🕵️ discovery problems

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Why executives don’t care about “visibility”

Most AEs stop discovery the moment they hear a surface-level problem.

They get a vague pain point, jump in with “We can help with that,” and start pitching.

The problem is, surface pains don’t close big deals. Executives don’t care about tactical issues like “visibility” or “enablement gaps.”

Big deals come from uncovering the real business impact - the kind that shows up in boardrooms and leadership meetings.

Chris Orlob breaks this down perfectly.

Here’s how a $0 “visibility” problem turned into a $500K+ business issue by peeling back the layers one by one:

Starting point: “We need visibility for better sales coaching.”

No urgency. No executive weight. No business impact.

If discovery stopped here, the deal would have gone nowhere.

Time to peel back the onion 🧅 layer by layer.

🧅 Layer 1: Coaching gaps

✔️ “Why do you need visibility for coaching?”

Their response: “We need to coach reps on selling to power.”

That gave more clarity, but it was still a tactical issue.

Not yet something your executives would prioritize.

🧅 Layer 2: Sales cycle drag

✔️ “What’s driving you to focus on that among any other gap?”

The answer was: “Selling too low has led to a 9-month sales cycle.”

Their problems connected directly to revenue impact.

🧅 Layer 3: Cash flow crisis

To push further, the AE asked:

✔️ “This may sound redundant, but why is decreasing the sales cycle critical right now?”

That’s when the SVP of Sales jumped in: “It’s causing cash flow issues.”

Cash flow problems affect company survival and growth.

🧅 Layer 4: Valuation risks

One more question led to the core problem:

⇢ “We’ll have to raise another round. If it’s a down round, we lose millions in valuation.”

What began as a $0 problem around coaching visibility had now become a $500K+ problem connected to business valuation.

Keep in mind, your true mission is to uncover problems that executives bring up in leadership meetings.

How to prove your value using discovery

Andy Neary breaks down an eight-step discovery process that moves clients forward.

Use this discovery checklist to remain structured and land your second meeting.

Step 1: Pre-call

🔑 Send a welcome email, and include agendas.

💬 Example: Send a short video clip saying,

“Hi Sarah, looking forward to our meeting Thursday. I’ll be covering X, Y, Z, and attached is a quick agenda so you know what to expect.”

Preparation always starts before the meeting.

Step 2: Promise

🔑 Go over the agendas and explain your sales process.

💬 Example: “Today we’ll spend 20 minutes learning about your goals, 10 minutes walking through how we typically work with clients, and leave 5 minutes for next steps. Sound good?”

Lead the conversation effectively with a promising flow.

Step 3: Players

🔑 Quickly identify the decision-makers involved.

💬 Example: “Besides yourself, who else would be involved in evaluating a new partner on this project?”

Get clarity early so you can present to everyone.

Step 4: Power four

🔑 Ask four essential questions:

1. “What is your number one goal right now?”

2. “What would it mean if you could achieve it?”

3. “What challenges are keeping you from the goal?”

4. “How is that challenge impacting you right now?”

Uncover your prospect’s story - their primary goals, and obstacles.

💬 Example: Prospect mentions: “Our top goal is cutting renewal times in half.”

💬 Follow-up: “If you achieved that, what would it mean?”

💬 Response: “It would save reps 10 hours weekly and improve client satisfaction.”

Step 5: Process

🔑 Explain how your process bridges the problem - solution gap.

💬 Example: “We typically start with a 30-day assessment, then build a 90-day roadmap. By month 4, you’ll see measurable progress toward cutting renewal times.”

Keep everything clear so they understand exactly how you can help.

Step 6: Proof

🔑 Bring in a case study of someone “just like them” who achieved results.

💬 Example: “A similar company had the same problem with renewal times. We implemented this process, and within six months, they reduced turnaround from 14 days to 6.”

Make your prospects believe in your ability to solve their problems.

Step 7: Pivot

🔑 Ask difficult questions: “Based on what you’ve seen today, is there anything that would prevent you from doing business with us?”

💬 Example: Prospect says, “Honestly, we’ve worked with our adviser for 25 years.”

Now you know loyalty is the barrier and can decide how to address it.

Step 8: Proceed

🔑 If they’re positive, lock in the next meeting.

💬 Example: “Great. Let’s schedule a 45-minute follow-up next Tuesday to review a draft proposal with you and your CFO. Does that time work?”

That’s how you keep the momentum alive.

Free resource 📚

Gain answers with better questions

Monica Stewart points out how most reps start pitching, with little to no real discovery.

Keep your customers engaged by presenting well-rounded business use cases.

➤ Future agendas

📌 Set your customers’ expectations right away.

↳ Example: “Here’s what we’ll cover today, what I need to understand about you, what you’ll learn about us, and what usually happens next.”

Clear agendas prevent unexpected surprises.

➤ Introduction

📌 Ask questions about their position and responsibilities.

↳ Example: “As VP of Operations, what parts of annual planning are you responsible for? How do you work with finance?”

Leading with their perspective builds trust and lowers resistance.

➤ Current situation

📌 Investigate how they’re managing workflows now.

↳ Ask: “What’s working? What’s not?”

Fix problems by understanding their current situation.

➤ Context/impact

📌 Uncover why the problem matters.

• “What happens if this doesn’t get solved?”

• “Who else is currently getting affected?”

• “What’s placed at stake if things go down?”

Without direct impact, urgency won’t exist.

➤ Performance metrics

📌 Quantify your meaning of success.

Ask:

• “How do you measure this today?”

• “What would good look like in numbers?”

• “How would you track success?”

Metrics turn vague interest into business cases.

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