Hello everyone and welcome back to 33 voices. I am delighted today to welcome someone I have long admired and it's a real privilege that this opportunity to speak with him. Not only with for the work that he does but more importantly for the human being that he is in the example. He is Jerry Kelowna is the CEO and co-founder of one of the Premier leadership coaching firms in the world, and I hate to use the word coaching Jerry because I think you guys do much more than that reboot the depth of experience not only in business in Venture in private Equity that he brings makes them especially gifted for those who work with him. But as you're about to find out I think now the world gets a glimpse of what he does and what is firm does so Jerry great to be with you.
Well, well, thank you for having me Mo. It's really a delight to be here. So anyone
who knows you understands your uncompromising belief?
In radical self inquiry so I am curious for you personally. You've been so open in your book and it's just so open I think as an individual how have the questions that you've been asking yourself changed say over the past year or
so.
Over the past year.
Yeah, we're just generally because I know that you did that that's really critical for you and the people that you work with
well if we can expand the time Horizon just slightly to say the past few years. You got it. What I would say is, you know, when I when I talk about radical self inquiry and I talked about this sort of process of stripping away the ways in which we delude ourselves and I over the last few years. One of the things I found that I've had to do was stress again and again the notion of doing so with compassion because when I first, you know to back up many of the questions that I ask others are questions that I myself have been asked
Right and so, you know famously I talk about three magic questions. What am I not saying that needs to be said what's being said that I'm not hearing and what am I saying? That's not being heard and those three questions for example evolved out of me answering those questions for myself, but over the last few years one of the phenomena that I noticed was that as people started to look at the internal structures of their lives what I often refer to as the subroutine programming of their childhood that carries over into adulthood and defines how they lead and how they live that there's been this corollary response that happens which is self-criticism and it kind of goes like this. Can you believe that? This is the way I behave right?
It's and so what I've had to do and how I've had to evolve the process over. The last few years is to give people the warning that radical self inquiry is not licensed to beat oneself up that we're not doing it to find fault. So it's not the other person's fault. It's all my fault. No, no, no we're doing is trying to sort of cut through with discernment and figure out what the what the hell is really going on here so that I can then consciously make choices about what I want to change not so that I can find
fault.
One of the things you mentioned before we started this was this whole idea that's really fascinating to me about the permission for each of us to step into who we are and to be ourselves. And as you you mentioned these three questions, they're not easy obviously, especially if we if we understand the truth what makes it so difficult for most of us who are truthful to not only give permission to ourselves but to do it in a way that's meaningful.
Well here again, this is one of those moments where
The Temptation might be there to the Temptation might exist to use the difficulty as a nefarious way to sell criticized. Why is it why do I find it so difficult and I think that the Jujitsu move that's really important to make in that moment is to ask oneself a slightly different question. You ready? How has it served me for me not to see these things.
Okay, and the reason for that subtle shift is behaviors persist because they serve us.
Now they may not serve the better part of ourselves. They may not serve the part that our conscious mind wants to be in service, but they serve us.
And what's really important is that when one you know to go back to your question, why is it difficult?
What you know and I'll reframe it. Why has it been of service to me for it to be difficult?
It all of a sudden that line of inquiry gets to a much more helpful piece, which is how I maintain a kind of blindness to the structures of my life because it keeps me
safe. Absolutely.
Right? And so when I see that it's just a five-year-old and me trying to keep myself safe with a five year olds logic then I get to be very gentle and compassionate and remind the five year old that I am no longer five and that I am now an adult
And that I can do other things to keep myself
safe.
Will you talk about a lot of your very open about a lot of the turning points that have taken place in your life? Was there a moment or two when you knew that you had to make the shift that you're talking about?
Well sure. I mean there were there were several of those and I continue to have those confrontations with myself maybe not quite as dramatic but certainly impactful and meaningful maybe the most famous of which was in 2002 where the way I think about it, February 2nd 2002 standing at Ground Zero me choosing do I live or do I die?
