The Secrets of Great Remote Teams

"Find people who can succeed in your environment"

Hiten Shah is an expert when it comes to building SaaS companies in a remote environment.

Over the last twenty years, Hiten has started multiple software companies, including: Crazy Egg, KISSmetrics, Quick Sprout, and his current company, Nira, all while working remotely.

In addition to being a serial entrepreneur, Hiten is also a startup advisor and investor. Some of his notable investments include: Front, Loom, and Truebill (Rocket Money).

Hiten has spent practically his whole career building great remote teams, so I sat down with him to learn about some of his secrets.

We also talk about:

  • How to create and sustain momentum on your remote team.

  • Why regardless of where you work, you'll still be doing async work.

  • What management is truly about and how that helps your team find success.

  • How Nira screens candidates for its "measure twice, cut once" engineering culture.

If you're looking for practical ways to accelerate the velocity of your remote team, then you don't want to miss our conversation.

You can watch it on our YouTube channel, or you can read it below.


Quick note before we get into it:

Running a distributed team can be chaotic. That’s why we built Almanac – to give remote teams structure and transparency without having to hold more meetings or buy more tools.

And I’m proud to say that Almanac has helped hundreds of world-class teams, like Credit Karma, Indeed, and Cisco, to document knowledge, collaborate online, and manage projects in a single place.

If you find it hard to escape the gravitational pull of chaotic processes, often caused by office-first ways of working transplanted into remote contexts, and you want help, shoot me an email ([email protected]).

I’ll have my team personally walk you through Almanac, help you set up your workspace, and I’ll give you a $35 credit to use on any of our plans.

Hope to hear from you soon.

Nira has been 100% remote since day one. Tell me why you set up the company that way.

I'm one of those people who doesn't know any better. For the last 20 years, I never really worked at a company where everyone was in the office. For example, at KISSmetrics, we had an office a couple of times, but we never had 100% of the people in the office. Prior to that–back in 2003–I started a consulting company that was remote. And at that time, we were using different tech–like Skype, AOL, and AIM. And then when Google came out with Chat, we actually used Google Chat, believe it or not. Very similar to how everyone uses Slack today.

So for me, I don't know any better. I guess the parallel to that is, I grew up as a Jain, which is a religion in India. It's a little more obscure, but it's similar to Buddhism and Hinduism. And in my family, we don't eat meat. So because I grew up like that, I don't know any better. With work, I never actually had a job where I had to be in an office, except for an internship in high school at a medical devices company. I'd go into an office every day, and that was my only personal office experience. But I was in high school, and I was an intern, so it didn't really count.

As I started to get into the workplace and start my own companies, we just naturally gravitated towards having remote teams simply because, at the time, when we started our consulting company, we didn't really need an office. No one was coming there. We weren't even going to other peoples' offices. A lot of the work we did was marketing work which could be done asynchronously and remote.

Martha Stewart and David Sacks said that people can't get anything done working remotely. You've said that remote work is a game changer because it treats adults like adults. What are they not seeing here?

I don't think it's about what they're not seeing. I think it's more about what they are seeing. And what I mean by that is–you're going to do what you're used to doing, especially when it comes to management and leadership. How you manage and how you think about managing are some of the hardest things to change. If you're used to managing everyone in an office, then you're going to want to manage that way.

It takes such a high bar to change. And that high bar came, and it got lowered with COVID. I've been known to say that COVID remote work was not remote work in the traditional sense. It was forced remote work under duress.

And then you had this whole crop of tools that came out that tried to mimic our office environment. Everyone was trying to mimic the way they worked in the office, in an environment that was not the office or an in-person form of working. So all that people are missing or seeing is what they're used to. Anything like that is just a pattern of behavior that folks got very used to over their whole careers.

And a lot of people join in on this debate and start blaming employees, which is the piece that really bugs me more than anything else. I like to ask, is it the team's fault? Or is it the fault of management and leadership? It's always the fault of management and leadership. So I would say that these remote work failures are management failures.

Sam Altman and Elon Musk say it's hard to manage people well in a remote environment. If they were here right now, what framework would you give them to help them manage a remote team?

I'll start with one thing–which I know you're very familiar with at Almanac–we're all doing remote work, even if we're in the office. That's the one highlight I need to really stress here. We can thank Writely–which was acquired by Google–for this because they built the online version of Microsoft Word.

The bottom line is this: most people are trying to mimic in-person work environments on remote or distributed teams, and that really doesn't work. So this is actually the root cause of most failure, and I can't really blame people who fail for it. They're used to a world where going into the office was the norm. It's the work environment that the majority of leaders and managers are used to, and that's the problem. So the real secret to getting people in any type of work environment, office or not, to be productive, is to focus on finding people who can be successful in that environment.

Here's the way I think about that: I actually start with the recruiting process and emphasize tests during the recruiting process. At my company we have a "measure twice, cut once" culture on our engineering team, and we hire for culture and process fit. So that's the difference between us and many other companies. Most companies hire for culture and aptitude, but they don't hire for process.

