Wisdom @ Work

But back in 2013, when I first met Chip, Airbnb was still just getting started. Though we had nearly four million guests staying in homes around the world, most people saw us as strictly a technology company. But Joe, Nate, and I knew we had more to offer. We knew that we weren’t just in the business of home sharing. We envisioned a community that helped people with not only where you stay, but what you do—and whom you do it with —while you’re there. In other words, a complete end-to-end trip. What we were actually selling was hospitality.

And from how he’s translated Maslow’s hierarchy of needs into a hierarchy of hospitality, to his deep understanding of Joseph Campbell’s revolutionary approach to storytelling, I knew his knowledge would be invaluable.

He affirmed that we all have a story to share and something to learn from one another. That if we take time to connect, we can learn anywhere and from anyone.

It is not by muscle, speed, or physical dexterity that great things are achieved, but by reflection, force of character, and judgment; in these qualities old age is usually not only not poorer, but it is even richer.’

—Cicero (106–43 BC)

If there’s one quality I believe defines wisdom in the workplace more than any other, it is the capacity for holistic or systems thinking that allows one to get the “gist” of something by synthesizing a wide variety of information quickly.

Ninety-two-year-old Brother David Steindl-Rast, whose TED video on how happiness is synonymous with gratitude is legendary, told me, ‘Yes, I’d agree that the first task of an elder is to listen with genuine interest to younger people: how much we might be able to give them will depend on how well we have been listening.

Science fiction writer William Gibson wrote, ‘The future is here. It’s just not evenly distributed yet.

How can you be so wise and so clueless at the same time?

I was learning the less there is of me, the more room there is for the person I was mentoring.

Perhaps most significant for my future role as a Modern Elder at Airbnb was the fact he did his best to intern publicly and mentor privately.

She believes we need to move from mentors to sponsors because a sponsor advocates on your behalf.

Sallie says, ‘All the important decisions about your career are made when you’re not in the room. People decide to hire you, fire you, promote you, fund you, send you on the overseas assignment, all when you’re not there. So how do you ensure that you have someone in the room fighting for you? I would strongly argue that you need to have in place your Personal Board of Directors. Those are your mentors, your sponsors, your confidants, the people you can turn to when you’re thinking about a career transition—for the kind of advice your boyfriend, your parents, and your best friend from college just can’t give you.

Whether it was the pace of growth of a “unicorn,” cultural trends of millennials, or how to size up the needs of Silicon Valley investors, Brian taught me as much as I taught him.

If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.

My friend Gina Pell, forty-nine, coined the term “Perennials” in 2016 to define the idea that people may be in their prime much longer, in ways that defy traditional expectations about age.

...distinguished three key phases in a typical rite-of-passage ceremony: (a) “severance” from the past; (b) a “threshold” that is the uncomfortable space of being in between two phases of your life; and (c) the “incorporation” of reentering the community in a new role.

He sees his role more as a translator of youthful vision into operational excellence.

Elizabeth White felt that sense of liminality when she was fifty-five and in between jobs; and it didn’t help that her phone had stopped ringing. This fierce, smart African American had graduate degrees from Harvard Business School and Johns Hopkins and had been a project officer for the World Bank and was eminently qualified to make a difference in so many ways and yet she was barely eking out a living through occasional on-and off consulting gigs. She felt invisible and in free fall. It was as though, as she puts it in her TEDx talk, she had ‘entered the uncertain world of formerly and used to be.

I woke up every morning, meditated, and then listened to k.d. lang croon “Hallelujah” as my way of emboldening myself for another day.

I came across all kinds of fascinating studies in researching this book, but one of my favorites comes from Jack Zenger and Joseph Folkman, called “How Age and Gender Affect Self-Improvement” (Harvard Business Review, 2016). Drawing on Carol Dweck’s work on fixed versus growth mindsets, they studied seven thousand businesspeople through self assessments and 360-degree reviews from coworkers. They found that older people were more open to self-improvement and less defensive to criticism because they had evolved over time to focus on improving instead of just proving themselves. And the researchers found that the more self confidence individuals have, the more willing they are to change.

Sufis, like the poet Rumi, were the first to become “whirling dervishes” as a means of shedding the earthly identities to achieve a transcendental state.

It meant I could evolve to make my new costume, as Sylvia Townsend Warner put it, ‘not just a thing one wears,’ but rather ‘a thing one does and is.

