Leading a team requires putting aside the fear of failure and rising to new challenges. When tasked with both guiding and encouraging a group of direct reports, often of varying skill levels, managers become role models for resilience. In uncertain times — like pandemics and transitions to virtual work, or strategizing for new rounds of funding — leaders are the organizing and supportive force behind a team’s success.
That success comes from a series of checkpoints; depending on outcomes, any one of them can be a boost or a pitfall for morale. Pitfalls are some of the most challenging, but necessary, areas for leaders to reinforce their team’s resilience and the value of trial and error. Andrew Cunningham, vice president of product at Mothership, recognizes that failure is a core requirement for growth — and like most educational opportunities, learning is maximized with guidelines at hand.
When building new projects, Cunningham helps his team aim for the best and prepare for the worst through the scientific method, creating a hypothesis at the outset and refining it as results eventuate.
“The confidence someone gains from failing and then succeeding teaches them to feel more comfortable with failure — they understand that it’s just part of the process,” he said.
While it can be taxing for teams to face their misses, having a foundational expectation and process around improvements can empower people to see through the negative and focus on a new direction.
How do you, as a leader, model resilience for your team? What does that look like in action?
On the Mothership product management and product design teams, we know that failure is central to the process of building great products. Nobody gets it right the first time, and that’s OK. Without failure, you don’t learn and you don’t grow. But failure can be taxing.
Our team leverages the scientific method to keep everyone focused on growing from failure. Whenever we kick off a new project, we start with an observation describing a problem we notice. We create a hypothesis and test it, but most importantly, we draw conclusions, refine the hypothesis and iterate.
That last part is the most important, and I try very hard to focus on learning and iterating instead of reprimanding or micromanaging. People grow immensely from understanding what went wrong and correcting the course. The confidence someone gains from failing and then succeeding teaches them to feel more comfortable with failure — they understand that it’s just part of the process!
Trusting your team to make great decisions and do the right thing motivates them to trust each other more.”
What are some actions you take to keep your team engaged, happy and motivated to come to work every day?
I believe that people need three things to feel engaged, happy and motivated: trust, care and sincerity.
People need to feel trusted, both by their peers and by their managers. Nobody wants to start their day with people who assume the worst of them or with people who won’t empower them to solve problems. Trusting your team to make great decisions and do the right thing, in turn, motivates them to trust each other more.
Care often gets overlooked, but if you don’t care about how your team is feeling, they can’t truly be themselves at work. So, I try very hard to check in with the team, understand how they’re doing, and motivate them to do the same with their teammates.
Finally, sincerity is key to developing trust and care on the team, but it’s also vital to build respect. I try my best to not only be transparent about business goals, metrics, and strategy but also about what I’m thinking, what I’m worried about and how I feel.
When people feel connected to and trust their colleagues, it’s easier for them to weather the challenges that come their way. What are some activities or rituals your team does to strengthen bonds and create the kind of team camaraderie that supports resilience?
When I joined Mothership, the team developed a manifesto that outlined who we wanted to be, both individually and as a team. Some highlights included wanting to be customer-focused, leveraging the scientific method, and maintaining a growth mindset. This decision set a solid foundation for the team’s development.
We’re fully remote and have found that seeing each other in person significantly helps develop trust, care and sincerity. Humans evolved to create in-person connections, and sometimes, you just can’t find a substitute. So, we do quarterly planning in person as a team. We also try to get product pods together for launches to celebrate wins and build morale.
We also do quarterly retrospectives, which give everybody on the team a chance to talk about mistakes and losses, and to crystalize what they learned and how it’s impacted their work. These normalize failure in a healthy way and show team members that everybody experiences it.
How do you, as a leader, model resilience for your team? And what does that look like in action?
DoubleDown has evolved significantly over the last few years, most recently after the acquisition by DoubleU Games, a Korean-based social casino publisher. Resilience through major cultural moments has required creative and diverse practices. It goes without saying that Korean and American culture aren’t incredibly similar, but what I’ve found particularly exciting is that our skills are rather complimentary.
