I paid a sales coach over $100k. He said ask these 7 questions...💸

“Help me close bigger deals.”

“Help me close more deals.”

This is the most common question salespeople ask me.

Gives me flashbacks to 26-year-old Chris trying to really make it in sales.

Make it in life.

What does make it mean?

Never think twice about swiping the credit card.

26-year-old Chris read every sales, communication, psychology book available.

Ask my wife. I've read close to 400 books to be a better salesperson.

(I might change the newsletter to "To Be A Better Salesperson.")

I can’t even begin to talk about the frustration I had.

Read 10 books, get 10 contradicting sales views. Both bestsellers. It made zero sense.

“Figuring out sales” is the most frustrating career.

Why? There's no degree. You don’t graduate with a Masters in Sales.

At 27, I hired a coach.

At 27, I got a sales masters degree.

My coach made tens of millions selling Hollywood movie scripts.

He was my real-life Ari Gold.

And damn, he could sell.

We had months of questioning sessions - how, what, when, and why to ask.

We came up with the 7 most important questions you can ask.

7 questions to win the deal if the prospect answers truthfully.

The truth is on you to unlock.

These questions can be used to sell a product, a service, an idea, a job.

The questions I’m spoon feeding you are for B2B Sales.

These questions will double or triple your income.

Before we get into that, we need to establish a baseline. What do the other 99% of salespeople ask?

The 7 most common (not good) questions salespeople ask.

You have an assignment. Before scrolling down, ask yourself what these questions do for your perception.

Do they make you a trusted advisor? Problem solver? Do they make you seem high status and professional? Or the opposite? Do they make you breathe, sound, look like a salesperson?

These are the most common 7 I found via Google, ChatGPT, and Claude

• "What are your biggest challenges/pain points right now?"

• "What are your goals for this year/quarter?"

• "What's your decision-making process for a purchase like this?"

• "What's your budget for solving this problem?"

• "What other solutions are you considering?"

• What does success look like for you with this project/purchase?"

• What concerns do you have about moving forward?"

Are you thinking “Chris, these are good. I ask these exact questions.”

Or are you thinking?

“These questions suck, Chris.”

Be honest.

One promise: After reading my questions, read the top 7, then reply with the difference.

We call this async coaching. I’m going to give every one of you a session for free.

Onto the questions

The 7 Most Important Sales Questions You Can Ask (And Need Answers To).

1. “What’s the problem? Why are we talking today?”

No problem. No sale.

Remember writing 10x each on the chalkboard in elementary school?

“No problem. No sale.”

Write that 10 times.

Read the question : “What’s the problem? Why are we talking today?”

It’s one sentence.

We need them to tell us why we're talking. What’s wrong that made them call a salesperson?

Why do we need them to tell us?

“Well, Chris, we can’t convince anyone they have a problem. They have to believe it and know it. Mostly, they need to want to solve it. Without their admittance, they have no problem,” said the woman in the back booth of the 164th floor sipping a cocktail and smoking a cigarette.

Fight for it.

If the response isn’t enough, let them know.

“We're just shopping around,” the prospect says.

“I don’t have time for window shoppers. You understand, right?”

2. “Why is that a problem?”

Is the problem a “nice to solve” or “need to solve”?

Big difference between the two.

Nice to solve are vitamins.

Need to solve are painkillers.

When in pain, you’ll do whatever it takes to fix it.

“We're missing budget by 10%.”

“Is that really a problem, you mentioned last year you beat budget by 26%?”

Everything we do is trying to find conviction in the prospect.

“Do I believe them?” should be constantly running through your head.

You only work with them after saying "yes."

3. “Why now? Why not 6 months ago?”

You can’t create urgency.

Just capture it.

This is the best question you can ask.

This will tell you everything. The urgency, priority, and likelihood of you getting a deal.

Let’s use a real-life example.

You’ve got a gentleman who’s been a bit heavy his entire life. Every year he goes to the doctor and every year the doctor says “Fred, you’ve gotta lose the weight.”

Every year Fred comes back the same weight, maybe a pound up or down.

Well, this year what does the doctor tell Fred?

“Fred, you’re pre-diabetic. If you don’t lose the weight, you’re going to develop full-blown diabetes.”

To avoid diabetes, Fred's life is about to change.

Urgency.

Why now?

