Earlier this year I was accepted into a leadership coaching program through the Co-Active Training Institute (CTI) and it’s leveled up my skills as a business coach and mentor, as well as made me a better question-asker and listener. So much so that during a recent dinner with a few girlfriends, one of them remarked, “You’re making me think about things I don’t think anyone has ever asked me.” She was talking about wanting to leave her cushy full-time job and lean into brand consulting, but was really doubting herself, so I asked two powerful questions, “What’s on the line if you leave or stay,” and “How will you know when you’re ready?” It was a beautiful moment and one that all of us at the table could relate to as we’re venturing into new jobs, motherhood, dating—and really anyone reading this who’s putting themselves out there in new ways.
It made me think about how we network (whether it’s a virtual or formal connect, or simply gathering at a friend’s house) and how we can ask more thoughtful questions to build relationships versus the expected “so, what do you do for work?” prompts.
Years ago when I worked for SXSW, we hosted meet ups all around the US to get to learn more about the community and what they were excited about. Speaking to hundreds of humans in a calendar year reminded me of three things: everyone has a story; everyone wants to be seen; and if you want to build trust, start with being genuinely curious.
I’ve discovered there’s a real art to getting to know someone better. So, to help you on your way, I’m sharing some of the questions I like to ask when I meet someone new to avoid the cheesy, surface-level moments and get straight into the real talk.
- What brought you here tonight?
- How do you know the host?
- What are you excited about right now?
- What are you looking forward to this week?
- What is a current challenge for you at work?
- Where are you finding inspiration?
- What does a day in your role look like?
- What organization or brand is fun to watch right now?
- How do you spend your time away from work?
- What’s the newest concept or idea you recently discovered?
- Who is your favorite person to follow on social media (or podcast to listen to)
- Who are you hoping to meet tonight?
- What are your favorite tools for organization?
- What app do you use the most?
- What makes (insert their name) unique?
- What are you most proud of right now?
It might feel different to kick off a conversation with “Hey, I’m ____, I want to know more about you, what brought you here tonight?” but I guarantee their answer will provide so much more insight into who they are instead of “How are you?” Because it’s unlikely we’re going to tell a stranger how stressful our day was.
I once had a friend who hosted an event and instead of introducing me as “This is Kelly, she works for SXSW,” she shared, “This is Kelly…” along with a fun fact about me and one of my hobbies. It was so cool and something I’ve adopted as well when I play host.
This self exploration had me intrigued. So I enlisted a few of my favorite people who also happen to be top networkers to share the questions they always ask when they want to get to know someone better. Here’s what they shared:
- What advice or insight would you share with your 16-year-old self? — Siraad Dirshe, Producer and Storyteller
- What can I help you with right now? — Jane Ko, Founder of A Taste of Koko, Austin Food & Travel Blog
- What does rest look like for you? — Shauntavia Ward, Founder of eleMINT Skin
- What was your most enjoyable phase of life and your most stressful? — Jen Pinkston, Founder of La Paloma
- What is your nickname? (There are so many back stories on how they got it or the rare people that have none.) – Melissa Farrar, Director of Communications, Fairmont
- What other careers did you consider or explore before choosing this one, and why did you rule them out? — Jessica Sanam Hekmat, Brand Strategist
As I’ve learned through my training, the best questions are open-ended and are always coming from a place of curiosity and inquiry, and of course, leaving space—even if it’s an uncomfortable amount—for the other person to share their thoughts and experiences.
Everyone wants to be seen and heard and in my experience, powerful questions show that you are interested and interesting, and those are the relationships that tend to evolve into something beautiful over time.
