There's a great chance that you're about to spend the next 36 days trapped in conversations you don't want to have.
Thanksgiving dinner with relatives you see once a year who immediately ask what you're doing for work - then glaze over when you answer.
Your spouse's company holiday party, where you know exactly zero people, and spend the first 20 minutes pretending to be fascinated by the cheese table.
New Year's gatherings where someone inevitably corners you to talk about their workout routine, their kid's travel baseball team, or why they're finally going to start that side hustle in 2026.
These aren't just awkward social obligations.
They're leadership training grounds you're probably wasting.
Being Interesting...Kinda Sucks
I spent my early twenties trying to survive these gatherings by being more interesting.
I'd prep stories. Polish my elevator pitch. Find clever ways to work in my wins, my goals, my perspective on whatever topic came up.
I thought if I could just be interesting enough, I'd be accepted. Respected. Remembered.
All I really did was talk past people while wondering why I felt like an outcast.
The shift didn't happen in some profound moment. It happened slowly - over dozens of uncomfortable holiday parties, networking events, and conversations where I finally noticed a pattern:
The people I most wanted to talk to weren't trying to be interesting at all.
They were interested.
My buddy literally has to cut me off during our tequila happy hours because I'll spend 90 minutes asking about his work, his wife, his kids - and forget to update him on anything happening in my life. He has to force the conversation back to me.
That's not because I'm some conversational saint.
It's because I learned something that changed how I show up everywhere - from conference rooms to family dinners:
Being interested in someone builds more influence than being interesting to them ever will.
Research backs this up.
A study from Harvard Business School found that people who ask more questions - especially follow-up questions - are better liked by their conversation partners.
But here's the kicker: It also makes you more influential.
When you're genuinely curious about someone, they don't just like you more. They trust you more. They listen when you eventually do speak.
They remember you.
Another study from the University of Pennsylvania found that asking questions increases your perceived competence. People don't see curiosity as weakness - they see it as confidence. Only secure people can make conversations about others instead of themselves.
Translation: The more interested you are in them, the more interesting you become to them.
Think about it.
Who doesn't love it when someone actually wants to know about us?
When they ask a real question and then (here's the rare part) actually listen to the answer and ask a follow-up?
It's magnetic. Not because it's manipulative, but because it's rare.
Most people are waiting for their turn to talk. You can be the one who's actually listening.
Here's your holiday gathering game plan:
Before you walk into your next party, gathering, or family dinner, set one intention. Not five. One. Pick the one that stretches you most:
Option 1: Ask 2 questions for every 1 thing you share about yourself: This keeps you from monologuing. It keeps the focus on them. It builds connection through curiosity, not credentials.
Option 2: Avoid any yes/no questions: Yes/no questions kill conversations. Open-ended questions create them. Force yourself to ask questions that require real answers.
Option 3: Talk to 3 people you've never met before: Push past the comfort of talking to people you already know. Seek out the person standing alone. The spouse who got dragged along. The new hire who doesn't know anyone yet.
Then ditch the default small talk. You know the questions I'm talking about:
- "So where are you from?"
"What do you do?"
"How do you know [host name]?"
Those aren't conversation starters. They're conversation fillers.
Try these instead:
- "What are you most excited about before the end of the year?"
- "If 2025 could be different in one specific way for you personally, what would it be?"
- "What's the bucket list item you want to cross off in 2025?"
- "If you weren't doing what you do now for work, what would you be dying to do?"
- "What's something you're working on right now that most people don't know about?"
Notice what these questions do: They skip the surface and go straight to what people actually care about. Their hopes. Their goals. Their dreams.
And when they answer?
Ask a follow-up. Don't just nod and pivot to your story. Dig deeper:
- "What made you decide that?"
- "How'd you get into that?"
- "What's been the hardest part?"
You're not interrogating them. You're showing them you actually care about their answer.
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Ready for the challenge?
Between now and January 1st, you've got multiple opportunities to practice this. Holiday parties. Family gatherings. Year-end networking events. Even random conversations at the gym or the coffee shop.
Pick your intention. Use the questions. Actually listen to the answers.
Track how many conversations you have where you learn something that surprises you about someone.
Where they light up because you asked about what they actually care about. Where they follow up with you later because you made them feel seen.
Don't do this to manipulate people into liking you.
Do this because being genuinely interested in others is how you become someone worth following - at work, at home, and everywhere in between.
Leadership isn't about being the most interesting person in the room.
It's about being interested enough to make everyone else feel like they matter.
You've got 36 days to practice before the year ends.
Go make someone feel heard.
I'm cheering for you, Reader,
Say hi π on Instagram or LinkedIn
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P.S.- If you want to go deeper on building the kind of competitive mindset that makes you someone others naturally want to follow, check out my book Lead Better Now.
It's the same system I use with sales, construction, and leadership teams who want to build cultures where people actually want to show up and make an impact.
Competitive Reflection
Think about your last three conversations - were you trying to be interesting, or were you genuinely interested? What's the difference in how those conversations felt?
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