How a Military Background Blends with Startup Leadership

by | Sep 10, 2020

Chances are the first word that comes to mind when you think of the US military isn’t “entrepreneurial.” But reality is that this isn’t your parents’ military. Today’s veterans came of age after 9/11 and are just as likely to have spent their service negotiating with a local magistrate or installing drip irrigation in a village as serving in combat. To succeed in today’s military, leaders must be determined, flexible, and compassionate. They must be able to lead diverse groups of women and men, while also being able to adapt to unforeseen circumstances in unfamiliar environments – all skills that serve leaders well in entrepreneurial surroundings. To say that today’s business leaders are facing unique challenges would be putting it mildly. Right now we are grappling with the worst pandemic in 100 years, the highest unemployment rate since the Great Depression, the most societal unrest since the 1960s, and a cavalcade of natural disasters brought on by climate change. While there is no playbook for this, I do think that some of the lessons from modern, small unit military leadership can be helpful, particularly for resource-constrained startups.

My current startup, Resilience Insurance, claims several veterans among its executives and is committed to hiring veterans throughout the company . Here are some of ways our military backgrounds have played a helping hand in these unprecedented times:

Grit and determination.

Startups are incredibly hard and founders fail way more often than they succeed. To be successful, they need to have determination in the face of seemingly insurmountable obstacles. Fortunately two of the first things you learn in the military are determination and endurance. If you’re assigned a mission, you complete that mission; no matter how hard it seems, how uncomfortable you might be, or even how long it might take. You also learn how to deal with failure and proceed anyway. Once you learn that you can not only endure challenges but also succeed, it frees you to focus on your goals and on your people.

Focus on your team.

When a young officer is commissioned in the military (often right out of college), that person immediately outranks 80% of the service. Additionally, a military leader is responsible for almost all aspects of their troops’ lives, not just their work product. You have to ensure they have housing, get continuing education, take time off when needed, stay healthy, and often resolve any domestic issues to name a few. You quickly learn that the only way to survive this “management by fire” is to listen to and enable your people. It’s both the hardest and simplest job in the world because your team’s success is your success. At Resilience, we have taken efforts to continuously listen and enable our team. First, like many startups, every employee is also a shareholder so everyone rises and falls together. We also have clear work-from-home policies and have spent company resources allowing employees to make their home-office environment more comfortable. We also established constant lines of communication, from individual chats (often using the Donut Slack app), to bi-weekly all-hands. We also established weekly educational sessions where employees could teach the rest of the company more about their jobs. This culminated in a virtual “hackathon” where diverse teams were encouraged to collaborate on solving new problems.

Deal with reality.

It used to be that businesses, especially tech businesses, could keep their heads down and focus on product. That’s not true anymore. Whether it’s concern about social media disinformation, co-workers who face deportation, the need for social justice, affordable housing, childcare, or people impacted by floods and fires caused by climate change, we can’t ignore problems facing our communities. While a single small company cannot change these massive issues, we can try to make things just a little better. That’s why Resilience drafted a progressive and affirmative immigration policy, provided offers of housing and support to potential fire evacuees, donated to social justice causes, and are creating a corporate social responsibility policy. We will also be allowing employees time off to engage in civic participation this fall, whether that’s working a polling station or building tech to stem the flow of disinformation. The old thinking was that these types of activities detract from the bottom line. Not so. At Resilience, we firmly believe that you can be a good corporate citizen and a financial success and aim to prove it.

Keep your eye on the objective.

Everyday seems to bring a new challenge. Don’t panic. Managers will have to make hard choices but don’t do so irresponsibly or from a position of fear.  Help people stay focused on their mission and provide calm, steady leadership. Most companies will have to tighten their belts but keep resourcing people and R&D to the extent possible. When the economy comes back, you will need both to outpace your competitors and delight your customers.

In the past, military leaders were seen as a different breed than corporate leaders but the lessons learned in the military can serve you well in a number of arenas if put to good use. At Resilience, we’re thankful to blend together those with a military background, our team members from tech and startups, as well as team members with other unique skills. A team made up of diverse inputs and backgrounds brings unique and diverse problems solving capabilities and, we believe, helps move the entire industry forward. Sign up for updates from the Resilience team or follow us on LinkedIn for regular information, educational resources, and more.