Coaching for Leaders — Episode 746

How to Make Small Talk with Executives, with Lorraine K. Lee

Host: Dave Stachowiak
Guest: Lorraine K. Lee
Release Date: August 25, 2025

Episode Overview

This episode delves into the often awkward but crucial art of making small talk with executives and other influential stakeholders. Host Dave Stachowiak welcomes Lorraine K. Lee, LinkedIn Top Voice in workplace communication and author of Unforgettable: Get Seen, Gain Influence, and Catapult Your Career. Together, they explore strategies for going beyond “autopilot” small talk, preparing for chance encounters, and connecting authentically with people in positions of power—especially as an introvert.

Key Discussion Points & Insights

1. The Challenges and Value of Small Talk

• Awkward Beginnings: Both Lorraine and Dave share personal stories of feeling awkward or wanting to “run and hide” rather than engage executives in small talk ([02:47], [04:26]).

  "Just a lot of awkwardness, I think." — Lorraine ([02:47]) “My default setting…was I think I would most commonly default to one of two things. Either I wouldn't show up... or I would...run and hide.” — Dave ([04:26])

• Reframing Small Talk: Small talk, when done well, is a strategic tool for relationship-building and career advancement.

  "Small talk is one of the most powerful ways that we connect with each other and make conversation. If we're doing it well, which is hard." — Lorraine ([05:43])

2. Escaping “Autopilot” Small Talk

• The “How Are You?” Trap: Too often, small talk is perfunctory and surface-level. Make it intentional to build real connection ([06:56]).
• Intentionality: Elevate small talk to spotlight yourself or your team, especially when face-to-face with executives ([08:31]).

3. Elements of Effective Small Talk

• Preparation for Predictable Situations: Most situations leading to small talk with executives are predictable—think all-hands meetings, conferences, or presentations ([09:03]).
• Conversational Threading:
  • Introduce multiple “threads” in your responses to encourage dialogue.
  • Respond to even dull questions (like “How was your weekend?”) by adding specific, interesting details ([10:24]):

    “My weekend was great. It was really relaxing. I was able to go to the spa and then I ran my usual three miles.” — Lorraine ([10:24])

  • Ask thoughtful questions, e.g., “What was the highlight of your weekend?” to break autopilot ([11:54]).

4. Creating Natural Back-and-Forth

• Mirroring Comfortable Relationships: Emulate the rhythm of conversation you have with friends—add depth, be intentional, and allow for a natural give-and-take ([13:05]).

  "Small talk gets a really bad rap, but it's because we're not doing it in the ideal way." — Lorraine ([13:05])

5. Proactive Approaches and Mindset Shifts

• Be the Person Who Offers Threads: Rather than waiting for the other party to deepen the conversation, give them something to grip ([13:41], [20:29]).
• Positive Language: Use uplifting, positive prompts (“What brought you joy this weekend?”) to prime a more engaging interaction ([14:51]):

  "Those positive words and phrases...prime people to think more positively in that interaction with you." — Lorraine ([14:51])

• The Power of Brief, Intentional Encounters: Even 20 seconds in an elevator can make a lasting impact if approached strategically and with preparation ([16:47]-[19:01]).

6. Crafting Memorable Introductions

• Go Beyond Titles: Prepare a Unique and Powerful Introduction (UPI). Include your current focus, project details, and name-drop associates the executive may know ([19:01]).

  “By taking 10, 15 extra seconds, that's really where the magic is....so that, again, the executive has the context of who you are, and now they also know...the impact you have and the value you bring.” — Lorraine ([19:01])

• Be the CEO of Your Own Career: Don’t assume others (even your manager) know what you do—advocate for yourself ([20:46]):

  “We can't assume that people know what we do, even our managers...You are going to be your own best advocate.” — Lorraine ([20:46])

7. Strategies for Social Events and Chance Encounters

• Offer Work-Adjacent Details: In quick encounters, mention recent articles, podcasts, or hobbies relevant to your organization’s priorities ([27:29]):

  “It shows that you are staying up to date...and someone who is thinking about company priorities.” — Lorraine ([28:23])

• Pre-Event Preparation: Before events, think of 2-3 interesting, professional topics or personal hobbies you can confidently share ([24:27]).
• Help Executives too: Even executives feel awkward at social events; by being prepared and open, you help them as well ([25:11]).

