Why Finance Leaders Need Courage, and How They Can Learn It

Why Finance Leaders Need Courage, and How They Can Learn It

When you think of what’s required of finance professionals, courage may not be the first thing that comes to mind. We’re often seen as cautious and conservative—the ones who are putting the brakes on spending and insisting that companies look before they leap. However, I’ve found that courage is something I've called upon in my career in finance almost daily. As companies look to finance for business strategy and increasing levels of leadership, courage is more important than ever, both for the present and the future.

The good news is, you can learn courage through experience. During my 10 years in the U.S. Army, I was guided by FM 22-100, the classic field manual that covers everything a leader must be, do, and know. The “be” part includes the four Cs of individual character, and the first C is courage. The others are candor, confidence, and commitment.

The army offered many lessons in courage, but probably what impacted me most was learning how to jump from planes and helicopters, which is how air assault soldiers get inserted into the battlefield.


Going into the military, I thought I had courage, but in hindsight, I would say it was more like bravado. As in, "That looks like fun. It's a little scary, but let's do it." That being the case, you would think jumping out of planes would be right up my alley, but a childhood experience gave me a healthy fear of heights. When I was a kid, I was climbing a tree when the branch I stood on broke, and I fell about 30 feet to the ground. It ended with me getting a pretty good concussion and thinking twice about climbing trees.

I knew I needed this training to be a better soldier, so I signed up for the jump. Of course, you’re working with instructors who have trained hundreds of people using methodologies that have been refined over decades, and equipment that’s been rigorously tested and maintained.

And while that seems reassuring, you get up there and quickly realize no sane person would jump out of a perfectly good airplane. When it comes time for you to stand in the door, you have to look at the horizon and move out before the fear paralyzes you. No amount of rationalization makes it easier to get out that door.

Fear that never goes away

I’ve now jumped out of more aircraft than I can count, and I’ve never overcome the fear. You do all you can to control the variables, but success is never assured until you’ve safely landed, released your chute, and moved into the next phase of your mission. Even when you’re out the door and your parachute has opened, and you look up, and the lines aren’t tangled, you can see drop zone, the wind is in your face, and the view is spectacular, you can never relax and enjoy the ride.

I've been on jumps when high winds have carried people in between power lines, across highways, into the woods and other places that are not ideal landings. A friend of mine who was a Ranger Battalion jumped under fire in Grenada. His chute opened. He looked up, and everything was fine. Then he looked down, and he sees a man running over people in a truck in the landing zone. There’s only so much you can do to steer your parachute. Upon landing, he got hit by the truck and broke his hip. Fortunately, he survived and went on to serve with honors, but that was a pretty tough break.

What courage means to me now is something along the lines of, "This probably isn't going to be fun. There is probably going to be collateral damage, but we need to do it anyway for the greater good."

Cultivating courage

I’m not recommending that everyone who aspires to financial leadership learn courage by jumping out of planes, but I do believe it’s essential to identify opportunities to learn it in your own life.

The way to do that is by putting yourself in situations that challenge and scare you a little bit. So why do finance leaders need courage, and why is it under-appreciated?

When setting forth an annual plan, for example, we try to come up with something that is reasonable. To a lot of people, especially those who want to set a more aggressive course, this looks like the opposite of courage.

But as CFO, you quickly realize that in a world of limited resources, whatever recommendation you make is not going to satisfy everyone. The individual contributors who are creating their parts of the masterpiece in the life of a business have a picture in mind of what success looks like, and many times, you will get pressure from them to move things in one direction or the other.

But we are equipped as leaders to deliver decisions made in the best interest of the business and to move boldly toward that future, even if those decisions are perceived as unpopular. This takes courage.

Courage to shape the future

It’s no secret that technology and data are changing finance, presenting us with an opportunity to shape the future and not just report on the past.

Any time you change companies or roles, implement new technology, restructure your organization, or undertake an untested strategic initiative, it’s like jumping out of a plane. And while you aren't falling toward the earth from a couple thousand feet up, it’s still scarier in a way.

When you're jumping out of a plane in the Army, the odds of a successful landing are very high and many of the finite number of known risks can be controlled.

However, as CFOs look at any given scenario, there are usually far more risks and unknowns than a parachute jump. Our job is to understand and prepare for as many risks as possible and to rein in the bravado of those in the organization who may not have the bird’s eye view. That’s one kind of courage.

The other kind, the kind that’s demanded of us as we move into a competitive landscape increasingly driven by automation, data, and artificial intelligence, is to have the courage to take calculated risks and deal with the downsides. We have to channel the cautious, analytical side we are known for and complete our due diligence. And when we spot a good opportunity, knowing that there’s no such thing as a guarantee for safety, we have to look toward the horizon and jump.

John Ewert is the CFO of Nvoicepay. After serving his country for four years on active duty in the U.S. Army, John began his business career with a Big Four public accounting firm. Over the last two decades, he has served in financial management roles at PwC, Sun Microsystems, Oracle Corporation, Palo Alto Networks and AWS Elemental, an Amazon Web Services company.

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