Leadership and the Art of Growing Up

Jerry Colonna: I guess it’s a silly attempt at humor. Not really, though – there’s a serious intent behind making the assertion around adulthood. And that is that I think that there’s an opportunity somewhere in our… Starting, say, in our 30s, [extending to] well into our 60s, to establish ourselves really more fully, in a more “actualized” way as an adult.

So, we’re not talking, obviously, about chronology, but we’re talking about becoming more fully ourselves, more fully the person we were born to be. And the relationship between the two is that I think that the leadership challenge – the challenges implicit in leadership – represent an opportunity to complete that work.

Rachel Salaman: And your book helps us with that. You were a journalist and a venture capitalist before you moved into coaching. Now you run Reboot – an executive coaching and leadership development firm, as I said. How would you describe your approach to coaching?

Jerry Colonna: It’s a combination of what I would say is a kind of “Buddhist aware” understanding of the way the mind can work, infused with an understanding from a Western psychology perspective (an almost psychoanalytic tradition), coupled with a very pragmatic and practical experience that comes from having helped launch, or establish, or grow more than 120 organizations over the last 20 years.

For me, in particular, it’s this combination of those three that represent a little bit of a different approach to coaching.

Rachel Salaman: Now you say in the book that some people assume that your type of coaching is some sort of, quote, “yoga-inspired, soft-bellied call to leadership.” I guess that’s hinting at the Buddhist side of it.

Jerry Colonna: Right.

Rachel Salaman: For anyone who might be thinking something similar, could you explain how it is not like that?

Jerry Colonna: Sure – and I smile when you reflect that back to me, because I was just actually having a conversation with a client last week who said to me that, when we first met, he described his experience of meeting me as kind of “woo-woo.”

Because there I was, wearing these Indian mala beads on my wrist, and I had a quote from His Holiness [the] Dalai Lama on the wall. And then I pointed out I also had photographs from Yankee Stadium when the Yankees beat the Mets in the World Series. So, I was like, “Well I’m a little bit of a different kind of guy.”

I think that the heart of your question is, how is it, in fact, not that soft-bellied kind of light approach? And my answer to that is, I think that the most challenging, most brave, thing that we can do is actually to look inside of ourselves – at our demons, at the structures of mind – and to understand the roots of our fears, the roots of our aggression, the roots of the choices that we have made. I think that takes a tremendous amount of courage and strength.

So far from being soft, I think it’s one of the hardest things possible.

Rachel Salaman: Your Reboot boot camps, as I said, famously make CEOs cry. Could you give us some context for that?

Jerry Colonna: The notion of tears started something as a joke. Wired magazine did an article on me, and it said, “This man makes founders cry.”

You know, what I often say is: it’s not about the tears, it’s actually about the feelings. And when you slow someone down… And sometimes it’s not just at the boot camps. I might do a speaking engagement where I stand up on stage and I slow down the pace of the room. You know, I did this a few weeks ago with 700 people in the room and there was just a buzz in the room that was exciting, but awful at the same time, and I just stopped everybody in the room, and I said my infamous question that makes people cry. I said, “How are you?”

That’s all I did, was to say, “How are you?” But asked it in a way in which they actually inquired within, and they began to pay attention to their feelings. What I have found is that when we get people to slow down and pay attention to their feelings, sometimes – oftentimes, because of the stresses of modern life – tears flow.

Rachel Salaman: And then how does that move forward to something positive, to some kind of development?

Jerry Colonna: Well, you know, if you look at the structures that impede the progress of an organization, or you look at the structures that perhaps stop a leader from fully actualizing as a leader, oftentimes it’s the things that are not being said. Oftentimes it’s the fears that they’re carrying.

So, for example, I was just speaking with someone last week who… Their “presenting challenge” as a leader is conflict avoidance. And we’ve all had leaders who avoid difficult conversations within organizations.

And this can spread, kind of like a cancer, within the organization, where people are just not dealing with tough issues, and the result is that the organization actually is impeded in its growth. Well, as we started to unpack it, we really made a connection to the fact that he is scared of being alone. And why is he scared of being alone? Because when he was eight his father walked out on the family.

Now until he understands that about himself, and takes back that experience and internalizes it, processes it, and then puts it away, he’s going to maintain the structure of conflict avoidance, which is then going to impede the success of the organization.

Rachel Salaman: Clearly this “radical self-inquiry,” which is what you call it in the book, is very powerful. Is it something we should attempt by ourselves, either individually or with the people that we coach ourselves?

