Jerry Colonna is the CEO of Reboot.io and the author of “Reboot: Leadership and the Art of Growing Up”. In this episode, Jerry teaches us how to expand our mindset to become a more compassionate leader, while tapping into our past experiences to turn them into positive outcomes. 

Listen to this episode (or read the transcript below) to learn how you can harness your adolescent experiences and transform them into favorable leadership qualities. 

1 What were some mistakes that you may have made early on in your management career? 

One of my first experiences was probably when I was in my 20’s and I was a reporter, then an editor, and then I eventually became one of the managers at the magazine. It was a print magazine in the technology sector and most of the people that reported to me were more senior than I was in age and experience. As a result, I was deeply insecure about judgment calls I had to make, and I probably put way too much pressure on those judgment calls. I thought I had to have all the right answers if I were to lead and I believed that in order to be a good leader you had to be the smartest person in the room and that led to a whole bunch of mistakes. 

2 How do you make the decision to promote someone to a certain role? 

One of the really profound challenges in human nature is when we’re confronted with the reality that we can do absolutely everything right and still not be rewarded. Good things happen to bad people, and bad things happen to good people all the time. As one of my B Buddhist teachers once said at a wedding, pain is not punishment, pleasure is not reward. What’s lost is the opportunity to develop true grit and the opportunity to develop resilience, which in my mind is the most important character trait of any leader but more important, the most important character trait of any adult. As I wrote in the book, True Grit resilience leads to equanimity and all we really want is the ability to feel okay, regardless. 

3 What does it mean to grow up as a leader and why do you need to do it to become a great leader? 

The task that exists before all of us is to use the challenge of leadership to grow up. You don’t have to grow up to be a leader, but those who don’t use the challenges of leadership to complete the process of becoming a better person, a better human, miss out on an opportunity. 

The real effort is in building the capacity to withstand the changes that occur and applying that not only to our job as leaders, but also to the process of growing up. Grownups should use every experience that they have to dive deeper into their own development. We use that challenge to unpack who we are as people so we can be in charge of our own lives. We have to ask ourselves who we are, how we are wired, and identify why we do the things that we can do so we can choose the way we’re going to respond to the world. 

4 How do you view self-inquiry versus radical self-inquiry and how do they differ? 

I call it radical more often than not, because we typically don’t do the work. A good example to go back to is if somebody makes you really mad. What do you do? You call a friend? What do you want to talk about, do you immediately start talking about how awful the other person is or do you identify the other feelings that may have arisen? We rarely ask those questions because we like to live comfortably behind our masks, but we have to remember that we’re somebody else’s awful person. 

So maybe what we should do is use the experience of being triggered, to radically enquire within and ask ourselves how ever been complicit in creating these conditions. We don’t train ourselves to strip away the masks and we need to in order to be radical. 

5 Can you change your belief systems or learn to embrace new ones? 

It’s a two-step process. The first thing you have to do is recognize that the subroutines are up. The second thing you want to do is ask how those subroutines continue to serve you or if they continue to serve you at all. I might have had a subroutine that says anger is dangerous, therefore, anytime I’m angry, I become anxious and then as an adult, I’m walking around anxious all the time. I would recommend shying away from the notion of replacing one set of programming with a new set of programming. What I would do instead is have a more adaptive learning system that doesn’t require as much programming and make sure that your ability to be discerning about certain situations matches your chronological age. 

6 You state that a conflict avoided is a conflict postponed. If you sense a conflict, do you believe in addressing it right away? 

You should get curious; moments of conflict can be scary and if we’re socialized as children, that conflict, and anger might lead to yelling, and other forms of violence and we’re going to avoid them like the plague. Sometimes conflict occurs because two people are acting from, their lesser selves, they’re acting from their own subroutines. But sometimes there are genuine disagreements about ways forward. When we avoid the conflict, not only do we kick the can down the road, and ultimately have to deal with conflict anyway, but we miss the opportunity to really go deep and be curious,

If we are brave in those instances, we get to examine what the various positions are that are in conflict, and then lift up and out of the conflict through innovation. There’s a tight correlation between positive conflict within an organization and high innovation because high innovation requires changing things as they are and there’s almost always somebody invested in keeping things exactly as they are but if we approach all conflict as a source of fear, we stifle innovation and the most innovative thinkers in our team will leave because they like the new concepts and ideas. 

7 How do you decide where to focus your attention? 

I spent a lot of time journaling every day and these are the kinds of things I journal about. I recommend using discernment. Consider it a tool. Nearly every opportunity is an opportunity for growth. I remember writing to one of my Buddhist teachers one time about being stuck in a middle seat on an airplane on a long flight two or three seats on the side, and I was stuck in the middle and I’m tall I am a big guy and my Buddhist teachers’ words kept coming to mind in which he would say that everything is workable. Everything is the middle seat on a shitty flight and it’s workable.

8 Do you have any tips, tricks, resources, or words of wisdom for managers or leaders that are looking to get better at their craft? 

The most important thing to remember is that you already have the answers you’re looking for. I often see leaders struggle with accessing the answers that they already have inside, and any good coach will help you understand that you already have all of the answers you’re looking for inside, you just have to be brave enough to access them.