Why Curiosity Wins Deals Published July 16, 2026
The last few months have been a stress test for small business lending, and the business environment right now is asking a lot of leaders. Teams are being pushed to do more with less, and automation continues to (re)shape how work gets done. Margins are tighter, and hiring decisions can feel riskier. For many small and mid-sized businesses, the road ahead can feel uncertain.
That uncertainty is showing up in meaningful ways for borrowers and lenders alike. Rates are still high, credit is still tight, SBA delinquencies haven’t recovered to where they were before the pandemic. The agency is also working through a massive backlog of pandemic-era loans flagged for fraud—which adds to an already complicated picture. Throw in a quarterly tax payment deadline that just passed, and a lot of executives are feeling the squeeze from multiple directions at once. The SBA has also moved to expand lending capacity, which is good news in principle, but more deal volume in a stressed environment can also mean more complexity for everyone involved.
The data flowing through these transactions can be immense and hard to interpret. When information piles up, people can default to moving it around rather than actually making sense of it, and that is where things can go sideways.
Today, we can take a call transcript or dozens of Excel sheets of financial data, run them through AI, and get a polished analysis back in seconds. But output is not insight. The core principle of sales has stayed the same: you still need to understand what the other person needs. A polished check-in email is no longer proof that someone is paying attention. The most important work begins outside of any document or inbox.
What I’m talking about is being curious about your customer. Are you interested in who they are, how they think about their business, what they are worried about right now? Or are you passively moving information around? That genuine interest in your customer’s well-being is how deals are won or lost—and where customers either walk away feeling like they have a real partner or just another vendor who sent them a nice-looking report. As Samantha McKenna notes, manners go a long way. The willingness to take that extra step for your customers in a complex, data-heavy environment adds a critical human element to the sales process.
Here’s how I encourage my sales team to stay curious.
Curiosity Makes Conversations About Risk Feel…Less Risky
For lenders, few conversations carry more weight than the ones where a borrower’s financial exposure suddenly comes into focus. A curious approach—one focused on understanding how those issues developed and what the borrower is trying to accomplish next—shifts the dynamic away from a binary decision. That positions the lender as a partner and problem-solver, which is where stronger relationships and better-performing plans tend to come from.
Our customers rely on the information we provide to assess risk, and something as foundational as whether payroll taxes are up to date can materially influence a lending decision. Recently, one lender noticed that payroll tax filings appeared to be missing on a report for a borrower they were in the process of funding. It would have been easy to assume a compliance issue and escalate concerns. Instead, they asked a few more questions. And what they uncovered was far less worrying: the borrower had transitioned to a new payroll provider, which changed how those filings were being submitted and reflected in the data.
Taking the time to understand the ‘why’ behind what they were seeing turned what could have been a difficult conversation, into a productive one, and gave the lender confidence to move forward with the right information. This personalized attention is what separates authentic, white-glove customer service teams from the rest of the pack.
Curiosity Is What Turns Tax Data Into Foresight
Accessing detailed IRS data can be its own challenge, but it’s equally—if not more—difficult to know what this information means for a borrower and a deal. Curiosity turns a balance, a filing pattern, or a change in behavior into a closer look at how the business operates and where it may be headed. Teams that ask questions and reflect on what the data implies are the ones that can be the most forward-looking.
By nature, data is static—it tells you what has already happened. Curiosity is what introduces forward momentum. It pushes teams to connect signals across filings, timing and behavior, and to ask what might come next. Going from reading the numbers to interpreting the factors behind them is what allows you and your team to anticipate risk and take the necessary next steps.
Curiosity and Empathy Are the Only Advantages You Can’t Buy
Technology levels the playing field—any competitor can access the same tools, data sources, and models. Genuine curiosity and empathy are now the true differentiators, because no one can buy or copy the way you understand your customers.
We saw this firsthand during a period of IRS system delays earlier this year. Every customer was dealing with the same systems, the same delays, and the same incomplete information. Technology wasn’t the differentiator because everyone was facing the exact same challenge.
What made the difference was how people responded. Our team focused on understanding how those delays were impacting customers, kept them informed, and helped them navigate the situation. In turn, the lenders who communicated openly with their borrowers and took the time to understand their circumstances were able to maintain trust despite the uncertainty.
Technology identified the problem, but it took people working together to provide context, build trust, and move forward.
