The Stacking Benjamins Show

Episode SB1771: How to Actually Enjoy Holiday Small Talk (And Give Better Gifts for Less)
Date: December 8, 2025
Guest: Charles Duhigg, Bestselling Author ("Super Communicators")

Episode Overview

This episode dives into two timely holiday topics: how to master small talk and excel at networking during events like work and neighborhood holiday parties, and how to give better gifts for less, even if they’re thrifted or secondhand. Joe and OG welcome back Charles Duhigg, author of Super Communicators, to unpack how anyone—even introverts—can build meaningful connections at social gatherings. They also discuss the growing trend of gifting thrifted treasures and share practical ways to save money while still spreading cheer.

Key Discussion Points & Insights

1. How to Actually Enjoy—and Win At—Holiday Small Talk

[10:19–36:44]

• Challenge: Many find holiday parties stressful—especially those who identify as introverts or “faux extroverts.” It’s a prime time for making (or blowing) career connections, so how do you not just survive, but thrive?
  • Joe Saul-Sehy [10:31]: “For those of us, Charles, who are introverts... it's also just a difficult time in general. We're in far more holiday parties… And how many times have you and I heard stories about people and their hearts beating out of their chest and they step in it? Their one opportunity to talk to maybe that big client or the boss's boss.”

Top Tips from Charles Duhigg ("Super Communicators")

• Be Prepared with Questions—Research has shown that merely having a few questions or topics in your back pocket empowers you to face any social setting with confidence.

  • Charles Duhigg [11:02]: “Super communicators are really, really good at inviting other people to have conversations… Have a couple of questions ready to ask.”
  • Harvard Study: MBA students wrote out questions before meeting strangers—not to use them, but so they’d feel prepared. This reduced anxiety even though the questions usually went unused.

• Ask Deeper Questions—Move from surface questions ("Where do you work?") to questions about values or motivation (“Why did you decide to go into your field?”).

  • Charles Duhigg [13:10]: “A deep question is something that asks us about our values or beliefs or our experiences… It invites the other person to tell you about something real.”

“The goal of communication is for us to connect with each other.”
—Charles Duhigg [14:56]

• Match The Setting—Be mindful of the environment and the other person’s needs. Sometimes, just making a quick genuine connection is enough for a party; “inviting” deeper conversation can follow up later.
  • Charles Duhigg [15:50]: “What do you think your boss needs out of that? Why is she having this conversation with you?... Put a question in their head, and don’t require them to answer it.”

Prove You’re Listening—Not Just Hearing

• Demonstrate Real Listening—Show you’re present using verbal and non-verbal cues. Use “looping for understanding”: ask a question, paraphrase what you heard, and ask if you got it right.
  • Charles Duhigg [22:04]: “We have to prove that we’re listening… by repeating back what we hear the person saying, not in the same words.”
• It’s OK to Exit Gracefully—If you’re not vibing, politely acknowledge the exchange and move on. Announce you both have more mingling to do, which diffuses awkwardness.
• Recognize Conversation Types:
  • Practical (solving problems, making plans)
  • Emotional (sharing feelings, empathy desired)
  • Social (identities, relationships)
    Match your approach to the situation and your conversational partner.

2. The True Nature of Charisma: It's Curiosity

[30:33–32:54]

• Charisma ≠ Just Storytelling—True charisma is about making others feel like THEY are great, not you.

  • Charles Duhigg [31:25]: “Charisma is not about proving to you that I’m great. It’s about making you feel like you’re great... That’s what charisma actually is... willingness to go places with a person, to really try and figure out who is this person, what makes them tick.”

• Set a Manageable Social Goal—Don’t aim to be the funniest in the room; aim to have one meaningful exchange and learn something new about someone.

  • Charles Duhigg [32:07]: “If I have one real conversation at that party... that party and that conversation was a huge success. You were the best version of yourself at that party.”

