Pain Point Discovery Tiers

We've all been there. You ask a prospect about their challenges, they give you a surface-level answer, and you move on thinking you've done discovery. Then the deal stalls, or worse, you lose to a competitor who actually understood what was really going on.

So we built a framework that forces deeper discovery, not through more questions, but through better ones. And recently, watching a prospect's reaction when they saw it in action reminded us why this matters so much.

The Problem with Surface-Level Discovery

Most sales conversations stop at the first layer. A prospect says "our team struggles with discovery calls" and we nod, make a note, and move on to the next topic. We've checked the box. We've identified a pain point.

But we haven't actually discovered anything meaningful.

What we're missing is the why behind the what, the impact on the person we're talking to, and the business consequences if nothing changes. Without these layers, we're just collecting symptoms whilst our competitors are diagnosing the disease.

The Four-Level Framework

Here's how we structure pain point discovery in Tiller, and why each level matters:

Level 1: Surface Identification

This is where most discovery stops. The prospect mentions a challenge: "Our discovery calls aren't consistent" or "We're missing revenue opportunities."

What it tells you: There's a problem worth exploring.

What it doesn't tell you: Literally everything else that matters.

Level 2: The Reason Why

This is where you start to understand causation. Why is discovery inconsistent? "We keep trying to do workshops, but people don't have time" or "Everyone forgets what they're supposed to ask."

What it tells you: The root cause, not just the symptom.

Why it matters: You can't solve a problem you don't understand.

Level 3: Personal Impact

Now we're getting somewhere. How does this affect the person you're talking to? For a sales leader: "We're not creating enough urgency around closing deals" or "I'm spending all my time coaching the same basics instead of strategic selling."

What it tells you: Why this person actually cares.

Why it matters: People buy solutions to their problems, not their company's problems.

Level 4: Business Consequences

This is where urgency lives. What happens to the business if nothing changes? "We're losing deals we should win" or "Our sales cycle is 30% longer than it should be" or "We can't scale the team without fixing this first."

What it tells you: The cost of inaction.

Why it matters: This is what gets deals across the line.

How It Works in Practice

During a recent demo, we showed how Tiller's Pitch Co-Pilot tracks pain point discovery in real-time. As you uncover each level during a conversation, the system scores your depth from 1/4 to 4/4.

The prospect's reaction was immediate: "This is exactly what we need."

Why? Because they could see how it would change their conversations. Instead of reps thinking they'd done discovery after identifying a surface problem, they'd have real-time guidance pushing them deeper. Instead of managers reviewing calls and wondering why deals stalled, they'd have clear visibility into whether their team actually understood the prospect's situation.

But here's what really resonated: the framework doesn't just help during the call. It transforms everything that comes after.

Why This Changes Deal Progression

When you've genuinely discovered pain at all four levels, several things happen:

• Your proposals write themselves - You're not guessing at what matters; you're addressing specific, understood challenges with clear business impact
  
  

• Your follow-ups are relevant - You can reference the actual problems that keep your prospect up at night, not generic pain points from a template
  
  

• Your champions can sell internally - They have the language and business case to advocate for your solution because you've helped them articulate it
  
  

• Your deals move faster - When everyone understands the cost of inaction, urgency becomes natural rather than manufactured

This is why we built the framework into Tiller's Insights feature. It doesn't just track which pain points come up most often. It shows you how deeply you're discovering them, and which ones correlate with closed deals.

The Coaching Opportunity

Managers can now see exactly where their reps stop digging. Some consistently get to Level 2 but never push for personal impact. Others are great at identifying business consequences but miss the emotional drivers that actually motivate buyers.

And because the Co-Pilot prompts reps to go deeper during live calls, coaching becomes proactive rather than reactive. Instead of reviewing a recording three days later and saying "you should have asked about impact," the system nudges them in the moment.

Making It Work for Your Team

The framework is simple, but implementing it requires intention. Here's what we've learned:

1. Train on the levels explicitly

Don't assume your team knows the difference between surface problems and root causes. Make the four levels part of your sales methodology and reference them constantly.

2. Use it in deal reviews

When reviewing opportunities, ask: "What level of discovery have we reached on their main pain points?" If the answer is Level 1 or 2, the deal probably isn't as qualified as you think.

3. Celebrate depth, not just activity

It's easy to reward reps for having lots of conversations. It's more valuable to reward them for having deep conversations. Track discovery depth as a metric.

4. Let the system help

This is exactly the kind of thing AI should be doing, tracking complexity in real-time so humans can focus on the conversation. If you're doing this manually, you're making it harder than it needs to be.

Why This Matters Now

Buyers are more sophisticated than ever. They've done their research. They've talked to your competitors. They don't need another vendor asking surface-level questions and pitching generic solutions.

What they need is someone who genuinely understands their situation, not just what's broken, but why it's broken, how it affects them personally, and what it costs their business.

The four-level framework isn't magic. It's just structured curiosity. But in a world where most sales conversations barely scratch the surface, structured curiosity is a competitive advantage.

And when a prospect sees you using it, when they watch their pain points being discovered and documented at every level, they don't just see a better sales process. They see someone who actually gets it.

That's when they say: "This is exactly what we need."