The Discovery Call

The six questions that help prospects sell themselves — and how to prepare, run, and follow up on every call

A discovery call has one purpose: understand the prospect's situation well enough to know whether and how you can help them.

Not to pitch. Not to sell. To understand.

The strange thing about discovery calls is that when they go well, when the questions are good and the listening is real, prospects often sell themselves. They articulate their problem clearly, they realise how much it costs them to leave it unsolved, and they start to feel like you are the right person to fix it. Not because you said so but because the conversation helped them see it.

This lesson gives you the structure and the Claude prompts to run that kind of call.

Before the Call: 10 Minutes of Preparation

Do not go into a discovery call unprepared. The difference between a prepared call and an unprepared one is visible to the prospect within the first two minutes.

Run this before every call:

I have a discovery call in [TIME]. Here is everything I know about this prospect:
Name: [NAME]
Company or what they do: [DESCRIPTION]
What they said when they reached out: [PASTE THEIR MESSAGE OR INTAKE FORM]

Their website: [URL if available]

Anything else I know about them: [ANY OTHER CONTEXT]

My services and what I offer: from @MARKETING.MD and @SALES.MD

Help me prepare for this call:

1. Three things I should know about their business or situation before I start
2. The most important question to ask first based on what they have told me
3. Two or three potential needs I should listen for based on their situation
4. One thing that might make this a poor fit — a flag to watch for
5. What my "this is a great fit" looks like for this prospect specifically

This takes ten minutes and means you go in with a direction rather than an open question.

The Six Discovery Call Questions

Run these in order, not as a checklist but as a conversation. Let the answers take you somewhere. Ask follow-up questions when something is interesting or unclear. The six questions are the structure and the conversation fills it in.

Question 1: Open with their situation, not your services

"Before I tell you anything about what I do, can you walk me through what's going on on your end? What made you reach out?"

This question puts them at the centre of the conversation immediately. It tells you how they think about their own problem and gives you language you can reflect back to them later.

Question 2: Get specific

"When you say [THING THEY JUST SAID], what does that actually look like day to day? What's the specific part that's most painful?"

Generic problem descriptions like "I need more clients" or "I need a better website" need to become specific. The specific version is where the real problem lives.

Question 3: Find the cost

"What does it cost you to leave this as it is? Either in time, money, missed opportunities — what's actually happening because of this?"

This is not a manipulation tactic. It is a genuine question that helps both of you understand whether the problem is worth solving. Some problems people describe turn out to be minor annoyances. Others turn out to be costing serious money. The answer shapes everything that comes after.

Question 4: Understand what success looks like

"If we solve this, what does good look like on the other side? What changes?"

This tells you what to promise, what to build, and what to measure. It also tells you whether their expectations are realistic. If they say "I want to triple my revenue from this" that is important to surface now and not after you have delivered the project.

Question 5: Ask about previous attempts

"Have you tried to solve this before? What happened?"

You learned this from the qualifying lesson. In the discovery call go deeper. What specifically did not work? Why did they stop? What would need to be different for it to work this time?

Question 6: Timeline and decision

"What is your timeline for getting this sorted? And is it just you making this decision or is there someone else who needs to be involved?"

Timeline tells you urgency. Decision-maker tells you whether there is a second conversation needed before anything gets signed. If someone says "I need to check with my partner" or "I need board approval," you need to know that now and not after you send a proposal.

During the Call: How to Listen Well

Do not take notes while listening to the answer to a question. Listen completely then write the important parts down in a pause.

If they say something that could mean multiple things, ask what they mean: "When you say X, do you mean [interpretation A] or [interpretation B]?"

If they say something important, reflect it back: "So if I understand correctly, you need [SUMMARY OF WHAT THEY SAID] — is that right?" Reflection confirms understanding and makes the prospect feel heard.

If you do not know something, say so: "That is outside what I usually do. Let me think about whether I can handle that before I commit to including it."

After the Call: Turning Your Notes Into a Summary

Within 30 minutes of the call ending while it is still fresh, run this:

I just finished a discovery call. Here are my rough notes:

[PASTE YOUR NOTES — even messy bullet points work]

Using @MARKETING.MD and @SALES.MD — help me produce:

1. A one-paragraph summary of their situation and what they need
2. The core problem in one sentence
3. What success looks like for them in their words
4. Whether this is a good fit for what I offer and why or why not
5. The scope of what I would need to propose
6. Any flags or concerns I should address in the proposal

Format this clearly so I can use it as the input for writing the proposal.

Save this summary. It becomes the direct input for the proposal lesson.

Adding to SALES.md

## Discovery Call Questions

1. Walk me through what's going on — what made you reach out?
2. When you say [X], what does that look like day to day? What's most painful?
3. What does it cost you to leave this as it is — time, money, missed work?
4. If we solve this, what does good look like on the other side?
5. Have you tried to fix this before? What happened?
6. What's your timeline? And is it just you making this decision?

Post-call: run the discovery summary prompt before writing any proposal.

What to Do at the End of the Call

Always end the call with a specific next step agreed out loud.

"Based on what you've told me, I think there's a good fit here. What I will do is put together a proposal that covers [SCOPE SUMMARY] and send it to you by [DAY]. Does that work?"
If the call revealed it is not a fit: "Based on what you've described, I do not think I am the right person for this and here is why. But [REFERRAL OR ALTERNATIVE] might be a better fit for what you need."

Never end a call without one of these two outcomes: a concrete next step or an honest exit.

Your Action Right Now

Update SALES.md with your six discovery call questions written in your own voice. Then book a practice call with a past client, a peer, or someone in the community who will play the prospect role. Run through the questions. It feels clunky the first time and natural by the third.