Coaching and Difficult Conversations (VSLive Vegas 2026 Workshop Slides)

March 20, 2026
Coaching and Difficult Conversations (VSLive Vegas 2026 Workshop Slides)

This is Module 6 from the "Mastering Human Factors in Engineering" workshop that Angela Dugan and I co-presented at VSLive Las Vegas 2026. (See also: Module 1: The Leadership Shift, Module 2: Why Does Everyone Hate Agile?, and Module 3: Words for Leaders.)

The Scrum Master Is Dead

The dedicated coaching role is largely gone from most organizations. But the skills didn't disappear — they got distributed. Somebody still has to remove obstacles, ask the hard questions, and have the conversations that nobody else wants to have. That somebody is probably you.

The coaching stance is fundamentally generative. A manager assigns tasks, checks on progress, gives answers, and drives the team. A coach asks questions, removes obstacles, helps find answers, and enables the team. Both are needed, but if all you have is the manager side, you're building dependency instead of capability.

Three Levels of Listening

This module starts with something deceptively simple: how to listen. Level 1 is listening to respond — you're already formulating your answer while they're talking. Level 2 is listening to understand — you're actually tracking what they're saying. Level 3 is listening to the room — you're noticing the energy shifts, the things that go unsaid, the moment when everyone suddenly gets quiet.

Level 3 is the coaching superpower. When the energy shifts, say what you noticed. You're not diagnosing. You're making the invisible visible. That's a generative act.

Difficult Conversations Don't Age Well

The back half of the module covers the framework from "Difficult Conversations" (Stone, Patton, and Heen). Every difficult conversation is actually three conversations happening simultaneously: what happened, feelings, and identity. Most of us only address the first one and wonder why things don't get better.

The practical framework is simple: Observe (state what you observed, facts not interpretation), Impact (share the impact on you, the team, or the project), Ask (ask for their perspective — you might be wrong). And sometimes the most important thing is not solving anything at all. When someone is upset, sometimes you just need to be with them. Presence can be the solution. Resist the urge to solve.

One last thing that I think is worth highlighting: the more senior you get, the less honest feedback you receive. How you react to bad news defines your culture. The hero can't be coached. Be coachable yourself.

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—Ben

Categories: generative-leadership