I recently fell down a YouTube rabbit hole and discovered something fascinating: Jordan Rudess, the keyboard virtuoso from Dream Theater, jamming to Jay-Z and Alicia Keys’ “Empire State of Mind” — a song he’d never heard before.
What struck me wasn’t just his technical brilliance. It was how he approached unfamiliarity with absolute confidence and turned it into an opportunity for creativity. As I watched his fingers dance across those keys, adding unexpected flourishes and complementary runs without missing a beat, I realized I was watching the perfect metaphor for great sales conversations.
Think about your last discovery call. You had your talk track and qualification questions ready, but then the prospect went off-script: “Actually, our biggest challenge isn’t what you’d expect...” Did you freeze? Or did you do what Rudess did — lean in, listen intently, and begin improvising something meaningful?
The best sales conversations feel like musical collaborations. Your prospect drops a pain point (that’s their melody), and instead of interrupting with your rehearsed feature pitch, you complement it with questions that create harmony. You build on their theme rather than competing with it.
I’ve noticed that when I enter sales conversations with Rudess-like curiosity rather than rigid preparation, I uncover challenges the prospect hadn’t even articulated yet. Last month, what started as a standard discovery call revealed that my prospect’s stated problem (implementation timelines) masked a deeper concern about internal adoption. Had I stuck to my script, we’d have solved the wrong problem entirely.
The magic happens in the spaces between the notes — those moments when you stop talking and truly listen for the underlying rhythm of your prospect’s needs. Then, like Rudess adding unexpected chord progressions, you can introduce novel perspectives they hadn’t considered.
What makes Rudess’s improvisations so compelling isn’t just technical skill; it’s his playful enthusiasm. He approaches the unknown with genuine joy. When’s the last time you brought that same energy to a sales conversation? That sense of “I don’t know exactly where this is going, but I’m excited to explore it with you”?
Next time you’re heading into a sales call, try thinking less like someone with a presentation to deliver and more like a musician ready to jam. Come prepared with your fundamental skills and knowledge, but hold them loosely. Listen for your prospect’s melody, and instead of rushing to play your own tune, find ways to complement what they’re already playing.
The most memorable sales conversations, like the best musical improvisations, don’t follow a rigid structure — they create something new that neither party could have created alone.