Jerry Colonna: Let’s back up and describe more fully “radical self-inquiry.” So what I often say is it’s simply the process by which, with compassion and skill, we strip away the masks that protect us. And the most important person from whom we are stripping away the masks is ourselves.

So, with that as a framing and an understanding – compassion, skillfulness, cutting through your own delusion. “Who, me? I’m not afraid!” That’s a delusional statement. If we look at it from that perspective what we see is it’s actually a practice that one can live every single day.

Now, here’s a little bit of the Buddhism that I was talking about before: imagine waking up to your life, imagine spending a few minutes every day saying, “Why did I have that conversation that I just had?” or, “What is it about this failing that is going on in my organization that’s so scary?”

That’s the kind of day-to-day practice that one doesn’t need a coach for, doesn’t need a therapist for. You just sort of look at your life instead of looking away.

Rachel Salaman: So, would you in fact advise us to do that by ourselves, or is it better to be guided by an experienced coach, such as yourself?

Jerry Colonna: I think one should do it in all instances. I mean, for example, take a romantic relationship: imagine sitting down with your partner at night and not just saying, you know, blithely going through the recitation of what your day experience was like, over some reheated food, but to actually look across the table and say, “How are you doing? What are you carrying? What might you be afraid of, what might you be excited about? What are you looking forward to?” And imagine being able to share from your heart, that!

So, I know it can feel scary to open up and look in. Here’s a visual for yourself: imagine all of these feelings, all of these experiences, all of these complex structures from our childhood are kind of in a jumble in the closet. And it’s scary to open up the door, because everything may tumble down upon you. But imagine just sort of taking it all out, sorting it through, handing off a bunch of things to charity that you no longer need, and putting it back in nice neat little boxes and appreciating it. That’s what I’m talking about doing.

It’s great to have a community of people around you, it’s great to have a partner who reflects back to you – it’s also wonderful to be able to do that on your own.

Rachel Salaman: Your book is a kind of memoir – it shares lessons that you learned through your own experience. Could you tell us a bit about your early life?

Jerry Colonna: First, let me frame it by saying the reason I did tell stories from my own life was because, as I say in the introduction, I don’t really feel comfortable asking you, or a client, or a reader to examine their life without being willing to show an examination of my own life.

I think that too often we’re given leadership books where people, forgive me, wag their finger and tell somebody else how to do it. And I think that we learn best by having someone model for us that which they are talking about. So, I’ll say that.

Then, with regard to my childhood, there are a number of stories that I share that have shaped who I am. One, for example, occurred when I was 10 years old, in which my father, after about 30 years working for the same company, had come home just before Christmas and announced that he had lost his job and that he was for the first time in his life without a job.

It was the first time I ever saw my father cry, and it stuck with me. It was only years later that I came to understand that that experience shaped so many of my career choices.

So, for example, I get a little nervous if I’ve worked for the same company for more than eight to 10 years. Because there’s a part of me that wonders, “Is some guy going to come down and fire me?” Right?!

So I’ve always gravitated towards jobs in which I was the one making the decision. I’ve always gravitated towards jobs where it was my company, and I’m much more comfortable that way.

Rachel Salaman: As a young man you say you were, quote, “desperate and anxious,” and actually nearly dropped out of college because you couldn’t pay your tuition.

Jerry Colonna: That’s right.

Rachel Salaman: Yet four years later you were the editor of a successful magazine. So how do you account for that turnaround?

Jerry Colonna: It’s a very specific path. When I look backward I see the path – when I was in the middle of it I saw no path, but when I look backward I see the path – and the path went like this: I was desperate and I went in to see my college advisor, and I explained to him that I wasn’t going to be able to pay tuition and I had to drop out. And he was such a kind man, such a thoughtful man (and kind of an angry man, in some ways – angry at the system), he said, “Well, that’s not going to happen, not on my watch.”

He happened to be the sole judge of a scholarship contest, a brand-new scholarship, and he said, “It’s my decision, you’re getting the scholarship.” The scholarship, not only did it pay my tuition for the rest of my college career, but it came with a summer job, a summer internship. And with that opportunity, I ended up staying in that journalistic enterprise, that magazine, for nearly 10 years.

Yes, I worked hard. Yes, I found my way. Yes, I impressed my supervisors. Yes, I was innovative, and all of those things. But I was also really fortunate and had the privilege of running into someone who said, “Not on my watch. You’re going to remain in school and you’re going to get an opportunity.”

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Rachel Salaman: From journalism you moved into venture capital, working at J.P. Morgan and also founding your own investment company. How and why did you move from there to becoming an executive coach?

