How should rapport be built with a counterparty in a conversation or sales meeting?

Stevie Case · Jan 25, 2023

The best way to open people up in a difficult sales meeting is to give them comfort with your own vulnerability, because being human and flawed makes others comfortable being imperfect

This was the lesson her mentor taught her in a hostile sales meeting

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Stevie Case · Jan 25, 2023

Salespeople can be vulnerable and openly flawed with clients while still projecting competence and confidence, and holding both is what makes selling work

People still buy from people, so being a knowledgeable expert and an uncertain human being at the same time is what creates connection

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Gili Raanan · Mar 18, 2024

To get founders to open up about painful memories an investor must strip away VC status signalling — no offices, a quiet non-corporate setting, no flashy clothes — and share their own failures first

Without mutual openness and transparency the two sides cannot be terrific partners, and he is effectively joining as another cofounder rather than buying into an existing company

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Harry Stebbings · Aug 4, 2025

Running a visible rapport-building playbook destroys rapport; making the other person feel safe and being a little vulnerable yourself is what actually builds it

When he senses someone is running a playbook on him it doesn't work, whereas sharing something personal makes the other person feel they're getting to know him

Scope: drawn from his experience as an interviewer

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Ron Gabrisko · Aug 4, 2025

Rapport is built by starting small and asking about where someone grew up, their interests and their family rather than weather-style small talk

People are heavily influenced by where they grew up and their families, and family is a super important thing to most people, so it's the fastest route to knowing them

52:05 Start small with personal questions about hometown and family

Emil Michael · Oct 24, 2022

Opening a serious negotiation with small talk about flights and hotels betrays naivety; better to build rapport by asking the counterpart how they saw the shared competitive events.

In a serious negotiation nobody actually cares about the pleasantries — they care about what you're trying to do — whereas comparing perspectives on the same incidents builds real rapport and trust.

18:06 Comparing shared competitive experiences not small talk builds real rapport