Brutal Honesty: What the Military Taught Me About Startup Success

Business Success - Military

There is one key to ensuring your best chance at startup success: “Brutal Honesty.” Without that, you likely will not succeed.

Startup Success

My experience in a military career, twenty-five years of entrepreneurship and a brief foray into local elected office has shown that humans have an amazing propensity to fool themselves. This manifests itself as both outright deceit as well as simple “wishful thinking.” Regardless of its nature, the failure to understand and accept reality (life as it is, not how we want it to be) is a key indicator of impending failure.

I first learned this lesson as an Aide for a General Officer in the Army. I sat through innumerable post-operation debriefings. He was a hard-nosed Patton-like character who tolerated little incompetence and no excuses.

He was always a cheerleader for the troops. He lauded them for their accomplishments, motivating and encouraging them to strive even harder. There was always raucous cheering, reminiscent of the celebrations of a sports team after a big victory.

That was the public face – optimistic and full of energy. This is the same face that an entrepreneur must portray to the external world. Despite any problem or setback, a startup must be pushed forward, often by only the sheer will of the founder to succeed. As Winston Churchill once said, “Success is the ability to go from failure to failure with no loss of enthusiasm.”

However, my General’s tone when we were behind closed doors was another matter entirely. When he was with the leaders, the tenor can only be described as “brutally honest.” Yes, we must always acknowledge successful actions, but the key is to clearly admit our shortcomings. This was an overriding imperative in military training and operations. Failure isn’t measured in profit or loss; the cost is counted in the lives of those wounded or killed. It is “unlimited liability.” For a startup, the lives of people might not be at stake, but the survival of the company is.

Improvement only comes once the problems are identified and acknowledged. This is the first step. It is also the hardest. People are loath to admit their mistakes, particularly in an environment where “heads might roll.” Therefore, the key is to “never shoot the messenger,” even if they may have culpability. Rather, the trick is to “tease out” the cause and effect relationship.

Hold “after action reviews.” Encourage dialogue and participation. You must make it clear that at some point, everyone will be on the hot seat; no one is perfect, including the founder. Admit your own flaws. In fact, it can be helpful to start out by stating what “you” did wrong and ask your subordinates for their comments on your performance.

Once it is all on the table, it is time to identify what can be done to “fix” things. My brother was a Naval officer and his wife was an astronaut on the ill-fated Columbia space shuttle. He once told me that there were two components to an accident investigation.

  • Find and fix the technical problem. What was the failure and how do you prevent it from happening again?
  • Improve Crew Survivability. If it does happen again, how do you mitigate the effects and increase the likelihood of keeping the crew alive.

It seems that this is a pretty good template for assessing and correcting problems in a startup: prevent reoccurring failures and mitigate the effect of a problem on your operations and financial well-being. The former is generally straight forward. Sadly, it often comes down to “human error;” someone just makes a mistake. After all, human beings are, well “human.” Nothing is perfect and there is a good chance it may well happen again. You want to be prepared for it.

Mitigation is often harder to address. The problems here are not entirely technical. Often they are procedural. Milestones and check-steps can help identify and stop the spread of a problem after it occurs. Likewise, training in problem identification and trouble-shooting can be key. However, employee improvement and training are often low on the priority list in the startup process when funds are scarce.

In the end, failure is not just an option; it is a near certainty. The issue is not whether you will stumble; it is how you address and correct the problems. Actually, the story of how you have overcome setbacks can be turned to your advantage. Rather than “hiding” them, a great story of good leadership and perseverance can sometimes help investors gain confidence in your management team.

In order to be successful, you must adequately and coherently address problems as they arise. The very first step in that process is “brutal honesty,” particularly with yourself as the founder and leader of your startup company.


Dave Clark

Dave Clark taught Strategy at West Point and is a co-founder of FundingSage, which provides valuable information, tools and resources to entrepreneurs seeking to start, grow and fund a business.