The third eBook in the Retention category. It's about the second sale, the third sale and the steady rhythm of repeat purchases that quietly underwrite a small business. The work is mostly about timing, helpfulness and offer design - not pressure.
Members ebook·7 chapters· 45 minute read
Chapter 2
Designing Genuine Upsells
How to offer a bigger, better or more complete version of what the customer already chose, in a way that feels like service rather than selling.
An upsell, at its best, is the offer the customer was hoping you'd make. The bigger room. The longer course. The fuller package that includes the bits they were going to buy elsewhere anyway. At its worst, an upsell is the chip-shop trick of asking if you'd like a large for fifty pence more on something you didn't want in the first place. Both are called upselling. They're not the same activity.
This chapter is about the first kind. The kind that makes the customer feel looked after and the business slightly more sustainable. The kind that doesn't require a sales script, a pricing psychology workshop or any technique that would make you cringe if your mother saw you using it.
By the end of the chapter you'll have a short list of upsells you could genuinely offer in your own business, the wording to introduce them and the moments in the customer journey where they belong.
The full chapter covers the four shapes of genuine upsell, the language for each and how to test one without redesigning your price list.
What makes an upsell genuine
Three tests. First, the customer is better off taking it than not. Not just nominally. Actually. The bigger package solves more of their problem, the longer course gives them more of what they came for, the fuller service saves them a job they were going to have to do themselves. Second, you'd recommend it to a friend in the same situation, without flinching. Third, the price reflects honest extra value, not a rounding up that exploits the customer's reluctance to seem mean by haggling.
If an upsell fails any of these tests, it isn't really an upsell. It's just a markup. Customers can usually tell the difference, and they remember.
The four shapes of genuine upsell
Most small business upsells fall into one of four shapes. Naming them helps, because each one wants different language and different timing.
The first shape is the bigger version. The same offer, scaled up. The longer therapy course (eight sessions instead of four). The bigger photography package (the full day instead of the half). The larger product (the family size instead of the single). The customer wanted the thing. You're offering more of the thing.
The second shape is the more complete version. The offer plus the things the customer would have had to arrange separately. The wedding photography package that includes the album and the print release. The plumbing job that includes the bathroom seal and the radiator bleed. The web design project that includes the basic content writing. The customer wanted the thing. You're offering it without the holes.
The third shape is the next-tier version. A genuinely different level of service, with a clearly different price. The premium consultation. The on-site visit instead of the phone call. The hand-finished version instead of the standard. This shape needs the most care, because tiers are easy to design badly.
The fourth shape is the longer commitment. The annual contract instead of the one-off. The ten-session block instead of the single session. The yearly subscription instead of the monthly. The customer wanted the thing. You're offering it for longer, usually at a small per-unit discount.
The four shapes of genuine upsell
The bigger version - more of the same thing
The more complete version - the thing without the gaps
The next-tier version - a real step up in service
The longer commitment - the same thing for longer, usually at a small per-unit discount
Designing one for your own business
Pick one offer in your business that has only one version. Now write down the four shapes for it. What would the bigger version look like? What would the more complete version include? What would a genuine next tier feel like? What would a longer commitment look like? You don't need to launch all four. You're trying to find the one that fits your customers and your delivery.
A few worked examples. The plumbing firm with a one-off boiler service. Bigger version: a full system service that includes the radiators and the controls. More complete: the service plus a winter check. Next tier: the priority service with same-day response. Longer commitment: the annual maintenance contract.
The therapist with a four-session package. Bigger: an eight-session course. More complete: the four sessions plus a written summary and a follow-up review. Next tier: in-person sessions with a longer slot. Longer commitment: a six-month support arrangement with a fortnightly cadence.
The online shop selling a £40 candle. Bigger: a three-candle gift set. More complete: the candle, the matches and a wick trimmer. Next tier: a hand-numbered limited edition. Longer commitment: a quarterly subscription.
How to introduce an upsell without making it weird
The tone matters more than the technique. The wording that works in small businesses tends to be quiet, factual and customer-first. A few patterns that travel well.
For the bigger version: 'Most people in your situation actually find the [bigger] more useful than the [smaller], because [reason]. It's £X more. Happy to do either.'
For the more complete version: 'A lot of people end up needing the [extra bit] anyway, so we offer the two together for £X. If you'd rather just do the [main thing], that's fine too.'
For the next tier: 'There's a [premium version] if you want [extra benefit]. Most people don't need it. It's there if you do.'
For the longer commitment: 'If you think you'll want this regularly, the [annual] works out at £X a month rather than £Y. No pressure either way.'
Notice what these have in common. They name the upsell, give a reason, name the price and explicitly leave the door open to the smaller option. That's the difference between offering and pushing.
When upsells go wrong
Three common failures. The first is upselling too late, after the customer has emotionally committed to the smaller version. By then the offer feels like a sales add-on. The second is upselling something the business can't actually deliver well at the higher price, which damages trust. The third is making the upsell so big a jump that it no longer feels like the same purchase. A 30 to 50 per cent step up usually feels like an upgrade. A 200 per cent step up usually feels like a different product.
What to do this week
Pick one offer in your business and write down the four shapes for it. The bigger version, the more complete version, the next tier, the longer commitment. Choose one of the four to test in the next month. Write the two-line introduction in the tone above and use it on the next ten customers who buy that offer. Track how many take it. You'll know within a month whether it deserves a permanent place on your price list.
The recurring principle here is the same as the rest of the category: keep existing customers close. The earlier eBook to revisit is Pricing for Small Businesses, which covers how to price tiers without damaging trust. The next chapter, Cross-Sells That Feel Helpful, takes the same care into the territory of related products and services.
The rest of this chapter walks through the practical steps, the templates and the checklists you need to put it into action. It includes worked examples, copy frameworks and the small decisions that make the difference between a plan that sits in a drive and one that gets used.
Inside you'll find a step-by-step playbook, a downloadable template, a checklist you can run this week and a short list of common mistakes to avoid before you start.
The full action plan, broken into weekly steps.
Ready-to-use scripts, templates and checklists.
Worked examples for different sized businesses.
Common mistakes and how to avoid them.
Members-only chapter
Become a member to read the full chapter
Members get the complete chapter, the step-by-step plan, the templates and the checklists. Cancel anytime.
