The Power of a Professional Wing Person

In this conversation of What One Thing, co-host Devon Montgomery Pasha chats with Shaena Harrison, professional wing person and CEO of Wing People, a boutique agency dedicated to bringing genuine human connection back to business events. After years of producing major conferences and watching attendees struggle to move beyond surface-level networking, Harrison launched a team of trained wing people to help guests skip small talk and spark meaningful relationships. 

Drawing from her lifelong instinct for connecting others and her belief that events succeed when people feel they belong, Harrison explains how her team creates conditions where real conversations can happen through facilitated connection corners and subtle behavioral cues, such as forming a croissant instead of a closed-circle donut. She also shares how her work bridges the gap between data and dialogue, where AI can support personalization but humans still carry the heart of connection. 

Produced by: Eming Piansay

Transcript

Devon Montgomery Pasha
 Welcome to What One Thing, a Smart Meetings podcast where we ask successful people what made all the difference in their life and career, so listeners can learn from their journeys and spark their own growth. Good morning, everyone. I am Devon Montgomery Pasha, delighted to be the newest member of the Smart Meetings podcast family. Today’s guest is on a mission to make human connection easier and a lot more fun. Please welcome Shaena Harrison, founder and professional wing person behind Wing People, a boutique agency dedicated to bringing genuine human connection back to business events.

Shaena Harrison
 Thank you. I’m so excited to be here with you, Devon. And congratulations on becoming a co-host.

DMP
 I’m thrilled. When I was thinking about new voices in the industry and the human experience, you were the first person who came to mind. Before we get into your work, can you explain what a wing person is and how the term became part of your career?

SH
 It actually came after being laid off four times in three years. I call it my “redundancy rodeo.” My confidence took a hit, but a few things happened at once. I’ve always been a connector. My brain naturally says, “You do this and you do this. Why haven’t you two met yet?” My mom started the first Make-A-Wish organization in Canada, so I grew up around connection and service. In November 2022, a friend called and said, “I’m starting a new company. You introduced me to everyone when we met eight years ago. Can you be my professional wing person?” I typed “professional wing person” into ChatGPT, and it thought I was trying to help people find love, which was not the case. But we launched the idea in March 2023, and it’s been a wild ride ever since.

DMP
 Before recording, we were talking about how you and I met at the College of Extraordinary Experiences. You introduced yourself as a professional wing person, and while we were there, you were collecting information about people and asking who they wanted to meet. You connected strangers with ease. You’ve said events aren’t about the stage. They’re about the people. What does designing for connection look like for you?

SH
 When people hear “go network,” they often don’t know what that means. Do they grab a coffee and stand awkwardly in the corner? Designing for connection means understanding your audience and creating conditions where real conversations can happen. One example is our connection corners, facilitated by wing people. We learn who attendees are, why they’re there and how we can help. Sometimes AI supports that process, but the human element accelerates meaningful connection. These interactions have turned into partnerships, friendships and, occasionally, accidental love.

DMP
 You create conditions where true conversations happen, which is very different from the usual networking reception with wine, cheese cubes and awkward small talk. How do you build that sense of belonging?

SH
 Everyone wants to feel like they’re part of something. When people are standing alone, especially introverts, sometimes all they need is a nudge. One of my favorite techniques from the College is the extra chair rule. If you sit in a group of chairs, keep an empty chair. When someone joins, add another chair. It signals, “There’s always room for you.” Those tiny shifts create inclusivity. I also love the “donut vs. croissant” method. People form donut circles, which are closed. A croissant shape leaves space for someone new to naturally join the group. It’s a behavioral cue that changes everything.

DMP
 It’s such a human reminder to include others in the way we’d want to be included. You mentioned using AI early on, but your work is about genuine human connection. How do the two work together?

SH
 AI can open the door, but humans have to walk through it. AI is good at matchmaking and personalizing suggestions, but it can’t sense nervousness or pick up on body language. That’s where wing people come in. We bridge the gap between data and dialogue. But AI still misses a lot. For example, I recently introduced a client from Kenya to one of the founders of Skype. The app never would have matched them. I facilitated it using one of my techniques, the LinkedIn game, where you guess how many mutual connections you share. They ended up meeting in Kenya. That outcome would never have happened with AI alone.

DMP
 Your smile says everything about how meaningful this work is. What has this journey meant to you personally?

SH
 It’s been uplifting and challenging. I’m building something that didn’t exist. I’m educating, selling and working solo while leading a global team of wing people. Traditional KPIs can’t measure the impact of a connection that changes someone’s life. But hearing stories about partnerships, friendships or even a letter from someone I winged eight years ago makes it worth it. Those moments remind me why I do this.

DMP
 We’ve reached our signature question. What is the one thing that made all the difference in your life and career?

SH
 Resilience. Getting pushed off the cliff and getting back up. My career has been a squiggly line. I’ve worked in corporate, startups, nonprofits and NGOs. Every role taught me something. If I hadn’t tried so many things, I wouldn’t be doing this now. And your network is everything. I have anchors, high-fivers, cheerleaders, obsidian rock stars. Know who your people are, ask for their support and return the favor.

DMP
 Before we wrap, I want to touch on your cheeky side project: Date My Mate. What is it?

SH
 People kept asking if I would do love events. As a recovering event producer, I finally said yes. At Date My Mate, everyone brings a wing person. Your wing person does the introductions. It’s old-school matchmaking with business cards and “my friend likes you” energy. People are dating from it. No “date my babies” yet, but it’s still new. Ultimately, people are hungry for in-person connection, whether for business or love.

DMP
 One last fun curveball. If you could be a wing person to anyone in history, who would it be?

SH
 Marie Curie. Imagine having a wing woman beside her saying, “Excuse me, gentlemen, she just discovered radiation. What did you do today?” I think she deserved someone lifting her up in rooms that didn’t welcome her.

DMP
 A perfect answer. Shaena, thank you for sharing your insight and your spark with the Meet Smart community. Conversations like this remind us that small moments can make a big difference. You can find more brilliant voices at smartmeetings.com/podcast or wherever you listen. I’m Devon Pasha. Until next time, keep shining bright and share your one thing with the world.