By Chip Conley for HBR
A growing number of people feel like an old carton of milk, with an expiration date stamped on their wrinkled foreheads. One paradox of our time is that Baby Boomers enjoy better health than ever, remain young and stay in the workplace longer, but feel less and less relevant. They worry, justifiably, that bosses or potential employers may see their age more as liability than asset. Especially in the tech industry.
And yet we workers “of a certain age” are less like a carton of milk and more like a bottle of fine wine — especially now, in the digital era. The tech sector, which has become as famous for toxic company cultures as for innovation, and as well-known for human resource headaches as for hoodie-wearing CEOs, could use a little of the mellowness and wisdom that comes with age.
I started a boutique hotel company when I was 26 and, after 24 years as CEO, sold it at the bottom of the Great Recession, not knowing what was next. That’s when Airbnb came calling. In early 2013 cofounder and CEO Brian Chesky approached me after reading my book Peak: How Great Companies Get Their Mojo from Maslow. He and his two Millennial cofounders wanted me to help turn their growing tech startup into an international giant, as their Head of Global Hospitality and Strategy. Sounded good. But I was an “old-school” hotel guy and had never used Airbnb. I didn’t even have the Uber app on my phone. I was 52 years old, I’d never worked in a tech company, I didn’t code, I was twice the age of the average Airbnb employee, and, after running my own company for well over two decades, I’d be reporting to a smart guy 21 years my junior. I was a little intimidated. But I took the job.
On my first day I heard an existential tech question in a meeting and didn’t know how to answer it: “If you shipped a feature and no one used it, did it really ship?” Bewildered, I realized I was in deep “ship,” as I didn’t even know what it meant to ship product. Brian had asked me to be his mentor, but I also felt like an intern.
I realized I’d have to figure out a way to be both.
First, I quickly learned that I needed to strategically forget part of my historical work identity. The company didn’t need two CEOs, or me pontificating wisdom from the elder’s pulpit. More than anything, I listened and watched intently, with as little judgment or ego as possible. I imagined myself as a cultural anthropologist, intrigued and fascinated by this new habitat. Part of my job was to just observe. Often I would leave a meeting and discreetly ask one of my fellow leaders, who might be two decades younger than I was, if they were open to some private feedback on how to read the emotions in the room, or the motivations of a particular engineer, a little more effectively.
That brings me to the second thing I learned, which can be summarized in a one-line trade agreement: “I’ll offer you some emotional intelligence for your digital intelligence.” Many young people can read the face of their iPhone better than the face of the person sitting next to them. I’m not saying young people don’t understand emotions. Our digital world is full of emojis, and the term “emo” didn’t exist back in my schoolyard days. But emojis don’t create interpersonal, face-to-face fluency. I was surrounded by folks who were tech-savvy — but were perhaps unaware that being “emo-savvy” could be just the thing to help them grow into great leaders. I realized that we expect young digital-era leaders to miraculously embody relationship wisdoms, with very little training, that we elders had twice as long to learn. Over time, I learned that being an intern publicly and a mentor privately was essential, since no one wants to be criticized in a meeting by someone who sounds like their dad.
I also learned that my best tactic was to reconceive my bewilderment as curiosity, and give free rein to it. I asked a lot of “why” and “what if” questions, forsaking the “what” and “how” questions on which most senior leaders focus. I didn’t know any better. Being in a tech company was new for this old fart. My beginner’s mind helped us see our blind spots a little better, as it was free of expert habits. We think of “why” and “what if” as little kid questions, but they don’t have to be. In fact, in my experience it can be easier for older people to admit how much we still don’t know. Paradoxically, this curiosity keeps us feeling young. Management theorist Peter Drucker was famously curious. He lived to age 95, and one of the ways he thrived later in life was by diving deeply into a new subject that intrigued him, from Japanese flower arranging to medieval war strategy.
Although some older folks in the tech world feel they have to hide their age, I think doing that is a missed opportunity. Being open helped me succeed in tech; I’ve spent a lifetime being curious about people and things, which, I guess, means I’m well-read and well connected. I’m not sure there’s anyone in Airbnb who’s been asked to chat by a more diverse collection of employees. I always did my best to respond with an enthusiastic yes to these invitations. And I’m grateful. Because if I were to plot all of those conversations across the various islands (or departments) of the company, you’d see a rich web of relationships and knowledge. This served me even more as a strategic advisor to the founders, since I had a real sense of the pulse of the company and its various teams.
Boomers and Millennials have a lot to offer, and learn from, each other. Enter the “Modern Elder,” who serves and learns, as both mentor and intern, and relishes being both student and sage. The opportunity for intergenerational learning is especially important to Boomers, as we are likely to live 10 years longer than our parents, yet power in a digital society has moved 10 years younger. This means Boomers could experience 20 additional years of irrelevance and obsolescence. That the number of 65-and-older workers last year was 125% higher than in 2000 presages a national human resource tragedy.
Wisdom is about pattern recognition. And the older you are, the more patterns you’ve seen. There’s an old saying I love: “When an elder dies, it’s like a library has burned down.” In the digital era, libraries — and elders — aren’t quite as popular as they used to be. But wisdom never grows old