The right question can change everything

Some conversations fade the moment they end. Others leave you replaying them for years.

The difference is often a single question, the kind that makes you stop mid-sentence, tilt your head, and see your world differently. A good question can shift your day. A great one can change your career, or even your life. For me, there’s one I keep coming back to. A few years ago, a friend asked me:

Does your job actually provide meaning in a richer sense?

It wasn’t meant as a challenge, but it forced me to look hard at where I was going and whether I was building a life I actually wanted. That single question still echoes in my head whenever I feel stuck. Throughout my career, I’ve been lucky to meet peers and mentors who have shaped me—not just as a data scientist, but as a person—through questions like this. And that’s at the heart of what we’re building with Flynt. We're not optimising for clicks or time spent scrolling. Our north star is high-quality conversations (HQCs), lovingly named in one of our earliest brainstorming sessions. It's why we went back to first principles to break down what separates polite small talk from a true breakthrough. And it's why, with every Flynt introduction, you don't just get a match, you get conversation starters tailored to the unique dynamic between you and your match. It's an area we're obsessing over: using AI to identify which questions will create the deepest conversations.

A framework for breakthrough conversations

A forgettable conversation dies in small talk. A memorable one lands in the territory where trust, ideas, and breakthroughs live. Here are five types of questions from our playbook, designed to help you make that leap.

Fresh perspectives

Inviting unfiltered outside views Your Flynt match isn't your colleague, that's the point. They can give you the brutally honest external view you'll never get in the office.

• “From where you sit, what’s the most obvious mistake my industry is making right now?”
• “What’s one ‘unspoken truth’ in your field that you think is completely wrong?”
• “If you stepped into my role tomorrow, what’s the very first thing you’d change?”

The real story

Moving past the polished version into lived experience The biggest lessons rarely come from glossy success stories. They come from the messiness, the scars, the what it was really like.

• “Tell me about a project that looked like a huge win from the outside, but was a nightmare on the inside.”
• “What’s the most expensive mistake you’ve been part of, and what did it teach you?”
• “What’s a piece of common industry advice that turned out to be useless in practice?”

Honest guidance

Stress-testing high-stakes problems with help from someone outside your bubble It’s easy to get stuck inside your own perspective. A good question can turn your match into a consultant, surfacing angles you’ve missed. One I find particularly revealing is: “What’s the riskiest assumption we’re making here?” It cuts straight to where our reasoning might be weakest. Other powerful ones:

• “Here’s a problem I’m stuck on: [briefly state the problem]. What am I not seeing?”
• “If you had to play devil’s advocate on my current approach, where would you attack first?”
• “What’s a counterintuitive way to solve this that most people wouldn’t think of?”

What matters most

Surfacing values and deeply held beliefs The best questions cut through professional posturing to reveal what a person genuinely admires and prioritises. One of my personal favourites in this category is: “If you were starting a new company tomorrow and could only bring one person you’ve ever worked with, who would it be and why?” I use this often in interviews because it reveals both what someone values and sparks reflections on the game-changing people in their career. It shows who they trust when the stakes are high. Other powerful ones:

• “What’s a belief you hold strongly that many people in our industry would disagree with?”
• “When you’ve felt most proud of your work, what underlying value was being honoured?”

Future horizons

Exploring possibilities and ambitions Looking ahead creates space for imagination - and often, surprising overlap in ambitions.

• “What are you most excited to learn in the next six months, outside your direct responsibilities?”
• “What are you most excited to learn in the next six months, outside your direct responsibilities?”
• “If you weren’t in your current role, what’s a problem you’d love to spend a decade solving?”

These kinds of questions take courage to ask, but the insights they unlock can reshape your path. We're solving this by using profile data to automatically generate the most impactful questions for each specific match, turning every introduction into a potential breakthrough. The right introduction puts you in the room with the right person. Flynt handles the connection and gives you the conversation starters.