of us do what has been modeled to us,, and most of us have worked in traditional companies where the company owns your time and the company tells you exactly what to do. So you really need to bring in managers who are a hundred percent bought in on this. I think one of the keys to trust, which really this works in any size company, is that it goes both ways. It’s not just me, as a manager, trust my employee to get their work done, say they’re doing what they’re going to do. It’s also employees really trusting their manager and leadership. It’s really trusting my manager to be super candid with me about what’s going on in the business and how my performance is. We’ve all been in the experience where we go into our quarterly or our annual review and we got our fingers crossed that we get a good review. And that should never happen.
Your manager should be telling you how your performance is weekly or biweekly or whatever your one-on-one schedule is. So part of trust is me, as a manager, being willing to say the hard things. Being willing to say, “Hey, your performance has not been good. You need to pick it up.” Or “Hey, I know we give you a lot of flexibility to set your schedule. You’re not producing. I don’t really care when you work, but you’re not producing, and you’ve got to do that.” So it’s really managers saying hard things, which is hard. Having those hard conversations is hard.

Rob Walling:
That was the hardest part of learning to manage for me. I see management as there’s leadership, and then there’s supervision or management. It’s two components. And the leadership was always like, “I know where I’m going, and I’m excited about it. Anything I do, I’m stoked to do it. Otherwise I’m not doing it.” And so, to get other people stoked about it has never been a challenge for me. The hardest part has always been, man, I’ve got a good team, I really like them. How do I tell this person they’re dropping the ball? And I do it now. But it took me years and years of practice.
And I think that if you’re hiring people who are generally good people who are generally nice as well, and they’re becoming managers, and you’re training them, that might be the number one thing that I try to communicate is, “You have to do this. You just have to learn how to do it.” And if we need to role play it, if we need to buy books, if we need to watch YouTube videos or buy courses or whatever, learn how to give constructive feedback. There is a book called Crucial Conversations that I read. It was recommended to me by Ruben from Seinwell, where I still almost all my good ideas. That book had a real mental shift for me. So I think if you’re listening to this and you’re wondering, how can I get better at that? I really liked it. Andrew, do you have any other resources you use to get better at that?

Andrew Berkowitz:
I think one thing that’s really helped me as a manager is create an atmosphere, in my one-on-ones with employees, where it’s really clear that we are going to spend time in every one-on-one talking about the negative things. So I used to manage a lot of designers. And designers are notoriously stoic, for whatever reason. And so basically in our one-on-ones, I would basically say, “You have to complain about three things in this one-on-one. And one of them has to be something about me.” So I basically force them, “You cannot say nothing.” And they can always come up with something. “You don’t give me enough feedback” or whatever it is. So basically, every time we get into a one-on-one, we’re not just going to talk about happy, positive things. We’re going to talk about the problems.” And some weeks they’re very minor problem.
Some weeks, you have to complain about something like, “Well, I felt like this release came out a little bit too fast, and we should have had a different color of blue.” But then some weeks it’s going to be like, “I think our parental leave policy sucks.” So you need to prime that. And when you start priming that, then I think it becomes easier for you as a manager to realize, okay, well, I’m going to have some too. So we’re going to talk about some things that were negative here too.

Rob Walling:
Touching on a couple points we’ve talked about and some critiques of this approach that I think would be interested in going down is one thing you said is, “You have to hire great people for this to work.” There are only so many great people. Where does everyone else work? If you’re great, are 10% of worldwide…? Or let’s say you’re hiring in the US because and I are in the US. For the sake of this, even though we both hire outside the US.
But just for simplicity, how many potential employees, team members are there in the entire US of working age? Then how many have any skills that maybe you and I could hire for? And then what percentage of those are quote, unquote “great” and would work with this? Is it 10%? Is it 50%? It’s not 90%, right? So where do those people go work? And how do you make sure that, as you scale this, again, can I find 10 great people remote? Probably. Can I find 500? I don’t know. I think, at a certain point, the bell curve kicks in, and a certain percentage of your employees are not great by definition.

Andrew Berkowitz:
I think that’s true. And maybe great is too high a bar. Maybe solidly good with good intentions. I think that fundamentally, up until a few years ago, the world of work was predicated on this theory that, left to their own devices, my employees will goof off. If I don’t police my employees, they will goof off. If I’m not watching them, they won’t work. And also, if I don’t police my employees, they will steal from the company.
That is how we have thought about employment for years and years. And I just think most people are better than that. I think the vast majority of people are not going to steal from the company. The vast majority of people, they want to do good work. And they want to do good work because they want to accelerate their careers. It’s great when somebody is totally bought into your mission and wants to help you build the widgets that you’re building and wants to change the world.
But it’s also okay if they just want to do great work because they want to make their resume better because they want to move up in your company, they want to make more money, they want to grow that way. Either way. And I think most people do. Now, are there bad apples out there? Absolutely. There are people who will try to steal from you. There are people who will goof off and not do the work. But when you build your company policies around the lowest common denominator, you end up punishing everybody, and you end up ultimately punishing your company.
So you need to think, what is the penalty for getting this wrong? For example, if I have a super flexible vacation policy, and somebody books a three-month vacation, what is the penalty for that? Well, for one thing, you’re probably going to fire that person. But is your company out of business? You’ve been embezzled? You haven’t. So just think about, don’t make policies for the lowest common denominator.

