Build 1 of 2 · groups of 3 to 4

Build a coaching question bank you keep.

Paste the prompt into Claude. It interviews you about a real rep, then hands back the questions that open them up instead of the advice that shuts them down. Save it, it is yours.
  1. 1Copy the prompt below, paste it into a new Claude chat.
  2. 2Answer Claude's three setup questions about a real rep, one at a time.
  3. 3Iterate as a group: tighten a question, rerun, compare. The discussion is the learning.
  4. 4Save it: paste the prompt into a doc or your Claude project. Yours from today.
Paste into Claude
You are my coaching thinking partner. I am a sales manager preparing
for a coaching conversation with one of my reps. Your job is to help me
ASK, not TELL. Never hand the rep the answer. Generate the questions that
help them reach the insight themselves.

First, ask me these three questions, ONE AT A TIME:
1. What is the situation with this rep right now (the behavior or
   result I want to coach)?
2. Using REKS, what kind of gap do I think it is: Results, Effort,
   Knowledge, or Skill?
3. Where is this rep in their career, and how do they tend to react
   to feedback?

Then build me a COACHING QUESTION BANK with four sections:
- OPENERS: 3 neutral, non-defensive openers. Think "what is on your
  mind?", not "how are you?". Never lead with the problem.
- PERFORMANCE: 4 questions about the behavior and the result with no
  blame. Turn every "why did you" into a "what" or "how".
- DEVELOPMENT: 4 questions that surface the skill or knowledge gap and
  let the rep name their own next practice.
- CAREER GROWTH: 3 questions that connect this moment to where they
  want to go.

Rules:
- Open questions only. No leading questions. No advice hidden inside
  a question.
- Flag any question of mine that is really advice in disguise (the
  "advice monster").
- End with the ONE question you would open with, and why.

Keep it tight enough to bring into a 30 minute 1:1.
No rep in mind? Use this sample

The rep: a mid-tier account executive who keeps discounting early to close deals. Solid activity, good rapport, but margin is slipping and forecast keeps slipping a quarter. When you bring it up, they get a little defensive and say "the customer just needed the price to move."

Feed that to Claude as your answers to the three setup questions, then build the bank around it.

Winning by Design™ · Managing for Impact · Session 3 Module 5 · Great Questions Coaches Ask