Remote Work Interviews

Conversations with leaders and innovators about how industries and organizations think about the future of remote work.
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Shane Metcalf: Co-Founder and Chief Culture Officer of 15Five
February 4, 2019
Interview by Sophia Bernazzani
Photography by Shane Metcalf
Shane Metcalf is the co-founder and Chief Culture Officer of 15Five, an employee management and performance software company.

Shane Metcalf is co-founder and Chief Culture Officer of 15Five, an employee management software to help companies bring out the best in their people. He believes in the power of freedom, flexibility, and creativity to transform companies and their cultures. In this interview, he shares with us his thoughts on how to get hybrid distributed teams right, and where he believes the future of remote work is going.

Owl Labs (OL): Tell me a little bit about your product, 15Five.

Shane Metcalf (SM): We launched our employee performance management software, 15Five, in 2012, and the product has evolved a lot since then. One of the biggest shifts is that we're now leading with a philosophy behind the product, which is something we call "best self management." It's the idea that companies should stop focusing on simply the external results of employee performance and the results of performance, but actually start to help people shift towards being their best selves at work in order to unlock high-performance, creativity, loyalty, and all of the other things that we actually want as business leaders from our team.

It's a shift in thinking about how you invest in and cultivate the humans in your company. We went from a product that was primarily a weekly check-in tool, which is still the heartbeat of the whole platform, but now we also have tools for objectives and key results and goal setting. We have one-on-one agendas. We have personal development objectives, a reinvention of the annual performance review into what we call "a best self review" on a quarterly or biannual basis. It's actually designed to help cultivate your strengths and reflect on what impact you want to have on the company. Using it, employees get peer feedback around strengths and weaknesses, 360 feedback for and from their managers, and more. It's an integrated platform designed to improve communication, develop strengths, and increase productivity, clarity, accountability, and effectiveness at work.

OL: When you first started and you were thinking through the idea for 15Five, what was the mission?

SM: We wanted to create something that would give business owners and managers superpowers. We wanted our product to create transparency in what people were working on and what they were struggling with to take away a traditionally very opaque employee-manager relationship and create greater transparency. We believe transparency is one of these things that improves all facets of relationships, teams, and businesses. Everything that transparency touches, it improves. It surfaces stuck issues, it surfaces problems, and it allows us to actually recognize the wins and the good things that are happening.

OL: To what degree have you felt that the company has been successful in achieving that aim so far?

SM: Very successful. And with where we're bringing the product next, it's going to do that even more effectively. For example, one of our customers, the Chief People Officer of Credit Karma, uses 15Five to essentially create X-ray vision. It gives her X-ray vision into who are the good managers, and who are the crappy managers, at her company. 15Five reinforces the basic principles of great management, which include inquiry-driven coaching, asking questions, and helping employees solve problems and develop the skills to solve those problems on their own the next time. As we know, highly-engaged managers are infinitely more effective at helping their employees succeed, and 15Five really gives leaders that X-ray vision into where active, engaged management is and isn't happening.

We believe transparency is one of these things that improves all facets of relationships, teams, and businesses. Everything that transparency touches, it improves. It surfaces stuck issues, it surfaces problems, and it allows us to actually recognize the wins and the good things that are happening. Click to Tweet.

OL: What's the structure of the 15Five team? Do you work remote-only, remote friendly, or in-office?

SM: We're a hybrid team. We have three headquarters in San Francisco, CA, in Raleigh, NC, and in New York, NY. We also have employees working remotely in six countries in Europe and five other states in the U.S. We're a team of about 75 people, and about half of those are in offices and half are distributed.

OL: What works about the company's current remote work structure, and what's challenging?

SM: I think people tend to think that remote teams are culturally weak, and that it's a huge risk to be a distributed company because it's going to make company culture hard to maintain outside of the office walls. We decided to take what is commonly perceived as a weakness and turn it into a strength. We did that by saying, "Okay, we're distributed, so we need to be hyper-focused on the culture in order to create a cohesive culture that everybody feels they're a part of and connected with, even though they haven't met their teammates and only see them once or twice a year."

