Mentorship, lifelong learning and the multigenerational workplace: A conversation with Airbnb’s Chip Conley

Chip Conley [00:00:00]:
Wisdom is not taught, it’s shared. And when it’s shared on a team, you are tapping into someone else’s wisdom so you don’t have to make the same mistake. So that’s valuable. It creates candor. It creates transparency.

Hannah Beaver [00:00:14]:
You’re listening to How to Make a Leader a leadership development podcast from Big Think plus, where we take the best ideas from the biggest minds in learning and development and distill them into actionable insights. I’m your host, Hannah Beaver. In today’s episode, we’re diving into the ever popular topic of the multigenerational workplace and how to lead and thrive in an age diverse environment. According to the US Bureau of Labor Statistics, there are currently up to five generations at play in the current workforce environment. Data from Glassdoor indicates that Gen Z is set to overtake baby boomers in the full time workforce this year, which will see a huge shift in workplace dynamics, culture and generational priorities. These transitions can be complex, but if led correctly, multigenerational teams can bring new ideas and tackle problems with valuable depth in insight, experience and varying viewpoints. However, recent data from Deloitte showed that only 6% of their survey respondents showed that they strongly agree that their leaders are equipped to lead a multi generational workforce effectively. And this is all to say that age and generational differences simply can’t be ignored, especially when it comes to work.

Hannah Beaver [00:01:28]:
So who better to hear from in today’s episode than Chip conley, hospitality industry executive, founder and CEO of the Modern Elder Academy, and esteemed author of multiple books, including Wisdom at the Making of a Modern Elder and most recently, Learning to love Midlife. Twelve reasons why life gets better with age Chip’s journey entailed transitioning from the CEO of his own hospitality empire to working with and learning from Brian Chesky and the founding Airbnb team. At 52, an age considered advanced by most tech industry standards, his experience taught him the power of remaining curious and the viable benefits of mentorship programs at any age. In this conversation, Chip shares wisdom from his time at Airbnb about lifelong learning breaks down how to be an effective mentor no matter your generation. So just kick it off. Would love to hear what inspired you both to write this book, and also, more broadly, what inspired you to found the Modern Elder Academy.

Chip Conley [00:02:32]:
For those who don’t know, my career really has had three chapters. The first chapter was at age 26. I started a boutique hotel company in the mid 1980s, when boutique hotels were the language. Even the lingo of boutique hotels was not known in the United States and was proud that I created what became the second largest in the US, Joie de Vivre. Based in San Francisco. We had 52 boutique hotels around California and each had its own name. And so I loved that until I hated it for 22 of my 24 years running that company. I really did love it.

Chip Conley [00:03:09]:
And then my last two or three years during the great Recession, everything in my life that could go wrong did go wrong, including the company having challenges. And it was a period of time in my late forties where I was having what might be considered a midlife crisis. I now consider a midlife chrysalis, because the chrysalis is the in between stage for the caterpillar and the butterfly. So it’s basically midlife for the butterfly. And I got to the other side of it and I was like, okay, I’m done with this. And I sold the company at the bottom of the great Recession. And I had a couple years off to think about what was next, to sort through what is midlife? And I was asked by the founders of Airbnb over eleven years ago to come join their little tech startup as the in house mentor to the founders. They called me the Modern Elder.

Chip Conley [00:03:59]:
I didn’t like that at first because I thought it was ageist, but then they said, no, chip, a Modern Elder is someone who’s as curious as they are wise. I was like, okay, I like that. And so for four years full time and then three and a half years part time, I was the Modern Elder at Airbnb, helping the company grow into the most valuable hospitality company in the world. During my ladders part of that time, I decided I was going to write a book called Wisdom at the making of a Modern Elder around the importance of intergenerational collaboration at work and the importance of wisdom. And so while I was writing that book down in Baja, where I had a home on the beach, I had a baja aha. I had an epiphany. And so for those who don’t know where Baja is, Baja is in Mexico, south of California. Baja California is how it’s called.

