Hello Reader,

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The best sales conversations flow naturally.

But that’s a lot easier said than done.

What is the best way to accomplish a natural flow in sales?

It's done by the questions you ask.

The reality is that there is an art to asking questions in sales, and it comes down to timing.

Last week, I gave you insights into how to get control in sales. And in order to get control, you need to be asking the right questions, in the right way, at the right time.

Now while I explained those and gave you the 52 Sales Questions Guide to help you even further, this week I plan on diving deeper into the last part. “At the right time.”

The reason why timing is so critical with questions is because it can either make your prospect instantly lower all their guards and let you in, or reinforce their guards to never let you in!

What I always like to say to get people to understand this is, “Would you ask a person to marry you on the first date?”

And I did touch on a similar statement last week.

Now, I hope you wouldn’t ask someone to marry you on the first date. But if things become serious, and a year of happy courtship goes by… you’ve learned a lot about each other, you’re both ready for commitment… and then you pop the big question…

That right there is, “the right time.”

But had you popped the question on the first date, you would’ve most likely scared that person away for good.

And it’s the same in sales.

So timing is critical. But how do you know how timing works in sales?

Simple. You have to consider what stage your prospect is in.

• Are they only just hearing of you, or have they had interactions with you before?
• Are they aware they have a problem, and if they do, are they aware your solution even exists?
• If they’re aware your solution exists, are they aware of your competitors?

I can go on with the bulleted list above, but to shorten it, think of your sales conversation like a three-course meal:

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Starter questions: Setting the stage

Your starter questions are like an appetiser. They ease your prospect in. They’re light, open-ended, and designed to get them talking.

Great starters help you:

• Build rapport
• Uncover surface-level needs
• Set the tone for a deeper conversation

Examples:

1. “What’s made you look into this now?”
2. “Where does this fit within your current priorities?”
3. “What impact is this issue having on you personally?”
4. Notice that these aren’t about selling, they’re about understanding.

Main course questions: Digging deeper

Once you’ve built rapport, it’s time for the main course. These are the heavier, insight-driven questions that uncover pain points, urgency, and decision-making factors.

This is where you get to the real problem.

Examples:

1. “What happens if you do nothing for the next 3 to 6 months?”
2. “How much is this currently costing you in time, energy, and money?”
3. “What’s the ripple effect this challenge is having across your team?”
4. “Is there anyone else we should be involving in this discussion?”
5. “What would be your budget to solve this problem?”

These questions help the prospect connect their problem to a real, tangible cost. And once they see the cost? They’re much more likely to act. It also makes the price of your services seem a lot more digestible when compared to how much they stand to lose without your services.

Pudding questions: Moving the deal forward

Dessert is the final part of the meal. In sales, this is where you test readiness and guide the deal to a close.

But just like dessert… you don’t serve it too early.

Examples:

1. “What would achieving this be worth to you and your team?”
2. “How will you know when you’ve found the right solution and provider?”
3. “Can you envision anything that could cause delays on your side?”

Now this is where most salespeople make their mistakes. The mistake is that they ask these pudding questions (closing questions), when they’re supposed to be asking starter questions.

So they’re asking the right questions, just at the wrong time.

Like I said last week, asking, “Would you like to move forward?” before the prospect even acknowledges they have a problem, won’t work.

Think about when you’re walking in an airport, and someone tries to force a flyer onto you. Some people may take it, because they don’t want to risk being rude. Others will ignore and keep walking.

The point is, nobody wants the flyer.

Because you’re in an airport, most likely in a rush.

You have no idea what that flyer is about, and you don’t have the time of day to stand there and listen to someone explain it to you.

Your prospects are exactly the same. They’re busy, and they don’t have time. But you have one advantage over people who hand out flyers at airports. While they’re handing flyers out to everyone and anyone, you’ve got a list of qualified leads!

Which means you know these people need your services.

So respect their time by asking the right questions, and getting the timing right in the questions you ask.

Now, as I mentioned earlier, last week I gave you one of my most downloaded resources – 52 of the best sales qualifying questions to ask, to help ask better questions. I hope you went through them or shared them with your team to go over. Because this email should now help you understand when to ask those questions.

But if you want to step it up a notch and be able to qualify leads better and eliminate timewasters, check out my BANT course. It’ll give you everything you need, and it’s available at a steal of a price.

Until next week, keep working on that timing…

James

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