1. What have you found most challenging as a CEO or executive of a large enterprise?

There are seemingly endless challenges for senior leaders. But when a CEO or other senior leader coaching client is most transparent with me, I'll often hear some variation of the imposter syndrome.
One CEO told me that, on the night before her first day with the title, she was Googling "how to be a CEO". She was deeply qualified. But she doubted herself. I've found that's a more common challenge than is talked about.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

I started my company 20 years ago, jumping from a corporate leadership track to becoming an entrepreneur. At the time, I looked at the next level up and didn't see anything attractive about it. It was not a painless journey in making that jump but one that I will forever be thankful for making.

3. How do you structure your work days from waking up to going to sleep?

The two most important things I do in the morning are both physical and spiritual. There's a stretching routine that starts and ends each day, which I'm finding increasingly important as I get older. On the spiritual front, a mentor told me over 25 years ago about the benefit he gets from reading through the Bible each year. I thought I'd try it for a year and haven't stopped. There's something about the daily perspective it offers that spills over to my day-to-day life.
I track my time in Toggl so I can watch for trends. I block out all Monday's--no speaking or coaching, with few exceptions. It provides an opportunity to plan the week and work on longer term priorities.
We try to have dinner together as a family each night, unless I'm on the road. Time with my wife and family is a big priority. I'm a fan of quantity time--it's hard to predict when quality time will hit if I'm not investing in quantity....

4. What's the most recent significant leadership lesson you've learned?

While prepping for an interview of the author of the book How to Think Strategically, I came across a quote that I haven't been able to shake. The author Greg Githins stated that "Leadership is a practice of kindness, but it's not always a practice of niceness."
Of course, that lesson can come down to definitions. But as someone who can err on the side of niceness, that's caused some helpful reflection on how I lead.
I've also recently come across Montaigne's observation that "a man who fears suffering is already suffering from what he fears." We'll have to forgive Montaigne's pronoun usage--obviously it's not gender specific. But in a year that has been characterized by a lot of fear, that single quote changed how we, as a family, faced the pandemic. We decided to not put life on hold. We're going to be responsible, but we're also going to support local restaurants and businesses. We're going to physical distance, but not social distance. It allowed us to flourish in a year when the opposite would have been easy.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Asking for my favorite book is like asking which child is my favorite. We have over 300 episodes on the podcast and nearly every book has impacted me in helpful ways.
James Clear's book Atomic Habits is a must-read. It's not about leadership. per se, but much of what we do as leader has a compounding effect. If we develop effective leadership habits, the compounded benefits are astounding.
I highly recommend Unleashed, from Harvard's Frances Frei. Her definition of leadership is worth contemplating.... "Leadership is about empowering other people as a result of your presence--and making sure that impact continues into your absence."
Her point? Things certainly need to be better when we're present (and that should not be considered a given--sometimes our presence makes things worse!). But what about in our absence? After someone moves to another company? Or we leave? Did we unleash them--inspire them--to continue to grow. What's left in our wake is a reflection of how well we lead.

6. How do you build leadership capacity in a large enterprise?

If it's up to me, we're in trouble. We make it part of everyone's job--to see themselves as a leader, and that means a developer of people in their span of control.
Gary Hamel makes it clear in Humanocracy--there's no such thing as a low skill worker. We find that tapping into the insights of the people lowest in the organization helps them reframe how they see themselves. And it yields insights we'd never see from an ivory tower, so to speak.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

I asked a CIO once, "What's the source of your greatest joys?" I'll never forget his reply: "The source of my greatest joys is the same as my greatest pains: people!"
A direct report from 25 years ago recently reached out to share a story. He said I had pulled him into my office and said something to the effect of, "Ken, when you walk down the aisle, there are a bunch of bodies in your wake. You're destroying the people on your teams."
I don't remember that conversation, though I do remember that he struggled with balancing his brilliance with his people skills. Ken told me he was upset that I was so graphic--so blunt--with him. But he said that it was a wake up call that served him well for the next decades. In fact, he said it's the most important leadership conversation he's had in his career.
Ironic that I don't remember it. But it's a good reminder to us all that the most important influence we can have on someone's career might be a conversation that you have today. Or should have today.