Back to Basics – Week 2

We’re starting with the easiest fundamental of all — and it’s one that even seasoned sales pros forget to do.

When a prospect shares a pain point, challenge or goal, dig deeper.

That’s it. That’s the whole thing.

I call it “peeling the onion,” and it’s the difference between surface-level conversations that might land you an average contract in uncertain economic times and the kind of discovery that leads to higher-impact partnerships.

Here’s what I see time and again, even with the smartest of subject-matter expert founders:

You: “What’s your biggest challenge right now?”
Prospect: “We need better processes.”
You: “Yes, I get that. Most of our clients come to us saying the same thing. Let me pull up some slides and take you slide by slide through our process for the next 20 minutes, not letting you get a word in edge-wise.” 

Stop. Rewind. You just missed the golden opportunity to peel the onion and go deeper. 

Here’s what peeling the onion looks like:

You: “What’s your biggest challenge right now?”
Prospect: “We need better processes.”
You: “Tell me more about that?”
Prospect: “Well, it’s taking too long to go from idea to execution.”
You: “Hmm, and what’s happening as a result of taking too long to execute?”
Prospect: “We’re losing money with every day we take, and the team is frustrated.”
You: “I’m sorry to hear that. Say more about the team being frustrated — what’s the worry there?”
Prospect: “We’re in a highly competitive industry, and we need to retain our best talent. If they can’t do the work they want to do, we could lose them pretty easily.”

See the difference? By going deeper, you’re getting a better understanding of what’s at stake for the prospect if they don’t commit to fixing the problem — and so are they. 

Plus, when you do share about your solutions, you can better position your value:

“Our approach is a bit different. We start with X, so that your team immediately feels some relief — which means you’ll diminish the risk of losing them.”

“Compared to other larger consultancies doing the same work, our clients have told us that our small size allows us to move faster — which is meaningful when you’re losing money every day that you don’t fix the process.”

Always, always connect the dots between what you do and what they shared when you peeled the onion. 

So, are you spending enough time peeling the onion — or you playing “beat the clock,” thinking you’ve got quickly get through all your questions on a 30-60 minute sales call? 

Remember: When selling premium B2B services, you will almost always be better served by going an inch wide and mile deep, rather than a mile wide and only an inch deep. 

Going even one layer deeper can reveal the most critical intel needed to get to a contract:

• The real pain points (not just the surface symptoms)
• Budget implications (“This is costing us $50K a quarter”)
• Urgency factors (“Our board is asking about this monthly”)
• Internal politics (“Half the team loves the old way”)

Your homework this week: In every sales conversation, practice asking “Tell me more about that” at least three times.

Watch how much richer your discovery becomes when you resist the urge to rapid-fire through your question list.

What you’ll discover might surprise you — when you truly engage your prospects, they’ll grant you more time, be less likely to ghost and be more willing to advocate for you internally.