Historically, the boss typically has been older than the staff. But in the last few decades, several trends converged that made it more common for employees to have younger managers. One catalyst is the shift from seniority-based promotions toward those based on merit, according to a research article in the Journal of Organizational Behavior. Also, as the pace of technology innovation increases, companies promote more tech-savvy younger workers into supervisory jobs. Meanwhile, older workers are staying employed longer due to such things as the disappearance of early retirement schemes.
Entrepreneur Chip Conley knows first-hand what it feels like to have a younger boss. The former hotelier works at Airbnb, where the CEO is two decades younger, as its head of global hospitality and strategy. But Conley believes that diversity of ages makes for a better workplace. His new book, Wisdom At Work: The Making of the Modern Elder, argues the case for this “intergenerational potluck” where everyone brings something to the table. He recently joined the Knowledge at Wharton radio show on SiriusXM to explain how one generation can learn from another.
An edited transcript of the conversation follows.
Knowledge at Wharton: Does older really mean wiser?
Chip Conley: There have been a number of studies on this, and they’ve shown very little correlation between age and wisdom. As a guy who’s 58, it’s hard to hear that, but there is some evidence that shows that it is not necessarily a correlation. What is correlated is that people actually make sense of their life and their mistakes and their experiences along the way. If you have a process for doing that, then age is correlated with wisdom because you create a pattern recognition.
Wisdom is about being able to see the patterns in things faster than when you’re younger because you’ve seen a lot of patterns and you’ve seen the implications or results of certain things. I think wisdom can be correlated [with age], but it isn’t necessarily correlated. So, just because you’re older doesn’t mean you’re an elder.
Knowledge at Wharton: How do you fit that into your experience of going to Airbnb in your 50s?
Conley: It’s interesting. For 24 years, I was the founder and CEO of a company called Joie de Vivre based in San Francisco that created 52 boutique hotels. We were the second-largest boutique hotelier. In the Great Recession, I decided to sell the company. I had been doing it for a long time. I was ready to move on. Then I spent a couple years thinking about what was next [for me].
There is a great Robert De Niro quote from the movie The Intern [about a senior citizen who became an intern at a shopping startup], which is, “Musicians don’t retire; they quit when there’s no more music left inside of them.” I knew I had music inside of me; I just wasn’t sure whom to share it with.
I was lucky enough that Brian Chesky, the CEO of Airbnb, asked me to be his in-house mentor and then come in as the head of global hospitality and strategy, which was supposed to be a part-time job but quickly became full time.
“The modern elder is appreciated for their relevance, not their reverence, because they’re as much of an intern as they are a mentor.”
The thing that was interesting about the partnership that Brian I have forged over five and a half years is that we often think of the traditional elder as having all that wisdom and being held in reverence. Instead, I think the modern elder is appreciated for their relevance, not their reverence, because they’re as much of an intern as they are a mentor. That’s what I learned. I have this mutual mentorship relationship with Brian, and we really learn from each other.
Knowledge at Wharton: Do you think that is a bit of a microcosm of what’s going on in business now, where we are seeing many older people working for younger managers?
Conley: Here’s the reality of the situation, and it’s been written a lot about and there’s empirical evidence to show it: Power is moving to younger [people] in the business world and in organizations because of our increasing reliance on DQ or digital intelligence. In fact, some studies show that power is 10 years younger today than it was 20 years ago. But we’re all living 10 years older. So, if power is moving 10 years younger and we’re living 10 years older, society has created a new 20-year irrelevancy gap for people in mid-life and beyond.
What does that mean? There’s a social justice piece to this of helping older people to still have some relevancy. But the bigger question that really helped make my experience at Airbnb successful was that I saw that we expect these young, digital leaders to somehow miraculously embody the relationship wisdom and leadership skills that we older workers have had decades to learn.
I started to realize that there are some things they could teach me, like digital intelligence, and there are things that I could teach them, which is emotional intelligence, leadership skills, strategic thinking, etc. That is the opportunity. How do we create an intergenerational collaboration like we’ve never seen before because we have five generations in the workplace at the same time, for the first time?
