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Reboot: Leadership and the Art of Growing Up

3.93  ·  Rating details ·  1,149 ratings  ·  144 reviews

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

Kindle Edition, 288 pages
Published June 18th 2019 by HarperBusiness (first published 2019)
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Average rating 3.93  · 
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Brad Feld
Jun 28, 2019 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
Bartosz Pranczke
Aug 11, 2019 rated it really liked it  ·  review of another edition
Shelves: 2019
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
Jun 21, 2019 rated it really liked it
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
Sebastian Gebski
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 ..
J. Pablo
Sep 06, 2019 rated it did not like it  ·  review of another edition
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.
Christopher Mahussier
Nuggets of wisdom are there, but need to be panned for. Book is far from uplifting and has a flair for the dramatic. Criticizing crow and nobel soldier were good characters to meet.
Dylan Mason
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?”


“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
Apr 11, 2019 rated it it was amazing
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.
Jul 16, 2019 rated it really liked it  ·  review of another edition
If you have questions about your life, this book will invite you to ask even more.
I found myself drifting off and then rewinding as questions sparked thoughts.
I think any business owner or leader will find thought provoking questions here and develop a desire to attend a Reboot boot camp!
Sep 09, 2020 rated it it was amazing  ·  review of another edition
Vulnerable, authentic, refreshing take on what it means to be whole, to practice radical self-inquiry, and to be a human.
Judy Phin
Feb 29, 2020 rated it it was amazing  ·  review of another edition
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
Jul 16, 2019 rated it liked it
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
Jun 29, 2019 rated it really liked it  ·  review of another edition
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
Eoin O
Aug 15, 2019 rated it it was ok  ·  review of another edition
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
Jun 26, 2019 rated it it was amazing
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
Kathy Durand
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
Nov 23, 2019 rated it it was amazing  ·  review of another edition
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.
Barry O'Neill
Aug 19, 2019 rated it it was amazing  ·  review of another edition
Essential reading for entrepreneurs. Or anyone.
Aug 25, 2019 rated it it was amazing  ·  review of another edition
Not your typical leadership book. In fact, this book is for anyone seeking to live a whole and authentic life.
Adam Nowak
Aug 25, 2019 rated it liked it  ·  review of another edition
Recommended to Adam by: Bartosz Pranczke
Shelves: 2019, audiobook, be-better
"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 (
Dec 24, 2020 rated it it was ok  ·  review of another edition
This was the audio book, and his voice was so victim based and depressing as if he was the only person in the world who suffered. Terrible.
Ethan Nguyen
Nov 22, 2020 rated it it was amazing  ·  review of another edition
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.
Ruslan Zaydullin
Jan 14, 2020 rated it it was amazing
The kindest and gentlest book about leadership

It just tore my heart open. True, clear messages, based on amazing storytelling by the kindest author. I was in tears many times. Absolutely happy I’ve found this gem. As a CEO of a 70+ people startup, there was a lot of insights for me.
Pritesh Pawar
Sep 02, 2019 rated it really liked it  ·  review of another edition
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
Richard Kriheli
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
Nov 02, 2019 rated it really liked it  ·  review of another edition
Shelves: 2019
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
Warren Parad
Nov 10, 2019 rated it did not like it  ·  review of another edition
Shelves: dropped
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
Scott Wozniak
Dec 12, 2019 rated it really liked it  ·  review of another edition
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
Oct 09, 2019 rated it did not like it  ·  review of another edition
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.
Claudia Mangeac
(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.
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