In healthcare especially — where buying cycles are long, stakeholders are many, and budgets are tight — there needs to be clear, compelling, and costly reason to act.

That reason is pain.

I don’t love the term, and you won’t catch me asking a buyer, “What’s your biggest pain point?”

It’s clumsy and it puts people on guard.

Instead, I’ll ask:

• “What’s not working the way you’d like it to?”

• "What led you to take this meeting?”

And then I listen.

Not just for one issue, but for multiple signs of pain — across different domains:

• Operational inefficiency (e.g., too much manual work, lack of integration

• Financial pressure (e.g., rising costs, missed revenue opportunities)

• Compliance and risk exposure (e.g., audits, CMS penalties)

• Reputational or experiential gaps (e.g., provider complaints, member churn)

Once several pain points surface, I’ll ask them to rank them. “Which of these issues is most important to solve? Why?”

This is where it gets interesting.

You’ll learn what’s driving urgency — whether it’s cost savings, external mandates, internal visibility, or plain old frustration.

These are where deals come from.

The better you are at identifying, prioritizing, and framing pain in their terms, the more control you have over the sale.

Because a polite conversation about vague improvement goals doesn’t get you decisions or customers.

But identifying and solving for real, validated, prioritized pain?

That’s what matters.