A bedrock principle I hold dear is that leadership is mostly learned from experience: it is developed through venturing into new territory with the courage to think critically about oneself, reflect on strengths and weaknesses, and learn from feedback.

That’s why I was delighted to read Jim Schell’s new book, Where Wisdom Comes From: How Our Experience Makes Us Wise.  It is filled with every day stories explaining the lessons Jim learned, and how he learned them, told in a most memorable and entertaining way.  I was thrilled he agreed to do a follow up interview to dig deeper into the habits and personal characteristics that enabled him to learn so much from his experience.


Jim, you are an 83-year-old, super-charged learner from experience.  When I moved to Central Oregon, I found out that you are a serial entrepreneur, author of a dozen books, mentor to dozens, starter and fixer of businesses and non-profits, and an insatiable connector of people.  I discovered your fingerprints all over many incredible civic and business breakthroughs in Bend.  

Thanks for talking with me to dig a little deeper on what you know about learning to lead from experience.

Q & A:

Q: Jim, we all have experiences but many of us do not learn from them—or take away the wrong lessons.  What is it about you that made you such a fantastic serial learner from experience? 

A: For me, my infatuation with learning comes from a couple of sources. Firstly, I am, by nature, curious. That curiosity leads to a penchant for asking questions and we can’t help but learn if we’re a lover of asking questions. It’s cause and effect at work.

Secondly, genes helped too. My mom passed on to me her affinity for learning. She was an indefatigable reader and so am I. Even today, at age 83, I’m still devouring nonfiction books on my favorite topics such as wisdom, aging, mentoring, and entrepreneurship.

Michael Gerber, in his iconic book The E-Myth, made one of my favorite observations as it relates to becoming a successful entrepreneur. “The number one common characteristic of a successful entrepreneur is an insatiable appetite to learn,” Gerber wrote. He was spot on.

Q: In your book, Where Wisdom Comes From, you take us through the stages of your life from Growing Up, to Grown Up, to Growing Old, to Looking Back. You learned at every stage. Did you get better at learning over time and if so, what did you do to enhance your skill to learn from experience?

A. In my early business years my primary learning tool was trial-and-error. There was no such thing as an “entrepreneur” back in those days, we were “small business owners” or “moms and pops.” We didn’t have anything close to the learning tools at our disposal that are available today. No college courses on small business and entrepreneurship, few books on the subject, no Inc or Entrepreneur magazines, no internet to search for solutions to our problems. 
Like most entrepreneurs, I was always taking chances of one sort or another, and, for better or for worse, I learned something from every chance I took. As a result, I learned both the “how to’s” of building a business as well as “how not to’s.”  

The good news about learning from trial-and-error is that we never forget the lessons we learn. The bad news is that those lessons are so damn expensive. I’m not espousing trial and error as a learning tool, mind you, but as Barry Manilow sings, “we learn more from our mistakes than we do from our successes.”  Well, sometimes, anyway.   

So yes, I enhanced my learning skills as the years passed, thanks to books, magazines, the internet, and the wide variety of resources in my community’s entrepreneurial ecosystem. Sadly, I never had a mentor, which is part of the reason why I choose to mentor so many younger people today. I know what I missed. 

Q: I would like to zero in on the period when you became an entrepreneur managing other people versus being managed by someone else.  What did you most need to learn to lead people?  How long did it take and how did you learn it?

A: As previously commented, I initially learned how to manage people by trial-and-error, just like I learned most everything else. Like most entrepreneurs, the HR part of starting and growing a business is the part of growing a business we like the least. 

If you ask an ex-entrepreneur what he (or she) liked the most about business and what he liked the least, the answer will usually be the same. “The people.” We enjoyed the people we worked with but having to manage them was an ongoing frustration. Entrepreneurs weren’t born to manage things we were born to create and grow them.  

For me, there were two things I needed to learn to become a better leader. The first was empathy, which comes from learning to see things through the eyes of others, rather than through just our own eyes. The second thing was accountability, I had a difficult time holding my employees accountable. “Why don’t they just do it right the first time” was the question I’d ask in my early days. I needed to learn that the two of us are cut from different cloth. “Employees are from Mars and employers are from Venus” is an acute observation: the two of us see our business differently. We, as employers, need to understand that.

Q: Say I am the CEO of a growing company with the ability to invest in leadership development. The head of HR wants to spend money on leadership training. I am not sure that will yield the best results.  What would you advise me to do to develop leaders?

A: Every entrepreneur needs to understand that in order to build a successful business, our number one duty should be “to assemble a team of superstars in gamebreaker positions.” Then, once we have a team of superstars in our business’s gamebreaker positions, we can delegate whatever our number two duty is. 

Assembling that team of superstars is a four-part process; skip any of those four steps and we’ll never have a team of superstars working for us. Those four steps include 1) hiring the right employees in the first place, 2) giving them the training they need to succeed, 3) motivating them to want to be a superstar, and 4) when necessary, firing those that don’t measure up. Skip or downgrade any of those four steps and our team of superstars will end up as a team of mediocrity. Those gamebreaker positions include, in most businesses anyway, operations, finance, sales, marketing, HR, and in some cases technology.

Finally, there’s a parable in business on the topic of training that is timeless. The parable begins with a well-intentioned CFO who is looking for ways to cut training expenses saying to his CEO, “What if we train our employees and they leave?” The CEO then responds; “What if we don’t train them and they stay?” 

Savor More of Jim’s Lessons That Have Made Him Wise

Reach out to him at him at JimSchell5@gmail.com to order his book, Where Wisdom Comes From: How Our Experience Makes Us Wise.