Jerry Colonna: Well the story of leaving venture capital to become a coach feels like it was, when you look backwards, it feels like it was a natural progression, but in fact there was a long period of wandering in between.

I knew that I had hit a point in my life in my late 30s, 38 years old, where the inner part of me was not matching the outer part of me, and that no amount of approbation and affirmation was enough to assuage the internal parts of me that knew that something was wrong.

I had outward success and inwardly I was miserable. So much so that I was suicidally depressed. This was no joke because in my late teens I had attempted suicide. So, what had been a life-long relationship to depression came back, with a kind of meanness and power that really stopped me and made me just walk away from the life that I had created.

It was during that period, say 38 to maybe 44 – classic midlife, classic second adulthood, if you will – that I became aware that there was a different way for me to live and a different way for me to make a living, which was to dive into these deeper questions with people and really bear witness to them. In a sense, going back to my old skills as a journalist where I would ask a lot of questions and take notes on their answers and reflect back what I had heard.

Rachel Salaman: Yes, I can see that it’s quite a similar skill set. Why do you focus on senior executives as coachees?

Jerry Colonna: Well we don’t focus, “we” as the company and myself, we don’t focus exclusively on CEOs or senior executives, but I will say that there is a sort of underlying wish that we have, which is to affect culture. And if you want to affect culture you have to go where power is.

So I’m really intrigued by working with people who have power, because those who have power, who don’t do that work, can really do harm to all those around them. Whereas if you can work with someone who has the authority and agency to affect a culture, then you can help the lives of many, many other people around them.

Rachel Salaman: In the book, you make the point that people always want to know that they are on the right path and always expect their trajectory to be upwards. But you don’t necessarily subscribe to that idea, do you?

Jerry Colonna: I think that I understand entirely the wish and the impulse – it’s about mitigating fear. And I think if anyone looks back over the course of their lives, they will find moments in which their life seemed to be taking a step backward, only to take them in the right direction.

I think this is how lives unfold. We do a lot of careful planning, we do a lot of anxious anticipation of what the future will hold: “I’m going to graduate university, I’m going to get a job, here, I’m going to put enough money away to pay my bills, and then somewhere in my 30s or 40s I’ll start to be happy.” You know, the deferred life plan, as we say.

Then things happen (it doesn’t necessarily have to be bad things) all of a sudden: at 29, you meet the love of your life, and all the plans are tossed out the window. Or you lose a job, or you have a parent get ill, or the company that you thought was the perfect company turns out to be led by a fraudster. I mean, things happen!

And I think one source of suffering is the belief system that it’s all knowable, it’s all discernible, it’s all something we can plan for. And then, when [the] normal events of our lives happen, we are rattled, and we start to believe that we did something wrong.

Rachel Salaman: So what value does career planning have, in your view?

Jerry Colonna: I think career planning, like any planning, is really important. But we need to understand what we’re really trying to do there – we’re trying to mitigate fear.

And this is true for the entrepreneurs who are out there, as well. I often say this about business planning: in the 150 companies that I’ve ever invested in, not one ever executed precisely according to every step in their business plan. So, is a business plan worthless? Is a career plan worthless? Of course not, but you hold it loosely.

Rachel Salaman: Another really interesting quote from your book is, “Work is an opportunity for a daily realignment of the inner and outer, a daily do-over of life expressed with integrity.” Could you expand on that idea?

Jerry Colonna: Sure. To link it back to something we were talking about before, from my own experience I came to understand that when my outer actions are not in alignment with my inner beliefs and values, that not only do I act in a way that is perhaps either passive or actively aggressive, hurting those around me that I love, but also hurting myself in creating a kind of discomfort and disease.

Now, why does that happen? Well it happens because there are all these forces at play, in the world at large, that kind of move us to act in certain ways. If you’re leading an organization, you might every day have a real reassertion of your value system that “we put people first,” and then you have public shareholders who are saying, "But what about profits?”

So every single day you’re presented an opportunity to realign those and say, for example, that putting profits at the top by itself may not be in alignment with your values. But, simultaneously, putting people at [the] top by themselves, without also understanding that the fiscal health of the organization is equally important, means you might be living out of sync as well.

So, every day you get this opportunity to sort of sync up and make choices based on an alignment between your inner belief systems and your outer actions.

Rachel Salaman: Earlier you were talking about “opening up.” What are the benefits of opening up to employees and other stakeholders in an organization?

