The 3 Questions That Turn “No” Into A “Yes”

Over a number of years I’ve developed a three question system that I use to land better meetings, move deals along quicker, and sweep the objection mine field clear to close more deals.

I wish I could say that this came to me easily, quickly, and naturally in my sales career, but that’s not the case. In all honesty I discovered this technique because I had to.

Ten years ago I put myself in the ultimate ‘no looking back now’ scenario: I joined a startup as a cofounder and the first full-time salesperson.

In other words, if I failed then we all failed, even if everyone else involved succeeded.

I had never felt pressure like this before.

Within a few days I had already set up my first meetings with prospects. It was go time.

Yet I realized it wasn’t my company’s name on the line this time, it was mine. Wow. I bet you can think of a time you had the same feeling I had that day. It wasn’t about selling something, it was about making a mark.

Before my first meeting I asked myself, “If these were going to be my customers forever and ever, how would I treat them?”

That question changed the course of my sales career in an instant.


Three months later we all huddled to talk about how 2007 was going to be a big year for us.

After all, I was forecasting an absolutely massive month. Not only was I projecting a good number of new orders, I had promised a boatload of new customers. Not in Q1. Nope. I promised they were all coming in right now, in January.

Have you ever committed to a big number? I had before, except this time I was sweating bullets. It was one thing to pull off a big quarter. It was another to promise the biggest month yet after coming off a slow holiday season.

The other three cofounders all wondered if this kid they had bet the company on would pull it off.

If I missed this month – not this quarter, this one month – the gig was up. Either we’d fold or I’d get fired.

And what happened? I delivered. Oh, did I deliver. The pipeline I had built was so good that I was closing at least one deal every single day. New customers were lining up for their first order and existing customers were placing even bigger second orders. One of the cofounders nicknamed me Cal Ripken because I landed an order every single business day like clockwork.

(I finally missed on 2 days the final week of the month, but the nickname stuck)

I wish I could say that was the beginning of an amazing run but alas, startups succeed for the same few reasons yet can die a million different ways. Before the year was out, before we landed the funding we needed to stay afloat, the other cofounders split and we ran out of cash.

Thankfully I walked away with the closing system that had changed my life.

You too can learn this system. I know, that’s a corny as hell line. It’s true, though.

I’ve taught this approach to dozens of sales reps over the past five years in different industries. Could it work for you? I’ll let you be the judge.


Closing – whether you’re closing a meeting, a next step, or finalizing a deal – comes down to doing one thing and one thing only.

Guiding the prospect through the buying process.

Notice I didn’t say SELLING them. Notice I didn’t mention features, benefits, value propositions, or showing them ROI. None of that matters if you don’t understand the most fundamental rule up front.

Prospects BUY, and your only job is to guide them down that process, whether it means you personally close a sale at the end of the process or not.

This is all about showing the prospect HOW to buy something. If you take only one thing away from this post, you should literally write down what a “How to buy my product the best way possible” process looks like.

After all, if you can’t help a prospect figure out how to buy something, how do you expect they’ll figure out how to buy from you?

The best part is that it doesn’t matter if we’re talking software or services, automobiles or analytics, plane tickets or Lear jets. A sale doesn’t happen unless the prospect goes through a process to buy something.

Here’s the fun part: when first you meet a prospect you have absolutely no idea where they are in the buying process. Even worse, your prospect probably doesn’t know where they are in the buying process.

And you were wondering why they paid sales people the big bucks!

You get to be the one who figures out where the prospect is in the buying process. Your goal is to help them along the rest of the way without getting lost or distracted, but if that’s going to happen anyway I’d recommend letting them wander off sooner than later.

Back when I had that conversation with myself about how I’d treat my new customers, the ones I thought I’d have forever and ever, I started acting differently. Specifically, I stopped using all the silly tactics I had picked up trying to push, pull, prod, and pummel prospects into signing on the dotted line.

These were going to be my customers for life and I realized I needed them to want to buy from me.

I knew that the only way to guide someone in a buying decision was to ask them questions. I needed to act more like an advisor than a quota carrying sales person. Specifically, my forever customers’ advisor.

The first question I knew to ask was one I had used for years. It was my best friend at every step of the buying process, from cold call to close.

CLOSING QUESTION #1

“If we’re in agreement here, will you take the next step?”

The classic A/B close. Strong enough for a personality Type A, soft enough for a Type B.

Now before you start going out asking this exact question, let’s take a step back to understand what’s going on here and how to ask this question. This one can be used at every step of the buying process, so pay close attention to how it transforms based on the situation you’re in.

Say you’re calling to schedule a first meeting. The prospect has given you just enough information that you’re ready to book it.

Your close would be, “It seems like X and Y are your big priorities, and that’s an area we’ve helped dozens of companies get even better results. If you’d like to have a deeper discussion on how we might be able to do that for you, when could we set up a 30 minute meeting next week?”

At the end of that call (great call, btw!), you know the next step in the buying process is to give the prospect a test drive. You might call it a trial, you might call it a proof of concept. Whatever it is, you know the best way for them to experience your product is to actually get them to use it.

Your close would be, “It seems like this could be a great fit for you. The next logical step for you to take would be to set up a 14 day trial so you can really understand how much easier X and Y will be for you and your team. If that sounds like something you’d like to see, when can we set that up?”

The test drive goes great and then you’re ready to move forward. This is where things get sticky. This is where you’ll run into objections – budget, timing, pricing – and you’ll realize your prospect has suddenly wandered away from the buying process and straight into the Tire Kicking cul-de-sac.

