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Reboot: Leadership and the Art of Growing Up
by
One of the start-up world’s most in-demand executive coaches—hailed as the “CEO Whisperer” (Wired)—reveals why radical self-inquiry is critical to professional success and healthy relationships in all realms of life.
Jerry Colonna helps start-up CEOs make peace with their demons, the psychological habits and behavioral patterns that have helped them to succeed—molding them
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Kindle Edition, 288 pages
Published
June 18th 2019
by HarperBusiness
(first published 2019)
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Start your review of Reboot: Leadership and the Art of Growing Up

Jun 28, 2019
Brad Feld
rated it
it was amazing
·
review of another edition
Shelves:
entrepreneurship
Jerry Colonna has written a “must read for everyone on planet earth book” titled Reboot: Leadership and the Art of Growing Up.
Jerry and I are extremely close friends and have been for 23 years. I first met Jerry when he was beginning his partnership with Fred Wilson at Flatiron Partners. But, I didn’t meet him through Fred. I met him through NetGenesis, a company I was chairman of at the time that had been started by Rajat Bhargava (who we still work with as CEO of JumpCloud), Matt Cutler (who w ...more
Jerry and I are extremely close friends and have been for 23 years. I first met Jerry when he was beginning his partnership with Fred Wilson at Flatiron Partners. But, I didn’t meet him through Fred. I met him through NetGenesis, a company I was chairman of at the time that had been started by Rajat Bhargava (who we still work with as CEO of JumpCloud), Matt Cutler (who w ...more

The book was not what I thought it would be. And I'm grateful because I'd probably not read it. I didn't even know that I needed such a book.
I needed it.
I've read a lot of leadership books and almost all of them focused on one's external work. How you scale, delegate, have one-on-ones, motivate, what manager's tools you should use, etc. It's all about work focused on other people. Obviously, a very important topic. But the more experience I have the more I think that leaders should primarily w ...more
I needed it.
I've read a lot of leadership books and almost all of them focused on one's external work. How you scale, delegate, have one-on-ones, motivate, what manager's tools you should use, etc. It's all about work focused on other people. Obviously, a very important topic. But the more experience I have the more I think that leaders should primarily w ...more

So many gems in this book 💎💎💎
In the introduction, Colonna frames the rest of the book with a series of questions you can ask yourself. Questions like:
💰 How did my relationship to money get formed?
🏃♀️ In what ways have I depleted myself, run myself into the ground? Why have I allowed myself to be so exhausted?
👨🏻🏫 Who is the person I've been all my life? What can that person teach me about becoming the leader I want to be?
👨👩👧👦 What was the story my family told about being real, being vulnera ...more
In the introduction, Colonna frames the rest of the book with a series of questions you can ask yourself. Questions like:
💰 How did my relationship to money get formed?
🏃♀️ In what ways have I depleted myself, run myself into the ground? Why have I allowed myself to be so exhausted?
👨🏻🏫 Who is the person I've been all my life? What can that person teach me about becoming the leader I want to be?
👨👩👧👦 What was the story my family told about being real, being vulnera ...more

This definitely ain't a book for me (but that's a conclusion AFTER I've read it).
It's not that I'm not a CEO, the reason is different.
It's a book about leading which looks (sounds, in my case) like it was written by Virginia Woolf - very personal, all about feelings, impressions, moods, etc. Probably there are some people it will resonate with - people of very similar sensitivity, or ones who have similar observations, or ... I don't know, but I guess there'll be some.
In my case it was simply .. ...more
It's not that I'm not a CEO, the reason is different.
It's a book about leading which looks (sounds, in my case) like it was written by Virginia Woolf - very personal, all about feelings, impressions, moods, etc. Probably there are some people it will resonate with - people of very similar sensitivity, or ones who have similar observations, or ... I don't know, but I guess there'll be some.
In my case it was simply .. ...more

I pre-ordered the book while listening to Jason Calacanis interviewing Jerry Colonna on his podcast This Week in Startups. That was a very enjoyable episode that felt like it contained a lot of good lessons for people like me, entrepreneurs. Sadly, this didn't happen with the book.
Based on other reviews and the interview, I'm confused. Did I miss something? Did it go over my head? I couldn't get anything from it. It felt like rambling stories with a touch of woowoo. ...more
Based on other reviews and the interview, I'm confused. Did I miss something? Did it go over my head? I couldn't get anything from it. It felt like rambling stories with a touch of woowoo. ...more