For many of us, there’s a gradual “molting” that occurs before the world sees our new identity.

I was no longer the ‘sage on the stage’ but was instead transitioning into the ‘guide on the side.’ More than anything, in those first few months, I just listened and watched intently with as little judgment or ego as possible.

As I wrote in my book Emotional Equations, leaders are the emotional thermostats of those they lead, and our habits as leaders can spread like a contagion.

Our reputation is one of the few portable assets we can count on our entire lives.

The cult of productivity has its place, but worshipping at its altar can rob us of our sense of curiosity, joy, and wonder and rob a company of its ability to self-reflect.

We can take eighth-century Buddhist sage Hui-Neng’s advice: ‘Show me the face you had before even your parents were born.

And, then, what qualities are you ready to part ways with? In other words, which qualities are like toxins best removed from your system? The capacity for change with a ballast of continuity defines the Modern Elder.

Gandhi clarified the connection of beliefs to destiny in the following linear, poignant way: ‘Your beliefs become your thoughts. Your thoughts become your words. Your words become your actions. Your actions become your habits. Your habits become your values. Your values become your destiny.’ So, at your core, what beliefs define your reputation?

Older brains often flourish with a diverse set of sensory and intellectual inputs.

For many of our hosts, the better they feel about their hosting, the better they feel about themselves as a human.

What if improving our review system could create a more effective feedback loop so guest satisfaction might surpass the hotel industry, even though those delivering the service aren’t our employees?

Alan Eustace was a fifty-seven-year-old Silicon Valley engineer in free fall. No, I’m not referring to the sad truth that many older engineers are discarded by their employers. I’m referring to the fact that Alan holds the world’s record for the highest altitude free-fall jump. In 2014, after years of preparing, he fell from 135,889 feet in the stratosphere, becoming a human projectile falling at a rate of 821 miles per hour. I get a nosebleed over ten thousand feet, so I was particularly impressed when I had the honor of spending a few minutes talking with him about the near decade he spent as the head of engineering globally at Google during their most significant early growth years.

Alan was a rock star technologist in 2002 when he joined Google, which was then just four years old and bringing in very little revenue. And he was about fifteen years senior to its founders, Larry Page and Sergey Brin, who had set out to hire very senior technical leaders who’d become available in the wake of the disintegration of some of the great research institutions like Xerox PARC and Bell Labs. Yet “Larry and Sergey weren’t interested in how you did things before,” Alan says. ‘They just wanted it done the smartest way and they wanted to have confidence that you weren’t taking the easy path by just repeating what you’ve done before.

As the greatest basketball coach of all time, John Wooden, put it, ‘It’s what you learn after you know it all that counts.

Author David Cooperrider suggests in his book Appreciative Inquiry, ‘Human systems grow in the direction of what they persistently ask questions about, and this propensity is strongest and most sustainable when the means and ends of inquiry are positively correlated.

Show me the typical question that emerges from a meeting of any company’s leaders, and I’ll show you the culture of that organization.

When Eric Schmidt was CEO of Google, he said, “We run the company by questions, not by answers.” Their Friday afternoon company wide meetings were famous for the wise questions that were posed from line-level employees to leadership.

Here’s how to avoid the traps that inhibit a questioning culture in many organizations:

1. Avoid Using Questions Like a Hammer. In companies that swing the questioning pendulum too far in the direction of intense inquiry, you often find know-it-alls using questions as a way to stroke their ego and show off. When questions are used as a hammer to drive an existing viewpoint rather than as a flashlight to shine light on new ones, you don’t elicit productive reflection. To remedy this, focus on empowering rather than disempowering questions, which we’ll outline in the ModEl Practices section of this chapter. When in doubt, offer a healthy mix of authentic empathy and sharp curiosity in your questions. I once offered the following private feedback to a constant questioner who was grandstanding a bit and creating unneeded tension in the room: ‘Wisdom is whatever is left after you’ve run out of your opinions. Be careful not to use questions as a means of just expressing a strongly held belief.’

1. Know When It’s Time for Questioning and When It’s Time for Efficiency in Decision-making and Execution. A questioning culture can slow things down and, if it’s a hierarchical organization like the military, it can lead to confusion in strategy or lack of leadership direction. So it’s important to recognize if your organization isn’t built for questioning at times when the pressure is on, deadlines are looming, and stakes are high.