Being distributed created a fierce dedication to figuring out how to do culture well. One of our guiding principles is that a distributed or hybrid team culture is hard, but it's just an excuse to say you can't create a strong, powerful culture if you're distributed, so you shouldn't do it.

We try to find ways that teams in offices build a culture of rapport and trust, and figure out how to build similar methods for our hybrid teams.

One example is watercooler talk, where in-office employees have the opportunity to connect on a more human level, unrelated to our roles and to work. What we've done is create consistent and repeatable opportunities to connect on a human level, remotely. And that is I think the most important thing for distributed teams is to create opportunities for people to connect as humans, not as employees.

At 15Five, we have three weekly stand-ups for the whole company. We call them "boosts" because we want them to boost the energy of the team. On Mondays and Wednesdays, we have a process where we go over all of the numbers  we're looking at the transparency and how we're tracking on all of our objectives. But before we do that, on Monday mornings, we start the week off right with a gratitude meditation. One of us will lead a reflection on a particular obscure topic to explore our gratitude for. Then, people in the office will find someone else to talk to, and remote folks will write in Slack in the gratitude channel, to discuss gratitude further. Every week, we host a mini-workshop to explore gratitude and catch up with our teammates on a more human level. The first five minutes of our Monday stand-ups involve human connection over an emotional, inner-state experience, followed by 25 minutes of business operations.

On Fridays, we host Question Fridays, which is the crown jewel of how we've built a highly cohesive, empathetic, distributed culture. Every Friday, the company gets on a boost, and we ask a non-business related question. We rotate who's the question master every month, and they're responsible for coming up with a question that they've encountered during their own journey of self-discovery. They ask the question, and everybody answers.

OL: What's a question that you've loved from one of those meetings?

SM: There have been varying degrees of vulnerable questions and more playful, superficial questions asked. A question asked last week that I loved was, "What's the last sh*tty thing that happened to you, and how did you deal with it?" Question Fridays is so beautiful because people get vulnerable. They lean in, they actually share the hard things that are happening to them in life, and it creates rich, open listening. You get to hear the different aspects of the people you work with every day. I've been working with people here for almost 7 years, and on Fridays, I always learn something new about them.

And it's purely human. There's no business value to it  except that there is, because it helps our business' humans. All of these are very deliberate exercises that create tremendous business value, but that's secondary, honestly. The primary value is that you create opportunities for people to share their story about who they are as individuals, and not just as professionals. And what happens is that really connect with each other. "Wow, that's so cool. I never knew that about you." Or, "I can totally relate," or, "Wow, their experience is completely different from my own." The full spectrum of human emotions can include humor and sadness and humility, and we try to bring those feelings out among our team so they can bring their whole selves to work, too  just like our customers.

"I think people tend to think that remote teams are culturally weak, and that it's a huge risk to be a distributed company because it's going to make company culture hard to maintain outside of the office walls. We decided to take what is commonly perceived as a weakness and turn it into a strength. We did that by saying, 'Okay, we're distributed, so we need to be hyper-focused on the culture in order to create a cohesive culture that everybody feels they're a part of and connected with, even though they haven't met their teammates and only see them once or twice a year.'"

OL: Have you gleaned any insights into the differences between remote and in-office employees — both positive and challenging — within your own company that have highlighted some of the processes you've put in place?

SM: One of the biggest rewards of working in an office is the social connection and the in-person camaraderie. Humans are social creatures, so if there's a healthy office environment, you can thrive and be nourished by a sense of community at work. If you're cultivating emotional bonds with people and cultivating high trust and vulnerability within your team, people are going to feel nourished by coming into work and spending time with their team every day.