And fortunately I chose to live and in the rest of my life unfolded from that nator moment, but there have been many many such moments moments of change and transition in my life moments where I have to you know, say what is true when I've been denying what is true in my own life moments where I've had to work with people that I love and who love me and recognize that I have been hurtful. There have been many of those moments. I will say this each moment has become
Marginally easier, but each moment is difficult.
Jerry is you have gone through this Evolution. You have a beautiful family talk about those you love and those who love you how has the shift that you've made for yourself impacted your family. How is a perception that you've started to have for you over the last decade or two impacted how the perception of your family that your family especially your kids have had.
Well, I want to be fair. One of the things that I am really really careful about is maintaining their own lives and their own separateness from me. So I'll I'll respond but by honoring that that's a question for them to answer in some ways. Now that said I will say this I remember a few years back. I was on CNN And the reporter was asked me a question about mental health and startup community and my response to her was to ask her a set of questions which then helped her connect to some deeper feelings. And then she cried and everybody on Facebook was watching commenting on this clip and my daughter Emma popped in and said something like yeah, this is great. But can you imagine what it's like growing up with a dad who asked you questions? You don't want to answer this.
I see that so, you know, I think that there's that going on. I think they what they have shared with me is enormous Pride kind of fierce willingness to look at their own lives in one form or another and a gentleness with which they're looking at that I will also add that they were insistent that I would be the one who recorded the audio of the book and not hire a voice actor. So that was kind of sweet. Well, you got a great
voice many of the people that I know who have worked with you say things like having a heightened sense of awareness after having worked for you with you of their feelings and of their discomforts and
How to sit with their pains and their experiences for those of us who were still in this figuring it out stage. What does it really mean Jerry to sit with your discomfort and sit with your pain?
Well, I think that so much of the what we identify as suffering right stems from our inability to sit still I think it was Blaise Pascal. I'm going to mangle the quote who said something like all of humankind's problems, then from people's inability to sit still by themselves in a room. I think that you know a client will call and say I got to get a hand on my schedule. It's incredibly busy. I don't understand what's going on and then we start to probe and we start to say things like well, how does it serve you to have no space in your day?
And then with a little bit of presence, they start to realize that it means that they don't have to answer questions that they don't want to answer. Like am I happy in my job as CEO?
And so I think that one of the most important adulting
skills
is learning to be with and be in a relationship with our conflictual ambivalent confusing uncomfortable perceptions and feelings, which is one of the reasons why I go into such detail about struggles mine and those of others is to really try to normalize it and to get people to realize that if they just pause and stay still and they're overwhelmed by those conflictual difficult feelings while they need to remember that they're not the only one who's having those feelings. And then from that place they begin to experience those feelings and then begin to make conscious choices around their life.
Rather than just acting out of a fear of feeling pain.
It's only me right the feeling that I'm the only one feeling it.
It's it. Not only is it only me but because I'm feeling these things I must be uniquely broken.
And that that just compounds the era of the ways.
Will one of the more important insights that you share about struggles is you know that the one of the common denominators in all of our struggles is always people right yet most of us still Overlook that what causes that
well because it's easier to think that the problem is a process or the problem is a product. Well, the problem is code or the problem is business model. It's much more challenging to think that it's wet where that's a problem and not Hardware or software running because it we start to die. We start to live in the realm of not knowing for sure what to do people people.
What works today with one person may not work with that person tomorrow or may not work with that person's colleague the next day and so we have to constantly tuned our leadership to the demands of the moment and that's can be exhausting.
So knowing that Jerry and if we were speaking to this emerging generation of leaders, this next generation of leaders who are going to probably make the most significant contribution to the world. What is it that they should understand about this notion that almost all struggles are related to people and how should they start to approach that?
Well, they should first of all recognize that if if what we just said is true and you and I both believe it to be true. Then the skill that they have to focus on is actually Communications.
