The 4-step secret to upselling

Annie Gray
4 min readJun 28, 2021

Before I started working in Account Management and Customer Success, I didn’t understand upselling or cross-selling but then I realized this was something that I’d been doing my whole career in Hospitality I had just never thought of it this way. When I suggested a more expensive dish or convinced the customer to add sides, I was upselling and I knew how to do that well.

What’s the secret? In essence it’s simple, trust.

Wouldn’t it be great if we could just end it there, “oh great, thanks Annie, that’s really cleared it up”. Alas, the real secret is how to gain that trust and how to gain it quickly.

This weekend I got to witness a master of upselling and it got me thinking how servers are the best at this art. We were in a restaurant celebrating the anniversary of me moving to Spain and decided to be more adventurous with our food choices than perhaps we normally would be to compliment the biggest adventure I’ve taken so far — migrating. We started to order and had listed a few items, the waiter gave descriptions of what was in each dish and then made a few suggestions for some dishes that we might like. The waiter then told us to stop ordering as we probably had enough so we thanked him and started to salivate thinking about the dishes that were coming our way.

4 images of dishes, Duck and accompaniments, Pâté with candy floss, cherries and eel, seabass taco and a medley of shellfish with a spicy leek sauce
Top — Duck hoisin style. L-R Pâté with cherry, eel and candy floss; Seabass taco; Shellfish medley with spicy leek sauce

The food was incredible, every dish was as delicious and exciting as the previous one and they complimented each other perfectly without overwhelming our palettes. But this isn’t an advert for the restaurant (Can Gallina in case you’re interested), this is a look into how and why the waiter was so successful in upselling to us.

How was the waiter able to build our trust enough to spend around 30% more than we had planned? The same steps I used when I worked in hospitality:

  1. In-depth Product Knowledge
  2. Price point
  3. Value proposition
  4. Purposefully “un-sell”

In-depth Product Knowledge — In order to build trust quickly, you need to prove to the customer that you know what you are talking about. In a restaurant this is being able to describe the ingredients in a dish, in software it’s being able to explain the functionality in layman’s terms. You need to demonstrate, without showing off but with confidence (a tricky balancing act), that you know what you’re talking about and are the most knowledgeable person on the subject in the room.

Price Point — Arguably this is easier in a hospitality setting than in business but the way that this step works is you don’t automatically suggest the most expensive option. By suggesting the second most expensive option, or third, you are still encouraging the customer to spend more money but you appear more trustworthy as you haven’t obviously pitched the most expensive item to sell to them just to get them to spend the most amount of money possible. We, as customers, make a mental justification for buying something if there’s something more expensive available that we don’t go for. It works the same way as me telling my partner how much money I’ve “saved” when I buy something in the sale instead of how much I spent. However it could be that the most expensive option is actually the best solution for the customer and that’s where the third element comes into affect.

Value Proposition — This is selling in it’s most basic form. In a restaurant you would be selling the flavors, how they balance on your tongue. In tourism you’d be selling the feeling of the sand between your toes. In business you’re selling the quickest win that this functionality will give them. This could be that it would save X hours per week, Y fewer clicks, shortened deal length by Z days etc. I’d always recommend that you lean towards getting an emotional response, even in business. Find out the biggest pain point that your customer has and establish a tangible benefit that they would get from whatever it is that you are trying to sell to them. If you aren’t able to find one…the customer won’t be able to find a reason to buy it either.

Purposefully “un-sell” — This is where the waiter told us we didn’t need to order another dish as we’d have enough with what we’d ordered. By doing this, you are actively telling the customer to not spend more money and this makes the customer trust you that you wouldn’t let them spend money on things that they didn’t need. This therefore reinforces the feeling that everything they have purchased so far, they do need and is justifiable. In software this could be moving to the next software tier for example. It’s helpful to subtly mention this unnecessary item early on in the conversation so that later you can bring it back up to let the customer know that they don’t need it.

I have always tried to practice what I call “moral sales” by this I mean I can only sell something to someone if I think they absolutely need it and would benefit from it. If I can’t convince myself that the customer needs it, I’m never going to be able to convince the customer. That also helps with the trust element as when I build the relationship with the customers that I manage, I reassure them that I’d never try to sell them something just because I have to hit a target. This (among other reasons) is why I don’t like Account Managers being commission based on a sales target but that’s a conversation for another day.

If you want to know more about how to serve your customers better, or what software could help you provide that personalized experience reach out to me at annie.gray@livehelpnow.com

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Annie Gray

I love Customer Experience, Customer Success, Relationship Building…basically if it’s customer related — I’m in!