If you're a distributed team, the benefits are freedom and flexibility, and one of our values as a company is to embrace freedom and flexibility. And so that you get to actually have a choice of where you live and work and still feel connected to a larger purpose and to a larger mission that can really provide more than just employment, more than a paycheck but actually fulfill our human need for purpose, while not compromising on family or work commute or location.

One thing I love about the distributed 15Five team members is how different and uniquely awesome all of the locations where they work are. It broadens my circle of care and concern among the places that are on my radar. Before we opened an office in North Carolina, Raleigh wasn't on my radar at all. We have a team in San Diego and so now I feel like San Diego's a part of the 15Five family. We have people working remotely throughout Poland, Ukraine, Portugal, and Spain, so there's this growing sense of a global community. As individuals, I think that helps us have a broader view of life. For distributed folks, one of the biggest benefits for them is not having to choose between life and work.

OL: What are the feelings and needs that have to be managed on hybrid or distributed teams?

SM: One of the first things you need to factor into the hybrid team culture equation is Maslow's hierarchy of needs. Those needs include physiology and safety, and then the third need is a sense of belonging. One of the great dangers of remote work is that people might not feel involved in or attached to the company, and there are some simple solutions to that risk. First, you need to create opportunities for human connection online. But then, you need to create opportunities for people to interface in-person. In-person connection is a huge part of a remote employee feeling like they belong to the greater team.

We can't always do this, but once a year, we bring everybody together from around the world, and that experience gives us enough juice to keep running for the next year working apart from each other. About two years ago, I think our VP of Product was considering leaving the company because she may have wanted to work for a company in-person. Then, she came to one of the in-person retreats, she connected with everybody, and it completely changed her perspective. Now she's in it for the long haul. It's important to balance the freedom and flexibility of letting team members work remotely with some degree of in-person connection.

OL: For other teams besides 15Five — whether it's 15Five partners, clients, or otherwise — what do you think are some of the biggest missteps that companies make when it comes to distributed or partially distributed teams?

SM: Keeping things overly formal and too serious. I think that some of the best remote or remote-friendly companies bring a lot of personality to the virtual channels. They make custom emojis for every employee on Slack, and they're constantly having a lively and creative flow of communication — work-related or not. There can be a tendency with distributed teams to think about stripping down the business to its essentials, and that can make the team lose a human element to it.

That perspective makes people focus purely on being productive. Work talk is the only thing that can kind of happen in virtual spaces, which means no playfulness, jokes, or silly memes and questions that would otherwise spark at the virtual watercooler. The biggest mistake I think remote team leaders can make is being overly serious with virtual communication.

The 15Five Team Retreat

OL: Virtual communication tools, like Slack, let remote coworkers use the space to have honest conversations with one another in a form that feels personal. It's easy when you're in a room disagreeing with somebody to feel uncomfortable or emotional, versus doing it over Slack, where it feels different.

SM: Absolutely. And that's where asynchronous check-ins within 15Five are so critical and so much of why remote teams love using us. It creates a psychologically safe space to bring up issues that are a little more awkward to bring up. It's easier than when you're in person or on a video call, which can feel impersonal. Remote teams need a consistent series of prompts to get people to surface the issues they're struggling with and not expressing to their manager.

OL: Is there a particular part of the product that you think is crucial, like maybe more so than others for companies that are distributed or partially remote?

SM: The weekly asynchronous check-in prompt is so important for virtual teams. I manage folks who are remote, and when I sit down and I review their 15Five on a Friday, one of the first questions asked is "How are you feeling?" That's something that seems like a simple question, but it's actually hard to gather when I'm having regular meetings with my team. From the prompt, I can get an instant pulse-check or where my team is at, and if they're having a tough week.

Answers to these prompts help managers answer questions they have about where their team is getting stuck, and what they need help with. The asynchronous check-ins also enable me to have a more meaningful one-on-one with my team. As a manager, you have to put in the effort to make sure you're connecting on an emotional, human level, where your employees really feel that you genuinely care about them. You have to do that regardless of whether they're distributed or not, but you have to put in more effort if they are distributed.