You’re going to need to keep the A/B question by your side. You’re also going to need some reinforcement to get the buyer back on track.

CLOSING QUESTION #2

“What would prevent you from moving forward?”

Wait, did I just invite the prospect to throw objections at me?

You’re absolutely right I did. This was my first golden discovery when I was building the startup.

When you ask your guiding questions, the ones designed to get a “yes”, what you’re doing is painting a picture of what things could be like. These feel safe to you because you feel in control. You’re avoiding a “no”. You’re avoiding everything that could derail the deal. Right?

Nothing could be further from the truth.

Whether you choose to surface those objections or not, they’re still there.

A sales professional understands that objections are likely lurking in the shadows. What you gain by inviting the prospect to point out the important land mines that are right next to both of your on the buying process is that you’re asking them to guide both of you through the tough spots.

The prospect feels safe because they’ve said “no” to you. They get to keep status quo for another moment.

Except that’s not entirely the truth.

You’ve empowered your buyer to be the leader on their buying journey by letting them tell you “no” and giving them the illusion of control.

Now that their objections are in PLAIN SIGHT!

Ah ha, they’ve shown you all the rough terrain before you’ve gotten there!

The best part is that the prospect suddenly feels more relaxed. Calmer. All those fearful emotions that you’re used to battling through disappear.

Your prospect is relaxed, focused, feeling in control, and ready to talk to you to see if they should buy.

What should you do? You show the prospect how both of you can overcome them. After all, the only way the prospect can complete their journey through the buying process, the only way they can get all the amazing benefits you’ve been discussing, is by joining forces with you to overcome them.

They’re more than open to having this conversation now that they’re calm, cool, collected, and feeling in control.

How do you handle these objections? By asking a variation of Question #1, of course.

Before I show you how, let me give you the why. The inexperienced sales rep hears an objection, panics, and spits out a canned rebuttal, praying it works.

You? You’re a professional. You’re better than that. You ask them your A/B close BEFORE addressing their objection to make sure nothing else is holding them back at this point.

Let me give you three different ways you can ask this.

“If that’s something we can do, will you be ready to move to the next step?”

“Other than this objection, is there anything else holding you back from moving forward?”

“Before we dig into this I need to ask you, if we can iron this out will you be ready to move forward?”

Some of you might have noticed that there are two things you’re asking with this question.

First off, are we discussing everything that could end the buying journey? Because there’s no point in turning land mines into guideposts if there is another one still buried in the ground, waiting for you to step on it.

You won’t be able to move forward without getting all the objections out in plain sight as soon as possible. Once they’re all clearly defined, yes, go about handling them (and get the prospect to help).

Second, the prospect is committing to moving along the buying process with you.

This one is so simple and super important. Do you really want to waste your time with a prospect who needs something you can’t offer? Of course not! They’re not going to buy from you. You’re a sales professional, and you focus your time with prospects who can buy from you.

There’s no point in continuing along if the prospect flat out says, “You know, I need Z,” and Z is something you absolutely cannot do for them.

However, what if the prospect is confusing must haves with nice to haves? What do I do then?

You still have one more question in your arsenal.

CLOSING QUESTION #3

“Have you given up on this?”

This one is so amazingly powerful in all its variations.

The last thing most people want to do is give up on someone else. When you ask this question you’re communicating that the prospect is letting you down.

That’s right. The prospect has failed you, not the other way around.

You’ve spent all this time trying to guide the prospect through the frightening buying process and now you’ve fallen short. Except it’s the prospect’s journey, not your’s. You’ve been their guide. And now the prospect isn’t going to finish the journey you’ve been helping them along.

What kind of person gets all this help only to stop short?

Oh, and it eats at the prospect! They have a moment, thinking, “What can I do to help this person who I’ve clearly failed?”

There’s only one way to make things right, and that’s for the prospect to see if they can save you.

Now, this doesn’t always work. This is your last ditch effort when it’s clear the prospect is stuck on their buying journey with you. The interesting thing is that it will work more often than you’d expect, and far more often than anything else you could do.

By asking the question, by letting the prospect choose to re-engage with you (not the other way around), they’ve committed to you that they will deliver one more strong effort to complete their buying process.

Their mindset is much like when you asked them to put their objections on the table. Your prospect is calm and relaxed and ready to see what you can do together.

The prospect is your partner again.

There are different ways of phrasing this, depending on your situation.

If you’re talking with them in person, you might want to say:

“It seems like there’s nothing we can do to move forward today.”

Pause and see how they respond. Give them a good ten seconds if need be.

If you’re sending an email to try and get back in front of them, all your subject needs to say is:

“Did I lose you?”

Especially if you’re forwarding along all the past conversations and outreach you’ve had. That subject line has worked like magic for me.

It’s always worth trying to get the prospect back even when it looks like you’ve lost. You’ve gone on a long journey through the buying process with your prospect, and you might be on the verge of closing the deal. All they need is someone to help them take those final steps.

CLOSING THE SALE WITH QUESTION #1

Now that we’ve helped the prospect through the buying process and gotten to the very end, you have to ask for the sale. It’s time to close them.

We just need to say the magic words.

“Prospect, if this is all agreeable to you, when can we start?”

You might be wondering if this is all a dream. Or a hoax.

Can you really schedule more meetings, develop more deals, and close more sales all by asking 3 questions?

I assure you, yes, you can.

You can spend your days trying to trap prospects, or waiting until you trip over the people who are so far long the buying process that they’re ready to buy…

Or you can learn how to help your prospects buy from YOU.

The best part is this: not only will they buy, they will buy quicker and pay more because it’s clear you know how to help them make a great decision.

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