Every successful sale starts with one thing – understanding the customer’s pain. Without that, you’re just guessing.
The best salespeople don’t pitch first. They listen, question, and uncover what really matters. Here’s how to do it right.
1. Do your homework
Before the call, research the company. Look at recent news, reviews, or financial reports. Check LinkedIn to see what’s changing – new hires, funding, product launches. Go in knowing what might be keeping them up at night.
2. Build trust fast
People don’t share their problems with strangers. Start by showing genuine interest, not a script. Use openers like:
- “What’s been working well for you recently?”
- “What’s not going as planned?”
When they see you care, they’ll open up.
3. Ask open-ended questions
Avoid yes/no questions. Try:
- “What challenges are you facing in hitting your sales targets?”
- “What’s the biggest obstacle slowing things down right now?”
- “If you could change one thing about your current system, what would it be?”
4. Listen actively
Most reps listen to reply. Top performers listen to understand. Take notes. Pay attention to tone and emotion. If a topic triggers frustration or stress, that’s a sign you’ve hit a pain point.
5. Dig deeper
Don’t stop at surface-level answers. If they say, “We’re losing leads,” ask, “Why do you think that’s happening?” or “How is that affecting your team?” The real pain is often two or three layers below the first answer.
6. Quantify the impact
Turn pain into measurable consequences. “How much time does that cost your team each week?” or “What’s the financial impact of those delays?” Numbers make the problem real and justify your solution.
7. Confirm your understanding
Before moving on, summarize what you’ve heard.
“So, the main challenge is that your sales team is spending too much time on admin, and that’s costing productivity – is that right?”
This shows you’re listening and gives them a chance to correct or expand.
8. Connect pain to value
Once the pain is clear, show how your solution fixes it. Don’t just list features. Say, “You mentioned wasted time – here’s how we help teams cut admin hours by 30%.”
9. Watch for emotional cues
When buyers start saying things like “That’s exactly what we’ve been struggling with” or “If we could fix that, it would change everything,” you’ve hit the emotional core of the pain. That’s where deals are won.
10. Stay curious
Even if you think you know the problem, keep exploring. Every business evolves, and pain points shift. Curiosity keeps your pipeline full and your conversations valuable.
Pain drives action. Find it, understand it, and solve it – that’s how you turn calls into closed deals.
What question do you always ask to uncover client pain?