OL: Is there a company or leader that you admire that leads a remote-only or remote-friendly team?

SM: Buffer is a real inspiration to me. They have a fully distributed team and they're a good example of a company that has brought a ton of personality into their remote work.

OL: Why does that matter?

SM: Because then your team feels like they're a part of something. They're part of the tribe, and that's bigger than just having a job. You have colleagues that you're connected to, laughing with, and able to be vulnerable with. A brand with a personality actually connects to the human life, not just the business mind.

OL: What advice would you give to a leader in a remote position and it was their first time leading a team?

SM: A lot of companies will hold a virtual team meeting with one camera in a conference room that shows the whole room, but the remote participants can't see facial gestures or the microexpressions on a person's face in order to get closer to some semblance of in-person communication. Even if you're hybrid, leaders should treat meetings as remote-first. If the whole team is in a meeting and there are three people in the office and two people online, everyone in the office should log into the meeting on their own individual computers so remote participants can see each others' faces.

My other piece of advice is to create ongoing space for employees to be able to express their humanity. We need to elevate humanity inside of companies. We need to say, "This is valuable enough." At 15Five, we spend half an hour every week for 75 people to connect on a level that's completely unproductive. It doesn't have a direct correlation to business value, which makes it expensive. Those thirty minutes a week probably cost us tens of thousands of dollars. But it's one of the most valuable things that we do.

We need to elevate humanity inside of companies. We need to say, "This is valuable enough." At 15Five, we spend half an hour every week for 75 people to connect on a level that's completely unproductive. It doesn't have a direct correlation to business value, which makes it expensive. Those thirty minutes a week probably cost us tens of thousands of dollars. But it's one of the most valuable things that we do. Click to Tweet.

OL: When companies, leaders, and entrepreneurs are thinking about the bottom line cost of integrating remote-friendly practices or remote-only practices, do you have any insight for them?

SM: The amount of money that we save having remote workers is huge. By having a distributed workforce, offices are less expensive, especially in San Francisco. An office for 70 or 80 people in San Francisco versus an office for 30 people is a huge difference. We aren't paying for the remote workers' homes because they get to make that choice. We might help by paying for coworking spaces or home office supplies, but the savings on rent are a huge benefit to the bottom line.

There's also something to be said for giving people flexibility: We've only had three employees voluntarily leave the team in about seven years. Like I mentioned, there have been several people who would've left the team if they couldn't have moved to the city that they wanted to live in or go traveling for a little while and work remotely. Allowing that flexibility has increased our employee retention rate and lifetime value. To replace a high-performing employee, it can 1-4X their annual salary is the estimate.

OL: It must be expensive to bring all of your remote employees together for retreats.

SM: We pay more money for travel than other companies might, and our annual retreat is expensive. But to us, it's worth it.

By opening up your team's remote work policies, you get access to all of these incredible locations in the world, from which you get to hire the best talent. Another consideration is salary costs. If we had all of our engineers and designers in San Francisco, we'd be paying astronomically higher salaries because salary is based on local cost of living figures. We save a lot of money when it comes to salaries and rent.

Another benefit we gain from being distributed is greater team diversity. North Carolina has very different cultural values than northern California, and from Poland. Having a distributed team doesn't necessarily increase racial or ethnic diversity, but having geographical diversity helps us design a product that works for people using it around the world. We need that diversity of perspectives and I think having remote team members from around the world helps us do that.

OL: Sometimes when you're in a privileged bubble with an office in one place, you can run the risk of no longer solving problems that are relevant to the majority of the country, or even, world.

SM: I've noticed that myself. The problems or ideas that spring out of other places and other people in different cities always feel a little bit different than some of the ideas that you have over a dinner conversation in your city, with people similar to you, because the needs are different. This benefits a company as well, especially if people are building a tool that is intended to work for lots of different industries, businesses, and teams around the world.