Knowledge at Wharton: It is unique because of the recession. A lot of people who were planning to retire lost their savings and needed to continue working longer.
Conley: That is so true. Yet how bewildering and anxiety-producing it is to know that if you’re in your 50s or 60s and you’re going to have work longer, you feel like you’re invisible or irrelevant. Part of [my reason for] writing the book was my way of trying to give back to my generation, to say, “Listen, you can mine your mastery. And while you may not be running the company, you certainly can be an ally to a younger person, as long as we figure out how to create a fluency where we can learn from each other.”
The average longevity in the United States in the year 1900 was 47. In 2000, it was 77. So, we added 30 years of life in one century. But that created something that really didn’t exist before, which is midlife. That’s why in 1965 the term midlife crisis emerged. At that time, midlife was perceived as 45 to 65 or 40 to 60. Today, I think it’s 35 to 75 because people are going to work longer and people start feeling irrelevant earlier.
That means there’s this period of life where people are having to remake, reinvent and repurpose themselves in ways that they didn’t have to in the past because things are changing so quickly. This is part of the reason we created a Modern Elder Academy down in Mexico on three acres on a beach where we actually bring people in midlife. It’s a social enterprise, so half the people are on scholarship. The intent is to bring people for weekly programs where they learn a core curriculum that helps them repurpose themselves and mine their mastery to figure out how to make themselves relevant for the second half of their life.
Knowledge at Wharton: In the book, you focus on the fact that, even though we are in the digital age, wisdom is not something you can automate. Can you talk about that?
Conley: There’s a term that we’re all familiar with called knowledge worker. I was born in 1960, and Peter Drucker came up with that term in 1959 in advance of the computer age. He said we’re all going to be knowledge workers some day. I think knowledge worker is a term to retire now because knowledge is in the computer, it’s in the cloud. You can get out there and find knowledge. In fact, we’re sort of awash in knowledge. But what we could use a little more of is wisdom.
Wisdom is not a plus, plus, plus equation like knowledge is. Wisdom is more of a division equation. You distill the essence of something into what’s important, and that’s what is valuable. I really think that we should change the term knowledge worker and replace it with wisdom worker, because wisdom includes a certain amount of intuitive and human quality that you don’t necessarily get from AI or from your computer. The idea of wisdom making a comeback at a time when we’re so technologically advanced is not that surprising.
“We’re sort of awash in knowledge. But what we could use a little more of is wisdom.”
The three-stage life of the past — you learn until you’re 25, you earn until you’re 65, and then you retire until you die — that model is evaporating. We’re lifelong learners, and there’s an element of having to do that reinvention or that rewiring in midlife. That’s really what my book is about. It’s helping people to understand the process of doing that. It’s not easy because it requires you to shift out of some of your habits and mindsets that you’ve held onto for a long time.
Knowledge at Wharton: How do the professional relationships between older and younger workers affect both the younger workers and the company in general? Maybe this is something that we will get a handle on in the next few years because it’s still a relatively new idea.
Conley: It is a new idea, let’s be honest. The fact that almost 40% of workers have a boss younger than them — that number is going to be the majority by 2025. That’s a fascinating statistic. We didn’t have that before.
It’s not just because the power is moving to the young, it’s because there are a lot of people who are going to be working in their 60s and, frankly, into their 70s. It means that we need to start asking ourselves, how do we create an ‘intergenerational potluck’ so that people bring what they know best? The thing that we do in our Modern Elder Academy down in Mexico is help people to [recognize] what is it that you have to offer?
When I joined Airbnb, I think I had been brought in because I was a seasoned expert in my field, which was boutique hotels, hospitality and the travel industry. When I joined five and a half years ago, Airbnb was a very small company, and there was not one person in the company who had a travel or hospitality industry background. I was brought in initially because of that knowledge. That was helpful, and a lot of my networking of people I knew helped.
But ultimately, what I think I was able to offer them was this sense of emotional intelligence. How do you understand people? As they said to me, “A lot of your fact knowledge doesn’t matter here at Airbnb because how many rooms a maid cleans in an eight-hour shift isn’t really important in the home-sharing world.” But my process knowledge of how you get things done based upon understanding the underlying motivations of everyone at the table is something you learn as you get older, because emotional intelligence is something that can grow with time.
