Wingmen — Those Trusted to Go With You into Battle

When you lead your startup into battle, you need an inner circle of wingmen (and hopefully, wingwomen) backing you up. They are the trusted few who have earned the right to fly by your side and make an impact.

Before I jump into this topic, let me acknowledge that while the presence of wingmen has dominated my life experience, I believe that it is a role that can and should be played by any gender, so I mean to be gender inclusive when referring to wingmen (wing people sounds a bit silly to me!).

As I have often said, teams build successful startups. And as the startup grows, so the team grows. Nonetheless, in addition to building the team at large, a startup CEO must cultivate an inner circle of wingmen to grow, scale, and succeed. These are the special few, the A-players that significantly impact the startup’s success. The CEO cannot do it alone, so their ability to cultivate wingmen over time is a critical success factor.

Having wingmen and being a wingman is a great honor that incurs tremendous responsibility and requires risk, trustworthiness, hard work, and sacrifice. These are the people I rely on to get the job done. They are prepared, insightful, responsible, compassionate, disciplined, and strong. It is a role that must be earned over time through the repeated overcoming of shared trials.

Wingman is a military term grown out of the world of fighter pilots. While I am not personally an actual pilot, the fighter jet analogy seems to fit the world of a fast-moving, agile, intense high-potential startup. Screaming through the air to make an impact, a fighter squadron has a leader flanked by wingmen (I know this isn’t technically right, but in business, one often has more than one wingman). The group flies fast in tighter formation, relying on the well-honed skills of each other to charge into the action ahead while searching the horizon for signs of trouble in time to step in to prevent it.

As a startup CEO, I am always looking for potential wingmen to join me. While I value every member of my growing team at every level, only a precious few can earn the right to become a wingman. Here are some of the common characteristics of those I have been privileged to partner with at the level of a wingman:

• Most trusted inner circle:  A wingman is part of my most trusted inner circle of company leaders. They are mission-ready and trusted to go into battle because they have earned that trust, and I can count on their integrity and ability to get the job done. They are the ones (s) who are “in the know” about my most important goals, the threatening dangers, and the strategies and plans we often co-create to accomplish our evolving objectives.
  
  
• Deep and consistent communication:  With my wingmen, I try hard to keep them continuously in the loop regarding our dynamic situation(s) so that they have all the context around the mission at hand, can be fully aligned and clear on who has what role, and can, therefore, fly in tight formation with me. This also puts them in a position to be well-informed guiding hands for the rest of the team, creating critical leverage within the organization.
  
  
• Got my back: My wingmen have my back. Over time, we build a deep awareness of each other’s strengths and weaknesses so that we can rely on each other and play to each other’s strengths in each situation as it emerges. My wingmen back me up, always looking for danger, errors, and emerging problems, and with the confidence and insight to proactively intervene as needed.
  
  
• Leaders as well as followers:  Sometimes, people assume that because a wingman has your back, they are always following. And there is some truth to the follower idea because they are keeping an eye out to the sides and back of the formation and tracking the movements of the leader; however, it would be a gross misconception to think they are not also leading in their own right. In fact, I count on my wingmen to think and act as leaders as well. They bring their own ownership mentality to the mission at hand and must make critical real-time judgments and decisions to keep in formation with the rest of the leaders and achieve the objectives ahead of us. The multiplier effect depends on achieving that balance where we stay in sync while simultaneously each is acting with a degree of independence. My wingmen know the right things to do, and they will take action to do them.
  
  
• Often functionally specialized:  In a startup, there is rarely room for multiple general management executives like the CEO, whose leadership spans many or all functions. For example, until a startup grows very large, you will not typically need both a CEO and a President or COO. Therefore, in startups, wingmen are also typically functional leaders as well. In my experience, a wingman can hail from various functions. Personally, across different startups, I have had wingmen who are leading product development, commercial, and financial functions. Since I often find that I have functional leaders who are wingmen and functional leaders who are not, what differentiates a wingman from a functional leader is the depth of their alignment with and ability to co-drive the most important things as well as their ability to keep up with and help shape the fast-moving dynamics in a startup. They tend to be strategic thinkers whose skills and points of view complement my own.
  
  
• It is possible to have more than one:  As the organization grows, it is certainly possible to cultivate more than one wingman. In fact, you can get a small squadron going if you all train together and work to develop the communication cadence, network, and other skills to execute with excellence together.

I have always thought it was one of the greatest honors of my life as a startup CEO when one of my trusted inner circle declares that they are proud to be my wingman and have my back. That says that they trust my leadership and that they are inviting me to trust their strengths and integrity as well. Such a relationship is a great responsibility for both of us, bringing great multiplying power and rewards into a startup.