1. What have you found most challenging as a leader?

There are basically 3 levels to leadership and each one has its own challenge.
For New Supervisors:
I struggled with the “Buddy to Boss” challenge when I first became a supervisor. This happens when you become the leader of your former peer group and people on your team start to test you as a leader. I learned a lot going through those experiences and that helped build the foundation for my leadership courses.
The Buddy to Boss Challenge is easily overcome when you have the respect of your team. Jocko Willink, in his book The Dichotomy of Leadership, talks about managing the dual role of a leader - taking care of your team while also accomplishing the organization’s goals. Your team has to respect the fact that you can still be friends while off duty but that you’re their boss while at work.
For Mid-level managers:
Impostor Syndrome, where you doubt your abilities and achievements, usually creeps in at this point.
Know your stuff. Be an expert at your craft. Confidence comes from competence. It also comes from a healthy ability to ignore criticism. Marcus Aurelius said it best: “It never ceases to amaze me: we all love ourselves more than other people, but care more about their opinion than our own.” Learn from the Stoics to free yourself from unnecessary emotional baggage that doesn’t serve you and only weighs you down.
For Senior executives:
Any experienced leader will tell you that the higher up you go in your leadership chain, the harder it is to get people to be honest with you. That is one of the main reasons why I am sought out by CEOs, top executives and entrepreneurs - I provide an unbiased point of view that offers objectivity without judgment. Why is this so important?
Warren Bennis, an American leadership expert, revealed a startling fact in his research about leadership, which he called the “70% factor” - 70% of the hundreds of executives he surveyed over more than 15 years would not offer feedback or advice that is contrary to the norms and preference of the boss, even when they know that following a certain course will lead to disaster. Let that sink in. Haven’t we all worked for a boss who was like that?
A perfect example of this was what happened to Ernest Kanzler, who was a Vice President at Ford Motor Company. In January of 1926, he wrote a letter to the company’s founder and CEO, Henry Ford, where he identified that Ford Motor Company was losing their market share due to other competitors and strategic decisions made by Mr. Ford. All of the top executives knew that Mr. Ford needed to change course to help the company survive, but no one would say anything out of fear of reprisal. The end result was that Mr. Ford humiliated and embarrassed Mr. Kanzler until he was gone soon after. The sad part was that Ernest Kanzler was right about everything. Ford Motor Company survived in spite of Mr. Ford’s ego.
For ALL Leaders, especially CEOs, Top Executives, and Entrepreneurs:
As an executive coach who works with top executives and entrepreneurs, two things consistently prove to be career killers - excessive ego (internal) and a lack of trust (external), both of which can easily be avoided. Ego shows itself in many forms, but the most pervasive is a lack of introspection. I put my clients through a process that I call “Ego Inoculation”, which removes the excessive part of the ego that is holding them back from greatness.
I came up with this concept of “Ego Inoculation” years ago, while I was a quarterback coach for a high school football team. I realized that when we watched film of our games (to find ways to improve), most of my players were too consumed with their feelings about being called out for their mistakes in front of their teammates to appreciate the value of the critical feedback the coaches were giving. This is not just a teenage athlete problem - It’s a human being problem.
The “Ego Inoculation” system was created to help leaders maintain their confidence while getting out of their own way. Externally, leaders often miss one of the most basic tenets of effective leadership - Trust. As John Maxwell said, “People buy into the leader before they buy into the vision.” One of the main ways I help leaders is to show them their “blind spots” and provide them with growth-minded solutions. The only way I can do that successfully requires…Trust!

2. How did you become a leader? Can you please briefly tell the story?

I played sports growing up and I started out by being a Quarterback and Captain of my football team. This was my first lesson on the importance of leading from the front - showing up earlier and working harder than everyone else in that case.
I later joined the United States Marine Corps, which marked the beginning of my professional leadership career. I was named Guide of my platoon while at boot camp (basically it’s the team captain), which is a demanding position because in addition to taking care of your own tasks, you are responsible for everyone in the platoon as well. One day, we went on a run with our Commanding Officer. He led us faster than we ever had run before and, just as we got to the finish line, he kept going as a test. After expecting sudden relief at our normal finish line, I felt like I was about to die as we continued to run.
I had a decision to make - I could take the easy route - give up my position and stop running - or I could keep going until I passed out or finished, whichever came first. I decided to keep running and that moment became a major turning point in my life. I went on to graduate from boot camp as my Company Honor Man and I’ve carried the lessons I learned there into every aspect of my life with great success!

