As an adviser to family-owned businesses, I often talk with Gen Z clients clashing with their parents over whether, when, and how they will join the company. My friends sometimes tell me my work is like an episode of the HBO series Succession — and they’re right.
Recently, a twentysomething client asked me to help solve a conflict between him, his father, and the board of their family business.
The son, who was a part owner of the business but had little power, had drafted long emails articulating his position on why the company was declining and what to do about it, but no one seemed to be listening. His dad and most of the board were in Europe; he was not. Eventually I gave him the same piece of advice I’ve been telling so many people lately: Just book a flight.
As a Gen-Xer (55), I’m shocked at how often I’m dispensing this advice to young people averse to face-to-face encounters, even with relatives. Shouldn’t it be obvious that some disagreements can only be addressed during a real-life conversation? I understand that no one enjoys awkwardness. But even in the age of Zoom, we need to reestablish a clear social norm about the necessity of analog conversations.
If you’ve dated someone for a significant period of time, it is unacceptable to break up over text. It’s rude to resign from a job via email. And even as more of us consult AI about the best ways to communicate through difficult moments, we need to agree that spontaneous conversation with other people is not optional.
The reluctance to engage in real-life conversation is understandable. This generation of young professionals grew up communicating through messaging apps, social media, Slack, Zoom, and FaceTime. During COVID-19, that was the only way many of them communicated. They’ve grown comfortable endlessly editing text messages, iterating, and asking friends for advice before pressing send. In a 2025 YouGov survey, 65 percent of Gen Z said they favored text, email, or instant messaging when communicating with close friends or family, compared with 26 percent of boomers.
But relying on electronic communication can carry a cost. Experiments by Amit Kumar and Nicholas Epley found that despite subjects’ expectations that talking with old friends or strangers would be more awkward than texting or emailing, they weren’t — live conversations created stronger social bonds. And a study published in 2026 by Burint Bevis, Juliana Schroeder, and Michael Yeomans with 1,576 participants found that spoken disagreements produced greater understanding and less conflict than written exchanges — even though most participants expected the opposite.
Fortunately, people can get better at engaging in-person about difficult subjects if they practice. In my work teaching Harvard MBA and executive education students, I advise them to prepare for these moments. Ask questions. Go into the discussion with curiosity instead of a rehearsed argument, because understanding the other person’s perspective is usually more valuable than winning your case.
When they sit down, I say, Aim to listen more than you talk. Most importantly, remember that challenging conversations are rarely resolved in one meeting.
As we role-play, it’s clear how unnatural this feels to many of them. Sometimes they remind me of young tennis players who grow accustomed to serving mostly aces: They don’t know how to handle it when someone returns the serve. But we’ll practice the conversation over and over, bringing it in directions they don’t expect, and, slowly, I can see their skills improve.
AI only increases the need to know when and how to communicate face-to-face. When I began my career, someone who was quietly competent — great at building spreadsheets, slide decks, and memos — could get ahead. Today AI does many of those tasks. If young professionals don’t become adept at the messiness of real-life conversations — of reading the room, making eye contact, controlling their body language, displaying appropriate emotions, and responding without the convenient, deliberative pauses afforded by texting — the odds of AI displacing them only increase.
The future will belong to people who know when to put down the phone, sit down together, and start talking.
Christina Wing is a faculty member at Harvard Business School, founder of Wingspan Legacy Partners, and the author of Unspeakable: The Taboo Topics We Avoid and How to Talk About Them, to be published October 20 by Harvard Business Review Press.