Subscribe to Veteran Led


Episode 41

Episode 41: What the Military Didn't Teach Me About Decision-Making


The military teaches us two ways to make decisions: quick and reactionary or deliberate and meticulously planned. In this episode of Veteran Led, John Berry shares shares invaluable lessons on quick vs. deliberate decisions, exposing the blind spots in long-term planning, a gap often overlooked in military training. He emphasizes the critical importance of considering decisions through a 5-10 year lens, urging leaders to envision their organization’s future with a strategic, forward-thinking approach.


Welcome fellow veterans. From the tip of the spear to in the rear with the gear, I went from active-duty Infantry to reserve-component logistician. I’m your host, CEO, entrepreneur, trial lawyer, and Lieutenant Colonel Retired, John Berry. The military lessons that I learned helped me grow an eight-figure business that has maintained consistent annual double-digit growth, landing on the Inc. 5000 list of fastest growing companies in America every year for the past seven years and has allowed me to continue to serve America’s heroes. 

Welcome back to Veteran Led. In this episode, I’m going to talk about what the military did not teach me about decision-making. But to start, I learned a great deal about decision-making from the military. I learned how to make quick decisions. I learned how to make slower, deliberately planned decisions, but I didn’t learn how to make decisions in the 5-10 year context and to think about those long-term consequences.  

It seemed in the military we were always trying to solve the immediate problem, and I suppose that’s why the politicians were there; to solve the long-term problem. But we were there to solve the immediate problem and so while we did long-term planning, we never really did long-term decision-making. 

The first thing I learned was how to make quick decisions and decisive leaders have to make quick decisions. In training we had all sorts of exercises where we would do battle drills such as react to indirect fire, react to sniper fire, react to ambush. The goal was to train leaders to make split second decisions in combat. We don’t need leaders who freeze. And I can remember evaluating several training lanes where I would tell that officer, “Great decisiveness. Great initiative. Poor judgment.” While it was important that the leader acted decisively, made a decision on the spot and didn’t freeze, it was also important that the leader learn that that quick decision wasn’t always a good decision. 

Later in my military career, I learned that deliberate planning is preferred when we have the time to do it. One of the processes we used was called the military decision-making process. In this process, we would conduct a mission analysis, followed by a course of action development, where we would look at all the facts and all the assumptions and then try to deal with the assumptions and turn as many as we could into facts or kill the assumption. 

Then we would go through course of action refinement, wargaming, and we would even create a decision matrix where we would give each criteria a weight and a value, and then we’d add them up for each option to determine on our scoreboard, which was the best option before presenting to the commander. The point was that when we had a lot of time to make a decision, we should take all the time and use all the available information to make that decision. 

Now, there was also the Colin Powell quote of “If you have 80% of the information, you have too much information.” I like that quote, and I would always use that during the training exercise to try to just get us through the military decision-making process. Hey guys, we already have most of the information, we don’t need more information. Now, someone called me out on that, and we actually researched it, and we found out that the 80% quote came from Colin Powell’s 40-70 rule, which said that if you have no less than 40%, and no more than 70% of the information, you have enough information to make a decision. 

Now, one lesson that I did not learn in the decision-making process was how to consider how a decision will affect the team or the organization 5 to 10 years down the road. Now, even the ethical decision-making classes taught us to think short term. I can remember two examples; one was for the physical fitness test, the two mile course was 200 meters short, and you learned about it after you’ve run that two mile course and your team has, and they finished the physical fitness test. Do you make them retake the test? And the answer is, yes. That was the easy one. But then they would get a little more difficult. You have a top performer who violated a standard and you have to decide whether you punish the top performer the same way you punish the low performer. So that was a little bit more difficult question. 

Even the most difficult decisions we had to do in the training would in no way affect the unit three years from now when a new command team was in place and most of the soldiers had already moved on to their next assignment. But of course, that leadership example that we set would stay with those soldiers for their entire careers, if not their entire lives. And yet, there was no military decision-making exercise where we considered the true long-term effects of our actions. And when I transitioned to the civilian world, most of my decision-making only addressed the immediate problem. And I failed quite a bit because of this.  

I was short-sighted when it came to hiring. I was just trying to fill today’s org chart instead of thinking about the org chart that I wanted to build tomorrow. For physical space, I only looked at the buildings that I could afford, not whether it was in line with my vision of what I wanted in the next five years. And yet I would sign the five year lease for something that had I thought about it, I would have known I didn’t want after two years. 

Marketing at the time was mostly direct response. I didn’t consider investing in building a brand because I didn’t even know that I wanted a brand because I hadn’t thought about where I wanted to be in five years. IT costs were an annual expense rather than a long-term investment in building a culture of efficiency.  

