What Wisconsin Taught Me About Sales (And Why We’re All Moving Too Fast)

This past month, I found myself sitting around a dinner table in Wisconsin with three women who’ve been in my life for nearly three decades. We’re the kind of friends who can text about high school memories and inside jokes without missing a beat. We know each other’s stories, each other’s families, each other’s quirks.

But this dinner was different.

Instead of staying in the comfortable territory of shared memories, we asked the harder questions: What’s really going on in your life right now? What are you struggling with? What are you excited about?

The conversation made us laugh and cry. We talked about present-day challenges and small wins. And in that space of being truly seen and heard by people who know all of you - the messy, the beautiful, the complicated - something shifted. There was comfort, clarity, and a quiet reminder that we’re not alone in what we’re carrying.

A week later, I was running a virtual two-hour sales training lab with a founder. We were walking through each stage of the sales process when she paused and shared something that stuck with me. She noticed that she was often jumping ahead, thinking about how to handle objections or negotiate, before she had really spent time up front asking thoughtful questions and listening to what the other person needed.

And there it was, the same insight I’d just experienced at that dinner table.

In both relationships and sales, we’re often moving too fast. We think we know the story because we’ve heard similar ones before. We assume we understand the challenges because they sound familiar. But when we resist the urge to rush ahead and instead focus on what’s happening now, everything shifts.

She was onto something. When you slow down early in the conversation, when you ask better questions and actually listen, you’re not just collecting information. You’re building trust. You’re showing up as someone who’s curious, thoughtful, and focused on the other person, not just trying to get to the close.

And just like that dinner with my friends, when someone feels heard and understood, the rest of the conversation flows more naturally. The foundation is stronger.

Whether or not sales is part of your job, we all have moments where it helps to slow down and really pay attention to the person in front of us. To ask deeper questions. To listen for what’s actually being said, not what we assume we already know.

This is the heart of what I teach, as a sales trainer and a leadership coach. When we lead with curiosity and connection, everything else gets easier.

What would change in your next important conversation if you slowed down just a little bit more?