3. Foster Candor and Psychological Safety. Part of the reason many employees don’t feel comfortable asking tough questions is a fear of reprisal for being a ‘troublemaker’—or even losing their job. Author Edgar Schein poses a very important question that leaders can be asked as a measure to determine the level of psychological safety in an organization: ‘If I am about to make a mistake, will you tell me?’ If there is not enough candor and safety built into an organization’s culture to honestly answer yes, then the next question becomes, ‘What do we need to do differently to develop and create that kind of culture?’ Without it, people may take a less candid CYA (Cover Your Ass) approach to communication.

4. Be Clear That Alignment Is the Ultimate Goal of Questioning. A questioning culture is not synonymous with democratic decision making, although they’re often confused to be the same. Companies that do this well make very clear when it’s the right time for questions and potential disagreements and when it’s time to align. It’s critical to be explicit about this. Pat Lencioni’s book Five Dysfunctions of a Team (which we used as an Airbnb leadership team) gives good direction on how to clarify the difference between debate and alignment.

5. Make Sure Senior Leaders Are Actively Engaged in the Questioning Process. If senior leaders don’t actively take part in the questions and debate, whether it’s because they’re not in the room or because they are preoccupied on their phones or laptops, it sends a deadening signal to everyone else. Additionally, when a truth has been uncovered through the questioning process, but senior leadership doesn’t see it or take action, this can dissuade energy expended by the group in a future debate.

After interviewing thousands of candidates, I’ve found these three questions to be the most catalytic in terms of learning more about a candidate:

a. In some ways, we’re probably all occasionally misperceived at work. People see us one way, but—in truth—we’re different than that. What’s the most common way you’re misperceived?

b. What’s the biggest mistake you’ve made in your career? And why did you answer the question with this particular mistake?

c. At what skill are you world-class? And I’d be honored if you gave me some evidence of that talent?

We started by reading the book The Five Dysfunctions of a Team by Patrick Lencioni and hired a facilitator from the author’s company, the Table Group, to help oversee daylong and multiday off-site retreats every few weeks. This was quite a commitment of time and required a stripping away of old costumes and the summoning of our catalytic curiosity.

But, as evidenced by a film on intergen jazz collaboration I’ve listed in the appendix, Keep On Keepin’ On, masters almost always learn something from their superstar students as well.

Nearly 40 percent of the American workforce has a younger boss (a number that is growing quickly), but here’s a scary set of stats. When leadership development adviser Jack Zenger reviewed the seventeen thousand worldwide leaders who had gone through his leadership training program, he found the average age was forty-two. And yet the typical individual in these companies had become a supervisor at around age thirty and remained in that role for nine years—that is, until age thirty-nine—but had never received any other training prior to Zenger’s program. That’s a dirty dozen years between thirty and forty-two during which young managers are running the orchestra pit without any formal guidance.

Based on research from 10,000 founders, 65 percent of start-ups fail as a result of cofounder conflict.’ In many cases, this might be fixable with the introduction of a Modern Elder.

Your emotional contagion grows the higher you are on the org chart.

The Roman philosopher Seneca wrote, “If wisdom were offered me on the one condition that I should keep it shut away and not divulge it to anyone, I should reject it. There is no enjoying the possession of anything valuable unless one has someone to share it with.” Think of your workplace as a potluck with each person having their own special recipes and dishes to be shared. In the next chapter, we’ll take that perspective and apply it to the final lesson: how you can give wise counsel to those who seek it.

Her [Jessica Semaan] life has become a journey to help people believe in themselves. And it all started with believing in herself once again.

Author Neil Gaiman wrote, “Google can bring you back, you know, a hundred thousand answers. A librarian can bring you back the right one.” Google may be the best search engine in the world but it doesn’t yet understand nuance like a finely attuned human heart and mind.

Of course, the more you build a reputation for having a ‘personal network effect,’ the more people will seek you out. And your value to your company will only multiply to the extent that: (1) you are open to sharing your “know-who” and “know-how”; (2) you exercise confidentiality and aren’t seen as competitive; (3) you are reliable and empathetic; (4) you provide true insight often through the use of questions; and (5) you have a capacity for synthetic, ‘gist thinking’ to help the junior person understand what they really should be looking for.

I met Luther [Kitahata] at a Wise Leader retreat I was cofacilitating in May 2017. When I heard about his resilience as an engineering leader in his fifties, I was impressed. But I was more intrigued by Luther’s calm and contemplative demeanor (he reminded me of a Zen monk). I explored further and found a scientist and philosopher at heart. I discovered someone who has been asking big questions since he was young, and who started doing his own personal development work in his twenties.

