Does leverage in deal-making come from driving the conversation or from listening and reading the counterparty?

Larry Shurtz · May 10, 2024

Listening and empathy are the highest-leverage leadership skills, and customers and teams can tell the difference between someone genuinely listening and someone waiting to deliver a prepared answer

The leaders who most impressed him — Godfrey Sullivan and his long-tenured boss through Oracle and Salesforce — could hear that things weren't going as anticipated and leave the team feeling 'we've got this'

Scope: combined with preparation, knowing the details, and having a plan

47:56 20Sales: How to Build Vertical Sales Teams, Why No Customer Success is BS and Everyone Needs it, How to Hire, Train and Retain the First Reps and Lessons Scaling to $2.1BN Revenue and 1,300 People with Larry Schurtz, CRO @ Genesys

Winston Weinberg · Jan 19, 2026

In deal-making you should listen more than you speak, because deal-making is fundamentally people reading at scale rather than talking the most

People wrongly equate movement and talking with control and progress; the quiet party may hold the upper hand, and the real work is reading individuals, groups and verticals to figure out what they want

54:59 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

Jackie Reses · Mar 31, 2023

Deal making is not a zero-sum game; the key is first understanding what truly drives the other side's decision — whether they need to look good or need a specific economic outcome and when — which creates optionality in what you can negotiate for

Creativity about the other party's real needs yields both good long-term relationships and great economic outcomes

20:36 Deal making is not zero sum understanding the other sides true drivers creates optionality

Jackie Reses · Mar 31, 2023

You can extract enormous economics from a position of zero leverage by rebuilding trust and demonstrably putting the counterparty's interests first before asking for anything

At Yahoo she spent years rebuilding relationships in China and letting Alibaba shareholders do things she didn't have to allow, so that when she asked for equity back they trusted her and returned economics worth roughly $50BN to Yahoo shareholders despite a contract obligating the giveback

23:44 Building trust and demonstrating care for counterparty first can extract major economics from zero leverage

Jeff Lawson · Jun 28, 2021

Almost everyone believes they are a good listener, but genuinely good listening takes hard, deliberate work.

42:51 Genuine listening is a rare effortful skill despite near universal self belief

Harry Stebbings · Sep 11, 2024

Being comfortable with silence is one of the most important interviewing skills, and everyone should interview because it makes you a better spouse and friend

Asking a question and sitting in awkward silence is where the magic most often follows

26:54 Comfortable silence is the decisive interviewing skill

Emil Michael · Oct 24, 2022

Beyond the industrial logic, it was his personal relationship and accumulated trust with Jean Liu that got the Uber China–Didi deal over the line, sustained by clearing the air with her at the end of every day.

A week of negotiating together built trust; like a marriage, resolving grievances before bed each day kept the process alive through an extremely complicated cross-border consumer M&A.

19:17 Sustained personal trust built through daily reconciliation drives complex cross border deals