Difficult conversation

A conversation about something important that people find hard to raise, often because the stakes are high and feelings are involved.

Checked 9 Oct 2026 · 3 sources

Origin
Douglas Stone, Bruce Patton and Sheila Heen (1999)

What is a difficult conversation?

A difficult conversation is a conversation about something important that people find hard to raise, often because the stakes are high and feelings are involved. Telling a seller they are moving to a performance plan is one. So is telling the board the quarter will miss. The 1999 book Difficult Conversations: How to Discuss What Matters Most, by Douglas Stone, Bruce Patton and Sheila Heen, treats these talks as a skill people can learn.

Why it matters to a revenue leader

Revenue leaders face these conversations often, from a manager who is not working out to a forecast that will disappoint the sponsor. Putting one off leaves the problem in place, and the eventual conversation gets harder. The authors, whose work grew out of the Harvard Negotiation Project, focus on preparing well and opening in a way that lowers defensiveness. A CRO who handles these talks directly also shows managers that hard news gets said early on this team.

Example

A VP Sales at a mechanical services company has a branch manager whose team has missed plan for several quarters. She has postponed the conversation twice. When they meet, she opens with what she has seen in the numbers and asks how he sees it before discussing what changes next.

The question to ask

"Which conversation have I been putting off, and what is the delay costing the team?"

Sources

  1. Difficult Conversations: How to Discuss What Matters Most, Viking 1999 (Open Library record) checked 9 Oct 2026
  2. Difficult Conversations by Douglas Stone, Bruce Patton and Sheila Heen (Penguin Random House) checked 9 Oct 2026
  3. Sheila Heen, faculty profile (Harvard Law School) checked 9 Oct 2026

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