One of the most frustrating books I've ever read. Frustrating because the genuinely helpful insights about improving as a leader were drowned out by excessively poetic anecdotes.
For example…
“When our employees and colleagues leave our sides and our company, what do we want them to say about our time together?”
vs.
“Fearing broken skis, failed businesses, and the scars that come from skinned knees, we stay small—listening more to our Loyal Soldier’s fear-filled and protective whispered warnings ...more
For example…
“When our employees and colleagues leave our sides and our company, what do we want them to say about our time together?”
vs.
“Fearing broken skis, failed businesses, and the scars that come from skinned knees, we stay small—listening more to our Loyal Soldier’s fear-filled and protective whispered warnings ...more

I had the privilege and great chance to work with Jerry both as a member of a leadership team and individually and he has helped me/us break open our hearts, radically inquire within, and create strong backs with an open heart. Jerry has made me a better leader and I am grateful that he now shares his wisdom and personal story with the world through this book. Thank you, Jerry.

Initially when I had picked up this book, I must have been closed minded to the idea that it would have much relevance to me as I am not a leader in my field, my family or friends. But I was intrigued by the 'Art of Growing up' section on the title and from some reviews that I had read, it was enough for me to purchase this book.
By having this initial projection of myself not being a leader, I read the book not being able to relate to many of the stories, and thinking... 'he still has some good ...more
By having this initial projection of myself not being a leader, I read the book not being able to relate to many of the stories, and thinking... 'he still has some good ...more

As I started reading the book, I thought to myself "If Pema Chodron had written a business book, this would be it". By chapter 3, the author introduces Pema as his teacher. Ok, adds up.
The most valuable part of the book was the list of questions at the end of each chapter. They offer a great lattice for self-exploration. If you make the effort to write down answers to those via a deep and visceral examination of yourself, they can be edifying.
In general, I am not a fan of pop Buddhism - I find ...more
The most valuable part of the book was the list of questions at the end of each chapter. They offer a great lattice for self-exploration. If you make the effort to write down answers to those via a deep and visceral examination of yourself, they can be edifying.
In general, I am not a fan of pop Buddhism - I find ...more

Very interesting book, a strange mix of management philosophy, traditional belles-lettres and autobiography. I have “read” it as an audiobook, narrated by the writer. As usual in this case, it gives much more personal touch to the whole experience.
So many different layers could be found in its chapters that it requires several re-reads to fully digest their messages. The questions at the end of each chapter promote self-study. Highly recommended, though four stars only as I did find it time to ...more
So many different layers could be found in its chapters that it requires several re-reads to fully digest their messages. The questions at the end of each chapter promote self-study. Highly recommended, though four stars only as I did find it time to ...more

I listened to the audiobook. The narration was very slow and the seemingly endless anecdotes made me want to quit, which I didn't, but maybe I should have!
...more

To be a better leader, and human, read this book
Have you ever you come across a book that provides just the spiritual nourishment you were craving at the moment you needed it? To me, this is that book. I cannot express my gratitude to him to have written it. Jerry is an old friend and former colleague so I have a little personal experience with the magical insight he brings to his work as well as the forces that plagued him at the peak of his career in finance. He was always more honest about th ...more
Have you ever you come across a book that provides just the spiritual nourishment you were craving at the moment you needed it? To me, this is that book. I cannot express my gratitude to him to have written it. Jerry is an old friend and former colleague so I have a little personal experience with the magical insight he brings to his work as well as the forces that plagued him at the peak of his career in finance. He was always more honest about th ...more

There were some elements of this book I really liked. The journaling invitations were very good and were by far my favourite part. Not sure I would have kept going otherwise. I found it difficult to make connections between all the different stories used and after a while I tuned out. There were some really interesting insights in among the stories, but they were sometimes hard to find.
The other disconnect I haven't quite worked out is the combination of Buddhist philosophy and a fairly capitali ...more
The other disconnect I haven't quite worked out is the combination of Buddhist philosophy and a fairly capitali ...more

If you want to be a better leader, work to be a better person. This book explains why and how, through a deeply personal and affecting series of vignettes that unfold like a long walk with an old friend. I was both moved and challenged by it, the only questions left are the ones I need to answer for myself.

