Chasing Excellence: A New Weekly Journal
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THIS WEEK’S JOURNAL
Every generation wants something different.
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Your best sales strategy depends on who’s buying. You could sell the same product to two different people and find that one approach works better than the other.
One way to think about that is through the different generations in your audience.
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Here’s a broad overview:
Gen Z wants to feel like businesses understand their personality.
Millennials want the fastest, simplest path to what they need.
Gen X want proof they’re getting value for their money.
Boomers want to trust you before they buy.
If your product appeals to multiple generations, think about how best to approach each one.
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Same Offer, Two Ways to Sell It
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Take a restaurant I love. New customers get an extra pastry on the house — a small token of appreciation. I love that gesture, because it immediately makes a customer feel looked after.
But say they wanted to attract a younger crowd. They might change how they promote the same offer:
✅ Advertise the free pastry on their socials.
✅ Make sure the food looks good on camera.
✅ Make their reviews easy to find.
Same restaurant. Same offer. Two completely different ways of making the sale.
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★ A Little Fun
This feels like the closest thing we have to a business astrology chart.
(Virgos are perfectionists. Millennials hate talking to salespeople. Something like that. 😂)
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I’ve generally found these patterns to be true in my business. It’s worth paying attention to whether the same ones show up in yours.
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Here’s the full breakdown of what each generation looks for — and how to adjust. Save it so you have it on hand.
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How to Sell Across Generations
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Gen Z |
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What they value
The feeling of belonging. They want to feel like brands understand their personality.
How they want to buy
Fast and digital. They’ll vet you on socials before talking to you directly.
How to sell
| ✅ | Show the product being used in real life. |
| ✅ | Let reviews and comments do some of the selling for you. |
| ✅ | Make your online profiles appealing to follow. |
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Millennials |
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What they value
Time and simplicity. Remove a decision for them and they’ll pay for it.
How they want to buy
Seamlessly. Hunting for a price or information loses the sale.
How to sell
| ✅ | Put your pricing where they can see it without asking. |
| ✅ | Cut your booking or checkout process to the fewest steps possible. |
| ✅ | Create an FAQ page so they don’t have to message you first. |
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Gen X |
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What they value
Expertise and a clear return. They want to know what they’re getting and why it’s worth it.
How they want to buy
Efficiently — but they still want to talk to someone before they commit.
How to sell
| ✅ | Lead with the outcome, not the process. |
| ✅ | Have someone ready to answer questions before they buy. |
| ✅ | Back up your claims with specific results. |
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Boomers |
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What they value
A relationship they trust, and confidence they’re making the right call.
How they want to buy
Meaningfully. They want someone to walk them through things before committing.
How to sell
| ✅ | Offer a phone call or face-to-face meeting. |
| ✅ | Don’t shorten your pitch — they may want the fuller version. |
| ✅ | Take time for small talk; it builds trust before they buy. |
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How to Audit Your Sales Approach
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Step 1 · Know Who’s Buying From You
Pull up your last handful of sales and look for patterns. You might be making assumptions about your customer base without the full data.
Try this: look at your last ten customers. What generation do most of them belong to?
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Step 2 · Match Your Pitch
If you’re selling convenience to a Boomer or trust to a Gen Z, you’re working against yourself. Adjust the message, not the product.
Try this: pick your top-selling product. Rewrite the pitch for one generation you’re not reaching well right now.
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Step 3 · Test One Change
Don’t overhaul your entire sales process at once. Small tests show you what your customers actually respond to.
Try this: choose one lever — speed, proof, or personal touch — and test it for two weeks.
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YOUR TURN
Which generation makes up most of your audience — and are you selling to them the way they want to buy?
Keep chasing excellence.
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🎧 NEW EPISODE
Chasing Excellence with Tony Thompson
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Tony Thompson, CMB
Keynote Speaker, Founder & CEO, NAMMBA
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