And Communications isn't just one way speaking which is often times passes for communication. But it's also what it involves really active listening and which is why I like those three magic questions, right? The the second question what's being said that I'm not hearing is really really important because if you are actively listening you will hear things that are even going verbally unsaid but still being said within an organization and paying attention to that is essential to managing human beings.
Well,
well isn't the inevitability of leadership dealing with people
absolutely now that that's the definition of leadership is people and and and not even telling people what to do but listening to people asking questions prompting and provoking their own growth and their own capacity so that they can themselves solve problems that create scalability within an organization. It can be challenging because people can start to develop their own parallel processes. And so part of that leadership is to hold the holistic View and to understand what's happening, but not so tightly that you're in this position of telling people what to do all the time.
What do you recommend to individuals leaders out there who are dealing with very challenging people. I know that a lot of the people that you work with come to you to deal with people issues. So for leaders who were dealing with challenging difficult people, how do they serve them best?
We're out if we use radical self inquiry for a moment. One of the most important questions to ask is what were the conditions in which that person came to work at the company and and what was the setup
Right and so a challenging and difficult person had to have been hired by someone.
What was happening there?
Did the person actually change which I think is fairly rare or were they hired for the wrong position or were they hired with a different set of expectations or did they have a different set of expectations of what the job or company were about understanding that so that difficult and challenging person presents a whole set of opportunity for unpacking how effective is the organization and often times that difficult and challenging person is saying something that's quite true. They may not be saying it with skill, but they're saying something that's quite true. So what's the true thing that they're saying regardless of the
skill?
Why don't I want to go to a couple things that really stood out to me that about kind of the the whole idea of dealing with challenging people and really challenging ourselves. You sure a wonderful parable about coming to grips with our demons and I don't need to remind you that it can be terrifying for anybody who's going through it. What does it take to make this whole notion of eat me if you wish a little less frightening for people. I love that.
So so what you're referencing is an old Buddhist tale about a famous saint named Miller Epi who in the story comes eventually to get past his own ego based allusions to confronting in effect the true Challenge and he ends up facing the biggest most challenging demon.
It did that one. It's not just a question of surrendering but a willingness to put his head up to the mouth of the demon willingness to allow himself to be wiped out and destroyed by the truth of the that that demon represents. And in that moment. He says to the demon eat me if you wish and the magic is then the demon disappears right? It's the willingness to confront the most deadly the most dangerous the most fearsome.
fact
ttttt that makes the Fearsome fact that much more powerful to overcome. I think I forgot your question, but I wanted to re-emphasize the point of that story.
How do you that the idea was one? I love the parable because it makes a lot of sense to me personally, but my fault was obviously fear and doubt never leaves any of us. That's right. When they when you start to sense it when you start to sense fear or doubt or you start to sense of people you're working with are heading in that direction. How do you approach that?
Well to remember something like the fact that the demon disappears more often than not when you confront it. So for example client may come to me and say well what should I do? Should I tell the team that we're struggling with our finances and I which is a really scary thing and the fear is that they're somehow going to leave and what I often ask is well, would you rather have them stay for a lie? Right and that reframing can help them step into the fearful moment where they stand up and they get to say hey team we're struggling. This is our challenge now, I still believe in what we're trying to do, but you need to know the facts of the case. Well that moment that can be a really terrifying moment for a leader.
Sure.
So I think you know you made the point that the fear never goes away. The fear is quite sensible. It's coming from a place of protection. It's coming from a place of existential threat meeting as soon as existential threats, but what we know to be true and every wisdom tradition teaches us this that confronting the existential threat is actually the best way to deal with it running away hiding bypassing ultimately doesn't actually help it only makes the situation worse.
Hence the importance of the impermanence philosophy, right that impermanence is a fundamental fact of life yet again, we fail to see that when those types of things emerge.
That's right. That's right. You know, that's the gift of impermanence is that all things will pass all things change the challenging part of that is that all things change right and that we want only the
Things to stay the same way exactly. We want the bad things to to to change very very quickly only. It doesn't doesn't actually work that way.
