The Room I Didn’t Understand
Chip Conley had spent twenty-four years being the person a room waited on. He built Joie de Vivre into one of the country's best-known boutique hotel brands, sold it at fifty, and two years later Airbnb's founders called and asked him to come mentor them.
He said yes, and took the title Head of Global Hospitality and Strategy. When he walked into his first meeting, nobody waited on him. People were already talking about things he'd never heard of. He sat there and tried to follow along and couldn't. “They were talking a language I just didn't understand,” he said later.
He was fifty-two. The average age in that room was twenty-six.
He'd pictured it going differently. Twenty-four years running a company teaches a person a lot. More so, that others understand and work the conversation around what you know. He expected some version of that here, too. Maybe a little deference, even a small runway to get his bearings. Instead, he sat through that first meeting understanding almost nothing about the business he'd just agreed to help lead, and kept sitting through meetings like it for most of that first week. He started keeping a list of words people used, like onboarding, roadmap, and sprint. He'd write them down under the table and look them up that night, trying to understand what they meant just like a new hire does. Except, he was the Head of Global Hospitality and Strategy.
There was an easy way out of that feeling, and he could feel himself reaching for it. Say less, nod more, and let his resume speak for itself until the room settled around him. That's the ordinary version of this, and nobody would have necessarily called him wrong for choosing it. Twenty-four years earns a person the right to stop asking questions and start being asked.
Conley didn't take it and decided on a different approach. He took the more honest route and admitted he was as much a student in that room as anyone's mentor. He asked instead of answered. He let a twenty-six-year-old walk him through how the product actually worked, sitting at someone else's desk taking notes. In exchange, he taught them what two decades in hospitality had actually taught him: how to read a room full of guests who'd just had a bad flight, or a host trying to make a stranger feel at home for the night.
He started calling himself the company elder instead of the executive. Something close to a hundred people at Airbnb became something like mentees, though the relationship rarely ran in one direction only. He brought what he called “wise eyes.” They brought eyes that had developed inside a company he was still trying to understand. Most of those conversations left both people knowing something they hadn't walked in with. He'd later put a name to what he was doing: trading the expert-in-charge role for what he called “guide on the side.”
None of it made those first weeks comfortable. Feeling behind in a room full of people half his age isn't pleasant, no matter how it eventually pays off. There were meetings that first year where he said almost nothing because he genuinely didn't know enough yet to offer it responsibly. He could have decided, reasonably, that he'd already earned the right to skip that part. Some people in that position do exactly that and spend years holding a title in a room that never quite lets them all the way in.
He stayed for years, and by the time he moved into an advisory role, the company he once sat in meetings for and understood nothing about grew into a name almost everyone recognized. He'd spent the years in between being taught nearly as often as he taught.
Twenty-four years of running something well gets you into the room. It doesn't answer the one question that matters once you're sitting in it: what do you do the first time you realize you're the one who doesn't know the language.
Sources
• “Here's Why Companies Should Hire A 'Modern Elder,'” Forbes —
https://www.forbes.com/sites/nextavenue/2017/12/03/heres-why-companies-should-hire-a-modern-elder/
• “Airbnb Advisor Chip Conley On The Future Of Post-Pandemic Hospitality,” Forbes —
• “Chip Conley: A Modern Elder At Work” (interview transcript), Sounds True —
https://www.soundstrue.com/a/resources/transcript/chip-conley-a-modern-elder-at-work/
• “Episode 192: Chip Conley – Modern Elder Academy” (interview transcript), Bregman Partners —
https://bregmanpartners.com/podcast/chip-conley-modern-elder-academy/
