The Subtle Art of Asking the Right Questions: From Mundane Dates to Navigating AI and VC Connections
What’s the one question you think can tell you the most about someone?
“What do you like to do in your free time?”
That’s the question. The one that’s haunted almost every date I’ve been on. The moment it’s asked, my brain switches to autopilot, and I feel myself zoning out. It’s not that I don’t have an answer—it’s that the question itself feels so… flat. What are you really going to learn from, "I like eating out with friends"? Are you going to gain any real insight into who I am from that? Probably not.
But that’s the thing: a question like that doesn’t push the conversation anywhere meaningful. It’s small talk dressed up as a legitimate inquiry. And yet, it’s exactly in moments like this that I realized just how much power the right question can hold—whether on a date, at work, or even when dealing with artificial intelligence.
The AI Takeover? It's All in the Questions
There’s been a lot of chatter lately about AI taking over our jobs, lives, and who knows what else. Chatbots are writing poetry, designing graphics, and even diagnosing illnesses. It’s easy to feel like AI is creeping into every corner of our lives, leaving us humans with nothing left to do.
But here’s the twist: AI is only as good as the prompts we give it. Just like how a boring question leads to a boring conversation, a vague or generic prompt leads to lackluster responses from AI. If you ask, “What’s the weather today?” you’ll get a basic answer. But ask, “How will the weather impact the turnout at a beach event I’m planning this weekend?” and you’re suddenly tapping into AI’s true potential.
AI isn’t about replacing humans—it’s about enhancing what we already know how to do, as long as we ask the right questions. The fear of AI taking over stems from a misunderstanding: the real skill is in knowing how to communicate with it, how to extract useful insights from it. And at the core of that skill is the ability to ask the right question.
The VC Lens: Asking the Questions that Matter
In venture capital, the importance of asking the right questions isn’t that different from navigating a conversation with AI—or even from going on a date. But in VC, asking the right questions can make or break an investment. Let me share a moment that really drove this home for me.
I was in a pitch meeting with a founder who was doing all the typical stuff—going through growth metrics, market potential, and throwing out every buzzword you could imagine. It was tempting to ask the standard VC questions: "What’s your customer acquisition cost?" or "How soon will you hit your next revenue milestone?" But just as on a date when you want to move beyond the boring icebreakers, I wanted to know something real. So, I switched it up.
Instead of asking about metrics, I asked, “What’s the hardest day you’ve had since starting this company, and what got you through it?”
The founder paused and then opened up in a way I hadn’t expected. They shared a story about how they nearly lost everything when a key partnership fell through, how their team was on the verge of quitting, and how they had to dig deep to find a solution. That story told me more about the kind of leader they were than any data point could.
At the end of the day, it’s not just about whether the numbers make sense—it’s about whether I can see myself sitting on the same 12-hour flight with this founder on the way to our next investor meeting. Would I want to work alongside them when things get tough? These are the questions that really matter, because startups are full of unknowns, and it's the founders’ ability to weather those storms that sets them apart.
The Art of the Follow-Up
And it’s not just founders. When it comes to Limited Partners (LPs), the same principle applies. I used to make the mistake of focusing solely on the numbers: portfolio size, risk appetite, expected returns. But then I started asking more open-ended questions. One LP meeting stands out in particular.
Instead of diving straight into their financials, I asked, “What would make you excited about a new venture?” That question shifted the entire conversation. The LP opened up about their interest in sustainability projects and tech that could make a real difference in combating climate change. It wasn’t just about returns anymore; it was about aligning with their values. That was a turning point for us, and it helped me understand how to better position future investments to meet their personal goals.
The takeaway? Whether you’re talking to founders, LPs, or even AI, the art of asking questions isn’t just about gathering information—it’s about steering the conversation in a way that reveals deeper truths. It’s about understanding motivations, not just metrics. It’s about connection, not just data.
Bringing It All Together
In a world where AI is taking over more and more tasks, the human skill of asking the right question has never been more important. It’s the key to unlocking better answers, deeper insights, and more meaningful conversations—whether you’re on a date, managing a startup, or deciding where to allocate millions in venture capital.
So, what do you like to do in your free time? Just kidding. But seriously—what’s the one question you think can tell you the most about someone?