Chip Conley [00:04:46]:
And I had an epiphany. I had a baja aha. And that was like, why do we have no midlife wisdom schools? I had had a very rough last part of my forties, and then I had a beautiful fifties, and I was like, okay, I want to make sense of this. And so I started researching and becoming a bit of a geek on the subject of life stages and midlife and found that, gosh, there’s this thing called the u curve of happiness. That shows that people often have a low point in their midlife, around 45 to 50, but then get happier with each decade after 50. And there’s this thing by Becca Levy, this research that shows that when people shift their mindset on aging, they gain seven and a half years of additional life if they go from negative to positive. So all of that led me to creating mea. And we’ve had over 4000 people from 47 countries now come visit our Baja campus.

Hannah Beaver [00:05:40]:
With an understanding of Chip’s past. I turn the conversation to the present to understand how Chip has approached working with and mentoring colleagues of multiple generations. How does an intergenerational workforce change the way that we interact and work with one another?

Chip Conley [00:06:00]:
So here’s an interesting stat. As of 2025 next year, the US Department of Labor forecasts that the majority of Americans will have a younger boss. We have never had that before. I mean, generally speaking, you had a boss who was going to be older than you because you had to pay your dues to move up the chart. But when we have digital intelligence, DQ as one of the most important qualities that a leader can have. And when you have digital natives, younger people versus digital immigrants, boomers like me, there’s no doubt that there’s a lot, a lot of power is moving to younger people in certain industries. In some industries, no way. And certainly in politics, no way.

Chip Conley [00:06:41]:
But long story short is, I think what this means is we need to actually understand what are the qualities of a person who’s younger, on average, that they’re better at than someone older, and vice versa. And how do we create an intergenerational potluck so everybody can come to the table and bring what they know or do best. So I wrote a book called Wisdom at work, the making of a Modern Elder. And I that book really speaks to this idea of the value of intergenerational collaboration. And some of the things that I think people need to consider are, how are we searching for wisdom in companies? I love a question that is a great question for any company to ask on their employee satisfaction surveys. And that is beyond your boss. Who do you look to for advice or wisdom in the company? And what it does is it helps to create a heat map once you’ve got all the names of who’s perceived as wise. Often someone who may be an informal mentor to people, but you don’t even, people don’t even know that.

Chip Conley [00:07:40]:
So that’s a great question. Learning how to create mutual mentorship such that you may have someone who’s in an office in London who knows how to run a great meeting but wants to learn more about their iPhone, and someone in Los Angeles who knows how to run their iPhone but doesn’t know how to run a meeting, you match those two people and with using great technology like mentor, cloud and other kinds of applications that can create these mutual matches within a company. So I just think there’s a lot of opportunities for us to get better at this. And for those who are really intrigued by that, take a look at my last book, which was called Wisdom at work.

Hannah Beaver [00:08:20]:
Mentorship is one way at Airbnb that you experience kind of that intergenerational information sharing. And a quote from the book is that wisdom is not taught, it’s shared. Mentorship can come in different shapes and sizes. So what does it really mean to be a mentor? And could you perhaps break down the different types of mentorship?

Chip Conley [00:08:42]:
So I think there are two kinds of mentors. And I learned this at Airbnb, where I had over 100 mentees over the course of seven and a half years. The first kind of mentor, some people wouldn’t even consider a mentor, but I think it can be. And I call this person the librarian. The librarian is somebody who has the know how and the know who to offer you things, especially if you’re someone maybe younger. And typically the librarian is, is someone who you seek out if you’re a mentee because you want to actually tap into their brain and their heart and maybe actually their rolodex. For those people who don’t know what that is, it’s. It’s their network.

Chip Conley [00:09:18]:
A librarian is somebody who is going to answer your questions. So you’re asking the librarian about this or that. The librarian, the mentor, says, okay, here’s a book you should read. Here’s a white paper. Here’s somebody I know who I can introduce you to, and that’s great. And it might be very finite. And so most of my Airbnb mentor relationships were meeting with someone, on average, three times over the course of maybe a couple months, and then it ended and it would end fine, and we just move on because they got what they wanted. I was really just dispensing knowledge.

