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Many CEOs are often thrust into the role of leadership with very little formal training

The school of hard knocks—absent of mentors—is often our only teacher. 

But, there is something to be said for experienced-based learning. As I like to say, pain is where the learning happens

My former colleague and close friend Jen Plourde reached out to ask me five leadership questions. 

She was taking a masterclass in leadership and had some homework to complete.

“[John] Thanks so much for agreeing to answer these questions for me. In the first chapter we had to write down someone we saw as a leader, and I immediately thought of you! In the next chapter, we were given the assignment to have that person answer some questions.” 

The questions were thoughtful. 

The more I answered, the more I realized how much I had grown in the past two decades. 

Here is a summary of the questions and my responses. 


Here is a summary of the questions and my responses.

1. When did you first see yourself as a leader?

I may sound a bit nerdy, but the very first time I felt like a leader was when I was voted president of the Association for Computer Science Undergrads (ACSU). It was a chapter, at Cornell, of a national association (ACM – these are folks that give out the Turing Award) focused on college students.  

I was tasked with turning the sleepy old organization into a vibrant, fun community. I recruited a new team, we set our goals for membership, the design of the organization. We achieved every one. By the time I stepped down, we were among the top organizations to join.

2. What are some of the greatest challenges you’ve faced as a leader?

Oof, so many. To name a few:

  1. Letting a large percentage of my employees go because we were experiencing tough times.
  2. Dealing with a failed attempt to sell my company (only to start it back up again).
  3. Navigating the delicate process of asking my co-founders to leave.
  4. Feeling like I was not capable of leading my team where we needed to go–and considering firing myself.
  5. Telling a customer, I didn’t love them anymore.
  6. Wearing multiple hats during a crisis.
  7. Watching my relationship with my wife unravel just when she needed me the most.
  8. Giving an employee a hug as she shared how the company we built together was affecting her health.

3. What has contributed to your growth as a leader?

I believe it has been looking at each experience good or bad as an opportunity to learn. I have always found that things happen for a reason, usually a good one. I now realize that the good thing is the learning that occurs. 

My new mantra for 2020 is: Easy is BoringWhen things are hard, that is where the learning happens, and the fun begins.

4. What are you currently doing to grow as a leader?

I read, listen, and write.

read every book I can find about leadership, management, decision making, and personal growth. I try to read one book a week. I try to read in my field and beyond, hoping to expand my mind. I read blogs, articles, and books alike. I am relentless about it. I read about old leaders that lived during tough times and search for timeless lessons.

write about my experience and learnings as a CEO. It has been an incredible ride. It is both cathartic for me and a new opportunity to help others. It inspired this blog. And has become a passion for me. This past holiday I wrote a summary of my learnings over the past two decades. And, I have received incredibly warm notes from people about how it is helping them.  

listen to interviews and podcasts about people with the courage to create something from scratch and their journey along the way to becoming successful. I hope to do it live at some point, learning from their stories.

Finally, I stay in the leadership seat. As a CEO, remaining on “the bridge,” I get to navigate lots of waves of adventure seas. And, I have learned there is nothing but growth to be found out there.

5. What is the best piece of advice that you would have for someone who aspires to be an effective leader?

Leadership is not a destination.  

It is a journey.

In that journey, you will learn that to be a successful leader, you must turn your attention away from yourself and focus on others. The higher you climb, the more your success will depend on making other people successful.

To be a leader, you must genuinely care about people, cultivate community among your teams, and learn to become a coach–not just a mentor–to them.

To become a coach, you must be coached. (So, I suggest you find one you admire).

And lastly, it’s counter-intuitive, but your title may make you manager, but your team makes you a leader.  (Got that insight from a book – Trillion Dollar Coach. It’s stuck in my head now – probably forever.)


How would you answer these questions?

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