How to Train Restaurant Staff to Upsell (the Right Way)

“Do you want fries with that?” It’s the most cliché phrase in the business, but there’s power in that simple question.

Restaurant upselling is the process of persuading or influencing a guest’s purchase by enticing them with more expensive or higher-margin items and add-ons. With a little effort and strategizing from your front-of-house staff, it’s an easy way to increase average check size and get more out of your menu.

Here are a few ways to train your staff to upsell in your restaurant to boost sales while providing a stellar dining experience.

Upselling vs. cross-selling: What's the difference?

• Upselling: Encouraging guests to purchase a more expensive version of an item (e.g., suggesting a premium vodka instead of well vodka, or upgrading from a regular to a large size)

• Cross-selling: Suggesting complementary items to go with the original purchase (e.g., recommending fries with a burger, or a dessert after an entrée)

Both techniques might increase check size, but understanding the difference helps staff apply the right approach at the right moment.

Teach your team upselling techniques

Your employees are the greatest asset for upselling, and they should be constantly aware of their ability to do that. Almost every interaction they have with a customer is an opportunity to influence their purchase. Whether they’re a bartender serving guests at the bar or a server welcoming a guest at the table, nothing beats the power of suggestion.

The best upselling doesn't feel like upselling — it feels like a server who actually knows what's good. Make sure your servers are enlightening your guests rather than harassing them. Talk to your staff about why upselling is important and coach them on how to do it gracefully. By taking a consultative approach, like “That particular cut of steak pairs nicely with the blue cheese crumble and a glass of red wine” or simply, “Would you like some fresh-cut fries with your sandwich?” your staff is forming a relationship with the customer and doing good for the business financially.

Ongoing training, especially when new menu items emerge, is a great way to guarantee your waitstaff are comfortable upselling. Have your kitchen prepare the latest and greatest from your menu for your next pre-shift. Give each employee the chance to try the new item, making sure they’re aware of the ingredients and cooking techniques used to create the dish. Encourage them to pick a favorite item from your menu that they can describe elaborately to your guests, along with sides and drinks that pair nicely with the meal.

This is where Toast comes in to help empower your team. Menu Upsells by Toast offers recommendations, menu pairings, modifier recommendations, and item upgrades. These features make it easier to teach your staff how to identify the best moments in a meal to make a suggestion.

Motivate your staff to sell

For front-of-house staff, there’s a clear benefit in upselling: it increases the size of their tip. But there are other ways to motivate your team to land bigger checks. Run a competition to see who can sell the most Sunday specials, or keep a leaderboard for the server who sells the most add-ons. 

The rewards you offer in return can vary from a cash bonus to favorite shift preferences, or even just a bottle of wine you overstocked.

Build upselling into your tech

Restaurant technology can help you upsell. Your restaurant POS system can complement thorough staff training by reminding employees to ask guests those crucial upselling questions.

When a customer orders an entrée, your POS system should prompt your employee to ask follow-up questions by suggesting on screen to add drinks or sides. This gives your employees some support, especially when they’re newer to the team.

Toast IQ automatically suggests upsell prompts based on item type, guest behavior, and strategic goals, offering guidance in real-time to boost revenue and guest satisfaction.

Upsell in your online ordering system

Your staff might be great at upselling in person, but what about when customers order online? Upselling doesn’t have to stop at the front door. Your restaurant’s online ordering platform can be just as powerful when it comes to increasing check sizes. With thoughtful design and strategic prompts, your digital menu can do the suggestive selling for you.

Toast’s online ordering system allows you to insert upsell prompts throughout the customer journey, like suggesting drinks or sides during checkout, or highlighting premium modifiers as add-ons right on the item page.

For example, when a guest selects a burger online, your system can automatically ask, “Would you like to add bacon or a fried egg?” or recommend a combo deal with fries and a drink. These subtle, helpful nudges mirror the upsell tactics your staff use at the table, only this time, they’re built into the ordering experience.

Better yet, with Toast, you can rotate online upsells seasonally, track which ones are converting best, and adjust in real time, all while freeing up your staff to focus on dine-in guests.

Online ordering upsells are a low-effort, high-reward way to increase revenue, especially during peak ordering hours or holidays when off-premise demand is high.

Offer gift cards and promotions to guests

Your customers want to know their business is important to you. But are your servers simply expected to write “Thank you!” at the bottom of a receipt and be done with it? Of course not. Here are some ways you can tell your customers, “We love you,” that actually make them feel appreciated.

Gift cards

If you’re not offering gift cards at your restaurant, you’re missing out on a revenue channel and an opportunity to make more money with every guest. A June 2026 Capital One report found 43% of American adults have unused gift cards, totaling an estimated $23 billion in unspent funds nationwide.

In addition to encouraging repeat business, collecting money upfront, and being relatively inexpensive to offer, gift cards are a great way to encourage guests to buy more.

Capital One also found that 61% of consumers spend more than a gift card’s value when redeeming, for an average of $31.75 more than the card’s value. And, a Toast survey found that 64% of respondents are discovering new restaurants by receiving a gift card.

