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17 Unorthodox Questions to Rapidly Build Trust and Authentic Connection
How to skip the small talk and explore unchartered territory with unexpected questions.
Dave Kline
May 24, 2023
Read Time: 3 minutes 4 seconds
As you know, I spent last week in Barcelona with a company I advise. On Day 1, the founder dropped this into the group chat:
“During the offsite, it's the "ski lift" 🎿🚠🚡⛷️ conversations where so much of the magic happens. They're unstructured, unprompted, organic - just people talking. In order to have the most meaningful conversations possible, ironically, some preparation does help with serendipity... Take a few moments to write down some questions you'd like to ask people.“
This left me thinking: Had I become lazy with my questions? Was I settling for the mundane because they were safe? Could I speed to a deeper connection by taking more risks with my inquiries?
With a week of data fueled by his prompt, my answer to all of the above is a wholehearted Yes.
But this muscle had atrophied for me. So I needed to do some prep. I also got to overhear others trying their hand at this.
My conclusion: There’s a fine line between authentic and awkward, between novel and nonsense. In your effort to speed to meaning, you can overstep or overcomplicate and do just the opposite.
So what constitutes a great question?
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The Anatomy of A Great Question
While there is no recipe, here are the six characteristics that seemed to underpin the questions that launched the best conversations.
Simple » Compound - Questions that tried to open up too many vectors typically cause more confusion than connection. Start simple and save the “ands” for the conversation you’re trying to start.
Genuine Curiosity - It seems obvious, but you can’t fake genuine curiosity. Don’t fall in love with a question because it’s clever. Ask one you genuinely care to learn about. I start every MGMT Accelerator cohort by asking about everyone’s first concert because it’s typically a visceral moment of joy I want to know about.
Long Horizons - In our always-on, instant-gratification world, going back in time or imagining years into the future forced a distillation of core beliefs that people held.