Let the Sales Conversation Wander: Evolving Chats Unlock Powerful Sales Discovery

When Monday morning arrived and I didn’t have an article ready to go live, it was the first time ever (except during February/March recovery from surgery). Not having article ideas in the pipeline is new to me but hey, after 2,000 of them over the past 20 years, I guess it can happen. Later, while driving in the car, I heard three different Beatles songs so I opened a chat with Grok (xAI’s witty AI sidekick) and tossed out a random question: “How many songs did Lennon and McCartney write?”

What started as a simple Beatles brain-teaser turned into one of those unplanned detours that reminds me why I love a good conversation. We crunched the numbers on Lennon and McCartney’s output which, if you include their solo runs, is about 1,200 songs.  We then stacked that output against my own output of 2,000+ articles on sales. Before I knew it, we were knee-deep in Dolly Parton’s songwriting marathon (3,000 and change), my annual Nutcracker posts with the three big lessons for salespeople, and a debate on why the Eagles’ “Long Road” tour was so much better than the studio cuts. And here we are, full circle, collaboratively turning an hour-long ramble into this article. I actually allowed Grok to write the first draft and while it sounded too much like Grok, and not enough like me, a round of editing later, the article was belting out my own vocals.

The important thing is that the conversation began without a script. Just a conversation letting gravity do its thing. And that mirrored the best sales calls I’ve ever had or coached teams through.

Too many salespeople treat discovery like a grocery list. “What’s your biggest pain? Budget? Timeline?” Check, check, check. It’s efficient, sure, like a studio recording of a pop hit, polished and predictable. But it misses the magic. The real breakthroughs happen when you let the music, or chat, evolve. When you listen, poke gently, and follow the flow to uncover the previously hidden compelling reasons to buy, you can create urgency, which helps you qualify the opportunity, and turn possible sale into a done deal.

Data backs it up. According to Objective Management Group’s (OMG) assessments of over a 2.5 million salespeople, only 27% are proficient at qualifying prospects, yet those who master it see skyrocketing win rates, fewer “no decisions,” and pipelines that actually flow. Top performers are 4x more likely to exceed quota expectations compared to the pack (33% vs. 9%). Why? Because prospects aren’t linear. They start with “We need better vinyl,” but wander into “Our team’s burned out from bad hires,” or “Remote work’s killing our team’s ability to collaborate.” If you’re not surfing that flow and saying, “Tell me more about the burnout” or “What’s the one thing your team hasn’t been able to solve?” you miss the real compelling reason. And just like your solution is nice to have instead of must have.

I’ve seen it play out time after time with clients. Last quarter, a SaaS team was tanking with 12% win rates, blaming “tough competition.” We role-played a discovery call that went much like this article.  It began with a simple question: “How did you get here?” and instead of jumping to features, the conversation ebbed and flowed and settled in on the CEO’s frustration with lack of accurate real-time data which prevented the CEO from making timely decisions.  He recently missed out on a critical opportunity because he lacked the data to determine the assets he could leverage on December 31. Boom!  It turns out the C-suite was siloed, with leaders spinning tales more like old 45 RPMs instead of facts. The conversation that wandered and flowed reframed the solution from “our solution is cutting edge” to “let’s solve that data problem.”

The wandering flow isn’t controlled chaos, it’s orchestrated listening and here’s how to pull it off:

1. Summarize and Expand: From-time-to-time, summarize what you’ve been hearing, and then layer a gentle question: “Sounds like hiring’s your bottleneck. What shifted in the last six months to make it worse?” It’s like my chat with Grok: I said “early Beatles,” Grok asked which song.  I responded with “I Wanna Hold Your Hand,” Grok asked which song I liked playing on repeat and I said, “Hi, hi, hi.”  We went from Beatles, to Eagles, to Paul Simon, Michael Franks, Nora Jones, country, R & B, Big Band, live concerts and more.
2. Spot the Side Trail: When prospects veer (and they will), don’t course-correct. Lean in. In our conversation, Grok asked about lyrics and I said I was more focused on chord progressions and melodies.  That could’ve ended the thread, but chasing it led to live Eagles concerts and a fresh article hook. In sales? A prospect’s “off-topic” budget rant might reveal cash-flow fears tying back to your solution. On a call today, a CEO was bragging that he hired a new Sales Development Manager five weeks ago.  We weren’t on the call to talk about that but I leaned in and after a half dozen questions, I was able to ask and close, on, “What if he’s not the right guy?”
3. Know When to Fold ‘Em: As Kenny Rogers sang, “You gotta…know when to hold ’em, know when to fold ’em.” Not every flow will be gold. Set a mental timer where, if after 5 minutes of flow, you aren’t getting anywhere, you can say, “So let’s get back to the problem you were telling me about.”

Bottom line: Sales discovery isn’t a straight line to a proposal and it’s not a demo to a close. It’s a jam session that looks and sounds unstructured to anyone who isn’t in on it, but you know the milestones you need to meet, just like jazz musicians know to improvise around the original chord changes. My Beatles-to-article detour? Proof that the unplanned path often delivers the best cuts.

Next time you’re prepping a call, ditch the rigid outline. That rare “nothing on my mind” sensation is straight out of my first book, Mindless Selling! Listen. Let it flow. A tire-kicker might just become your next sale.  Need help improving your listening and questioning flows?  We can help.