How to Ask Better Sales Questions

Questions can be the difference between closing or losing a big deal.

Good Morning and Happy National Password Day! Using an easy password is like walking around without a case on your iPhone. Seems great, until something bad happens. A group of researchers pulled a database of leaked passwords from the dark web and found the most commonly used passwords are ‘123456’, ‘admin’, and ‘12345678’. If you’re using one of those, it’s probably time to change it up. 🤷 

  • Ask these sales questions 🗣️ 

  • Sales tip of the day 💡 

  • Sales news around the internet 🗞️ 

  • Sales jobs, LinkedIn & a meme 😂 

The Sales Questions You Should Be Asking

Sales is all about discovery.

Not the TV channel, but the process of figuring out a prospect’s current situation and pain points.

When you boil down a good discovery call, it’s made up of two things:

Questions and answers.

It’s our job to ask the right questions and the best sellers know how to ask the right questions at the right time.

And sometimes, a few good questions can be the difference between losing or closing a big deal.

In a recent HBR article, 3 professors broke down the types of questions that successful CEO’s ask to uncover breakthroughs about their business and make decisions about their company strategy.

Although most of us aren’t making strategic decisions about our billion-dollar companies (yet), we noticed these same questions can be used to drive sales cycles.

Here they are. 👇️ 

1. Investigate: What We Know? 🔎 

This is where most of the discovery is done.

These are questions that uncover the basics like the current situation, pain points, and need for change.


  • What is the biggest issue you’re dealing with right now? 

  • What is the problem you are trying to solve?

  • What provoked you to take this call with me?

The biggest mistake most reps make is not going deep enough. When you think you’ve scratched the surface, go a level deeper.

2. Speculate: What If? 🤔 

This is the part where you get to challenge your prospect.

Dig deeper on what they’re telling you, and force them to look at their situation from a different lense.


  • What happens if you don’t fix this issue?

  • What if you just keep doing things the same way?

  • What would your day look like if you changed this?

3. Productive: What’s Next? ➡️ 

Once you’ve laid the groundwork, it’s time to keep the deal moving. Productive questions are your tool for driving commitment and next steps.


  • How soon do you want a solution in place?

  • How can I make this a no brainer for you?

  • What is stopping us from getting this done tomorrow?

Use these questions to hold your prospect accountable, and make a timeline for the deal.

4. Subjective: What’s Not Being Said? 🤫 

The final piece of the puzzle is understanding the emotional drivers.

This is the part where you need to figure out what your prospect really cares about (and it’s typically self serving).

These are questions you can ask both yourself and the prospect directly.


  • How can my product make the prospect look good to their boss? 

  • How can I make the prospect feel good about the purchase?

  • Why does my prospect specifically want to get this problem fixed? To make things better for their company or to make themselves look better? 

  • Will my product threaten my prospect’s job security? (looking at you AI 👀).

We sell to humans, and humans have emotions. With the right questions, you can use those emotions to your advantage.

What is your favorite type of question?

Login or Subscribe to participate in polls.

Sales Tip of The Day 💡 

Send a recap + action items email after every sales call or meeting.

Hi Prospect,

As a recap, we covered:
1. What your current process looks like.
2. How our tool works.
3. Expected timelines to implement a new solution.

Next steps and action items:
1. You will get back to me by Friday with a day/time for our next meeting.
2. I set a meeting with engineering on Tuesday to see if we can do XYZ.

This keeps a record of everything that was discussed and allows you to hold the prospect (and yourself) accountable to keep the deal moving.

Sales Around The Web 🗞️ 

Remote Sales Jobs 💼 

Checking In On LinkedIn

Yes, he’s being serious… 😅 

Sales Meme of the Day

What did you think of today's newsletter?

Login or Subscribe to participate in polls.