📋 discovery playbook

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Turn feature questions into discovery

Salman Mohiuddin highlights a change that makes your discovery far more effective: don’t rush to answer feature questions — uncover the real problem instead:

Answer, then probe for the why

When asked “Can your product do X?”, don’t just say yes and go into a walkthrough.

Instead:

→ Answer in a straightforward, brief manner

→ Follow with a question that uncovers behind the ask

Example:

AE: "Yes, it can. If you don’t mind me asking — what’s the purpose behind the ask? Is it duplicative work, an IT initiative, data governance, or something else?"

Why this works:

✔ Uncovers the real business problem

✔ Creates space for deeper dialogue

✔ Shows you care about outcomes, not just features

Go deeper — one layer at a time

Once the prospect gives you the initial driver (e.g. legacy modernization), keep peeling the layers.

⇢ Ask about complexity:

“Could you tell me more about that?”

⇢ Ask about the impact:

“How is this affecting your KPIs?”

⇢ Ask about the cost of the status quo:

“What’s this costing you today?”

The example flow leads from “legacy apps” to “manual work” to “TCO doubled in 6 months.”

Now you have a clear business case and urgency.

Your answer to the original feature question is much more impactful.

Key Feature Reminders:

➤ Don’t let happy ears derail your discovery process

➤ Use every feature question as a window into the problem

➤ The deeper you understand, the stronger your positioning

Answering feature questions builds trust, positions you as a problem-solver, and leads to more value-based conversations — not just technical demos.

Set process that move deals forward

Will Aitken explains that a discovery call isn’t all focused on asking questions — it’s about surfacing real problems, understanding what drives the buyer to take action:

Understand the before state first

Before running a discovery call, review past deals:

→ What problems did successful customers have before buying?

→ How did those problems impact their business?

Knowing this helps you ask sharper questions and look for strong buying signals.

Place expectations before starting

Begin the call by setting a clear agenda and getting buy-in to ask questions:

✔ “The goal of today’s call is to understand what you’re doing today, what might not be working as well as it could, and see if we can help. Does that sound good?”

This avoids the conversation feeling like an interrogation.

If a prospect just wants a demo, match their urgency and still ask for some context first:

⇢ “Could you get me up to speed on why you’re looking for a solution?”

Follow a straightforward process

Run your discovery call in this order:

1️⃣ Understand their current state

2️⃣ Identify the problems faced

3️⃣ Dig into the main root causes

4️⃣ Uncover the business impact

The biggest mistake?

Focusing only on potential gains.

Problems and pain drive urgency — surface them clearly.

Use conversational questions

Examples:

→ “What made you want to have this conversation today?”

→ “How long has this been an issue?”

→ “What have you tried to solve it already?”

→ “What ripple effect does this issue have on your business?”

Avoid cliché questions like:

“What impact is this having on your business?”

Ask it naturally, and use specific follow-ups.

Map buying process and next steps

Before ending the call:

✔ Ask who else should be involved

✔ Understand their buying process

✔ Book next step and confirm in writing

If they resist moving forward, pressure test the deal by asking:

→ “Am I missing something here, or is this not the fit you were hoping for?”

Mindset shift is always necessary

Discovery isn’t just about qualification.

It’s about deeply understanding:

→ The buyer’s world and industry

→ What’s driving their urgency

→ What could resist the deal

Top reps see discovery like an art — not a checklist.

Pressure test when uncovering friction

Matt Green breaks down why most reps treats discovery like a checklist and miss the biggest deal killers — hidden potential risks:

Discovery is more than qualification

Most reps focus only on:

✔ Finding pain points

✔ Confirming budget

✔ Booking the demo

But great discovery insulates the deal.

It uncovers friction that can stop momentum weeks later.

The biggest threats aren’t on the call transcript.

They show up when:

→ Legal adds another review cycle process

→ A VP asks new questions late in the game

→ Budget priorities change, your champion goes dark

Seek for landmines, not just interest

Great reps ask risk-focused questions to find what could block the deal:

➤ “What could slow this down internally?”

➤ “Who usually gets involved late in the process?”

➤ “What else is competing for budget right now?”

They also map potential blockers early:

⇢ “What’s the typical legal or procurement process?”

⇢ “Has this kind of initiative ever failed before?”

⇢ “What’s the risk if we currently do nothing?”

This prepares you to manage — not react to — obstacles.

Use business risk to drive urgency

Once you surface the risks, use them to drive urgency:

➤ “If this doesn’t move by Q2, what’s the downstream impact?”

➤ “What happens if this stays status quo through planning season?”

When prospects voice the risks themselves, they’re more likely to stay engaged and push internally.

Find problems and kill loopholes

Discovery isn’t just about who wants to buy.

It’s about finding what could kill the deal — and building a strategy to handle it.

Top reps are not just curious.

→ They are risk-aware to possibilities, and know when to step up.

→ Pressure-test deals before the market or internal politics do it for them.

That’s what keeps deals moving when others stall.

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