Gift cards are also likely to be used on higher-priced items since they’re essentially “free money” for the holder, so there’s a good chance they’re even more open to upsell efforts than the average guest.

Gift card sales are easier than ever with digital or e-gift card options. Operations director of Ethan Stowell Restaurants, Michael Pagana, recounted the drastic change that e-gift cards had on his business when he first began offering virtual gift cards. “I got a call that our gift card sales were down. That’s because they were looking at only physical gift card sales,” said Pagana. “We had actually sold more in online gift cards than we had all gift cards in the entirety of last year.”

Additionally, many restaurants combine gift card purchases with promotional deals, offering things like a bonus $20 gift card for every $100 gift card purchase. This kill-two-birds-with-one-stone methodology rewards your customers while also encouraging them to spend more.

Holiday promotions

Holidays are an easy time to upsell your restaurant’s gift cards, but there are also other ways to promote your restaurant around the holidays. Offering seasonal or holiday-specific items, hosting Halloween costume contests, or giving out free entrées for moms on Mother’s Day are all great ways to get more guests in the door.

Build loyalty with your regulars

Proving that you appreciate customer loyalty is beneficial to both your restaurant and your client base. Give your frequent patrons an incentive to keep coming back by offering a loyalty program based on your menu offerings. You can even use your point of sale system to track customer loyalty and allow your guests to see their progress online. This rids you of the cost of purchasing punch cards and relieves your customers of the hassle of trying to keep track of those pesky things.

Logan Hostettler, general manager at The 1894 Lodge, spoke about his experience with offering customer loyalty incentives through Toast. “Customers were so crazy to earn points that they were buying the entire bar a round so they could redeem the rewards. They love how the loyalty program offers a gamified restaurant experience,” said Hostettler. By displaying your appreciation for your repeat customers, you’re simultaneously driving up your bottom line.

With Toast’s loyalty program features integrated into the POS, guests can track their points in real time, making repeat visits feel like a game, and giving your team even more opportunities to upsell.

Strategize your menu

While it helps to have tact when upselling to guests in person, there’s no reason to make your menu options subtle. Make guests aware of all the upsell options available by writing them directly on the menu, and train your staff to call these out in conversation.

If it’s possible to add bacon to a burger, include “Bacon $2” under the burger menu item. If your guests want to add chili to their nachos, put it right there on the menu, and you’ll get them thinking about how delicious that appetizer would be with a little something extra.

This also allows you to get more creative with your menu without feeling like you have to offer expensive items for every dish you send out. To automatically include bacon, a fried egg, and fresh jalapeño slices on a burger would cause that item to be pretty pricey, but giving your customers the ability to create their own meal gives them a sense of ownership and saves you from the common complaint of high prices. This can make for an overall better customer experience.

Toast IQ automatically uncovers your top-selling items and vital business trends behind the scenes, giving you the data-driven insights to build a more profitable menu strategy without digging through manual reports.

Most customers aren’t aware of how tight restaurant margins are or how important every additional sale is, no matter how seemingly small. By making sure your staff is well-equipped to work upsells into the conversation, to be polite, not pushy when upselling to guests, you’ll provide an experience that will keep your customers coming back for more.

Menu Upsell by Toast

Slim margins. Labor. Inflation. It’s tough out there, but so are you. Protecting your bottom line means making every transaction count, but your team shouldn't have to guess what to recommend to guests.

Cold hard data. Easy decisions. Toast IQ is your extra set of hands, helping tackle the little tasks cluttering your to-do list. Toast IQ makes AI work for you with actual actions on-demand, using your restaurant’s own data to spot top-selling items and vital business trends. This helps you build the marketing plan that keeps you busy and identifies which pairings and upgrades drive the most revenue.

Complexity? You’re too busy for that. Pair those insights with a connected POS that captures every modification, add-on, or substitution accurately, so the kitchen delivers exactly what the guest ordered. More insights. Less guessing. By giving your staff the tools to execute the perfect upsell, you don't just boost checks—you fill your dining room with familiar faces and build businesses that last.

FAQ

What is upselling in a restaurant? Restaurant upselling is the practice of encouraging guests to purchase higher-priced items, upgrades, or add-ons to increase the total check size while enhancing their dining experience.

How do you train servers to upsell? Train servers through menu tastings, role-playing exercises, and providing specific scripts. Focus on making recommendations feel like helpful suggestions rather than sales pitches.

What's the difference between upselling and cross-selling? Upselling encourages purchasing a more expensive version of an item (e.g., premium liquor), while cross-selling suggests complementary items (e.g., dessert after dinner).

What are examples of upselling phrases servers can use? Effective phrases include: "Would you like to add our house-made guacamole for $3?", "That pairs perfectly with our Cabernet," and "Can I start you with one of our signature cocktails?"

How much can upselling increase restaurant revenue? Effective upselling can increase average check size by 10-30%, making it one of the most impactful strategies for boosting restaurant sales.