The Best Business Mistakes I’ve Ever Made

Recently, I have been taking stock of my journey as an entrepreneur. I’ve realized that I had learned quite a bit the hard way. Making mistakes and learning from them, as an individual leader or as a team, is enormously beneficial. Now, I’m not advocating for making mistakes to make them, but I am suggesting that we don’t let a good mistake go to waste.

Making mistakes is part of leading. They are part of life. If we fear failure and bash those who make the occasional mistake, we stifle people’s ability to take risks and innovate and may find our competition leaving us in the dust.

In reflection on some of my most colossal blunders over the years, I came up with a list of key learnings that have helped me both professionally and personally.

#1. Bad decisions don’t get better with time. Decisiveness is critical in helping you move faster than the competition, but it also means sometimes having to make decisions without the benefit of reams of data to back them up. We all make poor decisions sometimes. The real shame is when we don’t admit the blunder and try to ride it out in hopes that things will get better. Being able to identify a misstep quickly and being decisive enough to course correct is critical to success.

#2. You’re not always the smartest person in the room. As an entrepreneur and leader of a team, I felt intense pressure to have all the answers. Looking back, I recognize my faulty assumption. I may have started the company, but I’m certainly not the only one with all the answers. We have a smart and creative team that analyzes things in very different ways than I do. This is an enormous source of strength for us as we discuss and debate business topics before making decisions. This diversity of thought helps keep me honest.

#3. Hope is not a plan. We started our business on a hope and a dream. What we quickly realized is that hope is not a plan. As our organization matured and we became more established leaders in our industry, we took tangible steps to be intentional about who we are, where we’re headed, and how we plan on getting there. With the assembly of our Board of Advisors, our market repositioning, our all-hands strategic planning processes and reviews, we developed a planning cadence that focuses our work effort throughout the year.

#4. Don’t be afraid to fail. Starting a new business was a terrifying experience. What I realized quickly, however, is that fully experiencing life is about taking risk. Now, I don’t mean a constant Vegas-style gamble, but I am an advocate for putting yourself out there in an uncomfortable situation where you very well may fail. Assess the situation and mitigate as much risk as possible to stack the deck in your favor, then execute with everything you’ve got and don’t stop until you’ve succeeded in your endeavors.

Theodore Roosevelt made a speech at the Sorbonne, in Paris, France on April 23rd, 1910. I’ve memorized and carried part of this speech with me throughout my business endeavors:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

There is no great effort without some level of error and shortcoming. And when you make a mistake, don’t get so caught up in wringing your hands that you don’t capitalize on the learning opportunity.

Smooth Is Fast, But Fast Ain’t Smooth

When I was a young Army lieutenant training at Fort Knox, Kentucky and learning how to take the fight to the enemy with a 68-ton Abrams battle tank, I had the good fortune to cross paths with a person whose simple advice sticks with me all these years later. His name was Gunnery Sergeant Mummey and he was just about the most crusty, battle-hardened Marine I had ever come across. Gunnery Sergeant Mummey spent his days and nights reveling in watching the newly minted officers who were his students flail hopelessly within the confines of their tanks, trying their best to manage a withering onslaught of tasks and priorities. He had many a good laugh watching us, I’m sure!

One day I was learning how to direct my tank crew in preparation for a field exercise at the gunnery range where we would finally get to test our skills with live ammunition. This was a big milestone for us and it was a test of our ability to direct the three other members of our crew against a series of “enemy threats”. In order to succeed on the gunnery range, each student would have to react to unknown situations and quickly issue clear orders to the crew to successfully manage the situation. Needless to say, new lieutenants are not so great at making all that happen at first go-round.

I was no exception. As I sat in my commander’s hatch trying (unsuccessfully) to get my crew to quickly respond to my orders before the presenting targets vanished, I felt a jolt to the top of my helmet. I ignored it at first, focused solely on getting my crew to do what I had so elegantly envisioned in my head for months prior to this moment. Again, I felt a jolt to the top of my helmet and this time I looked up.

Sitting above me was Gunnery Sergeant Mummey in an instructor chair that had been bolted to the top of the tank so that he could observe us in action. The heel of his boot staring me in the face he said in a surly and disapproving voice, “Lieutenant, smooth is fast, but fast ain’t smooth!” Not understanding exactly what he was getting at, I nodded in approval and went back to work at a frenetic pace. It only took one more kick to the head for Gunnery Sergeant Mummey to get my attention and reiterate himself a way only a senior sergeant can, “Lieutenant, smooth is fast, but fast ain’t smooth!”

I nodded again but this time something changed. As his advice made its way into my brain I realized that in my efforts to speed things up I was only slowing things down. Me yelling to my crew louder and more frantically didn’t actually have the positive effect I was looking for (go figure!). I took a moment to collect myself and I began issuing out orders in a clear, confident, and paced manner, which enabled my crew to understand what I was saying and execute. By slowing down and operating more smoothly, I was able to significantly increase the speed of execution of my crew.

I’ve taken that lesson with me over the years. Through combat and through my career in civilian life, the concept of slowing things down to speed things up has served me well time and again. In a culture where “speed is of the essence” and where “time is money”, I often find myself getting caught up in the fever of the moment. But a lesson learned many years ago in Kentucky comes back to me and I remember to slow things down and to challenge the assumption that we fall victim to on a seemingly daily basis, that fast is good and faster is better.

The next time you’re feeling frantic, I challenge you to take a moment to collect yourself, slow it down and smooth it out. I think that, like me, you’ll find that you will accomplish things much more quickly and effectively and you will feel much more in control and at peace with the demands of your situation.

Remember, smooth is fast but fast ain’t smooth!

The Culture Grinder

Peter Drucker, one of the most respected authorities on the topic of leadership, has been noted with coining the phrase, “culture eats strategy for lunch”. This saying permeates any discussion about organizational culture, but many leaders fail to realize the true reality that this statement has in day-to-day life.

We call it “The Grinder”. Over the years, we have worked with clients around the world who struggle to understand why they can’t seem able to actually execute their business strategy. For most, it’s not that their strategies are weak or ill-conceived; quite the opposite. Many have done thorough business analyses, engaged high-profile strategy consultants, and developed powerful strategies that detail out how the organization needs to evolve in order to achieve future success.

Unfortunately, when it comes to actually rallying the troops in order to implement the plan, oftentimes, things fall short. Sometimes they fall way short. I am reminded of the countless times I have walked into a client’s office to see binders full of gorgeous, well thought through strategies that never even made it off the bookshelf.

Even if leaders are able to effectively align around a well thought out strategy and they are able to clearly articulate it to employees at all levels, getting people to behave differently becomes the Achilles’ heel. When this happens, a sense of cynicism can develop, only making it that much more difficult to drive strategic change in the future.

But what’s at the core of this regrettable situation? If Drucker’s saying bears weight, then we might come to see that the culture that has developed over the lifespan of the organization may be reinforcing certain attitudes and behaviors that are in conflict with those that would be required to ensure successful execution of the strategy. If leaders do not realize this, or worse yet, make the conscious decision to downplay the role of culture on performance, they may find themselves being chewed up and spit out of the Culture Grinder.