4 Ways to Ask Indisputably Better Probing Questions in Sales

In my first article of this series, I spoke about how to structure your discovery meetings. In part two, we took a nosedive into what a successful meeting opening looks like with ILPA (Introduction, Last Time We Spoke, Purpose, Agenda. It’s now time to talk about probing questions in sales.

As we remember from ILPA, we have already set the expectation that you will have questions for the prospect. This is to make sure what you about your product/services will be applicable for them. You have also gained permission and agreement from your prospect that they are open to answering your questions because it will benefit them.

It always amazes me how sales reps know to “ask” questions but they typically have no direction or pre determined/thought out plan on how to ask these questions.

On a first call, regardless of what you’re selling, the questioning should always start the same. I like to start broad and then narrow down. I often see reps making the huge mistake of only asking leading questions that are not open-ended.

Steer Clear of “OR”

We want people to describe their goals and pains not just answer yes/no or provide one-word answers. To do that, we need to understand the curse of the word “or.”

Which question will you get a better and more informative answer from?

What are some of the biggest challenges your department has getting projects out the door?


Is the biggest challenge for your department getting projects out the door the of collaboration or project management?

The first question is likely to give you a descriptive answer with lots of powerful data points. The second question will probably only give you a one-word answer with not much else. The language you use is incredibly powerful for uncovering important information.

Furthermore, this is the opportunity to build a good rapport with your prospects and show them how you might be able to “help” them (again not sell them).

Always (ALWAYS) Start with Your Prospect’s Role

By having a thoughtful and deliberate line of questioning, you have the guidance and outline to ask probing questions or dig in without losing your way.

Your line of questioning should always start with the following:

1) Tell me about your role. I have your title and I peeked at your Linkedin profile. That’s not always indicative of everything you are responsible for!

2) Tell me a little about your team. How it is structured and where do you sit in the organization?

3) I purposefully ask this question broadly—what are you trying to accomplish as a team this year? What are the major initiatives that folks are working towards?

4) How is your team measured?

5) Are you going to hit those goals?

6) What happens if you do/don’t?

7) What top challenges do you face?

Asking someone to describe his or her role is hugely important in a sales process. It can give you insight into what they personally care about (the #1 reason why someone buys). It can also give you insight into additional responsibilities that you did not realize they had.

All of that data can be used to craft a compelling sales pitch that pulls on their personal heart strings.

Go Beyond LinkedIn to Research About Your Prospect/Their Team

Same goes for getting a better sense of their team and how it is structured. Every business is different and has quirks that cannot always be deciphered by just doing research using public information like Linkedin.

Getting of a sense of who is who in the zoo will give you a better idea of the biggest beneficiaries of your solution and who the ultimate decision maker or committee might be.

Understand Your Prospect’s End Goal

Asking what the team is trying to accomplish is your first step to tying your solution to the overarching business goals.

People buy products and services for personal reasons, but they always have to back up the purchase decision with how this will ultimately impact the business. If you can get initial insight into what those big goals are, you can use those as ammunition on why your solution is so critical. This is essential to overcoming potential objections.

We have all heard prospect use the excuse “We don’t have budget” or “Not good timing.” When you have taken the time to understand their business goals, you have ammunition to challenge and push back.

Try something like this:

“Mr. Prospect, if you are open to be challenged a bit here. You mentioned that you are trying to grow your top funnel leads by 50% this year. But, your current resources are spending 25% of their time just trying to report on goals. I have showed you how our software can enable your team to re-allocate that 25% back to executing projects so that you can ensure you hit your 50% lead gen goal. I would think this is perfect timing given that there are only 6 months left in the year and you’re only at 10% growth.”

Use This Data to Challenge Your Customer

Your line of questioning and starting broad provide massive advantages to connecting your products and services to business and personal needs. There are nuances to the additional questions that you ask based on what you’re selling.

Ensuring you always start with the above fundamental questions will give you ample information to make your sales pitch compelling and galvanize your prospect to take action NOW.

You might also like More from author

Leave A Reply

Your email address will not be published.