So, on our team, we require engineers to have 90% confidence in their plan before they write a single line of production code. We work everything backwards from there, all the way to the recruiting process to ensure that we're hiring people who we're 90% confident can be successful in the environment that requires them to be 90% confident in their own plans. Our planning process is so critical to our success as a company from a product standpoint.

So before we do any culture-related evaluations, we have candidates do a planning exercise up front. Because the way we look at it is: their ability to work in the environment we've created matters so much more than their fit into our culture. A lot of companies bias towards culture fit first, and then aptitude, and then call it a day without thinking about the environment they've created. What we do instead is give front end engineers a to-do list app to plan and back end engineers a link shortener to plan. We don't do any coding puzzles or any of the typical coding challenges you see at other companies. We also give them a two page brief that includes things like: holidays, time zones, availability of teammates, and other things like that. And then we score the plan and talk to them. Usually it's a 90-minute call where we break down things like: how thought about their plan, how they timed it, and thought about the kind of technical research that would go into the build. And then we rescore it after that conversation. If they hit a certain threshold after the second score, then they proceed with culture interviews (panel and 1:1 calls).

Our thesis is that if they can't plan to our satisfaction, then they won't be successful in our engineering environment. I tell you all of this because we've been successful with it–we've gotten lots of positive feedback on our interview process. And in the last two years, our team has built more than any other company in our space in terms of functionality and features that get used and upsold. Here's what folks have said about our engineering interview process:

  • One candidate said, "This process is really cool. I hate those puzzle tests."

  • Another candidate said, "This was the first interview where I learned something."

  • And then another candidate went a little further and said, "I would love to express my gratitude regarding the form of exercise presented. It is very important to be focused on a candidate's thought process and planning abilities, as that is what I believe to be the fundamentals behind software development."

So at Nira, we took–ironically enough–what Elon Musk, Sam Altman, and others call first principles (around the environment that people are in), and then pulled out the critical piece and made that the test. It feels so basic to me at this point, because I understand now how this can be abstracted to many other areas. It's very common, when you hire someone in marketing, to have them make a 90-day plan, because that's a good test, or if you're hiring a writer, to make them write a few things with a brief, because that's what they're going to do every day.

So I think the big thing here isn't about remote work versus office work. It's about the way we manage and the way we recruit and being able to get those things in alignment. Because the environment that's created is based on how you manage. And we like to pull that out in the recruiting process and say, "hey, shouldn't we assess their ability to succeed in this environment we've created?"

It sounds like you're testing for things that are often required across roles to be successful in a distributed context. Things you've learned from working remotely for the last 20 years that you know will help your team deliver value to customers and build a successful business.

Yeah, exactly. For example, on product, we truly believe in research. All of our exercises for any product people we hire are focused around research and analyses. So we might have them do a user test on a home page or an onboarding flow, and then we'll see how they do with it. We'll look to see how they analyze it and how they think about it. Even if they've never done it before, our brief and process help them to understand how to do it.

So I think you hit it spot on, which is that these are all things based on running these environments for teams for a long time. Because here's the thing: a lot of the leadership and management criticisms against remote work–or in favor or office work–are all very personal to the manager and the leadership. They're not abstracted out to what environment you're creating or what's going to happen with your team. Because really, management isn't about you. It's about creating this environment inside the entire company where everyone can be successful.

So if you're very deliberate upfront, then there's less dissent downstream. So the advice I would give to any of these folks is to realize that they're already doing async work. You already have to design the systems and tooling to make that work. To me, it's not really that different, but people are making such a big deal out of it. And that's because they failed at the concept.

I like to say that remote exposes how good you really are at management. Most managers who want to go back to the office don't want to change.

Yeah. It just goes back to the earlier point: if you're used to it, this is what you're going to do. Management and leadership styles are the hardest things to change. And if those aren't going to change, and someone like Elon Musk truly believes that his team should be in the office, then guess what? That's the environment. That's how recruiting happens, and that's how success is going to happen at that organization.

But there is one caveat: you're still going to do a ton of async work. So what happens when there are multiple offices? All this stuff breaks down really fast. And to your point, a manager can come into the office to make sure that there are butts in seats and that people are doing their job. That's a traditional way to do it, but it's not how remote work is done.

Remote work attempts to create more autonomy and more work that's designed to be asynchronous. Hence why companies like Almanac exist. Because even if you're in the office and you have all these assets, documents, workflows, and all these things that need to be documented, well, guess what? You're still doing async work. That's the thing I can't get past: regardless of where you work, you're still doing that type (async) of work.

What are some of the hard earned lessons you've learned over time from managing in a remote context?

I've said before that remote work is a game-changer because it treats adults like adults. It's absurd to me that the way schools are designed is also how work is designed, because they are two different constructs. At school, there is a schedule. There's scheduled time to go from one class to another, scheduled time to eat, and even scheduled time in summer school. That's how school is designed–everything is scheduled for you.

The work environment most people are used to, I believe, comes from this construct of structure that we become accustomed to in college, high school, and elementary school. It makes sense to have when you're growing up and learning new things, but when you apply it to how work works, that's where I have my biggest gripe. We could blame Google for this, if we want to, because they really got everyone to love coming into the office. They were the poster child for the longest time–with free meals and all that. To me, self discipline and self management is what I think everyone should have from a freedom of time standpoint (even if you're working).

