By Dr. Kevin Reynolds

My son is learning to walk.

Sitting on the floor of our living room watching my son, Samuel, standing up, holding the edge of our couch as he struggles to keep his balance moving towards our dog Zoey, who wants absolutely nothing to do with him, as he smiles and does his excited shriek and then plops onto the ground with a surprised look, and then begins the process again.

I say to him, “Bud, you have to finish the first step before you start the second,” but the concept of sure footing isn’t clicking with this 9 month old daredevil because his experience tells him that if he does fall, he will fall into the arms of his caregivers or onto the soft carpet below him. My son, not yet a whole year old, understands the concept of calculated risk vs. reward. #ProudDad

As a student and scholar on the topic leadership, I tend to examine lots of moments like this as a potential metaphor for leaders.

The idea of sure footing, for example, is an important principle in the development of young leaders, as calculated risk is critical for advancing in every industry. As leaders, we need to be mindful of how we approach risk within our organizations. Are we James Tiberius Kirk, known for leaping before we look, as we strive to boldly go where no man has gone before? Or are we Sherlock Holmes, working out the equations and seeing the next steps in our heads before speaking.

Do we see the whole chess board before moving our pawn?

I have found that there can be tremendous reward in having the courage to propose a new way of doing something, to offer an out-of-the-box idea, or attempt to solve a problem. Sometimes you will be right and sometimes you will fall face first into the dirt, but if you’ve done the math first, often the outcomes are irrelevant. You can fail and win at the same time. Leadership is not perfection, it is the act of making a choice to move forward and to bring others along with you behind a shared vision. But how do you maintain followership if your [idea, decision, program, argument, investment] failed?

Easy. Show your work.

Remember in math class when your teacher would dock points from your test even though you got all the answers right? Turns out they might have been onto something. The process is always more important to the leader than the outcome. You have to know how you got to your decision in order to learn from what happened next. There may be more than one way to make an omelet, but once you get your recipe right you’ll want to be able to recreate it, maybe even alter it with new ingredients to see if it can be even better.

Successful leaders talk with their teams about the “why” behind a decision, because whether people agree with the choice or not, they will respect the leader’s position if they understand how they arrived at it.

So how does the leader approach weighing risk or predicting the potential outcomes? How do we go from counting on our fingers to doing quick mental math? We start with practice.

When I was involved in Student Government in college, our advisor was the Dean of Students, Dr. Jeffrey Waple. In meeting after meeting with Dean Waple I would bring up new ideas or propose new programs, plans, buildings that I thought would make the institution better. His response was the same every time. “Kevin, think five questions ahead.” It drove me crazy. Why wasn’t he as excited as I was about my idea? Why did he have to instantly poke holes in every proposal I came up with? I took me a few years to figure out that the holes were already there. He wasn’t poking them, he was trying to help me fill them in before they caused the whole project to sink.

When you’re so focused on where you’re going, like my son as he excitedly moves closer to his furry roommate, you may stumble along the way, but if you’ve done the work to assess the environment and context that you’re leading within, you will be better prepared to mitigate the potential risks and keep moving forward.

When you prepare to pitch a new idea to your team or to your supervisor, what are the first five questions that you expect they will ask? Who is in the room when you’re proposing this idea and what is more important to that individual? For example, while the CFO wants to know what it costs the CEO will want to know what makes it profitable and (here’s the important part) why you think that. Examining the potential impact of your decisions will help you find that sure footing and will better equip you with the tools you need to bring others on board with your ideas. It will also make you an invaluable member of any team that you are on.

It is ok not to look before you leap sometimes, but thinking ahead might cause you to bring a parachute just in case.

Dr. Kevin Reynolds is the Vice President for Advancement at Thomas More University. Kevin has worked professionally in higher education for nearly a decade and speaks on leadership, Title IX, and bystander intervention. He and his family live in Northern Kentucky. Learn more about his signature programs at

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