Boost Your Win Rate by Reducing the Friction in Your Sales Process. Here’s How.

In 2008, Eleven Madison Park was one of the most celebrated fine dining restaurants in New York City. It was also bleeding money.

The financial crisis had hit the restaurant industry hard but rather than cutting costs and playing defense, restaurateur Will Guidara and his team decided to get creative.

One of the changes they made was not only psychologically powerful but seems almost embarrassingly simple in hindsight.

At lunch, they were struggling to drive dessert orders. Not because the food wasn’t good. It was extraordinary. The problem was that lunch guests, mostly professionals on a midday break, didn’t want to sit through the full ritual of perusing a dessert menu, placing an order, waiting for the kitchen to plate it, and then having it delivered. Dessert felt like a tax on their afternoon. So they skipped it.

The fix? Roll a cart of fully prepared desserts right to the table. Guests could see the options in front of them: pies, cakes, and tarts. With a simple pointing of their finger, the scrumptious desserts would instantly land in front of them. No waiting. No imagination required. No friction.

Dessert sales went up 300%.

Same food. Same guests. Same restaurant. The only thing that changed was how easy they made the decision.

There’s a powerful sales lesson buried in that dessert cart. And it’s one that most sellers miss every single day.

 

The Real Enemy Isn’t Risk. It’s Friction.

I’ve written before about the Power of Prescription, the idea that modern buyers are overwhelmed by choice, and that sellers who lead their customers through the buying process close more deals, faster, with less regret on both sides. Things like how to define the problem the customer is experiencing, the best way to evaluate solutions for it, and what next steps they should take after each interaction are all areas that create friction that slows deals down.

Research from Gartner backs this up: prescriptive selling produces an 86% increase in purchase ease and a 37% drop in buyer regret.

But the dessert cart story adds an important dimension to that idea. It’s not just about reducing choices. It’s about reducing the cost of the next step.

Think about that for a moment. The lunch guests at Eleven Madison Park weren’t opposed to dessert. They weren’t price-sensitive or skeptical of the quality. They just didn’t want to deal with the process. The dessert menu came bundled with delay, effort, and uncertainty. That bundle was enough to make them walk away from something they actually wanted.

Sound familiar?

 

Why Your Sales Motion is Hurting You

Every time you hand a buyer a task instead of an answer, you’ve handed them a dessert menu.

Every time you leave a meeting without a clear recommendation for what happens next, you’ve handed them a dessert menu.

Every time your proposal asks them to figure out which tier or package is right for them, you’ve handed them a dessert menu.

The buyer might be genuinely interested. But the friction of the next step is enough to make them go quiet.

Here are four places sellers consistently hand buyers high-friction dessert menus, and what to do instead.

1. The Solution Demo

Most demos are built around the seller’s product, not the buyer’s problem. You walk them through features, they try to imagine how it applies to their world, and by the end of the call you’ve made them do all the mental heavy lifting.

That’s the kitchen, not the cart.

Instead, build your demo around a pre-researched version of their specific situation. Show them output that already reflects their industry, their use case, and their pain. When a buyer can point at something and say, “Yes, that!” the decision friction evaporates. They don’t have to imagine the dessert. They can already taste it.

 

2. The Pricing Presentation

In a well-known behavioral science experiment at Stanford and Columbia, researchers found that shoppers were ten times more likely to make a purchase when presented with six jam varieties versus 24. Ten times! When buyers face too many options, they don’t pick the best one. They pick none.

Most pricing pages and proposals are 24-flavor displays. Three tiers, fifteen add-ons, custom configurations, volume discounts based on seat counts the buyer hasn’t figured out yet.
Roll the cart instead. Come to the pricing conversation with a small set of options and a single recommendation: “Based on what you’ve told me, here’s what I’d suggest, and here’s why.”

When I was a VP at Salesforce, where our solution toolbox consisted of dozens of products all with complex discount matrices and pricing options, this was the approach we encouraged our reps to take. Start with a curated basket of solutions based on the customer’s needs, combine it with a few different discount options based on contract length, recommend one with conviction, and let them choose.

Buyers don’t want infinite options. They want a guide.

 

3. Meeting Follow-up

After a strong discovery call, too many sellers send a follow-up that reads like a list of asks:

“Let me know when you’d like to reconnect.”
“Feel free to share this with your team.”
”Let me know if you have any questions.”

That’s the dessert menu. You’ve handed the buyer a set of decisions and walked away.

Prescriptive follow-up looks different. It specifies the next step, the reason for it, and makes it as easy as possible to say yes. Something like: “I’d like to set up a 30-minute call on Thursday or Friday to walk through what a 90-day onboarding plan would look like for your team. That tends to be the most useful next step at this stage. If you feel that makes sense for you too, would either of those days work?”

You’ve done the work. They just have to point.

Note: As I’ve spoken about in the past, the level of prescription you can take without putting the customer off depends on where they are in the buying process. Early on, interest-based follow-ups are the least scary and easiest to agree to. Come on too strong and customers become resistant and ghost you. Later in the process, buyers appreciate you taking a more hands-on leadership approach.

 

The Takeaway

Eleven Madison Park didn’t increase dessert sales by making better desserts. They increased dessert sales by making it easier to say yes to the desserts they already had.
Your buyers aren’t skipping the next step because they don’t want what you’re selling. More often, they’re skipping it because the process of getting there feels like too much work.
Every place in your sales motion where a buyer has to imagine, calculate, decide, or wait is a dessert menu. Your job is to roll the cart.

Plot twist! I was lucky enough to dine at Eleven Madison Park and wrote an entire post about the out-of-this-world experience and what it taught me about sales. Check that out here: What Dining at the Best Restaurant in the World Taught Me about Sales