15Five CEO David Hassell on best-self management and how Millennials are changing workplace cultures

CEO David Hassell founded 15Five in 2011  with a desire to help people reach their full potential at work. The company, which has since grown to almost 170 employees and stretched to three cities across the country, creates a platform that allows managers to cultivate an environment where employees can grow to be their best selves, and Hassell aims to have that culture at 15Five, too. Ladders spoke with the founder and CEO to hear his thoughts on best-self management, how 15Five fits into the future of work, and the most surprising aspect of being a CEO.

What are you most excited for at 15Five right now?

“I would say the thing that I’m most excited for right now is the big movement that we’re currently putting out in the world. I think one of the things that distinguish us from the other competitors in the space is our philosophical orientation to people management. We have a very strong point of view that the concept of performance management, which is the category of software that we play in is a bit of a misnomer. We believe that performance in the organization is really a byproduct of focusing on other things…that’s the result that you get. What you choose to focus on is going to have varying degrees of success in actually creating high levels of employee engagement and performance. So we have looked at all of the social science research and we looked at a lot of psychological science and models of human performance and whatnot. What we’ve come up with is we believe that when you create an environment that supports people in being and becoming their best selves, then performance is the natural byproduct. And we call if best-self management. The message and the concept have really been resonating strongly with folks, and so that’s the thing I’m most excited about currently.”

Do you think 15Five is a part of the future of work?

“Absolutely. Work is evolving thoroughly based on what is required for companies to be successful. We’ve long left the era where people simply working harder and longer hours is a competitive advantage because so much of what has made companies successful is the level of creativity and innovation that they have to create products and services that are new and novel, that help people in new ways, and that are aesthetically pleasing to use. People, especially this younger generation, is looking to buy from and support companies that they believe have a high level of integrity and authenticity. All of those things require a different level of care from the human beings that are creating them.

So even if you just think about your work, the quality of the article you’re writing isn’t going to be dependent on how many hours you spend in front of the computer or how fast you type on the keyboard. It’s more about, are you in the right creative space for that, do you actually care what you’re writing about, do you feel supported by your employer to do a good job? So that shift in the world is what we’re really speaking to with this idea of best-self management. We’ve found that when companies genuinely and authentically have their backs and care about them as human beings, not just as cogs in some machine that they’re building, they’re more likely to show up and do their best work.”

What would you say is the biggest industry trend to watch right now?

“It’s not necessarily an industry trend, but more of a demographic trend. Certainly, technology has changed the face of how and when we work because of ubiquitous cellular and informational networks, mobile technology…people can work from wherever. I’m in Portugal right now at our company’s R&D retreat and speaking to you on my cell phone. I pay $10 a day now to access all the cell phone and internet data that I want in most countries of the world. So that’s definitely changed things. We have teams now in Portugal, Ukraine, Poland, Hungary, and we all connect over Slack and 15Five. So the technology for sure has been a big trend that’s changed workplace dynamics.

But I think there’s also a generational shift. The Millennial generation is by and large the first truly digital native generation to have grown up with network internet technology and all sorts of things that have shaped their world view. They tend to go to their computers or phones as the first steps to do anything. They’re now not only in the workplace, but I think they’re the largest generation in the workplace and have moved up to management and leadership positions. So their perspectives are starting to shift what types of products and services that companies are gravitating towards and how they work.”

How would you describe your management style?

“I lean very, very heavily on inspiration and support. I would think of three things: context, inspiration, and support. What I mean by that is, first and foremost you need to create a really powerful context for people to be working in. They have to be connected to some real larger shared purpose or mission. They have to understand, what are my values and what are the company’s core values and how do they relate to their work and choose to be a part of that?

I think that there are leadership styles that are more dominant and domineering, that are based in fear and control. I skew very far to the other end of that spectrum where I want people to be working at our company because they’re choosing it. They really want to be there, they feel inspired by what we’re doing, and then I want them to feel supported. I have a lot of empathy for people and understanding that there are different walks of life and different roles and things like that. I feel like my biggest job is to create an environment where people can do their best work. So I listen a lot. I try to understand, I try to make sure that my immediate leadership team and their teams have what they need to do their best work. First and foremost that they’re inspired by what we do and feel intrinsically motivated and energized to come to work.”

