When I was younger, I ran the neighborhood. I was the most outspoken kid—the one who organized all the football, soccer, and roller hockey games. As I grew older, I set up Kool-Aid stands, hiring my friends at 50¢ an hour to work them (sure, I was making $5/hour, they they were gainfully employed!!).

As I grew older, this extrovert personality made me a leader in just about everything I did:

  • scouts, Senior Patrol Leader
  • wrestling, team captain
  • cross country, team captain
  • and on
  • and on.

I developed a knack for organizing people and getting a team to achieve more…it involved a lot of “rah rah rah” and inspiration.


Now, as an owner who has to lead people in my company, I am learning that leadership is still about inspiration, but it is quickly becoming more about listening than talking.

I meet monthly with half my team to discuss their challenges, wins, and how work/life are going overall (my partner meets with the other half). Instead of telling my team members what they need to do, I find myself asking, “What obstacles do you need removed? What has been great this past month, and what’s been frustrating?”

I’ve found that the more people talk and express themselves, the more I am able to ask questions that lead them to the answers and path they are seeking.

When we are young, it is easier to be told what to do and given a predetermined path. As we get older, we become more and more independent and want to carve our own path.

We Can All Be Great

As leaders, it’s important to not try and force someone down a certain path, but to help illuminate the various paths and options people have. This illumination can only occur inside oneself, though; it’s not like you can shine a flashlight down for someone.

They have to see it themselves.

This requires them talking through the issues and discovering the answer for themselves.

We all have the opportunity to be great leaders. My question to you is: are you leading by telling or are you leading by coaching?

As leaders, we are often called to switch back and forth. In times of crisis, people look to be told, but the majority of time, I’ve found that people want to be led through coaching and self-discovery.

Have a comment? Leave it here or email me at bdempsey(at)