Debunking Remote's Biggest Myths

One of the cool things about The Big Bet is the number of impressive people I get to talk to. From Harvard professors to venture capitalists to startup founders, I get to talk to all different types of leaders.

Today's conversation is no different: 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, so I sat down with him to debunk some of remote's biggest myths. We talk about:

• Why remote work is good for diversity.

• How remote teams can do mentorship well.

• Why our most creative thinking is done outside of the office.

• Why team size matters more than location when it comes to moving fast.

• Why you can expect to see more one-person companies in the next five years.

If you're looking for an in-depth discussion on remote work and how to do it well, then you don't want to miss what Tyler has to say.

You can watch our conversation on Almanac's YouTube channel, or you can read it below.

Enjoy.

You've been a Head of Remote multiple times. I haven't seen this position become mainstream–why do you think more companies haven't hired Heads of Remote?

One of the things from the pandemic is people really caught on to the idea that work is distributed and flexible, which led them to say we're just going to do it this way now. I think organizations that saw the light don't need to claim that word or that job title as a thing.

NetApp's Lara Owen, the VP of Workplace, hired Justin Tomlin to be the Global Head of Flexible Work there. This is a Fortune 500 company that is saying "we're going to thrive everywhere." These are the kinds of things that are happening in the market.

So I think Head of Remote is kind of like planting the flag on the moon. I'm very grateful for the organizations like Doist, GitLab, and Automattic, that really were the astronauts of remote work. Even going back further to the teleworking days. You can see it from thought leaders like Laurel Farrer–who planted the distributed consulting flag–and Sara Sutton at Flex Jobs.

The kinds of phrases that I think are going to win in the market long term are distributed and flexible. Because remote, unfortunately, has really been associated with that pandemic work from home experience. Hybrid has also soured based upon the experience of the return to office movement. Back when Matt Mullenweg's (CEO of Automattic) podcast was publishing more frequently, they used the phrase "distributed" to express their talent strategy.

I think it's really important for remote advocates, at times, to have that spiky opinion that says, "no, we're about remote!" And then there's other times where we're going to use future of work and other softer phrases that are off in the distance and not affecting us yet. I think there's times to be considered about which phrases we use and for which audiences we use them.

Martha Stewart and David Sacks have pushed back on remote work. I'm curious what you think is going on here–what are they missing?

I think it's very clear that their investment portfolio is showing. Commercial real estate is a huge part of the financial infrastructure of the world. And I think there are chickens coming home to roost here. This is a different mode of work, and office utilization wasn't very strong pre-pandemic, and it's even worse post-pandemic. It's really important for us to say to ourselves, okay, not every company should operate without offices.

The thing that needs sorted out is whether or not we're going to mandate that people work from offices. That's the key ingredient–who has the authority to decide where individuals work? Some organizations put managers in charge of their teams and let them decide when and where they're going to work. Other organizations, like Atlassian, let individuals choose when and where they work. That's really key to sort out–where does that authority reside? 

For some organizations–the ones that want to retain the talent they currently have or recruit new talent–you have to give the power to the individuals. Those individuals are seeking and desiring the opportunity to have the authority to decide where and when they work. Other organizations don't need to do that. In fact, it might be detrimental to their business to let that authority reside with individuals.

I know for myself and what I want from my career–I want to be able to work from Fort Wayne, Indiana. I have chosen to reside where I reside because of being able to live near family and raise our family in a relatively low cost of living metro area. But I'm also interested in being ambitious and joining organizations that are doing cool things and building cool products. So, how do you balance those things out? For me, I'm optimizing first of all for where I get to decide to work.

What would you say to the managers who believe that brainstorming or ideation sessions are best done in an office?