Aug 25, 2019
Adam Nowak
rated it
liked it
·
review of another edition
Recommended to Adam by:
Bartosz Pranczke
"To be a better leader, you need to be a better human!"
The thing I liked the most about this book was "Journaling Invitations" section at the end of each chapter. My favourites:
* What am I saying that’s not being heard?
* What am I not saying that needs to be said?
* What’s being said to me that I’m not hearing?
Self-reflecting on them has great power (stop for a minute and try to answer them), but I feel that sharing the answers and thoughts with other people is going to make the real difference ( ...more
The thing I liked the most about this book was "Journaling Invitations" section at the end of each chapter. My favourites:
* What am I saying that’s not being heard?
* What am I not saying that needs to be said?
* What’s being said to me that I’m not hearing?
Self-reflecting on them has great power (stop for a minute and try to answer them), but I feel that sharing the answers and thoughts with other people is going to make the real difference ( ...more

To grow as leaders, we need to be more mindful human beings who pay close attention to the things that have shaped our present behavior. This will improve and deepen the way we interact with colleagues and how we lead the team as a whole.
Above all else, it pays to become more humans, courageous people, because that is the path to less-toxic workplaces and companies that act responsibly regarding their employees, communitites and the environment.
So, take time for yourself outside of work.
Above all else, it pays to become more humans, courageous people, because that is the path to less-toxic workplaces and companies that act responsibly regarding their employees, communitites and the environment.
So, take time for yourself outside of work.

Good book and a reminder that in many ways work and life are not separate. When we are blind to this, we inevitably create conditions that are difficult for us and those around us.
Jerry describes all of this in a way that is unsurprisingly personal and heartfelt. By opening up himself, he demonstrates how radical self-inquiry and having the strength to step into the mouth of our demons and bring our colleagues along with us on this journey, can be an incredibly powerful way to lead.
A book that ...more
Jerry describes all of this in a way that is unsurprisingly personal and heartfelt. By opening up himself, he demonstrates how radical self-inquiry and having the strength to step into the mouth of our demons and bring our colleagues along with us on this journey, can be an incredibly powerful way to lead.
A book that ...more

I'm not big on leadership books but I thought I'd give a few a try this year. My biggest takeaway with what I've seen thus far are middle aged white-males adopting eastern religion practices and applying them to the workplace and their everyday growth. While this is a noble pursuit, a lot of these books can be summed up by this sentence: "Go learn buddhism, hinduism, etc - learn to let go and meditate, and return to work and apply some principles without too much disruption - and boom! you're a
...more

I’ve never struggled so much to figure out if I enjoyed a book or not. One page my heart would be racing because of a profound insight that made me consider life in a whole new light; two pages later I’d be rolling my eyes and skimming through a three-page description of an event that could have been half a paragraph.
It felt fairly indulgent and long, overall. I generally don’t love culturally glorification of people with dramatic backstories. (Would this book have come to be if Mr. Colonna hadn ...more
It felt fairly indulgent and long, overall. I generally don’t love culturally glorification of people with dramatic backstories. (Would this book have come to be if Mr. Colonna hadn ...more

Was very challenging to read as I found the personal story being told to focus on what happened without context. Many of the story points went something like "Then I was awesome, and they loved me for it." without explaining what was done, how the author came to that conclusion, or why it was the right thing to do.
The concept of Radical Self-Inquiry is what is shared here, and understanding yourself and nature is important. However, the expectation that this is a new thought and that every reade ...more
The concept of Radical Self-Inquiry is what is shared here, and understanding yourself and nature is important. However, the expectation that this is a new thought and that every reade ...more

This is a marvelous memoir and a mediocre book on coaching. I love his openness. And he's got a very poetic way of sharing his heart. But he stays at a high level with the psychology, with very little help on how to get from A-Z on the growth journey. And it's also very Buddhist, resulting in some part that I think are actually unhelpful in practice.
So don't read this for the actual methods on how to face your fears and grow as a leader. But he's so good at making the emotional journey feel leg ...more
So don't read this for the actual methods on how to face your fears and grow as a leader. But he's so good at making the emotional journey feel leg ...more

This book seems very similar to Fierce Conversations, which may be because I just finished that. They both speak to interrogating reality and being vulnerable as a leader, but Fierce Conversations delivers it in a much better way. This book was more like an autobiography than a leadership book and was condescending to those who are not CEOs, venture capitalists or engineers. Did not enjoy his narration.

(Gave up about 80% in)
On the one hand, as a coach myself, I really loved Jerry's approach to radical self-inquiry by looking deeper into your every day life and annoyances and understanding where that stems from - spoiler alert, it's never what it seems to be.
However, in my opinion the book didn't flow well enough and the mix of deep personal stories with client experience and pseudo-philosophical parts just didn't make it an appealing read. ...more
On the one hand, as a coach myself, I really loved Jerry's approach to radical self-inquiry by looking deeper into your every day life and annoyances and understanding where that stems from - spoiler alert, it's never what it seems to be.
However, in my opinion the book didn't flow well enough and the mix of deep personal stories with client experience and pseudo-philosophical parts just didn't make it an appealing read. ...more
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