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Selling to Yoda: How to Sell to People Who Know More Than You
4 steps to closing industry vets who know more about your product that you.
Good Morning! Pour one out for Skype this morning, which officially shut down yesterday after 20+ years in business. Though let's be honest. If you sent a prospect a Skype meeting link in 2025, I’ve got some questions for you. But that’s a discussion for another day. Let’s get into today’s Follow Up. 😁
When things are going ‘too smoothly’ 🗣️
Selling to people who know more than you 🧠
7 disco call mistakes ❌
Sales jobs & a meme 😂
Sales Tip of The Day 💡
When a demo or sales call feels like it’s going a bit too smoothly, make sure to push back.
❌ Awesome, looks like you’re good to go. Any other questions?
✅ I’m glad this feels like a fit, but just to pressure test it, what do you see as the #1 thing that could still kill this?
When you're too optimistic, you miss important issues that prevent deals from closing.
It's better to find out the ugly problems, doubts, or roadblocks early on. Which usually requires some poking.
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Selling to Prospects Who Know More Than You.
Ever tried explaining wine to a sommelier? Or pitched accounting software to a CPA with 30 years of experience?
It's like showing up to a lightsaber duel with a butter knife.
Your confidence evaporates. Your carefully memorized talking points suddenly sound elementary. And that voice in your head keeps asking: "What could I possibly teach this person?"
This is the new normal in B2B sales. 77% of buyers won't even talk to sales until they've done their homework. They enter calls knowing more about your competitors, pricing, and sometimes even your product than you do.
But here's the truth: You can still win deals with Yoda-level buyers. The magic isn't in trying to outlearn them (impossible). It's all about shifting your approach.
Today, we’re breaking down how to sell to people who know more than you do. 👇️
1. Leave Your Ego Behind
If you wanna kill a deal as quickly as possible, pretend that you know more than the expert you're selling to.
It's like mansplaining basketball to LeBron. Not a good look.
When your buyer has forgotten more than you'll ever know about their industry, lean into your ignorance. Make it a strength.
Say things like: "You clearly know this space better than I do. I'm curious how you've approached {problem} in the past?"
If they ask something you don't know, just say: "That's a great question. I don't have the answer at the moment, but I'll find out and get back to you tomorrow." Then actually do it.
They don't expect you to be the expert. They expect you to be the bridge to a solution.
2. Do Ya’ Homework
While you can't magically gain 20 years of industry experience overnight, you can use Google, Perplexity, and ChatGPT to get pretty close.
As David Ogilvy once said, "I'm a lousy copywriter, but I am a good editor." The same idea applies here. You don't need to be the smartest person in the room, just the most prepared.
Preparation gives you confidence. Confidence builds trust. Trust wins deals.
When an expert asks you a technical question, you should understand enough to have an intelligent conversation, even if you don’t know the answer.
Out-prepare them if you can't out-experience them.
3. Lead with Curiosity and Great Questions
When your prospect is an expert, become a student.
People love talking about what they know, especially to someone who genuinely wants to learn.
The fastest way to earn respect with a know-it-all is by asking questions that make them think:
You've been in this field for years - what changes are you most excited about?
In your experience, what's the biggest hurdle in {problem you solve}?
Take actual notes and reference their points later to show you're listening.
And then use those answers to tailor your pitch.
This flips the dynamic from "junior rep pestering an elder" to "business partner who values their perspective."
4. Talk About Outcomes (Avoid the Specs)
Steer the discussion to where you can add value: their business outcomes.
Even the most technical experts care about results, solving problems, saving money, and growing revenue.
As sales guru Jeb Blount says, seasoned professionals don’t care about your age or title as much as you probably think they do. They care about whether you can address their business needs or not.
Zero in on the business impact: "Our software helped a similar firm cut onboarding time by 30%, which would free up your engineers for new projects."
Frame your product as a means to their end. When you keep the spotlight on tangible value and ROI, you avoid going head-to-head on knowledge.
In short, sell the solution, not just the product features.
Do your prospects know more about your product or industry than you? |
