While some boomers command rooms with wisdom everyone craves, others trigger a mass exodus of suddenly remembered "urgent emails" – and the surprising difference has nothing to do with their knowledge or experience.
Ever noticed how some boomers can hold court at any gathering, with people of all ages hanging on their every word, while others clear the room faster than someone announcing they brought their vacation slideshow?
The difference often comes down to one critical skill: listening.
During my years in finance, I worked alongside plenty of boomer colleagues. Some became cherished mentors who everyone sought out for advice. Others? Well, let's just say the younger staff developed an uncanny ability to suddenly remember urgent emails whenever certain people approached.
What separated the beloved from the barely tolerated wasn't their knowledge or experience. Both groups had plenty of that. The game-changer was how they listened, or didn't, to the people around them.
After transitioning from analyzing spreadsheets to analyzing human behavior, I've identified nine listening habits that determine whether someone becomes the wise elder everyone adores or the one who gets those not-so-subtle eyerolls.
1. They ask questions instead of waiting for their turn to talk
You know that person who's clearly just waiting for you to pause so they can jump in with their own story? Yeah, the beloved boomers don't do that.
When my colleague's daughter was stressed about choosing a college major, one of our senior managers sat down with her and asked genuinely curious questions. "What lights you up when you talk about it?" "What problems do you wish someone would solve?" Not once did he launch into his own college story from 1975.
The eyeroll-inducing alternative? "Well, when I was your age, we didn't have all these fancy options. We just picked business or engineering and got on with it."
See the difference? One approach opens doors, the other slams them shut.
2. They resist the urge to one-up every story
Nothing kills a conversation faster than the chronic one-upper. You mention a tough day at work, and suddenly you're hearing about how they once worked 80-hour weeks uphill both ways in a blizzard.
The beloved ones? They let your story be your story. When you share something difficult, they might say, "That sounds really challenging. How are you handling it?" They save their own experiences for when they're actually relevant or requested.
I learned this lesson the hard way during couples therapy. My partner would share a frustration, and I'd immediately counter with my own "worse" example. My therapist gently pointed out that this wasn't connecting, it was competing.
3. They acknowledge before advising
Here's something I discovered while mentoring young women entering finance: everyone wants to feel heard before they feel helped.
The beloved boomers get this. They'll say things like, "That sounds really frustrating" or "I can see why you'd feel that way" before even thinking about offering solutions. They validate first, advise second, and sometimes don't advise at all.
The ones who trigger eyerolls? They jump straight to "Here's what you should do" before you've even finished explaining the situation. They skip the human connection and go straight to problem-solving mode, which often feels dismissive rather than helpful.
4. They update their references and examples
Want to lose a younger audience instantly? Compare everything to how it was in 1982.
The beloved boomers stay current. They might not understand every TikTok trend, but they make an effort to relate to contemporary experiences. They'll say, "I imagine that's like when..." and find a bridge between their experience and yours.
The eyeroll crew? They're still using references from M*A*S*H and wondering why nobody gets their jokes. They assume their cultural touchstones are universal and timeless. Spoiler alert: they're not.
5. They admit when they don't understand something
"I'm not familiar with that. Can you explain it to me?"
Seven simple words that separate the beloved from the dismissed. The boomers everyone loves aren't afraid to admit knowledge gaps. They treat not knowing as an opportunity to learn, not a weakness to hide.
Meanwhile, the eyeroll-getters either pretend to know everything or dismiss what they don't understand as unimportant. "Oh, all that computer stuff is just a fad anyway."
6. They share the conversational space
I used to be terrible at this. Coming from finance, where commanding the room meant credibility, I thought holding court showed expertise. Then a friend gently told me I was exhausting to talk to because every conversation became my monologue.
The beloved boomers have mastered conversational ping-pong. They share, then pass the ball back. They notice when someone hasn't spoken and create openings. They recognize that dialogue beats monologue every single time.
The ones getting eyerolls? They treat every interaction like their personal TED talk, complete with a 20-minute runtime and no Q&A session.
7. They remember what you told them last time
"How did that presentation go?" "Did your daughter get into that program she wanted?"
These follow-up questions are gold. They show you were actually listening, not just performing the act of listening. The beloved boomers take mental notes and circle back, showing they value what you share.
The alternative? Having the same surface-level conversation every time you meet, as if your previous interactions never happened. Or worse, confusing your story with someone else's entirely.
8. They adjust their communication style to their audience
The boomers everyone loves understand that how you talk to your peers isn't necessarily how you should talk to someone 30 years younger or older. They read the room and adapt.
They'll skip the formal titles with millennials who prefer first names. They'll text instead of calling Gen Z colleagues. They recognize that respect looks different to different generations.
The eyeroll crew insists everyone adapt to their communication style. "I don't do texts. If you want to reach me, pick up the phone like a normal person."
9. They choose connection over correction
This one transformed my relationships completely. I used to be the person who couldn't let a minor factual error slide. Someone would say "December 10th" when they meant "December 11th," and I'd interrupt to correct them.
Then I learned that being right matters less than being kind. The beloved boomers understand this intrinsically. They let small mistakes go because they're focused on the bigger picture: human connection.
The ones everyone avoids? They're the grammar police, the fact-checkers of casual conversation, the ones who derail every story to point out insignificant errors.
Final thoughts
The beautiful thing about these habits? They're not locked in by age or generation. Any boomer currently in the eyeroll category can shift to the beloved category by simply choosing to listen differently.
And here's the kicker: these habits work for everyone, not just boomers. Whether you're 25 or 75, mastering the art of truly listening will transform how people respond to you.
The next time you're in a conversation, try just one of these habits. Ask a follow-up question. Resist the urge to one-up. Admit you don't know something.
Watch how quickly the energy shifts. Because at the end of the day, we all want the same thing: to feel heard, understood, and valued. The boomers who get this become the ones we seek out, not the ones we sidestep in the hallway.
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