Creating a Winning Culture In a Remote Environment

Since the COVID pandemic, many workforces have become fully remote or hybrid. This means that more and more people leaders have had to adapt to not seeing people face-to-face yet still finding ways to keep the entire team motivated. This not only creates concerns about managing productivity of a team, but it also creates challenges around morale and engagement.

I’ve spent the last five years or so working remotely. To be sure, it has its challenges, and I absolutely have felt more invigorated at the companies I have worked for during this time period when I have gone to see my coworkers face-to-face. This includes visits to company headquarters and it also includes trips to offsite festivities, client visits, or conferences and tradeshows.

As a sales leader, I am always thinking about ways to build a winning culture in a remote environment. I certainly feed off the energy of engaging with my coworkers. When COVID first began, I started leading virtual workouts for my team every morning at 730am. We adoringly called the workouts “KirchFit” as a knockoff to CrossFit. KirchFit eventually grew to include friends and friends of friends. At its peak, there were between 50-60 active subscribers during the pandemic, and it was not uncommon for half of them to show up to a Zoom workout in the morning. Eventually, this led to other activities, like a weekly meditation session to start the week, or lunch meetups.

As time has passed, I’ve had to think about ways to build culture sustainably in a remote working environment. Part of that comes from the interview process. I always ask people what is their “why” in the very first interview. I want to know whether or not they actually have a core motivation and something they are working towards. If they do not, I rarely advance them to future conversations. Or if they lie to me and tell me something they think I want to hear (typically something related to my employer’s mission), then I at least begin to sense they might be dishonest. Long story short, this question tells me a lot about whether or not someone is additive to the team culture. 

I also think it is important to be realistic during the interview process. What I mean by realistic is not simply being measured about the role and not over-selling the opportunity. What I also mean is that I try to be as authentic as possible and present an honest version of myself to the people I meet with. It’s really no different than dating. If you try to be someone that you are not, eventually it will catch up to you. So I do not try to be overly formal. It’s important to determine whether or not you will get along with people, and the best way to do that is to be yourself.

In my early conversations with team members, I believe that vulnerability is very important. Simply put, people do not relate to other people who are perfect. And the reason for that is because humans are imperfect. We relate to people who are flawed just like us. When you reveal yourself as a flawed individual to your team members, they actually grow to respect you for having the courage to not need constant praise and attention. Most people respect others who are growth-oriented and self-aware. Therefore, vulnerability is an attractive trait.

I also think vulnerability is a great way for a team to raise its stakes. At our most recent onsite, I asked everyone to discuss their “why.” In the spirit of vulnerability, I went first and talked about how much my daughter and my family mean to me. We went around the horn and everyone told very personal and touching stories. This brought the team closer together. It also made everyone feel a greater sense of responsibility towards one another.

On top of that, vulnerability engenders the type of trust that fosters fun and creative relationships. When people start to feel comfortable together, they appreciate the high stakes of what they are working on and yet they also have a shared sense of perspective. What I mean by that is everyone knows there is more to life than work. This allows people to loosen up and have some fun with each other. One thing I love about the current team that I manage is the non-stop witty and sarcastic banter we have with each other in team meetings and on Slack.

Now, you might be thinking to yourself “Well, that doesn’t sound like work.” I think in a winning culture you can balance the right amount of levity with the gravity of getting things done. I have learned to publicly praise team members and call out their achievements while also calling out the areas we need to work on as a team and why it matters to our shared success. Privately, I can coach and critique as needed, but I will never throw anyone under the bus publicly. One of my favorite mantras is to “Seek to understand.” You should almost always do this privately to get to a source of truth with people. 

My high school wrestling coach Mr. Ward was not a very serious person and yet he still commanded the respect of his team. He did not tell people to work hard but they worked hard anyway. That is because when the team respects its leader, they want to do well by their leader. When you have a winning culture, the team aligns around a shared vision and trusts in the process. They do not need to be told what to do, they lead from the front instead.

Great teams tend to have different types of skill players who excel in different areas. It’s very important to make everyone feel special for their specific area of expertise. It’s also important for that success to rub off on others. When you find someone who excels in a specific skill set, let them lead others on winning in that arena. Mr. Ward had a phrase I love: “Lead, follow, or get out of the way.” Sometimes as a leader, I need to simply get out of the way. There are members of my team who are so good at certain things that it’s best that I let them show everyone else how to succeed in that specific area. 

For me, there are six pillars that make for a winning culture: accountability, resilience (staying centered), seeking truth, teamwork, growth mindset, and authenticity. 

Authenticity is presenting an honest version of yourself. Everything starts here. We can’t work together unless we are working with the honest representations of our peers.

Growth mindset is critical. We must always be working to get better. Our weekly meetings need to focus not only on why we win, but why we lose.

Teamwork is an obvious one. If anyone is not bought into playing their role on the team, they need to get cut just as if they were on an NFL roster. It’s no different. 

Seeking truth is also important. It is easy – especially in a remote environment – to make assumptions about what is going on. Whether it is with our colleagues or our clients, we need to get to the core motivations of others and give the benefit of the doubt otherwise.

Resilience and remaining centered are critical in the world of startups. I compare it to riding a rollercoaster…you have good times and bad times. Through it all, you need to have perspective and remember why you signed up. If it were easy, everyone would do it.

Lastly, accountability. Without it, none of this works. Why? Because unless people hold themselves accountable to these values, it all unravels. Accountability is the key ingredient to holding it all together.

There are surely many values that are important for building a great culture. These are the ones I preach, and I’m looking forward to seeing how they may evolve with time.