Last week, I attended a networking event where a CEO presented his SaaS platform for contractors. The guy had a compelling story: he grew up working with his dad's construction company, taught himself to code at 15, built and launched e-commerce platforms and did other work, and then spent the last several years building software that solves real problems for builders.

During Q&A, he mentioned something that made my product management brain light up: his small team moves fast, but he's worried that scaling up will slow them down like he's seen at competitors. That's literally what I help teams solve.

So after his talk, I walked up to introduce myself.

And I absolutely botched it.

I asked some questions about their platform, and made interested noises (because I'm legitimately interested in what they're building!), then tried to position myself as someone who could help with their scaling challenge.

His body language told me everything I needed to know: polite smile, brief answers, looking for an exit. We weren't connecting at all.

I walked away kicking myself because I knew exactly what I'd done wrong.

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The Three Conversations

I just started reading Supercommunicators by Charles Duhigg, and early in the book he breaks down something critical: every conversation is actually one (or a mix) of three types.

The practical conversation: "What's this really about?" Problem-solving, information exchange, and decision-making.

The emotional conversation: "How do we feel?" Processing experiences, sharing reactions, and seeking validation.

The social conversation: "Who are we?" Identity, relationships, values, and belonging.

The key insight? Both people need to be having the same type of conversation, or you're talking past each other.

(This mirrors the three-conversation framework from Difficult Conversations by Stone and Heen. If you've read my onboarding emails, you've seen me reference their conflict work. The same principle applies to connection.)

Where I Went Wrong

I came at this CEO with a practical conversation. "I understand your scaling problem. I can help solve it. Let me tell you how."

But that's not the conversation he wanted to have.

He'd just spent 20 minutes sharing his story—his dad's business, learning to code as a teenager, the mission to help contractors like the ones he grew up around. His energy was in the identity space. He wanted the "who are we?" conversation.

I should have asked about his father. Or about what motivated him to build this specific thing. Or about conversations with his family about the business. Or about the contractors he's trying to serve.

If I'd started there—if I'd actually connected as humans first—maybe we would have eventually gotten to the practical conversation about scaling teams. Maybe not. But at the very least, I would have built an actual relationship instead of fumbling through a transactional pitch.

The Mistake Product People Make

We do this constantly with stakeholders, partners, and potential customers.

We lead with solutions because that's how our brains work. Someone mentions a problem, and we immediately jump to "here's how to fix it."

But they might not be in problem-solving mode yet. They might need to process the emotional impact of the challenge first. Or they might be trying to understand how this fits into their identity and values.

When you mismatch the conversation type, even good ideas land flat.

What to Do Instead

You can often read the conversation type from what someone emphasizes, their body language, and their tone. Are they:

• Focused on details and solutions? → Practical conversation

• Sharing feelings and reactions? → Emotional conversation

• Talking about values, identity, relationships? → Social conversation

Then match them. If they're emotional, share a similar experience that validates their feelings. If they're in identity mode, ask questions about their background and values. If they're practical, then yes, problem-solve with them.

Duhigg recommends asking directly: "Are you looking for feedback on this, or would it help more to just talk through what you're experiencing?" Adjust the question to fit your context, but the principle is the same—clarify what kind of conversation they need.

The critical part is that your motivation must be a genuine connection, not manipulation. If you're just mirroring to get something, people sense it. The technique only works when you actually care about understanding them.

Monday Morning Action

Here's what Duhigg recommends, and I think this is the real lesson I need to internalize:

"The most effective communicators pause before they speak and ask themselves, 'Why am I opening my mouth?' Unless we know what kind of discussion we're hoping for and what type of discussion our companions want, we're at a disadvantage."

So next time you're building a relationship with a potential partner, customer, or stakeholder, pause before you jump in.

Ask yourself two questions:

1. What kind of conversation am I trying to have?

2. What kind of conversation do they want to have right now?

If those don't match, have their conversation first. Build the connection. The practical outcomes can come later.

I'm going to try this with the next person I meet. Maybe I'll even circle back to that CEO once I've finished reading Supercommunicators and have something more interesting to share than "I can help you scale."

I'm going to practice this "pause" thing before my next networking conversation. And I'd love to hear how you're using this successfully, or if you've found a better approach!

Cheers,

Matthew

P.S. - If you want to dive deeper into these communication tools, both Supercommunicators and Difficult Conversations are excellent. I'm finding they complement each other well.

P.P.S. - I'm launching a weekday podcast where I'll break down real product team conflicts in 3-7 minutes. Got a challenging situation with your team, stakeholders, or boss? Reply and tell me about it—I might cover it in an episode (anonymously, of course).