The data doesn't support that claim. Brainstorming is best done with a structured facilitator who sends out pre-work ahead of time. There might be a synchronous component to a great brainstorming session, but that's not where our best thoughts are done. Our best thoughts are done in the shower, on a walk, or in a conversation that has nothing to do with the other thing. Then, all of a sudden, lightning strikes, so you get out your phone or your voice memos and you get that idea out. That's when the best ideas appear. And that's not to say that there isn't time for bursty conversation, but it's usually done within a structured cadence.

Flo Crivello, a previous guest on The Remote Show podcast, just reverted his opinion on remote. Maybe he was looking for some investment from David Sacks. I think it's interesting to hear them echoing each other. Because what I hear them saying is that, "I'm most productive in the office. So, where would I choose to be? I'm most productive when other people are collaborating with me in person." I think that there will be people that feel the exact same way as they do and are going to choose to work in those companies.

We've seen a large shift from the AI companies choosing to go work together in the Bay Area. I think that's great. But you're also noticing that there are other AI companies that are in far-flung places like St. John's, Newfoundland. Well, there's not enough AI talent in Newfoundland to be able to really have a team, so they're going to hire across hubs, at a minimum.

Darren Murph has always said, "remote is a forcing function for intentionality." I think what we're hearing from these return-to-office champions is (i) they're afraid for their investment portfolio, and (ii) they're expressing that they intentionally chose to work for a company that uses in-person collaboration as a core component in its strategy. I think that's a good thing.

Do startups need to be in-person to move fast? How can remote startups move fast in a distributed context?

I think team size matters more than colocation. And I think you also see some companies, even before return to office mandates came down, that had core working hours they reserved for bursty conversation because that was a core part of their go-to-work model.

The thing that matters more than anything else is, "one size fits one." That's on the company level, team level, and individual level. It's important to optimize for those different groupings of people and for the different sizes that they are, and then to start with a shared reality and iterate upon your experience with that.

You see people like Sacha Connor, who works in the global enterprise space, concentrating on developing team level agreements, like: how are we going to work? Where do we work? When do we work? How do I get a hold of somebody? You have to be explicit about those implicit things that used to just come along for the ride by being in the same office.

We can't just assume that everybody knows how we're going to do that anymore. It doesn't work like that. It never did work like that. Everybody was still kind of wondering, when and where do I work? Just because we had to come to the office all the time, there were a lot of things that were unsaid and just assumed. We were mostly right for the most part, but then there were those times where we were wrong about those assumptions and by golly, there was some friction and some tension that now is front and center. If we don't say it out loud or write it down, it won't be understood.

Have you seen remote teams do mentorship well? If so, what are their secrets to success?

I think the key ingredient is actually caring about delivering on that outcome. If you actually care about mentorship, then you will develop a program that makes that happen. If you don't care about that, then it won't happen, even if it's in the office. That was the experience of young people in an office–they could tap on somebody's shoulder and say, "hey, can I watch you work today?"

I don't have a lot of experience working in a corporate environment or company environment in office. I pivoted from a previous career in school teaching, which is as colocated as it gets. I had a lot of shoulder to shoulder time with students, because that's what we needed to do.

So how do you do that in a distributed environment? Well, you get into a one-on-one. Getting into the same room and having a conversation with someone isn't exclusive to working together in person.

Elon Musk has talked about how its unfair that if some people have to go into the office, then the rest of us shouldn't be able to work remotely. If he were here right now, what would you tell him about the idea that remote is actually good for diversity?

I think the response of warehouse unions and other touch-the-product type workers is interesting. They answered in solidarity with the Amazon office workers, in terms of them not having to return to the office. It's very clear that it is a capital versus labor conversation that has been going on forever and ever.

Just to timestamp this conversation, we celebrated Juneteenth on Monday, and things like Labor Day, the 40 hour work week, and the weekend, are the outgrowth of the labor movement in the United States (and other places). I think it's really important for us to honor the fact that these improvements to how we show up and do our work are not things that are going to be driven by capital.

One of the common analogies we make to this time and space involves something Henry Ford said: "if I had asked my customers what they wanted, they would have said a faster horse."