Startups are all about momentum. You've started three other companies before, so I'm curious: what are the secrets to creating momentum in the first place? And how do you sustain it over time?

Yeah, and I've tried to do it more than three. You just don't see a lot of the other failures and unsuccessful starts. When it comes to momentum, the number one thing that matters is: how customer obsessed are you? Can you feel it when the customer is reciprocating? Because if the customer is reciprocating that obsession that you're providing them, then you know that you're onto something that they value. Because it's not about what you value, it's about what they value.

I'm always looking for that customer momentum. At the end of the day, you have a customer and they need to be happy with you. Not even just happy, especially at a startup, they need to be so ecstatic that they want to tell everyone about what you're doing for them and what they're capable of doing because of your tool.

Look at AI–a lot of AI gets the early hype because customers are so wowed, at least initially, that they want to tell everyone about it. ChatGPT is a great example of that–no one can easily catch up now, even if they build the same thing, because the word of mouth is out there. So what I'm really looking for is customer momentum and that word of mouth. As a founder, you're basically hunting for these things.

I'm sure there were moments in your company where you felt like you had it, and then you felt like you didn't have it, and then you felt like you had it again. What I'm looking for is how to keep that kernel of momentum top of mind for the team, and how to make sure it's real. Because if the customer doesn't love what you've built, then you have no momentum. If they do, then you have momentum.

You need to find those kernels of truth that the customer cares about, and you need to bring them to the surface. So a lot of times, I repeat what the customer says, how they say it, and what that leads to. Oftentimes, they say that product market fit is when the customer is pulling the product out of you. That's exactly the kind of thing I'm talking about. The customer will tell you, "hey, what you've done is great. Can you do this other thing for me? Can you add this thing on? Can you fix this bug?" And then it's your job to create an environment in your company where the team is ready to do the job.

And the job is: the customer said it, so we're going to do it. And I don't mean that you need to adopt the mantra that the customer is always right, no, I mean you need to understand what that means for the customer and how to deliver it. For example, on multiple occasions, when we've been in the proof-of-concept stage of a trial, we've delivered features and functionality, big and small, that our users have requested (not customers, because the users haven't paid us yet–they're still in a trial or proof-of-value stage). That's because I can go to our CTO and say, "hey, we heard this, this, and this." And I don't even need to tell him to go fix it, to go do it, or to do anything. I just give him the context, and because of the way our environment works, we're able to pivot and understand things quickly. And there is always a trade off to that, but that makes the customer feel like we care about them and that we're obsessed with their feedback. So that's how you keep the momentum going.

It's important to develop short feedback loops and to understand how to deliver when a customer asks for something. Now, you can't always deliver on things, because sometimes customer requests are kind of insane. Sometimes they don't matter to all of your customers, so you don't do it. But anytime that you can do it, you should. It all relates to the bottom line of how to keep the momentum up.

You've been down the founding road so many times. What's one thing you know now that you wish you'd known when you started your first company?

I didn't come into this with a different construct, so I had to learn it from scratch. Here's my advice to not just founders, but to leaders in a company: you're going to have to do things that you don't want to do, so you have to find a way to get good with that. You need to find a way that works for you– is it meditation? Taking a walk? Talking to your co-founder? Talking to your mom about it who has no opinion except she loves you?

You are 100% going to have to get 100% used to doing things you truly do not want to do. Layoffs are probably at the top of the list, but everything under that is still just as scary or just as disheartening. On one hand, I want to say this and commit to it. On the other hand, sometimes I think if people knew, they wouldn't start a business and we wouldn't have such brilliant products and businesses out there that serve the world.

So I fear saying this, but if someone really wants advice–the good stuff–then you need to be okay with doing things every day that you do not want to do. And you have to get good with doing them at a pace that feels extremely tiring and extremely uncomfortable.

I have to give props to Steve, Nira's CTO, because he probably has the hardest job in the company. And I know this because he's feeling it. We're a tech company–we build software. We have to do incredible things to service this market that we're in. So, it's not just founders that have to embody this, it's also the leadership team. And that's not for everyone. In a startup, it's even worse because you have way fewer resources.

So that would be my advice: are you sure you really want to do this? Because you're going to have to do things you don't want to do, but that you need to do. And you need to do them fast and make decisions so fast that it kind of makes your world spin, and oh, you don't have a choice.

Next Week on The Big Bet: Tyler Sellhorn, Head of Remote and Top 50 Remote Accelerator

Tyler Sellhorn is an experienced startup executive who's served as the Head of Remote and Head of Customer Experience at multiple companies, including Polygon Labs, Hubstaff, and Commsor.

Tyler is a staunch advocate for remote work, and was recently named a Top 50 Remote Accelerator in The 2023 Remote Influencer Report. He hosts "The Remote Show," a podcast by We Work Remotely, where he shares tips on how to be a successful leader on a remote or distributed team. He’s passionate about all things remote, and my full conversation with him is coming to your inbox next Thursday.

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