The Power of Identifying Pain in Sales by Dan O'Shaughnessy

Leveraging PITOP for Stronger Opportunities

In the world of B2B sales, the difference between a strong pipeline and a struggling one often comes down to a single crucial factor: the quality of opportunities entering it. One of the most effective ways to improve pipeline health and win rates is through a disciplined approach to Identifying Pain, a core component of the MEDDICC framework.

But simply acknowledging pain isn’t enough—we must go deeper to truly understand its impact and create compelling urgency.

A methodology that brings structure to this process is PITOP: Pain, Impact, Tried, Outcome, and Projects.

By applying PITOP effectively, sales professionals can elevate conversations, qualify opportunities more rigorously, and gain access to budget and executive sponsorship.

Let’s break it down:

Pain – What’s the Problem?

Every deal starts with a problem. However, many salespeople make the mistake of accepting surface-level pain points without pressing further. Pain needs to be personal, measurable, and pressing enough to justify action. Instead of settling for “manual processes are slowing us down,” probe deeper:

Who is affected?

What specific inefficiencies exist?

What’s the measurable cost of inaction?

Uncovering the real pain shifts the conversation from “nice to have” to “must solve.”

Impact – What’s the Business Consequence?

Pain is only meaningful if it has a tangible business impact. Understanding the financial, operational, and strategic consequences of a problem is what turns a sales conversation into a business case. Ask:

How does this issue affect revenue, cost, or risk?

Is it preventing the company from hitting key targets?

How does it impact key stakeholders, from frontline teams to leadership?

When sellers help prospects quantify the cost of inaction, they create urgency and a strong investment case.

Tried – What Have They Done Before?

Understanding what the prospect has already attempted provides insight into their frustrations, preferences, and openness to new solutions. If they’ve tried solving this problem and failed, what went wrong?

What solutions have they evaluated or implemented?

Why didn’t they work?

What lessons did they learn from past attempts?

This insight helps position your solution as the right approach—without making the prospect feel like they’ve failed.

Outcome – What’s Their Desired Future State?

Every prospect has a vision for success. If we can align our solution with their ideal outcome, we increase our chances of winning the deal. Key questions:

What does success look like?

What key metrics will indicate improvement?

What’s the timeline for achieving these goals?

A clear understanding of their desired outcome ensures that our pitch focuses on tangible, meaningful value rather than just features and functions.

Projects – Where’s the Budget?

One of the biggest challenges in sales is ensuring there’s budget available. Often, budgets are tied to strategic initiatives, not individual solutions. By identifying aligned projects or initiatives, sellers can position their solution as a priority.

Are there ongoing or upcoming initiatives tied to this pain?

Is budget allocated to solving this problem?

Who owns these projects, and how do we gain access?

Tying pain to a funded initiative significantly increases the chances of closing a deal.

PITOP: Turning Insights into Wins

Identifying Pain isn’t just about recognizing a problem—it’s about systematically

understanding its depth, business impact, past attempts at resolution, desired

outcomes, and alignment with budgeted initiatives. By embedding PITOP into your sales conversations, you’ll:

Improve qualification, ensuring better opportunities enter the pipeline.

Strengthen your business case, leading to higher win rates.

Gain access to key decision-makers by aligning with strategic priorities.

In a competitive sales environment, those who deeply understand and articulate pain—and tie it to impact, budget, and strategy—will consistently outperform their peers.

Don’t just sell. Solve.