How do you gauge somebody self-confidence I mentioned to you that I'm with a wonderful group of people here wonderful group of leaders who were talking about the next stage of growth for their organization is was a topic that we talked about yesterday's how do we identify our own self-confidence? And how would how do we develop an organization around ongoing growth of our self-confidence? How do you look at self-confidence?
I mean, what do I make of one's internal sense of self-confidence?
Yeah, and and from that do you tie it to self-worth as self-confident? Do you see that individuals who have a higher sense of self-worth tend to at least have a confidence level that they going to be there? They believe in what they're going to say whether or not it's accepted by others.
Yeah. So I see where you headed. I think that both that self worth and self confidence our are reflections of something much more profound going on that that is that they are the outcome of something much more profound going on and what comes to mind is how our Brock's notion of radical self acceptance. Sure.
And and I think that when one is willing to accept oneself all the way down to one's bones methanol self-confidence and self-worth grow out organically.
And so, you know just like I often use this metaphor and I use it in the book that staring at the sky looking for shooting stars is probably the worst way to see shooting stars that the right thing to do is to relax one's gaze and allow one's peripheral vision to notice the movement across the sky in the same way one needs to relax one's gaze. And then this case the hard gaze is the constant judgment and to allow oneself to say, I'm okay. I'm acceptable. I am enough as I am.
Even when I do things about which I am not proud, even when I do things of which I might even feel some shame.
And when you take that stance and you're in this place of acceptance self-acceptance, then self-confidence becomes a natural byproduct. Well, okay, I could be wrong but here's what I think or self-worth is becomes disconnected, right? We begin to start to see ourselves as worthy regardless of whether or not we fail and regardless of whether or not we're right or wrong.
And that's radical
one of the things you shared about that for you personally is your relationship with money and at some point or another again, I think all of us deal with it. Are you a piece now with your relationship with money is Bill Gates now just stay, you know, an individual who's making a great contribution to the world. Not the target.
It's great question. I would say that for the most part I am at peace and then there are times where gosh darn it. Why did I leave the Venture Capital business? Yeah, especially nowadays, right? Well, especially when I walk down the streets of Manhattan and I look at some gorgeous townhouse and my God if I'd only stayed in I could have bought that town exactly but but for the most part,
Yes for the most part. Yes, periodically I lose it. But here's what's really important. I
can recover
and that's really important to me. I can find my way back to Equanimity. Even when I lose it.
What do you do? Is it is it back to standing still is it meditation? Is there an approach that you take when you get that sense whether it's with money or other things?
What do I do? I think I talk to people I think I I have I have surrounded myself with a posse of wonderful people who help to remind me of who I am. There are times when you know that the community of people have to step in and intervene and say hey Jerry.
Look what you've done look at who you are. Just as I will do for them just as is is I often will do for them. And yes, you know lately I'll confess that I have felt a bit bedraggled and a bit overwhelmed by the number of inquiries and connecting points and yesterday just yesterday. I went through my calendar and and with love and care for the people who wanted me to come talk. I canceled a bunch of speaking engagements because it was too much and I needed to take care of myself and interestingly every single person wrote back and said I am so glad you're taking care of yourself.
Yeah, we need you.
Yeah, thank you.
The world needs you when you sit back and do that Jerry. Do you start to think about kind of the the next version of Jerry? I know that there are lots of more exciting things that you have in store. But how often do you sit down and evaluate? Hey, here's where I am today here is where I think I want to be tomorrow or next week or next year that a regular thing that you do.
It's kind of like I do every day. So it by doing it most days. I don't know. I
it's just a part of your life. So
it's just a part of my learning and Dad gasps sense
of how what you do there.
