This new installment of our exclusive series with Tim Wenzel, CPP, Co-Founder and President of The Kindness Games, explores the importance of not knowing, but asking the right questions as a leader.

The progression

I graduated high school in the year 2000. In 2003, I was part of the invasion of Iraq with the US Army, which ultimately would lead me down a new career path to executive protection…

In 2005, I bought my very first computer, because I needed to look for jobs outside of my cornfield…

In 2010, I got my first smart phone AND sent my first text message. Then in 2013, I downloaded the book, “iPhone 4S for Dummies,” because I was trying to understand how you work a phone with only one button as I was onboarding at Facebook…

Two weeks later, I was placed in charge of “fixing” the technology problems within the Executive Protection department at my job…

At that moment, I stepped into a new foreign world. The security meetings I attended centered around ports, V-LANs and certificates. 

Half of the time I wondered if we owned a ship I was unaware of… the other half of the time I was wondering how I would find my next job before I was fired from this one.  

This is not the security I was used to… Why did I move out here for this? I don’t know anything, except that I need this job…

This is the fifth installment in my Crossroads in leadership series and we’ve arrived at a pivotal moment in a leader’s journey. 

As we become comfortable with who we are, who we are becoming and how we are reacting to the stress of leadership, we begin to rise. 

Our stages become larger, our portfolios more critical and we are led outside of our core competencies. 

We’re given assignments which are less easily defined and the people, projects or programs we lead depend more than ever on us. Every now and again we arrive at a place where we are lost.

Sometimes challenges arise that no one is equipped to solve. Maybe it’s a problem no one forecasted. Or maybe, there was a changing of the guard and a new management team was brought in to fix broken programs. Such was my case.

Our journey through the Crossroads in leadership has brought us to this truth: leaders do not know everything.

How will you react when you’ve crossed into a world in which you do not know the answers? You may even find yourself in my world, where I did not even know the questions to ask.

It is here where the limelight’s intensity grows and you find yourself truly alone. 

Not because you’ve been abandoned. Not because you’re in trouble or being scrutinized. You’re all alone because everyone is asking: “Do you know?” and the truth is: you don’t.

The crossroad

When you find yourself “managing the gray,” dealing with problems and projects you do not understand, you’ve entered the realm of thought leadership.

We often think of “thought leaders” as those who know and have the most thought provoking insights… but you’d be wrong.

If you pay attention, thought leaders are those brave enough to ask the questions. They are brave enough to put their ego aside and find out what other people think and what another’s perspective might teach them.

By asking questions to enough people, they begin to understand what others don’t. 

Thought leaders are professional learners. They are secure in dealing with the unknown or misunderstood because they are comfortable leading conversations to paint a more interesting portrait of the world around them.

David Yang and Chris Spitler were integral to my success during this time. They saw my struggle and they took time to explain things to me. 

They helped me understand what the true issues were and what needed to be discovered in order to create the critical path forward. 

They wouldn’t leave me all alone in these meetings. Ultimately, they helped a knuckle dragging Executive Protection Manager understand technology’s role in this new world and what I needed to understand to be successful.

Do you know who to ask? Who are the people who might know some of the answers or have an idea about the way to proceed? 

Find them and buy them coffee. Tell them about the problem set you’re dealing with. Tell them why it is a problem for your organization, why it is a problem for you management, why it is a problem for your team… and why you’re having a problem forging a path forward. 

Then listen. Answer their questions and ask your own as they start to discuss topics you aren’t familiar with.

Do you know who to include? Now that you’ve asked a variety of people what their take is and how they would proceed, who is able to help you and your team solve this problem? How can you include them in the project?

This is where the insecurity in security will take hold. “How can I lead people who are smarter than me?” 

That is exactly the point. When you find the right people with the right knowledge and you bring them together to solve a complicated problem… you are already leading them.  

Do you know what success looks like? Have you asked your prime stakeholders, the people who will judge the quality of the outcome, what a successful outcome looks like to them?

How do we get from here to success? Map out all the opinions of successful outcomes and try to understand where the contradictions lie.

Meet with the stakeholders to go through these contradictions to create an aligned vision of success.  Often we are afraid to lead in depth discussion with business leaders, our clients, our bosses… but then how will we measure success?  

Now you understand what success looks like for your stakeholders. You have your project team. 

The next step for me came from a place of frustration. As all these really smart people began to filter into the conference room and everyone looked at me, I stood up and said:

“Looking around this room, I just realized that I am literally the dumbest person here. My problem is that I do not understand this technology or how to make it work, yet I own these programs. 

“I am physically unable to complete this work on my own, which is why I’ve asked you all to help me. I need you to design a successful outcome and solve these problems.  

“Here are the current problem sets as I understand them…  

“Here is the vision of success from our stakeholders…  

“What do we need to figure out to move forward?”

It turns out that very intelligent people love to be left alone to create really great outcomes. They also love working for people who are not trying to impose their will or their vision on a project.  

Over the next several months I would learn to lead these brainstorming sessions. I grew confident enough to ask the “stupid” questions when I didn’t understand.

I learned that being the dumbest person in the room qualifies as diversity of thought. The questions I asked – which often seemed basic – would inspire quick answers. 

When people have to simplify complex ideas, they have to think a little deeper than normal which naturally exposes small details that will not work. 

I would ask the next question and then the next… and soon we would find the kink in that line of logic, leading to better ideas.  

As you aspire to climb the ladder and grow as a leader, you need to become comfortable with not knowing. 

You need to become a talent scout, finding quality people who understand what you don’t and placing them in key positions to make the world go round.

You cannot be a leader of an organization at scale if YOU MUST know everything about everything.

The next time you feel lost, overwhelmed because you do not know – contemplate this question:

Do you know how to find out?

You can find Tim on LinkedIn here.

The next installment of Crossroads in leadership will be released on 5 October! To read the previous installment, click here.