Friday Book Club | Wisdom@Work: The Making of a Modern Elder.

December 18, 2020

Friday Book Club | Wisdom@Work: The Making of a Modern Elder.

May 29, 2023

An MEA alum recently asked me why I’ve never reviewed my last book, “Wisdom@Work,” for Wisdom Well. Honestly, I’d never thought of it...until this past week with the Airbnb IPO. So, here’s my attempt at giving W@W a new view based upon my past eight years as CEO Brian Chesky’s in-house mentor.

The evolution of this company is inextricably connected to the ascension of this founder from the Rhode Island School of Design who was 26 when he started the company.

When Brian reached out to me and said he wanted me by his side to help him “democratize hospitality,” I had very little clue what Airbnb was and a certain Boomer skepticism that this Millennial way of travel wasn’t ready for the mainstream. And, while I was impressed by Brian’s curious and visionary mind, I also wondered how we were going to vibe together. After two dozen years of being CEO of my own company, I’d now be reporting to a guy 21 years younger than me - who didn’t understand our industry and had never started a company - but I’d also be mentoring him. What was it going to feel like to get my first performance review from someone who was younger than my foster son.

We agreed on 15 hours a week with me receiving no compensation other than 10,000 shares of stock that would vest in six months (rather than the typical four years). We also agreed not to publicize my joining the company as we didn’t want the media scrutinizing our working relationship if I might only be there a few months. So, I had my parachute if I wanted to eject from this situation.

Within three weeks, Brian had added to my plate (as Head of Global Hospitality) being in charge of the company’s overall strategy and creating a leadership development program. I told him this isn’t a 15-hour-a-week job. It’s more like 15-hours-a-day. He smiled a Cheshire grin that said, “Fooled you,” as if I was now caught in his web and either had to be all-in or see this as just a short-term gig. I chose the former.

But, in order for me to commit myself completely, I had to come to grips with a few key facts. I didn’t know a thing about technology so being head of strategy for a tech company scared me. I was surrounded by a collection of employees who were, on average, half my age speaking a lingo I didn’t understand. And, as much as I was supposed to mentor Brian on the travel industry and how to be a great leader, he was mentoring me on Millennial travel habits and design thinking as much as I was mentoring him.

Soon, I earned the reputation of being the “Modern Elder” in the land of the young, someone who was as curious as he was wise. I recognized that I needed to “intern publicly and mentor privately” so I led with appreciative inquiry and gave Brian feedback weekly in my backyard cottage not far from our headquarters. I also came to realize that my rite of passage in this role required the following arc:

  1. Evolve. I had to be willing to shift my mindset and edit what was no longer serving me. Much of my past thinking (being a CEO, how many rooms a maid cleaned in an eight-hour shift, etc..) wasn’t as relevant to this new role, so I needed to lead with curiosity.
  2. Learn. My beginner’s mind felt fresh. I wasn’t living in fear that I might not succeed in this new role at age 52. Instead of trying to prove myself, I focused on improving myself, making notes every weekend about the key things I’d learned each week.
  3. Collaborate. My young co-workers had the DQ (digital and design intelligence), but I started to realize that my EQ (emotional intelligence) was valuable on all the teams I led or was a part of. Google has proven that psychological safety is the #1 common variable amongst their effective teams so part of my role was to ensure that teams - often full of young dudes trying to out-smart each other - saw the value of collaboration.
  4. Counsel. Over the past eight years, I’ve mentored more than 100 Airbnb employees, but there was no formal program and I often learned as much from them as they did from me. I came to realize I was often a “confidante,” who gave confidence to young leaders while also being the “librarian” as my know-how and know-who helped guide them to greatness

A few weeks into the job, Brian pulled me aside and said, “We hired you for your knowledge, but what we got was your wisdom.” Frankly, I’d never thought of the difference in 2013, but now a day does not go by when I don’t think about how the world is evolving to needing more “wisdom workers” since we’re awash in “knowledge workers.”

Writing this book and starting MEA reflected my early efforts to help the business world recognize that we ought to value wisdom as much as we do disruption. The start-up world is littered with unwise disruptors and most of them - whether it’s Travis Kalanick at Uber or Adam Neumann at We Work - lose their jobs as CEOs along the way. They didn’t have a “Modern Elder” by their side. I’m proud of the kind of leader Brian has matured into particularly based upon how he’s navigated this year. It feels like my work is done at Airbnb and I feel fortunate to be acting in this Modern Elder role now in a few other companies. Hope you enjoy the book!

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