So my mornings are predominantly taken up with meditation and journaling and it usually takes about two hours before I can really be
Conscious and engage with other human beings. And in that quiet time, I'm doing a bunch of different things. I'm assessing not so much with the prefrontal cortex that intellectually. Oh, you know, it's a life. I'm leading, you know, but it's something much much much simpler. It's more like, how am I feeling? How am I doing? What's happening for me today? What am I? What am I thinking about for today?
And it's such a foundational part of my day that I no longer sort of call it out. It's just it just how how I approach the world. And then I Journal before I meditate which you know again, it wasn't something I consciously developed but it's just something that organically grew out and I think that that two-step process the first step is kind of a clearing of the Mind in the second step is just sitting in that space of for the most part of cleared mind that said there are many many times where the journaling session is preoccupied with a particular anxiety or particular story that I'm telling myself and the same thing is true with sitting on the cushion is there's often times a moment where I'm just sort of just completely wrapped up in preoccupied with something.
So I have a couple more questions for you and I'll let you go and I promised again this group that I'm with it. I would ask those but you're also triggered something else that you just said. When you think about this whole idea of the routine that you have the meditation the journaling premeditation and so forth has that become a practice for the people that you work with you find that being a Common Thread amongst the leaders and Founders and so forth that you work with that finally that get to this point of big unanimity and and kind of live in that space.
I don't know for sure. But I do know that many of the folks whether it's direct clients or folks who've come to our boot camps pick up a journaling and or a meditation practice.
And sometimes it shows up in the coaching sessions on one-on-one sessions. I might give a piece of homework and ask something like I was on a call earlier and I and I ask the person to journal and the question of what kind of CEO they'd like to be because of course, it implies that there are multiple kinds of CEOs and I wanted them to see that and so but I'd say that many of the people whether they picked up journaling or meditation they've certainly begun to incorporate habits of mind that I learned from my teachers and so in some ways, I guess I'm transmitting that teaching
you're an amazing coach you continually redefine this industry again with all due respect to other coaching. I don't see what you do similar to.
A lot of other people do and one of the things we were discussing and I try to discuss with with the any leaders that I'm around this whole idea that today. I believe the best leaders or the most admired managers or the ones who become great coaches. What advice do you have for again? The emerging leader maybe this next generation of manager to become better coaches.
Well to rely more on questions open honest questions, then necessarily believing that they're supposed to have the answers. I think it's the number one challenge that leaders run into and it's the thing that leaders could internalize and learn from coaching better than anything else and to be clear and open honest question is an is a question the answer to which you couldn't possibly know and if CEOs walked around and asked open honest questions of their employees amazing things would flourish. And so that's that's my wish is that more leaders would become coach like rather than coach has become more leadership.
Lastly your despite not being in the city or in the
Lee or in Venture anymore, you're still have a front row seat to people who have become and will continue to become wildly successful in building companies for those who become wildly successful. How do you help them deal with Fame? And for those who set who suffer setbacks? How do you help them deal with shame?
I think the antidote to both challenges Fame and shame blame and praise is to remember the truth of who they are and often times that means helping them remind helping to remind them of what life was like before the incidents that they were talking about so much of the dislocation that people will feel from either of those sort of circumstances.
Dances is exacerbated by not remembering who they are, you know to go back to something that you asked before about when I lose say my sense of enough and one of the things I said to you is that I'm surrounded by good friends who remind me of who I am and so in a sense, that's what that's what any good coach can do is to remind their client. Oh, right. You are this person and this is what you have done with your life and no matter what the blame or praise or fame or shame that you might feel. Don't forget who you are and who you have been
there is our criteria that you have for that inner circle that you keep in your life.
Very good skill and mocking me and making sure that my ego doesn't run amok.
Well it obviously they love you and you love them. And I think anyone who's around you knows that you're a gift and a treasure. I appreciate you sharing your time with me certainly and sharing your wisdom with us and hopefully they'll be plenty more to come the website or the firm is reboot dot IO the book is called reboot anything you want to leave everybody with
no. I just want to say thank you what a delightful conversation. It's been mowed really has been a
blast.