Well, guess what Henry Ford did as soon as he started figuring out assembly lines–he said something along the lines of, "we need to give workers an opportunity to have some leisure so that they can drive their car, and we need to pay them enough for them to be able to purchase the car."

Suddenly, there was an entire new world, a new economy, that was generated out of this new way of doing business. Well, I don't know if you've noticed, but things are a little different here in 2023 relative to what it was like in 2019. Praise God that things are different! People are going to work, showing up, and living lives that are completely different because of this new distributed, flexible model of working and doing business.

What do you think will happen with work one year from now? What about in five or ten years?

I think it's going to be interesting to see how many people stop accepting employment contracts and agreements that do not place responsibility and authority in the individual. There's so much more opportunity for someone to be successful as a freelancer or as one-person company. You already see this inside of the bootstrapped indie hacker community. I don't think that that's going to take over the market, but that's on offer to anyone now. It's going to shift how work gets done–what's already being done by teams is going to be done by individuals. LLMs are helping me do things today much faster than I would have done them yesterday. These "robot teammates" are going to help us get work done even faster.

What's going to be really interesting to see is when we reallocate the time back from commuting and from optimizing our work using automation or AI. I'm not a big a fan of calling it AI–it's a large language model. These LLMs are going to help us do things that we couldn't do before, and they'll help us do them faster and better. Low level tasks will get sorted automatically or with a quick prompt, and I think these sorts of experiences will be more available to more people.

Almanac's team won't have to grow as fast, so funding models are going to change. There are all kinds of ways that LLMs will change and improve how people work, and people are going to live their lives accordingly. And it's not going to be dictated by whomever is saying we should go back to the office. We don't have to do that anymore because people will be interested in employing us on a fractional basis–even as an individual contributor.

What do you think is the biggest unsolved challenge with remote work?

I think it's helping individuals, who have vested interests outside of what remote has been saying all along, to recognize that the work being done now is as good or better than it was previously. There is inertia that has not yet been overcome. People are going to retire or pass away, or leave the workforce at the leadership level, or they're going to adopt this new way of working. And I think that "or adopt this new way of working" is not yet solved.

How do we get people to recognize and observe that remote is better? In fact, it's less expensive and more productive. For those who have seen the light, it's a no brainer. It's obvious and very clear. For the other folks, they seem to be retrenching and digging in.

So, how do we hold open the space for them to stop doing that and to try a new way of working? I think that we need to embrace less friction filled ideas and ways of expressing them. Make it distributed and flexible, not hybrid and remote. I'm not attached to any particular way to say it, because what I'm attached to is the outcome. It's where people get to live their lives with an identity stack that's optimized for them and not for corporate HR.

What's your top tip for remote managers?

The number one thing is to center the understanding of the listener of your communication. What you intend to communicate does not matter because what they actually received–as your communication–is the thing that matters. You have to check in with that person.

Go back to my previous career. Think of the algebra teacher teaching twelve year olds algebra. It doesn't matter when they learned something, it matters that they did learn something. So, how are you checking for that understanding? How are you checking that the people who you intended to receive communication actually received it?

Send recordings–show up and be recorded. Record your tone of voice, record your cadence of speaking, put yourself on video, include bullet points, include a concise and condensed version of the transcript, and then also include the full transcript. Go omnichannel–express it all the different ways that somebody's going to be able to receive it because you can't guarantee which way they're going to figure it out the quickest. Give it to them in all the different ways.

Next Week on The Big Bet: Guillermo Rauch, Founder and CEO of Vercel

Guillermo Rauch is the Founder and CEO of Vercel, the multi-billion dollar company behind the Next.js web development framework. Previously, Guillermo was the Co-Founder and CTO of Cloudup and LearnBoost, two companies that were acquired by Automattic in 2013. Guillermo is also the creator behind several popular Node.JS open source libraries like: socket.io, mongoose, and slackin. My full conversation with Guillermo is coming to your inbox next Thursday.