Jerry Colonna: Well, I often explain it in this way: there’s no value necessarily in vulnerability for its own sake, other than perhaps in an internal alignment between who you are and what’s going on.

But, more specifically, those of us who are in our life circle, whether it’s family or friends or employees or colleagues, they can feel how we’re doing. They may not understand precisely what’s going on, but they can feel it.

I often speak to leaders and say, “If you want to understand how trust is a problem in an organization, say one thing and feel another. Say, for example, that you think the product works when you know in your heart it doesn’t. And then ask how trustworthy you’re coming across.”

Worse yet, when our colleagues and those of us who have less power are in a situation where we can sense a dissonance between what the leader is saying and what feeling they’re projecting, then what happens is we start telling ourselves stories about how awful things really are, and the result is that our anxieties get triggered and our productivity goes down, and our trusting goes down.

Rachel Salaman: In the book, you do acknowledge that there is a risk that we can share too much. How much should we worry about that? Should that be a factor in all of this?

Jerry Colonna: I think we should pay attention to the effect that we’re having on other people. And I think that it’s not a function of sharing too many feelings, it’s a function of asking other people to be responsible for solving our feelings.

So, for example, I might say to you, "Be honest, Rachel, with your colleagues and employees.” That doesn’t mean you walk in and say, “I’m freaking out!” Because you’re implicitly saying to them, “Please take care of me.” Well that’s not their responsibility.

But, if you walk in and you had a terrible weekend because you had a fight with your life partner and it’s awful, they’re going to walk in, they’re going to feel the tension that exists in your body and they’re going to say, “Uh-oh, company’s going out of business! Better polish up my résumé, I’m on my way out.”

Whereas if you walk in… You don’t necessarily have to share the content of the argument, but you can say something like, “Hey, just want to give people a heads-up, I’m not feeling my best today, had a rough weekend. So if I come across as a little short, that’s what’s going on.” And that’s it, right? Just nice and light.

Rachel Salaman: And I suppose a lot of these tips and insights can be useful for anyone in the hierarchy. They’re particularly useful for leaders, as you’ve outlined, but for people at all levels this is useful insight, isn’t it?

Jerry Colonna: I think so. I mean, it’s why I think that so many folks have read the book and said, “Whoa, hold on. This is not necessarily a book about leadership, this is a book about being human and growing up.”

If you’re 21 and at the start of your adult career and you learn a lesson about just paying attention to how you are truly feeling, that’s a good lesson to hold on to. Whether or not you have authority and agency in an organization, that’s alright.

Rachel Salaman: Now a lot of the most insightful conversations that you recount in your book happen on walks. What is it about walking that helps people open up and dig deep, and do you think we should try and do more of it?

Jerry Colonna: I do, I think walking is amazing. What I often ask people to visualize is walking shoulder to shoulder, side by side. No one’s leading, no one’s pushing, no one’s following – two human beings walking and being human together.

There is a neurological hack that goes on there, which is that when two or more people are walking together, most people will find themselves bodily falling into cadence with one another, and this sends a signal to the body’s limbic nervous system that “I am not alone.” And in that “I am not alone,” all of a sudden, I find it safer to actually share what’s going on in my heart.

So if you’re having difficult conversations with employees or life partners, go for a walk.

Rachel Salaman: Now in the book you say that you’d like your book to act like a coaching session, and there are several searching questions scattered throughout it. What are the key one or two of these that you’d like to leave people with today?

Jerry Colonna: Well I think one of the most important questions to ask of someone who might be charged with shaping an organization is, what kind of company do you want to work for? That can be a little rattling, because people presume that it’s out of their control to define what kind of company they want to work for.

Then, as a sort of secondary, corollary question to that: if your child, or someone you love, came to work for that company, that organization, how would you feel? If the answer is any hesitation, I’d explore that a little bit. What’s happening?

Because we get to create and shape the culture of the organizations that we work for (regardless of our positions of power) every day. And that’s a kind of consciousness that I think we’re all well served by bringing.

Then, lastly, to me the most important question isn’t even about leadership but it’s about being human. And that is, what kind of adult do I want to be? There again, there’s something radically different about that, because it implies that I have a choice. And that’s actually the main message I want to convey: you have a choice as to how you would like to be. Choose wisely.

Rache Salaman: Jerry Colonna, thanks very much for joining us today.

Jerry Colonna: Thank you, Rachel. It was really a delight.

The name of Jerry's book again is "Reboot: Leadership and the Art of Growing Up," and you can find out more about him and his work at www.reboot.io.

I'll be back in a few weeks with another Expert Interview. Until then, goodbye.