Level Up Discovery With Your Very Own AI Coach
- John Hsieh
- Nov 21, 2024
- 3 min read
Updated: Jul 9
Goal: This interactive, AI-guided coaching module is built for new hires looking to ramp faster and for experienced AEs who want targeted discovery coaching. In just 30 to 60 minutes, reps will:
Practice writing discovery questions that surfaces high impact pain points
Respond to realistic buyer scenarios
Get real-time feedback at every step to improve their instincts
This module is fully self-paced, actionable, and designed to build stronger discovery skills, without needing a live manager or scheduled training.
✅ What You’ll Need
ChatGPT (or a similar AI tool)
30 to 60 minutes focused time
High level understanding of problems you solve and for whom
You’ve got the tools. Now let’s sharpen your discovery game, one prompt at a time.
🔹 Step 1: Clarify The Problem(s) You Solve
Objective: Get clear on the problem your company solves and for whom in your own words.
Your responses will also help generate tailored coaching and simulations in Steps 2 & 3.
Paste into ChatGPT/AI Tool With Your Responses Filled In:
Act as a SaaS sales coach. I’m an AE and I want your help improving how I explain the problem we solve and who we solve it for. I’ll provide 4 key pieces of context — please review my responses and give me feedback. Be specific: tell me where I was clear or vague, what I could improve, and how to make it stronger.
Here are my responses:
1. Company Name: [Insert Response]
2. Industry or Category: [Insert Response]
4. Top 3 Business Problems We Solve: [Insert Response]
Please give me:
- Clear, structured feedback on each response
- Suggestions for sharpening my language
- One clarifying question I should consider for each section
🛠️ Once You Get AI Feedback:
Pick one of your original answers and revise it based on the feedback. Then paste your revised version back into the chat and ask:
“Here’s my revision. Is this stronger? What else could I tighten?”
This step helps you lock in the skill and models the kind of iterative thinking great sellers use every day.
🔹 Step 2: Turn Those Problems Into Discovery Questions
Objective: Turn the problems your company solves into thoughtful, open-ended questions that help you uncover whether a prospect is experiencing them without pitching.
Paste into ChatGPT/AI Tool With Your Responses Filled In:
Act as a SaaS sales coach. I’m an AE practicing how to run better discovery. I’ll list 3 business problems our company solves.
Then I’ll write 3 discovery questions and ask you to coach me. Tell me if they’re clear, too vague, too leading, or not likely to uncover the pain. Help me sharpen them.
Here are the problems we solve:
1. [Insert Problem]
2. [Insert Problem]
3. [Insert Problem]
Now here are my first-pass discovery questions:
1. [Insert Question]
2. [Insert Question]
3. [Insert Question]
Please give me:
- Feedback on whether each question is likely to surface real pain
- Suggestions for sharpening or rewording each one
- One additional discovery question you’d recommend adding based on these problems
🔹 Step 3: React to Real Buyer Responses
Objective: Practice listening for buyer signals and writing thoughtful follow-up questions that help uncover deeper pain, urgency, or decision criteria.
Paste into ChatGPT/AI Tool With Your Responses Filled In:
Act as a SaaS sales coach. I’m practicing how to respond to real buyer discovery answers. I’ll paste 2–3 discovery questions below. Please generate one realistic, thoughtful buyer response to each — based on common pain points related to the problem.
Then for each buyer response, I’ll write a follow-up question to go deeper. I want you to coach me on:
- Whether my follow-up is relevant and effective
- If it helps uncover more pain, urgency, or decision criteria
- Suggestions to make it stronger
Here are my discovery questions:
1. [Insert Question]
2. [Insert Question]
3. [Insert Question]
Please generate one buyer response at a time so I can write my follow-up in between.

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