Chip Conley [00:09:54]:
Now, the other kind of mentor relationship is the confidant. And the confidant is how a lot of us think of with a mentor as somebody who, it’s an ongoing relationship. It’s not about dispensing knowledge. It’s actually about helping a person develop themselves. And your job as the mentor is not to answer questions. It’s to ask questions. So it’s sort of like a coach, and a great coach is somebody who knows how to ask really illuminating questions. And so a confidant, that relationship can last years.

Chip Conley [00:10:25]:
It’s definitely a deeper relationship. You’re helping to develop the person professionally and personally. So I think it’s helpful if you’re going to be a mentor to understand when someone shows up and says, I want you to be my mentor, which relationship are they looking for? And you can only have so many confidants. And let me just say also Lisa, who was at Airbnb and she was 25 and I was 52 at the time, she said to me, Chip, you’re my confidant. And this is after we’ve been working together for three months. And I said, you haven’t given me any juicy details yet. So I think of a confidant to somebody who has all the secrets. And she said, chip, in my part of France, where I’m from, a confidant is the one who gives you confidence.

Chip Conley [00:11:03]:
And I love that because ideally a great mentor is someone who gives you confidence and helps you to see the path to success. Last thought I want to just throw out there is wisdom. So Peter Drucker, in 1959 coined the terminal knowledge worker. And within 30 years, knowledge management became a practice that was available in Fortune 1000 companies. Because today knowledge is so we’re wash in it. It’s everywhere. AI is, you know, has all the knowledge of the world available to it. What’s really scarce and valuable is wisdom.

Chip Conley [00:11:36]:
And so I think we are going into the hero where wisdom workers, the corollary to knowledge workers are going to become a thing. And I think that wisdom management practices will become, and I want to just talk about one wisdom management practice that I think is really valuable and that is helping people once a quarter on a leadership team to actually talk about what their biggest lesson of the quarter was. If wisdom are the painful life lessons, which leads to the raw material for future wisdom, helping people to see what they’ve learned in the last quarter helps them to make sense of like, what am I going to do with this learning? And you said earlier, wisdom is not taught, it’s shared. And when it’s shared on a team, you are tapping into someone else’s wisdom so you don’t have to make the same mistake. So that’s valuable. It creates candor, it creates transparency. And then at the end of the meeting, after each of the eight people on our leadership team, let’s say, have talked about their biggest lesson of the quarter, the team talks about what was our biggest lesson as a team. So this is one of many wisdom management practices that MEA helps teach leadership teams when we do private retreats at our two campuses in Baja and in Santa Fe.

Chip Conley [00:12:53]:
So I just wanted to call that out because I actually do think wisdom management and wisdom management practices are going to be increasingly important in companies.

Hannah Beaver [00:13:01]:
If you are a leader listening to the call today and you’re looking to perhaps build a mentorship program from the ground up, or if you’re a manager on the call today looking to instill new mentorship practices amongst your team, what is the first step or perhaps some of the first steps that you would take to start reflecting that culture amongst your team or organization?

Chip Conley [00:13:22]:
Well, I would say two or three things. Number one is there’s lots of variables here, so I’m just going to throw out something generically, but this is not as appropriate for some companies. But mentoring is already happening in your organization. As an organization, how do you study what’s already happening? And that’s why that question of who do you reach out to for advice or wisdom? Or you could even get more specific and say, who do you see in your company that’s already an informal mentor to you? That question is helpful because then you can see, is it working? Is it not? And you can see like, what are the qualities that are making it work? And then you can from there then develop a program. But what I’ll say is that a lot of formal mentoring programs feel very stiff. They feel like it’s like creating a friendship based upon the following four steps. I do think it’s really important that in a mentor program that there’s clarity about what both parties want to get out of it and what commitment they’re making to it. So that does need to be formalized.

Chip Conley [00:14:19]:
But saying how often you meet or what kind of questions you should be asking, I mean, that’s like, that’s formalizing a friendship. And a good mentorship program is not like a job interview where you’re having to ask the same seven questions because that’s what the HR department says has to be done. You really want to foster a sense of collegiality and friendship that’s being built in this process. So, and I think this idea of mutual mentorship, where you can skill share with someone else who has the exact opposite interests and, and expertise as you, is also valuable.

Hannah Beaver [00:14:57]:
Fantastic. I’d love to ask you a question specific to your time at Airbnb, how this revolutionized your thinking about what it means to be both a mentor and an intern, what you called a mentor.