Knowledge at Wharton: Is this relationship helped by the increased collaboration in the workplace? Most companies now want diverse teams to come together on a project, rather than putting it in the hands of one or two people.
Conley: Totally. Exactly. People go, “Oh, it’s a tech company. It’s just all engineers and individual people in their cubicles doing their work.” No, actually it’s full of teams. And to operate well, teams need to collaborate. Google did a famous study two or three years ago called Project Aristotle and found that the No. 1 common factor among successful and effective teams was psychological safety — people feeling like they could collaborate well without any kind of retribution.
The idea that we are able to be better collaborators as we get older because we have more emotional intelligence is pretty well empirically proven. Again, there are individuals where that does not make sense, but as a group it does. I also think collaboration is going to become more important, so those collaborative skills are a really important thing that someone in midlife or later can bring to the table.
“The hierarchy of the past that says the physics of wisdom only flows from old to young doesn’t make sense anymore.”
And there’s no doubt that cognitive diversity is hugely valuable on teams. If you just have a bunch of 25-year-old guys on a team together, they’re going to compete with each other and try to one-up each other to see who’s the smartest. Put a couple of women in that group, people of color or some older people [and the dynamic changes]. When we think of diversity, we often think almost exclusively of gender, race, and maybe sexual orientation. We don’t think about age very often, even though age is one of the most obvious demographic changes we see.
Knowledge at Wharton: There is an assumption that younger knows more than older in this digital age, correct?
Conley: Absolutely. Younger people who are digital natives have a digital fluency that may be greater than someone 25 or 30 years older than them — that is true. But to think that someone’s acuity and fluency in one particular scope of work means that they can apply that to anything else is forgetting about all of the human element of business, which requires a certain amount of collaboration and emotional intelligence and leadership skills. Brian Chesky is an amazing CEO. But when I joined, he was 31 and I was 52, and I was his mentor and he was my boss. That was a fascinating relationship — to be mentoring my boss. But five and a half years later, I’m still here.
Knowledge at Wharton: There’s a chapter in the book titled, “Am I a Mentern?” What is that?
Conley: Mentern would be a combination of mentor and intern. When I joined the company, no one told me that it was a possibility in life — you could be both the mentor and intern. It’s funny relative to the movie The Intern. I came in as the mentor to Brian Chesky, but turned into an intern as well. Whereas Robert De Niro came in as an intern, but he really ended up becoming the mentor to Anne Hathaway. The hierarchy of the past that says the physics of wisdom only flows from old to young doesn’t make sense anymore. The physics of wisdom moves in both directions; it just depends on the subject matter.
Knowledge at Wharton: How does this idea affect the labor force going forward, as more people work later in life and encounter younger co-workers and managers?
Conley: We have an unemployment rate below 4% and an immigration policy that’s gotten tighter. That means we have to look for new employees somehow, including people later in life who decide to go back to work after retiring. Often, it’s a woman who’s taken 20 years off from the workplace because she was bringing up the kids and now wants to get back in. Yes, we want that person back in the workplace. Being a stay-at-home person means that you’re juggling a lot, and that’s what you do in business or in organizations as well.
We’re on the cutting edge of this. There are great examples of leaders who, if they had had a modern elder by their side, might still have their job. Case study No. 1 is Travis Kalanick at Uber. Uber and Airbnb have been compared an awful lot, and on occasion people have said, “Gosh, if Travis had had someone in house in that sort of modern elder role next to him, he might have been able to mature his leadership approach a lot faster, and he might still have that job.”
Knowledge at Wharton: Could you add Tesla founder Elon Musk in that category?
Conley: He’s 47 years old, if I’m not mistaken. Could he use someone like that? Sure. But he’s relatively far along in terms of his career. He’s a bit of a genius. The thing we have to put to rest is the idea that singular geniuses do this alone. There’s always more than one person involved. The question is, who are you surrounding yourself with? To me, the answer is that you should be surrounding yourself with a diverse group of people, including some people who have some seasoned wisdom at the table.