8. Letting Go of the Script

• Open-Endedness & Curiosity: You don’t need a script—share, then watch what thread your conversation partner picks up ([25:30], [26:48]):

  "Approaching conversations with curiosity I think is always a great thing." — Lorraine ([26:48])

• Adjust in Real Time: Be present, listen, and follow the other person’s lead.

9. Building Confidence Through Practice

• The Reps Matter: The more you put yourself in these situations, the easier and more natural it becomes ([29:02]):

  “There's something powerful about just reps of doing this...as you do that more, it actually gets easier.” — Dave ([29:02]) "I started just seeing someone alone and I would walk up to them...they were just so thankful to have someone go up to them." — Lorraine ([29:42])

10. Embracing Small Talk as Important and Strategic

• Mindset Change: Small talk isn’t just “fluff”—it’s foundational for building professional relationships and visibility ([31:47]):

  “Small talk is a good thing. It is so easy to feel like it's just this thing we have to do...But it's very...powerful way of connecting with each other, building relationships...” — Lorraine ([31:47])

• Public Speaking Parallel: Balancing spontaneous small talk with prepared public speaking both help you stand out ([32:46]).

Notable Quotes & Memorable Moments

• “My default setting…was I think I would most commonly default to one of two things. Either I wouldn't show up... or I would...run and hide.” — Dave ([04:26])
• “Small talk is one of the most powerful ways that we connect with each other and make conversation. If we're doing it well, which is hard.” — Lorraine ([05:43])
• “Conversational threading is a way to have better conversations...ask questions that elicit threads and then you want to also answer in a way where you're giving multiple threads for the question asker to pull on.” — Lorraine ([10:24])
• “You are going to be your own best advocate...you initiating that conversation, you chasing the executive to catch up with them. Right. That's such an important, special moment.” — Lorraine ([20:46])
• “By taking 10, 15 extra seconds, that's really where the magic is...” — Lorraine ([19:01])
• "Approaching conversations with curiosity I think is always a great thing." — Lorraine ([26:48])
• “There's something powerful about just reps of doing this...as you do that more, it actually gets easier.” — Dave ([29:02])

Timestamps for Important Segments

• 02:47 — Lorraine’s early experiences and awkwardness making small talk
• 04:26–06:16 — Dave and Lorraine discuss introversion and reluctance to engage executives
• 06:56–07:38 — The autopilot pitfall of small talk and intentional alternatives
• 10:24–12:32 — Conversational threading explained and illustrated
• 14:51 — Priming positivity with the right questions
• 16:41–19:01 — Dave’s “elevator moment” and preparing for impromptu encounters
• 19:01–20:46 — Crafting memorable, impactful introductions (UPI)
• 24:27–25:30 — Preparing for and navigating professional social events
• 26:48–27:29 — Staying curious, present, and flexible in conversation
• 28:23–29:42 — Using content and industry trends as conversation starters
• 29:42–30:31 — Practice as a means for overcoming nerves and building confidence
• 31:47–32:46 — Seeing small talk as valuable; the public speaking parallel

Resources Mentioned

• Book: Lorraine K. Lee, Unforgettable: Get Seen, Gain Influence and Catapult Your Career
• Related Episodes:
  • Ep. 316: “Executive Presence with Your Elevator Speech” — with Tom Henschel
  • Ep. 706: “How to Talk to People Who Intimidate You” — with Shandi Welch
  • Ep. 717: “A Key Tactic for Way Better Conversations” — with Alison Wood Brooks

Tone & Takeaways

Lorraine and Dave model vulnerability, approachability, and practical wisdom throughout the episode. Their tone is encouraging, practical, and empathetic, especially toward introverts and anyone feeling apprehensive about “up-leveling” their small talk.

Key Takeaways:

• Prepare purposefully for chance encounters.
• Use conversational threading to foster natural dialogue: respond with multiple “threads” for the other to pick up.
• Treat small talk as a strategic tool for both personal and team visibility.
• Initiate and offer information, especially when others may be just as nervous.
• Practice is the surest way to build confidence and fluidity.

For anyone seeking to improve their approach with executives or key stakeholders—or just be a more memorable, authentic presence in any workplace encounter—this episode is rich with actionable strategies and reminders.