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

I wake up at 5:30am on weekdays. I walk my dogs and then I exercise, so I have my workout completed before I’ve even had breakfast.
I start work around 6:30am and I incorporate “1% Breaks” into my day to work on my Pillars of Personal Success. (I’ll explain in a moment.)
There are 5 Pillars of Personal Success
- 1) Physical Fitness
2) Mental Fitness
3) Personal Pursuit
4) Professional Development
5) Financial Knowledge
They are listed in their order of importance. If you don’t have your health, you have nothing so physical fitness is paramount before all else.
Mental fitness is a combination of focus/clarity and overall mental well-being.
Personal pursuits are hobbies or areas of interest (ex. learning to play the piano, writing poetry, planting a garden, etc.) that make you feel like you “lose track of time” because you get so "into" what you’re doing.
Professional development keeps you in a non-stop learning cycle that builds your competence - and confidence. Financial knowledge helps you leverage your money and sleep better at night! (Financial stress ends 80% of all marriages.)
I was helping a top executive get his (stuff) together not long ago and he needed a “boot camp” to get everything in order all at the same time. Like many of us, he simply fell into a “routine of responsibilities” and forgot to take care of himself first. I created a system that worked for him that was simple and easy to follow. It was built upon only spending 1% of your day on each of the 5 Pillars of Personal Success.
(24 hours x 60 minutes/hour = 1,440 minutes in a day -> 1% of 1,440 is 15 minutes) This way, it is easy to start the habit and keep the consistency going. Too many people “dive into the deep end of the pool” and fail to follow through because they’ve made it too difficult to adapt all at once. Small wins create momentum. Momentum creates consistency. Consistency creates progress.
I’ve created a free document that I call the “Daily G.A.S.” (Goal Action Steps) which provides a daily “road map” of how to achieve your goals in small increments and I’m excited to offer it for free to any of your fans. Just send me a direct message on Twitter (“Sean Carroll - @aioleadership”) using the code “A.I.O. Jonno.”

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

I have been reminded numerous times recently about the power and value of trust, or a lack thereof. A Harvard Business Review study by Mark Murphy showed that 58% of employees trust a total stranger more than they trust their boss.
That’s a scary statistic - especially if you’re a boss! The late General Colin Powell tells a great story about his Drill Sergeant explaining the meaning of trust, and the relationship between trust and leadership, in the armed forces.
The instructor said, “Lieutenant, trust is getting your team to follow you up the highest hill or down into the darkest valley…even if only out of curiosity…because they TRUST you!” To frame it more clearly, Commanding Officers of military units who made bad decisions during the Vietnam War - that put their troops in unnecessary/deadly situations - were often intentionally injured (or worse) by their troops as a misguided way of keeping themselves safe and getting the supervisor removed from their command position.
If your team doesn’t trust you, they will only give you the bare minimum as you are leading with the lowest form of leadership - leadership by fear. Effective Leadership inspires others to achieve a common goal, not extort them into action through fear of discipline. (That’s another conversation entirely.)
Conversely, when you have the trust of your team, there is nothing they won’t do for you. I’m sure we all can think of people that take both of these approaches.

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?

That's a great question with no easy answer as there are so many books and people that have influenced me throughout my career.
If I may, I’d like to offer two books. The first is “Extreme Ownership” by Jocko Willink and Leif Babin. That book came into my life right after I became a Police Sergeant (First Line Supervisor) and it changed everything about how I viewed my role. I had to make some serious changes and they have served me well since then.
The second book is “The Way of the Shepherd” by Dr. Kevin Leman and Bill Pentak - it’s one of the greatest leadership books I’ve ever read in its power and simplicity. It tells a story that weaves leadership lessons through it in a way that is easy to understand and conceptualize in its application. This book has helped me relay leadership concepts to my executive coaching clients in a very powerful way.

6. If you could only give one piece of advice to a young leader, what would you say to them?

It's so hard to answer this with only one item. Here's what I would say –
Take care of your team and they will take care of you;
Believe in yourself (especially if no one else does);
Always have a growth mindset;
Remember the power of trust in your relationships;
Your network equals your net worth;
“Never forget where you came from” (aka stay humble); and
Always treat people how THEY want to be treated!

7. What is one meaningful story that comes to mind from your time as a leader, so far?

After I retired as a Commanding Officer of a capital city police department a couple of years ago, I created a new executive leadership development course for the FBI National Academy Assoc. and they flew me all over the country to work with top level leaders of all types.
One of the segments I teach is about using your leadership power to connect with your team. In the class, I discussed a man who had committed suicide. After his death, a note was found saying that he was going to walk to the Golden Gate bridge and jump off it. He added, though, that if anyone acknowledged him along the way, then he wouldn’t kill himself.
Some time after that, one of my students reached out to me to tell me that he had just been promoted to Sergeant and he had taken over a team of people that he barely knew. One morning, after working an overnight shift, he saw one of his officers just sitting in his truck in the police station parking lot. He waved quickly at him as he got into his vehicle and drove home. A short time later, that officer approached him and thanked him. He had no idea why. When the Sergeant asked, the officer told him that when he waved at him that morning, he saved his life because he had been contemplating suicide. If the Sergeant hadn’t waved, the officer would have killed himself. The Sergeant saved his officer’s life with a single wave of his hand (literally) and didn’t even realize what he had just done.
That's the power that effective leadership, coupled with compassion, can have!