The Power of Probing Questions in Sales

Start Asking These Questions On Your Sales Calls

Good Morning! In case you missed it, yesterday, Apple announced some shiny new AI features called ‘Apple Intelligence’. One of the new features will bump ‘priority’ emails to the top of the inbox. So, of course, it’s got us wondering… how can we bribe Siri to mark our cold emails as high priority? 😄 

In today’s Follow Up:

  • The power of probing questions ⚡️ 

  • Sales tip of the day 🧠 

  • Sales news around the web 🖥️ 

  • Sales jobs, job market & a meme 😂 

The Power of Probing Questions

As a sales rep, you already know that asking the right questions is the key to uncovering pain points and closing deals.

But asking the right questions can feel like a guessing game.

You don’t want to overstep, but you need to understand their current situation and motivate them to take action (aka, buy your product).

Enter, Probing questions.

These questions are intended to dig deep into the heart of what your prospect really needs.

So today, we're breaking down the 4 types of probing questions you should be using.

Let's dive in. 👇

1. Exploratory Probing Questions 🔍

These are open-ended questions that get the conversations started. They can be used at the beginning of the sales cycle and should help you understand your prospect’s current situation and pain points.


  • Can you tell me more about what you’re currently using?

  • Can you walk me through your current process from start to finish?

  • What other solutions or products have you tried so far?

2. Investigative Probing Questions 🕵️

As the title says, these questions let you do some investigative work. Use these probing questions to drill down into specifics about details they’ve already given you.


  • When did this first become a problem?

  • Can you walk me through the steps you've taken to address it?

  • What roadblocks have you encountered when trying to fix it?

3. Confirming Probing Questions

These allow you to confirm what your prospect has said, and pull out more information. In most cases, your confirming questions should make the prospect correct you, or provide additional context to the information they’ve already given.


  • If I'm hearing you correctly, the main issue is X. Is that right?

  • So, you said {insert their answer to a question}. Do I have that correct?

  • It sounds like your ideal solution would achieve X, Y and Z. Would you say that’s accurate, or did I miss something in there?

  • Is there anything that I overlooked? 

4. Leading Probing Questions 🎯

Leading questions are meant to manipulate gently steer the prospect toward your solution. Use leading questions to push the prospect to your solution, once you’re confident that your solution can solve their problems.


  • How important is this feature to you? (assuming your product has the feature)

  • If we took cost out of the situation, would this solution be your first choice?

  • What’s stopping you from implementing a solution like this one?

A few honorable mentions…

We love our sales questions, so we had to leave you with a few extras…

  • Do you think this issue is unique to your team or company?

  • Do you know how your competition is dealing with this?

  • Is this problem ultimately affecting your customers?

  • If you could wave a magic wand and create the perfect solution, what would that look like?

Do you have your go-to questions?

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Sales Tip of The Day 💡 

When setting a call agenda or next steps use the phrase: ‘Does it make sense to…’

  • Does it make sense to cover this part of our product today?

  • Does it make sense to get something on the calendar next week?

  • Does it make sense to get your boss on the next call?

Using this phrase gives your prospect ownership of the decision, and is likely to make them elaborate on any objections they have.

Sales Around The Web 🗞️ 

 💰️ Psychologist Adam Grant says that success at your job comes down to 3 words: work more hours. 

🗣️ David Sacks breaks down the importance of deal velocity in sales, and why all deals are not created equally.

📽️ Simon Squibb gives his 30 Years of Sales Knowledge in 28 Minutes.

👀 How enterprise sales reps spend their Mondays when they’re at the top of the leaderboard and have no meetings on the calendar.

Checking In On The Job Market

How many times can you ask a candidate how old they are? 😅 

Sales Meme of the Day

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