When it came to making tough decisions for the company, which was my job, I cared more about how those decisions would affect the company in the next 90 days rather than how they would affect us over the next three years. Just think of your biggest decision right now. How will that affect your organization in three years? In five years? Will that tough decision even matter in 10 years?  

Now when we use that type of frame, it really takes the pressure off. If we’re thinking in 10-year increments, a lot of decisions we’re making today will have no effect on where we are 10 years from now. Now if you’re concerned that your decision may not be popular with the team today, it’s worth asking whether the people who will be critical of the decision today, even be around in three years. 

Most importantly, what do you want to become in 10 years? Is this decision in line with your future self? As a captain in the army, I couldn’t imagine myself as a lieutenant colonel. Those were the old, boring guys. But they were wise, and they made good decisions. I needed to start deciding, like I was a lieutenant colonel, if I was going to achieve that rank. 

The other part of long-term decision-making is that we have a lot of options that we never had in the military, right? If we thought long-term in the military, we might think about the progression of our career or how long we were going to stay in, but as a civilian, we ask a lot more questions because we have so many more options. 

Number one, is this organization my legacy? If it’s not, do I want to exit in a few years? Number two, how big and how fast do I want to grow the organization? These all affect our decisions. If we care about legacy and the organization is our legacy, we are more committed than if we plan to exit in a couple of years. If we plan to exit the organization soon, we need to make decisions that will not box us in or box in the buyer. For example, signing a 30-year lease may be a bad idea if we want to sell the company in two years. And your investment in branding your organization will be less valuable to the person buying up your company than you because the person who’s going to buy your company is probably going to buy your three competitors as well and consolidate everything and your brand’s going to disappear anyway.  

Now, if you want to grow slowly, you want to make sure that you’re taking enough profit out of the business each year to save up for when you have the lean years, when you need the money, because at that point, you can be the bank. On the other hand, if you want to grow quickly, you will burn through cash in the growth process and you need to consider how you view debt and what risks you’re willing to take to grow quickly and think long-term about how those risks could affect the organization.  

In sum, the military taught me a great deal about decision-making, how to make great decisions, how to think through decisions, how to make quick decisions, how to be decisive as a leader. But, what it didn’t teach me was how to really think through the long-term consequences of those decisions. If you run a civilian organization, don’t make the mistake I made. Do not make all of your decisions through a 90-day lens. Think long-term. Many of your decisions will have long-term consequences. 

And if you can figure out what those decisions are, and you can see them through the right lens, the long-term lens, you will be a much more effective leader because you will make better decisions. And your job as a leader is to make those tough decisions. And as we’ve said before, in other podcasts, those tough decisions are rarely the most popular decisions, but if you make them with the long-term in mind, you will be serving your organization in a way that will build it for the future that you want.  

After Action Review: 

  1. Being decisive doesn’t mean making quick, on-the-spot decisions. If you have the time, slow down and deliberately plan your decisions. 
  1. Think about your decisions from a much wider timeframe lens. How will this decision affect your organization five years down the road? How will it affect it 10 years down the road? 
  1. Make your decisions with the long game involved. Understand what the end state is, what your end goal is. It will give you clarity about how to make the more difficult decisions in your organization. 

Three Down:  

  1. As a leader, sometimes you will have to make quick decisions, but you don’t have to do that all the time, and in every decision, your judgment matters. 
  1. When solving a problem, don’t just look to see how solving the problem will solve the primary, secondary, and tertiary issues, look at how solving the problem will affect the organization in the long-term. 
  1. Remember the 40-70 rule. I’ve erred on both sides of this. I’ve made decisions where I did not have enough information and made a horrible decision. And there are other times where I lost opportunities because I had over 80% of the information and I still wanted 5% more of the information and I really didn’t need it to make the decision. All it did was slow things down. The 40-70 rule says you need at least 40% of the information, but no more than 70% of the information to make that key decision. 

Thank you for joining us today on Veteran Led, where we pursue our mission of promoting veteran leadership in business, strengthening the veteran community, and getting veterans all of the benefits that they earned. If you know a leader who should be on the Veteran Led podcast, report to our online community by searching @veteranled on your favorite social channels and posting in the comments. We want to hear how your military challenges prepared you to lead your industry or community, and we will let the world know. And of course, hit subscribe and join me next time on Veteran Led. 

Berry Law

The attorneys at Berry Law are dedicated to helping injured Veterans. With extensive experience working with VA disability claims, Berry Law can help you with your disability appeals.

This material is for informational purposes only. It does not create an attorney-client relationship between the Firm and the reader, and does not constitute legal advice. Legal advice must be tailored to the specific circumstances of each case, and the contents of this blog are not a substitute for legal counsel.

Subscribe to our newsletter

The Service Connection

Our monthly newsletter features about important and up-to-date veterans' law news, keeping you informed about the changes that matter.

Skip to content