Chip Conley [00:15:10]:
So to be a mentor means you’re a mentor and an intern at the same time. When they said I was both curious and wise, what they meant was like, chip, you joined a tech company for the first time at age 52, and you didn’t understand any of the lingo. So I had to be willing to be curious and maybe the dumbest person in the room at times. And that’s hard, frankly, if you especially for me, I’ve been a CEO of my own company for 24 years, but I really wanted to learn. And I think that sort of lifelong learning, long life learning perspective is really important. So the idea that we are not just there to try to be the smartest person in the room, but we’re also there to be the most curious person in the room is, I think, really important at any age. But I think it’s actually particularly important as we get older, because as we get older, you can sort of feel like, well, I’m supposed to know it all, and as I know you know. And so the idea that you are asking questions may feel ill fitting because youre 20 years older than everybody else in the room, but you can make fun of it.

Chip Conley [00:16:08]:
You could actually sort of talk about that. But I think this is where if youre a younger person and a lot of people on the call are younger than me here, if you want to reach out to someone and really get their attention, you could say something like the following to them. Ive noticed in meetings or just in your writing or what ive heard from other people, you have a lot of wisdom, and you have particular wisdom in this area and then fill in the blank of what that is. Can I just spend 15 or 30 minutes getting some coffee with you just so I can tap into that wisdom and ask you a couple questions? That is a hard thing to turn down. And that way you just package that, which is like you’ve sort of said, hey, you have wisdom and I want to tap into it. I have just a couple questions, and I want to spend 15 to 30 minutes. That is a great way to sort of start the process of building a mentorship relationship. Similarly, I did that at Airbnb with some younger people, and I was like, I want to understand.

Chip Conley [00:17:08]:
In my case, I wanted to understand Ux and the idea of what works for the user experience. How do we know what works? What is a b testing like? Because I didn’t have any experience with that at all. So I went to people younger than me and I said, can you spend half an hour with me, teaching me? And so I think, you know, building a growth mindset organization. There’s an article that just came out about Microsoft, and Microsoft has done a ton of training on growth mindset. A growth mindset is when you are not trying to prove yourself, you’re trying to improve yourself. You don’t define success as winning, you define it as learning. And I deeply believe that. I think that we’re supposed to learn and we’re not supposed to pretend and, you know, that.

Chip Conley [00:17:54]:
We know things. We’re not supposed to feel imposter syndrome because we’re trying to act like we know it all. No, we’re supposed to actually learn from each other.

Hannah Beaver [00:18:05]:
For more from Chip Conley, check the show notes for a link to our full conversation and to learn more about the Modern Elder Academy. For more from How to Make a Leader, make sure you subscribe so you never miss an episode. We’ll be back next month and every month with more insights from another L&D leader. Thanks for listening. We’ll catch you next time as we learn How to Make a Leader.

With up to five generations now sharing the modern workplace, how can leaders bridge the gap and leverage age diversity as a strength?

Enter Chip Conley, founder of MEA (the world’s first midlife wisdom school) and Airbnb’s former advisor, hospitality strategist and resident “modern elder”. He draws on his experience joining the then-startup as a 52 year-old, navigating a youthful technology company as an experienced hospitality executive. 

In this episode, Chip offers actionable insights for any leader aiming to leverage generational diversity as a strength rather than a challenge.

To learn even more about Chip Conley’s approach to leadership, listen to the full interview. 

To learn more about the Modern Elder Academy, check out their website here. 

You’ll learn:

• How to embrace age diversity to create more collaborative and dynamic teams
• How Airbnb pioneered a “mutual mentorship” model to bridge generational gaps
• How to be both an effective mentor and mentee
• How to blend curiosity and wisdom in your leadership approach

Things to listen for:

(00:00) Wisdom is not taught, it’s shared

(02:40) What inspired Chip to found the “Modern Elder Academy”

(09:28) How an intergenerational workforce changes the way that we interact and work with one another

(12:08) The different types of mentorship

(16:37) How to build a mentorship program

(18:35) Being a “mentern,” both a mentor and intern

Order Chip’s most recent book, Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age.