Rob Walling:
Speaking of that, we have a flexible vacation policy. Every company I’ve ever run has had one. But I still approve vacation. I know you said earlier, you don’t. You say, “Go talk to your team.” Oftentimes, like if you look at the TinySeed team, there’s five of us. So it’s not, “Go talk to your team.” We are the team. We are just one team. So I still do that. And same on the MicroConf side. There’s five or six of us. And people do come in order to coordinate. We have to coordinate schedules. Like you said, you don’t want everyone out of… No, we have an event that week. Everyone can’t be gone. A few of us have to be here.
So what I’m saying is, even within this realm of trust in building these trustful companies and trustful teams, there is still flexibility because you know said, “You don’t need to run it by me, go to your team” Whereas I’m saying, “No, I still do that.” But I feel like we’re still in the same orbit compared to the bigger momentum of the last 50 or a hundred years of institutionalized work is what you’ve been talking about, which is nine to five and the lack of trust and a bunch of guardrails in place to keep people in line.
One thing you just brought up that I want to touch on is you said, “There will be bad apples.” People embezzling from you is one thing. And I think that’s a very, very… It’s possible; it’s a very small number. People who will slack off, I think, is a larger percentage. Is that just a cost of this approach? And is it just…? What do you call it? It’s collateral damage, right? If you build an amazing team using this approach and you get to the point where you’re at 40, 50 employees and you do have one or two people who slack off, that’s just the price you pay?

Andrew Berkowitz:
I think you’re going to see that whatever kind of company you run. You can have a company where it is strict nine to five, we’re watching you every minute, there’s no trust whatsoever, and you’re still going to have a couple people who are slacking off. Because again, whether somebody is actually being productive when they are sitting at their desk is highly questionable. So I think the beautiful thing about trust is it turns this conversation to productivity and to results. We are really gauging people on what have you produced? And when I hear founders say, “I’m afraid to give people this kind of flexibility ’cause I’m afraid I’m not going to know if they’re working…” If you don’t know if your people are working, you have a problem with understanding what the outputs are for your team. For a developer, I’m pretty clear on what the outputs are. And those outputs are not sitting at your desk from nine to five. Those outputs are pushing bug-free, workable code.
And if I’m hiring a social media manager, I’m pretty clear on what those outputs are. It is managing my social media. So I really don’t care anything other than what you’re producing. And it makes the conversation so much simpler because you stop having these conversations where people say, “Boy, I’m working really hard.” It’s like, “I don’t care how hard you’re working. I care about what you are producing.” It simplifies the whole thing. And you can find your bad apples really fast because they’re not producing.
And the magical thing about this is you can’t hide in this way of working. At a strict nine to five, sit at your desk, show up before the CEO shows up, follow all the policies and procedures, you can hide for a long time. Because you can look really busy for a long time.

Rob Walling:
Even more so at in-person.

Andrew Berkowitz:
Oh yeah.

Rob Walling:
Have you ever been in an office with cubes where it’s like, “Well, everyone had to show up at nine, and we leave at six, and we have an hour lunch,” And there’s five people in my department who were doing jack (beep) all day, but I knew it because I was on their team and I’m like, “I’m shipping five times more software than this person.” But they showed up, and so no one asked questions. Whereas if we had been remote… To your point, Tracy Osborne is also the biggest fan of remote. She always says, “Just because you show up at the office doesn’t mean you’re actually working.”

Andrew Berkowitz:
Yeah. You got to know what your outputs look like. And if you don’t know that, if you’re not sure how much a senior developer should produce in a week or a month, that’s something you got to get calibrated on because you just don’t know what your outputs are supposed to look like. Similarly, you can hide a lot as a leader if you’re not forced to stand up in front of your company every month and show the financials.
We’ve heard so many stories of like, “Oh, I was surprised that they just laid off a thousand people. Because as far as we heard, everything was going great.” So being forced to stand up in front of your company and tell them everything, it really makes that conversation a lot simpler. People really hate uncertainty. And people will write their own stories. So if you are not transparent with your employees and telling them what’s really going on, they will write their own stories. And you’ll lose far more people who just imagine that things are terrible than just telling the answer.
One of the great things I learned from a previous co-founder was he loved to stand up in front of the company and answer hard questions. And so we’d do a company meeting every couple weeks. And we’d have an anonymous form where people could just, in real time, submit whatever questions they had. And it was tough stuff. It was, “What is happening with our strategy? This makes no sense.” Or “Why don’t we have more diversity?” Or really hard questions. And he just loved to stand up and answer those questions because it built trust with the team. They knew we can ask whatever we want to ask, and they’re not keeping secrets from us. And it turns out that people don’t necessarily need to love your answer. They just need to know that you’re listening and that you have an answer.

Rob Walling:
And is one of the reasons that you built Suggestion Ox, at suggestionox.com, because you wanted people to be able to anonymously submit feedback to their teams and their managers and such?

Andrew Berkowitz:
Yeah, I think, as we talked about earlier, everybody wants to build a company culture where everybody can be a hundred percent candid all the time and say the hard things and ask the hard questions. But the reality is not everybody is willing to do that. And a lot of employees have been burned. A lot of employees have been in a company where you asked a hard question, and you got fired. It takes time to build that trust. So that’s why we built that particular product, is we just know people need psychological safety to say the hard things, ask the hard things. And as a manager, you need to know it. If there’s a problem, you need to know it.

Rob Walling:
Folks want to keep up with you and see the subsequent content you’re creating around this. I hear a book on the horizon. They can head to Twitter. And you are Andrew Berkowitz, just like it sounds, or suggestionox.com. Thanks so much for joining me today, sir.

Andrew Berkowitz:
Thanks for having me.

Rob Walling:
Thanks again to Andrew for coming on the show. Thank you for listening. I hope you enjoyed that talk. I enjoyed the spirited discussion and the ability to just bat ideas back and forth and talk that topic through. I hope you enjoyed it. This is Rob Walling, signing off from episode 639.