One of the most important lessons I’ve learned over the years is this: the best deals don’t get closed because we had the flashiest demo or the most persuasive pitch. The best deals get closed because we understood the customer’s pain better than anyone else. When we can pinpoint the real problem and articulate it back to the customer in a way that makes them feel heard, we’re not just selling — we’re partnering.
Lately, I’ve been working with my teams to double down on this mindset. Too often, sellers jump right into talking about features, roadmaps, or the competitive landscape without slowing down to truly uncover the pains that matter most to the customer. And those pains aren’t always obvious — they’re often buried under layers of assumptions, surface-level frustrations, or even internal politics.
So how do we get better at identifying those problems? Here are a few ways I’ve been encouraging my team:
1. Go Beyond the Obvious
When a customer says, “We’re struggling with efficiency,” that’s not the real problem — that’s the headline. The deeper story might be that inefficient processes are causing delays in customer onboarding, which then impacts revenue recognition. Or maybe inefficiency is leading to employee burnout, which ties into retention issues. Instead of stopping at the headline, keep asking “why” until you uncover what’s really at stake.
2. Bring Technical Sellers into the Discovery Process
This is where technical sellers can shine. They often see nuances that frontline sellers might miss. A solutions engineer or technical consultant can translate a customer’s pain into specific, tangible use cases that the customer may not have fully articulated. For example, a technical seller might hear a comment about “data challenges” and immediately recognize how integration gaps between platforms are costing hours each week — something the buyer didn’t even realize had a measurable business cost.
3. Tie Problems to Outcomes
Once you’ve identified the pain, the next step is to connect it to a meaningful business outcome. Customers don’t just want problems solved; they want to know how solving those problems gets them closer to their goals. Technical sellers can help bridge this gap by showing how a feature or workflow translates into a measurable outcome — faster deal cycles, higher customer retention, reduced costs.
4. Make It a Team Effort
I’ve been encouraging my sellers to treat discovery as a team sport. Sales reps, technical sellers, and even managers bring different perspectives. By collaborating, we avoid blind spots and increase the odds of finding the root cause of a customer’s challenges.
At the end of the day, identifying problems isn’t about being clever — it’s about being disciplined, curious, and empathetic. Customers will always gravitate toward the partner who understands them best. And when technical sellers are given the chance to do what they do best — uncover, validate, and connect the dots — that’s when the biggest wins happen.
So as we move into the next quarter, my challenge to you is this: slow down, dig deeper, and don’t settle for surface-level pains. The real problems are often beneath the surface, and the teams that find them are the ones that win.