Is your prospect “developing diabetes” or needing to lose weight”?

4. “What are you hoping I can do that [current vendor] can't?”

Stop pitching everyone who walks in.

Let them pitch you.

This creates a pattern interrupt.

“What’s a pattern interrupt, Chris?”

Well, glad you asked.

A pattern interrupt occurs when a person’s brain double-takes because the experience isn’t normal.

What’s normal?

A prospect saying “Here’s how we’re different from the competitor.”

Not you.

You get them to tell you why. What do they think you can do differently. And why.

They are pitching you.

They're telling you your value proposition.

Stop doing the hard work for your prospects. They are the ones with the problem.

Ever been to the doctor when you weren’t feeling well and kept your mouth closed like Fort Knox?

Of course not!

You want the problem fixed.

Let. Them. Tell. You.

5. “Why not just [insert most obvious solution that isn’t you]?”

You want to be a trusted advisor.

So be it.

Trusted advisors tell prospects how to solve any problem.

Even if it’s not with them.

This is my favorite type of question.

This forces them to explain why the alternatives won’t work.

Aka the competition.

Homegrown solutions. Paid solutions. Competing solutions.

Anything that you believe will solve their problem (that costs less than you) needs to be mentioned.

Remember: There are more reasons not to make a deal than to make one.

Ask them why the alternative didn’t work.

This uncovers their willingness and ability to execute.

Did they fail because the solution didn’t work?

Did it fail due to lack of discipline and execution?

6. “What else is this intended to solve?”

Never solve just one issue.

No problem has one issue.

Overweight?

It’s diet. Exercise. Sleep. Stress.

Profit problem?

It’s sales. Margin. Costs. Marketing. Leads.

Solve all those and get the deal.

Solve one? Probably not.

Here’s how this looks in practice.

Overweight person comes to you telling you they need an exercise program.

“Exercise for sure helps. What else are you trying to solve with your weight loss?”

They will give you a laundry list of their problems they are having.

If they don’t, this is where you pop in the previous question about possible solutions.

“Have you tried going to bed earlier?”

Funny how these questions work together.

7. “How will you know 6 months from now you made the best decision?”

Why sell something?

Not commission. Not quota. Not a fancy new car.

To help someone.

How do you guarantee success? By making sure they get the benefit of what you sold.

99% of salespeople believe the sale ends when the check is signed.

Not you.

That’s when it begins.

I don’t lose customers. Ever.

I make sure the implementation of whatever I sold is perfect. That they get exactly what I sold.

I want my customers to be evangelists (that’s what my current coach calls them)

I want them to be so happy they chose me that when I ask them “Hey! What other cool/fun/smart/nice people like you should I know?” that they cannot wait to introduce me.

This sets up your referral engine.

Weekly Challenge

This week it’s about getting answers to the questions that unlock bigger deals with more prospects.

This is a two-part challenge.

Part 1 is simple.

New prospects, you need to ask these questions.

Part 1 Checklist:

1. Go into Google Docs or get a blank sheet of paper.

2. Put all the questions I gave you down on paper.

3. Keep paper on the desk.

4. Make certain all new deals are being asked these questions.

Part 2 is to get your deals back on track:

Part 2 Checklist:

1. Column A is your current deal.

2. Column B is question #1 “What’s the problem? Why are we talking today?”

3. Column C is question #2 “Why is that a problem?”

4. Etc.

5. Etc.

6. You are going to write down the answer that your prospect gave.

7. If they didn’t give you an answer, you need to ask the question.

Closing Thoughts

This newsletter is for you.

My only purpose is to teach you everything I know about selling.

If the newsletter isn’t enough and you want to have the best quarter of your career.

Close more deals than you’ve ever closed.

I offer 1:1 coaching to sales executives, founders, and entrepreneurs ready to become top 1% in the world at selling.

I’ll show you my exact system that helped me go from average salesperson to top 1% and 7-figure earner. You’ll learn how to get exactly what you want out of life.

Reply with “Coaching” and I’ll tell you how it works.

First 15-minute phone call is free.

Until next week.

-Chris

PS - Don’t forget about that promise.

One promise I need from you: Once you’re done reading the questions I’m giving you, I want you to read the most common 7. Then you need to reply with the difference between the two.

We call this async coaching. I’m going to give every one of you a session for free.