Most leaders misread generational tension. These 5 habits resolve it
I spend most days in rooms where four generations argue about the same spreadsheet.
Boomers, Gen X, millennials, and Gen Z staff the same executive teams, often guided by directors from a fifth—the Silent Generation. Four different eras, four different mental operating systems, one quarterly earnings call. When leaders tell me, “We’ve got a generation problem,” what they usually have is a self-awareness problem.
A widely cited review of so-called generational differences at work found that many popular stereotypes don’t hold up very well when you look at actual data on values and attitudes. At the same time, more recent research shows that age-mixed teams can outperform when leaders handle the friction with care.
So, the data tell us two things at once: People from different birth years are less alien than we’ve been told, and they can be a strength or a liability depending on how leaders show up.
After three decades recruiting and coaching leaders, I’ve learned a simple rule: What you can see, you can shape. What you can’t see quietly shapes you.
How our eras built our habits
I’m a boomer. I grew up on a steady diet of “show up early, stay late, say ‘yes, sir.’” That wiring served me well in my time at the White House and later in boardrooms. It also produced a habit that took me years to spot: the urge to please.
In hard conversations, I’d soften the edges. Add extra words. Smooth things over. Younger colleagues didn’t experience that as kindness. They experienced it as dodging. They wanted clarity, not choreography.
Psychologist Jean Twenge, in her book Generations, shows how each cohort’s habits grew out of the era that raised them: boom-time expansion, layoffs and divorce, student debt and purpose-driven careers, social media and permanent comparison. None of that is virtue or vice. It’s conditioning.
Trouble comes when we treat our conditioning as the gold standard and everyone else’s as a flaw.
The most freeing move I’ve made as a leader was saying to myself, “My boomer urge to be agreeable is watering down the truth.” Once I named it, I could do something about it.
A good first question for any leader is small and uncomfortable: What do people my age regularly praise me for that might secretly be wearing my team out?
When senior leaders look in the mirror
This isn’t just a mid-career problem. Senior leaders wrestle with it too.
Elon Musk, a Gen Xer, has spoken openly about his “pathologically optimistic” timelines. That belief that nearly anything is solvable with enough grit, iteration, and contrarian thinking—is one of the hallmark traits of the Generation X worldview. For Elon, is has helped drive rockets, electric cars, and ambitious AI projects, and it has also pushed employees into impossible deadlines when reality didn’t cooperate.
A classic boomer, Jamie Dimon, notes that his vigilance on risk is a strength, and he knows it can land as sharp or impatient in the room. Warren Buffett has explained in shareholder letters that his strong loyalty to managers sometimes kept him from moving fast enough to replace them when performance lagged.
These leaders didn’t erase their blind spots. They acknowledged them, adjusted, and built teams that were allowed to tell the truth back to them and accelerated performance and massive shareholder value creation. The same move is available to the rest of us.
Caricatures versus real people
Generational caricatures are easier than real work. Boomers as workaholics. Gen X as cynical. Millennials as needy. Gen Z as fragile. They make for good jokes; they make for bad leadership.
A study of multigenerational teams found that most friction comes from mismatched assumptions about communication, career speed, and feedback, not from wildly different values. That lines up with what I see in succession conversations: People want to grow, feel useful, and be treated fairly, regardless of their birth year. They simply learned different ways to signal those desires.
You don’t need a grand theory to lead through that. You need a few habits that make your own lens visible to you and to others.
5 small moves to shrink the ‘generation gap’
Here’s a list I often give to CEOs who are tired of the generational blame game:
- Run a “shadow meeting” review once a month. After a key meeting, ask one person who’s at least 15 years older or younger than you: “Walk me through how that meeting felt to you—what landed, what didn’t?” Listen without defending.
- Add a two-question feedback round every quarter. Ask your direct reports: “What’s one thing I should keep doing? What’s one thing I should adjust?” No surveys. Just live conversation.
- Pair up for reverse mentoring. Invite a younger colleague to teach you one digital habit or collaboration tool they rely on. In return, offer one story about a time you failed and recovered. Research on reverse mentoring points to gains on both sides—skills and understanding grow together.
- Narrate your intent. In tense moments, say aloud what you’re trying to do: “I’m pushing hard here because I’m worried about risk,” or “I’m being quiet here because I want to hear others first.” You’ll be surprised how much misreading that removes.
- Pick one generational habit to bend. A Silent-era or boomer leader might deliberately leave the office on time twice a week and invite a younger colleague to walk out with them. A Millennial or Gen Z leader might choose one meeting a day where the laptop stays shut and the phone stays face-down.
None of that requires a task force. It does require an honest look in the mirror.
The real bridge across generations
When leaders learn to notice their own blind spots and talk openly about them, something changes in the room. Silent-era steadiness calms Gen Z anxiety. boomer grit reinforces Millennial desire for purpose. Gen X realism ties these temperaments together.
The bridge is not another app, policy, or slogan about generations. The bridge is a leader willing to see themselves clearly and invite others to do the same.