What’s the most surprising aspect of being a CEO?

“I’ve been doing this for a long time, so just the role itself I don’t feel is very surprising at this point. I would say that we’ve been on a really rapid growth trajectory the past couple years. We do this company-wide retreat every January and in 2017 we had 30 people there. Last January we had almost 70 people there. This coming January we’re going to have over 200 people there. To see so many new faces so quickly. I showed up at our R&D retreat here in Portugal yesterday and I walked into a room that was about the same size as our all-hands retreat just 8 months ago. And that’s just our R&D team. That’s been the most surprising thing to me. To see all of these new faces coming into something that we have created the foundation for many many years. To see so many people getting up to speed pretty quickly, and actually to see the culture getting even stronger as opposed to weaker with this kind of influx of people.”

Do you have any advice for someone scaling a company?

“At some point, it gets harder and harder to have personal relationships with every single person. I think its really important for the CEO to be listening and to understand what’s going on, what challenges are happening in the organization, and using tools like 15Five that will get you the information in written form that you can scan through and see like, what are the challenges that people are facing throughout the organization? To ensure that things are moving in the right direction and, I don’t think that as leaders we have the ability to control our cultures. At best we can have an influence on them. At Peter Drecker once said that culture eats strategy for breakfast, it feels like the most important thing to get right and it’s very hard to shift a negative culture and make it positive. So keeping a close eye on how things are trending is critical if you’re going to survive to have more people join the company every year. You have to have a really, really, really strong center of gravity with your culture in order to sustain that growth.

Some people ask me, ‘When should I start focusing on my culture? Should I wait until I’m 10 people? Or 50 people? Or 100 people?’ I will often say, ‘you need to do that on day one. You need to architect your culture on day one when there’s only one, two, or three people and continue to invest in it from that point.’”

What’s the most enjoyable part of being a CEO?

“I would say it’s two things. One is the people I get to work with. I really enjoy the relationships I have with my team. I work with some incredible human beings and I feel blessed to have those relationships. It feels more than just a typical professional relationship with my leadership team.

The second thing is just seeing all of the amazing ideas and things people are creating throughout the company. It’s now beyond the point where I’m involved in many if any, decisions. Things are just spontaneously being created throughout the company by our employees that I am consistently wowed by. So that’s really fun.”

How would you describe your company culture?

“One of the things that specifically stands out about our culture is the level of camaraderie and care that we have. We frequently have people share, whether it’s through high fives inside 15Five, where people can share appreciation or share something with everyone, or feedback we’ve gotten in Slack and our engagement surveys.

15Five has actually changed people’s lives in how they feel psychologically safe at work, how they self express as human beings outside of work. I think that that’s a real testament to the kind of environment that we’ve created. We put a lot of attention into creating a culture that’s not just positive, but that’s actually transformational, that actually supports people in becoming the best versions of themselves, and it’s amazing to actually see that realized.”

What advice would you give to someone interviewing at 15Five?

“The advice I would give to someone interviewing at 15Five is to be 100% yourself, not to posture, because what we’re looking for is people who are fully themselves to come and work at our company because we value that uniqueness and that diversity.”

Is there anything else you want people to know about the company?

“We just launched a podcast. It’s ‘The Best-Self Management’ podcast on iTunes. People can follow us there or on our blog. In general, people that know the company know that we’re a different type of company…that we’re authentically mission-driven, that we really care about people and see it as an entirely new possibilities for the world of work, having companies succeed and thrive because they support their employees in thriving and not at the expense of them. That’s the gist of what we see in possible and what we’ve realized here at 15Five. If you visit our Glassdoor you get a sense of just how unique that is. We have 60, almost 70, reviews and a 5-star rating of people sharing the impact that the company has had on them. So we’re out there doing our best to be a model for what’s possible. We’re just continuing to get that word out.”