...he’s tapping into his ability to provide wise counsel to inspire others as they scale new peaks and remake themselves. He summarizes his approach to change in this simple phrase (inspired by Aristotle’s “We are what we repeatedly do. Excellence, then, is not an act, but a habit.”): ‘We are what we practice and we’re always practicing something. Thus, to make changes we need to practice something new and different.

This means we don’t just obsess upon our financial results; we look at our long-term impact on the communities we serve and we adapt policies and programs to be a positive force. And, given there’s much less cofounders’ drama than most other companies, our employees can focus on how this start-up, which became one of the world’s most valuable hospitality companies nearly overnight, can live its mission helping our customers ‘belong anywhere.

Chinese philosopher Lao-Tzu, author of the Tao Te Ching, wrote, ‘The Sage holds on to the One and in this way becomes the shepherd of the world. He does not show himself off; therefore he becomes prominent. He does not put himself on display; therefore he brightly shines. He does not brag about himself; therefore he receives credit. He does not praise his own deeds; therefore he can long endure. It is only because he does not compete that, therefore, no one is able to compete with him.

I’m a particular fan of the Coaches Training Institute so I would recommend that you look at www.coactive.com . You’ve also seen that “presence” is a quality that I think Modern Elders embody. There are a couple of programs that specialize in presence and embodied leadership: Strozzi Institute ( www.strozziinstitute.com ) and Leadership Embodiment ( www.leadershipembodiment.com ).

Michael Dearing, longtime eBay exec, former Stanford School of Engineering professor, and founder of Harrison Metal, which invests in start-ups, found that each time he’d meet with a mentee, a floodgate of memories would open as many of the issues these young folks were facing mirrored his past.

As your dutiful author and “librarian,” I’d suggest you also look for the New York Times July 2017 article “Switching Careers Doesn’t Have to Be Hard: Charting Jobs That Are Similar to Yours” listed in “My 10 Favorites” under “Articles” in the appendix. This insightful article, with its accompanying charts and automated career counselor, can tell you which kinds of jobs are most similar to and different from what you’re doing now and help you understand what habitats might be most ripe for you.

Learning came naturally for Sherry Lansing, seventy-three, the most powerful female movie mogul of all time and the first to head a major studio. But first, she was a schoolteacher, actress, and film executive, before becoming chairman of Paramount Pictures for twelve years. While the overall movie biz may have been more gender diverse, the corridors of power were exclusively male until Sherry came along; perhaps it was a result of her unique perspective that her whole career, as she tells it, was often mentoring or being mentored without even knowing it. Like me, she loved what she was doing until her calling turned into a job and it was then she knew it was time to get curious.

If this sounds like an interesting path for you, some of the other resources you might consider include AARP’s Experience Corps volunteering in urban public schools, and Stanford’s Distinguished Careers Institute (DCI) or Harvard’s Advanced Leadership Initiative (ALI), which help proven leaders find a way to make a social impact in their communities.

I love this delicate African proverb: ‘When an elder dies, it’s like a library has burned down.

What is left once you have left the stage is an idiosyncratic image, especially the one presented in later years….One’s remaining image, that unique way of being and doing, left in the minds of others, continues to act upon them—in anecdote, reminiscence, dream; as exemplar, mentoring voice, ancestor—a potent force working in those with lives to live.’ —JAMES HILLMAN

FOR A NEW BEGINNING —JOHN O’DONOHUE

In out-of-the-way places of the heart,

Where your thoughts never think to wander,

This beginning has been quietly forming,

Waiting until you were ready to emerge.

For a long time it has watched your desire,

Feeling the emptiness growing inside you,

Noticing how you willed yourself on,

Still unable to leave what you had outgrown.

It watched you play with the seduction of safety

And the gray promises that sameness whispered,

Heard the waves of turmoil rise and relent,

Wondered would you always live like this.

Then the delight, when your courage kindled,

And out you stepped onto new ground,

Your eyes young again with energy and dream,

A path of plenitude opening before you.

Though your destination is not yet clear

You can trust the promise of this opening;

Unfurl yourself into the grace of beginning

That is at one with your life’s desire.

Awaken your spirit to adventure;

Hold nothing back, learn to find ease in risk;

Soon you will be home in a new rhythm,

For your soul senses the world that awaits you.