Remote work is this incredible invitation to really get good at building inclusive cultures where there's a wide variety of types of people, and to build a culture where everyone feels included and everyone is experiencing ongoing growth and development on a regular basis. That's the challenge, and it's not an easy one. But the business isn't easy.

Building a company is one of the hardest things you can take on doing. It's a jigsaw puzzle, and you have to get all the pieces right. If you can get enough of the pieces right as a leader, then magic happens, and other people will buy into the vision with you so you can create a deeply fulfilling experience for every person that works for you.

OL: What are the biggest changes you coming to the future of remote work within the next 5-10 years?

SM: I think we're going to get better at human connection. Remote work has been this thing that's almost been tolerated by some companies, and I think it's going to become more and more acceptable and common. It's going to continue to be embraced by the world, especially as the enablement technology gets better. The future of remote work is really about developing technology that can facilitate emotional intelligence more effectively.

That can facilitate some of the subtler cues that we can pick up on in-person that are much harder to perceive virtually. Virtual reality is probably going to be something that allows an unprecedented level of human connection across distributed teams, which is kind of ironic. But the purely virtual technology can enhance human connection and the subtleties that are involved in conveying feelings and hurt feelings and excitement and appreciation.

OL: How do you think that changing focus, acceptance, and integration of remote work into work changes the way people feel about work and do work?

SM: As remote work becomes more acceptable, and as technology improves more rapidly, I think work will start to liberate human creativity. Building cultures that aren't rooted in fear-based paradigms of management will be a big shift, and company leaders will be focused on building cultures based on freedom.

When you move your center of gravity from a fear-based life to a freedom-based life, so many cool things happen. Creativity increases, satisfaction increases, and your relationships get better. And as all of these positive things become more integrated and more synergistic, that's when the upward spiral of benefits gains momentum versus a downward spiral of negativity at work that spreads into the rest of your life.

I think remote work is a part of that, and I don't think it's the only part of it. There needs to be a wider strategy to learn how to get people to transcend the compromises they have made in their life in order to survive in a capitalistic society and actually start to discover what their intrinsic motivations are. What are their true feelings of purpose and passion, and how can they align their roles with those aspects of their life? That's where we get free, happy, competent and ultimately, effectively humans that can do great things.

A little more trust which is a little less fear which is a little more freedom which is more creativity which is more options which is more of an ability to envision positive futures will help us actually create those positive futures.

There needs to be a wider strategy to learn how to get people to transcend the compromises they have made in their life in order to survive in a capitalistic society and actually start to discover what their intrinsic motivations are. What are their true feelings of purpose and passion, and how can they align their roles with those aspects of their life? That's where we get free, happy, competent and ultimately, effectively humans that can do great things.

Key Takeaways

1. Asynchronous communication methods help remote managers and teams more effectively communicate challenges and feedback that may otherwise be tough to deliver in-person or via video conference.

15Five's asynchronous employee check-in tools allow managers of teams, whether remote or in-person, to get another perspective on how their team is doing, and how they can better support them. Shane encourages all managers to use asynchronous tools, like 15Five or Slack, but especially managers of remote employees, who might not be as willing to talk about challenges or obstacles via video conference.

2. If remote employee travel and lodging seem expensive, it actually might save companies money in terms of office rent and employee retention and lifetime value.

Shane explains how, in 15Five's case, the cost of travel and lodging for all of its remote employees to attend the company retreat is nothing compared to lower office rental costs for a smaller in-office team and the money saved by reducing employee turnover.

3. Successful hybrid or remote teams should build in time for non-work-related connection with the entire team.

Shane cites 15Five's virtual catch-up meetings throughout the week that aren't dedicated to work talk as integral to building and maintaining a successful and positive company culture.

To learn more, read our state of remote work report.

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