# Appendix A Coaching Questions by Challenger Pillar

Paraphrased from the Challenger Coaching Guide excerpt (Appendix A, _The Challenger Sale_). Use these question sets in the Understand and Embed steps of the PAUSE framework to anchor coaching conversations to specific observable behaviors per pillar.

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## Teach for Differentiation

**Before the call — preparation questions for the rep:**

1. What business problem are you planning to surface with this customer — and why this one, at this point in the relationship?
2. How do you know this problem is genuinely high-priority for them? What evidence do you have?
3. How have other companies in this customer's situation approached the same problem? What worked and what didn't?
4. How novel will your perspective be to this customer? Is it likely to teach them something they don't already know, or confirm what they already believe?
5. Why hasn't the customer solved this problem on their own already? What has stood in the way?

**After the call — debrief questions:**

- How engaged or provoked did the customer appear when you introduced your perspective? What signals told you that — their words, questions, body language, next-steps energy?
- Was the customer's reaction to your insight what you expected? If not, what surprised you?

**Coaching exercise — building a stronger teaching conversation:**

Pick one account together. Answer these:
- What are the customer's top strategic priorities over the next one to three years?
- Where are they outperforming their competitors? Where are they falling behind?
- How does your contact's specific role connect to those priorities and gaps?
- Where does your company's capability create a genuine advantage that connects to the customer's situation?

Use the answers to help the rep build a teaching conversation that links the customer's competitive position to your solution — without leading with the product.

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## Tailor for Resonance

**Before the call — preparation questions for the rep:**

1. What industry trends are likely top-of-mind for this customer right now, and how would those trends hit their specific company?
2. What is distinctive about this company's market position — what do they do better or differently than their peers?
3. Where are they most exposed or vulnerable in their competitive environment?
4. Which stakeholders will be in this conversation, and what does success look like from each of their perspectives?

**After the call — debrief questions:**

- What did you learn about this customer's business drivers that you didn't know going in?
- Did you encounter any goals, concerns, or motivations you hadn't anticipated? How did you adapt in the moment?
- Did your message land differently with different stakeholders in the room? Why?

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## Take Control

**Before the call — preparation questions for the rep:**

1. What specific next step does a successful outcome of this call produce — not a vague "move forward" but a concrete decision, date, or action?
2. What do you know about how this customer's organization actually makes purchase decisions? Who approves? Who blocks? What does their internal process look like?
3. Where in the buying process are you, and what does the customer need to do in their organization to get to the next stage?

**After the call — debrief questions:**

- Did this conversation produce a concrete next step that moves the purchase process forward? What is it, and who owns it?
- When tension arose — around price, timing, consensus, or commitment — what was your instinct: defuse the tension or hold your position? What did you actually do?
- What are your next steps to ensure the deal does not stall between now and the next interaction?

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## Which Questions to Use

Select the question set that matches the rep's weakest Challenger pillar as identified in `rep-profile-assessment.md`:

| Weakest subscale | Use |
|---|---|
| Teaches for Differentiation (Q2+Q3 < 7) | Teach question set |
| Tailors for Resonance (Q5+Q6 < 7) | Tailor question set |
| Takes Control (Q8+Q9 < 7) | Take Control question set |

If two subscales are equally weak, focus on one per coaching session — do not blend question sets. The Specify step requires the manager to land on ONE observable change, and mixing pillars makes that impossible.