Helping our teams recognize that we share common interests and driving them toward that recognition has taken many forms. We share our social and traditional values, allowing the teams to understand a little bit more about our fellow team members. We’ve played trivia and shared culinary experiences. We’ve also instilled a sense of patience and compassion among the team. Empathy is the strongest weapon in our leadership’s arsenal to create and maintain a thriving and resilient team.
Everyone at DoubleDown is important and part of the process in a fun and inclusive environment.”
What are some actions you take to keep your team engaged, happy and motivated to come to work every day?
Our first and most important task throughout the last 20 months has been to ensure that our team feels safe and supported during this challenging time. Working closely with our people and culture team became an incredibly important part of maintaining the integrity of our core belief that as a business, we’re only as strong as the team we have. We quickly opened dialog with the larger organization. We wanted to hear from everyone; what do they fear, what are their needs and how can we help. In order to keep our team engaged in this new environment, we’ve expanded benefits to help with mental health and crisis management. We’ve created virtual social events that cater to a variety of different interests. This is of course an ongoing process and we keep learning more about the needs of our team and the best way to protect our number one asset.
What are some activities or rituals your team does to strengthen bonds and create the kind of team camaraderie that supports resilience?
Because so much has changed both in the world at large and within our organization, we’ve had to get very creative to help the team feel connected. We recently expanded development to include work with our Korean counterparts. Without an initial face-to-face connection, we had to think of ways to build trust and develop working habits that benefit both teams.
First, we asked the teams in both locations to share something special about themselves. Then we utilized tools like Google Jamboard to put sticky notes on each other’s work. We also found a common time and opened up a “watercooler” type of environment in Slack where people can share their weekend stories, cultural holidays, homemade recipes and the like.
Recently during a virtual all-hands meeting, we surprised everyone with a game. We asked everyone to show up with a rubber band, and had them choose a direction to shoot their rubber band. Based on those answers, we put everyone into groups. Those groups are now building games together, and eventually we’ll prototype and work on the winning team’s game idea. When someone in CS or marketing gets to be a part of the game making process, they feel a connection to their peers.
How do you, as a leader, model resilience for your team? And what does that look like in action?
We believe the best way for people to get to know and trust each other is for them to collaborate. We try not to silo any engineering team member into a given area; we encourage multiple folks to work on the same components, and share in the design and implementation work. When new features come up, we encourage engineers that have never worked in a given area to give it a try. This helps them learn from their peers and expand their knowledge base. This also benefits the company as it builds more redundant knowledge across the team.
We strive to make sure that everyone is contributing to key initiatives and feels that they are contributing to the success of the company.”
What are some actions you take to keep your team engaged, happy and motivated to come to work every day?
We always give the team a solid understanding of how their project is important to the success of the company. Also, we offer a bonus plan and an equity plan based on company metrics so all employees share in the financial successes of the company as well.
We also encourage engineers who are troubleshooting an issue to get on a call with their peers, as opposed to working it out over chat or Slack. Software engineering, QA, IT and operations members are encouraged to coordinate cross functional initiatives, as opposed to putting the entire responsibility on managers. When people feel connected to and trust their colleagues, it’s easier for them to weather the challenges that come their way.
What are some activities or rituals your team does to strengthen bonds and create the kind of team camaraderie that supports resilience?
Pre-Covid-19, we’d have a fun outing at least every quarter. Remote employees were encouraged to join Seattle-based team members for these events — bumper cars, bowling, mini-golf and the like — which were always followed by a meal together. Company initiatives such scavenger hunts gave team members a chance to socialize with members outside of engineering and form some bonds with other colleagues from across the organization.
Covid-19 has certainly made maintaining team spirit more challenging, but we have continued to focus on setting aside some time for team members to socialize virtually. As Covid-19 restrictions are slowly being lifted, hopefully we will be able to begin incorporating some in-person activities back into our social calendar. That said, we can also see that the work landscape has changed, and some level of virtual activities will need to remain in place to better support remote working.