Notable Quotes & Memorable Moments

On Preparation:

“Spend 30 seconds thinking about it before you go to the party... But I felt so confident because I knew that if there was like a weird silence... I had these questions.”
—Charles Duhigg [12:33]

On Inviting vs Mandating:

“When we invite rather than mandate, what we do is we make the person feel safe.”
—Charles Duhigg [28:40]

On Listening:

“The goal is to say, you know, you said this thing before that's really interesting to me, or let me see if I'm getting this right. What you're saying is... Did I hear you correctly? Because... I’m asking for permission to acknowledge that I was listening.”
—Charles Duhigg [22:04]

On Charisma:

“What charisma is, it's not about proving to you that I'm great. It's about making you feel like you're great.”
—Charles Duhigg [31:25]

Important Timestamps

• 10:19 – Charles Duhigg joins to talk “Super Communicators"
• 11:02 – Prepping for small talk: the power of having a few questions ready
• 13:10 – Surface vs. deep questions
• 18:06 – Crafting great interactions with busy people (e.g., your boss)
• 19:20 – Nonverbal cues and being fully present
• 22:04 – “Looping for understanding” as a listening technique
• 24:28 – How to be prepared when you know nobody at the event
• 26:11 – Three kinds of conversation (practical, emotional, social)
• 28:40 – The power of inviting, not mandating, discussion
• 29:06 – Giving speeches or toasts: be brief and be vulnerable
• 31:25–32:54 – Redefining charisma as curiosity

Holiday Gifting on a Budget: Thrift, Re-Gift, Repurpose!

[45:21–61:27]

• Headline Discussion: The Rise of Thrifted & Secondhand Gifts
  • Thrift stores saw Black Friday sales and young people are spearheading the trend of giving (cool!) secondhand gifts to save money and reduce waste.
  • Examples: Vinyl records, classic books, nostalgic toys, cookware, sports equipment—all hot thrift store items.
  • Doug [57:05]: “One of the points of gift giving is to show that you really love and care and know about that person and made a choice to get them something that they would value… So, you gotta pick your spots.”
• Gift-Giving Etiquette: Be honest if something is secondhand; share the story (“I found this amazing vintage sweater and thought of you!”). Don’t pass used goods off as new.
  • Joe Saul-Sehy [52:07]: “If she had said, I know you're a finance fan. So, I read this already and I thought you would really like it—that was one thing. By the way, the same year she gave my father-in-law this VHS collection of all the James Bond movies… They got a new DVD player. She’s cleaning her house, giving gifts to family members and trying to pass them all off.”
• Context Matters: Used sports gear is great for growing kids, a funky mug or record for a collector is a win, but underwear? Maybe stick to new.
  • OG [48:37]: “Like underwear? Probably not a big fan.”

Top Tips for Thrifting Gifts:

• Inspect for quality (no stains, chips, or excessive wear)
• Choose natural fibers (better sustainability)
• Look for jewelry stamps (e.g., “925” for sterling silver)
• Wash and clean before gifting
• Share origin stories if it helps the recipient appreciate the treasure

The Meaning of Connection

• Beyond Money—Meaningful conversations and relationships are a greater predictor of health and happiness than wealth.

  • Charles Duhigg [34:09]: “There was really only one predictor of lifelong health and happiness and success… People who are happiest and healthiest and most successful... had at least a couple of close friends at age 45.”
  • Even a brief, “awkward” initial call to rekindle an old relationship can bring joy—don’t second-guess it.

• Stacking Benjamins Purpose—It’s not just about finances, but about “more life, and more meaning.”

  • Joe Saul-Sehy [35:53]: “Stacking Benjamins is all about... Not about more money, it's about more life, more meaning in our life.”

Takeaways & To-Do's

How to Win at Holiday Socializing:

• Prepare 3–5 open-ended or “deep” questions ahead of time
• Shift away from “fact” questions to questions about experiences or motivations
• Be fully present; listen deeply (try “looping for understanding” in tense moments)
• Don’t stress about being “charismatic;” focus on making others feel seen and heard
• If you want a deeper connection with someone (like your boss), use the party for a warm, brief check-in, then follow up later for more depth

Gift-Giving Wisdom:

• Thrift and secondhand gifts are cool—when thoughtfully chosen and cleaned
• Add a personal touch or story
• Match the gift to the recipient’s personality and preferences
• The spirit of the gift (and the intent to delight) matters more than the price or “newness”

Final Words from Charles Duhigg

“Conversations are what make life meaningful. And the more we lean into them, the better off we are.”
—Charles Duhigg [35:37]

Resources Mentioned

• Super Communicators by Charles Duhigg (book & audiobook)
• MarketWatch article on secondhand gifting (linked in Stacking Benjamins show notes)
• The Power of Habit by Charles Duhigg
• stackingbenjamins.com for show notes, resources, and upcoming events

Next episode sneak peek:
Lou Frankfurt (longtime CEO of Coach) joins to discuss fashion, career pivots, and leadership lessons.