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4 Tips for Asking Better Probing Sales Questions

Ask anyone who’s ever been on the receiving end of a poorly executed, template-based cold outreach campaign: sales is simply better when it’s personalized.

The closer you can come to understand what your prospects want to gain from a new product, service, or vendor, the stronger you can make the case in favor of your solution. But although you can do endless research and form educated guesses based on past sales conversations, you won’t know exactly what prospects need to hear from you unless you ask. 

To do that, you’ve got to move past “yes or no” questions that shut down sales outreach prematurely in favor of an approach that’s based on the kinds of probing sales questions that keep the conversation going. Use the four tips below to form better probing questions and to use them properly in your next sales call:

Be Prepared 

You might be able to come up with good probing sales questions on the fly, mid-pitch. But you’ll see even better results if you come to the conversation prepared.

Do your background research. Before a call with a prospect, search for them on Google, look them up on LinkedIn, visit their social media profiles, or stop by their company’s website. Pay particular attention to any company news or updates you see. For instance, did they recently:

  • Announce a new acquisition?
  • Share a major loss?
  • Bring on new leadership?
  • Shake up the board?
  • Put out a new press release?

These and other noteworthy events can give you insight into what their needs or buying behavior may look like in the moment. But they can also give you an “in” to the conversation and position you as the provider who understands what their company is currently facing.

Once you’ve identified one or more anchoring events, make a list of probing sales questions you could ask and practice asking them before the call. As an example, if your research reveals that the company’s recently brought on a new COO, you can better single out current decision-makers by asking, “Who will need to approve the final purchase?” 

Others you could ask, based on the types of news and events described above, include:

  • “Will your company’s latest acquisition affect your budget or purchase timelines?”
  • “How do you expect [company’s major loss] to affect your department?”
  • “Does your new board member share your perspective on this upcoming purchase?”
  • “How do you see [a new industry trend] affecting your [company or department]?”

Get creative. The more you tune into the factors affecting your prospect’s company, the more opportunities you’ll discover to ask probing sales questions.

Practice Active Listening

In an article for Positive Psychology, Birgit Ohlin, MA, BBA, notes that “Listening is more than the passive act of receiving or hearing. It is the conscious processing of the auditory stimuli that have been perceived through hearing.”

When it comes down to it, most of us are pretty bad listeners. We drift off when others are speaking to us, or we focus more on what we’re going to say next than on what we’re hearing in the moment. Often, we’re so busy thinking of how we’ll respond that we miss the information being shared that shows us what the most appropriate response would be.   

That’s why identifying and delivering probing questions is only half the battle. If you aren’t actively listening to your prospect’s responses, you waste all the background work you did in the first place.

A few active listening practices to work on include:

  • Remaining mentally present when prospects are speaking to you
  • Focusing in on prospects’ body language, vocal variation, or other subtle communication cues, to the extent possible
  • Repeating their responses back to them in a paraphrased form to confirm your understanding
  • Asking further questions if there’s anything you need clarified

These practices may sound simple, but they’re often easier said than done. Put the effort into practicing them, because listening attentively will go a long way towards building your relationship and ensuring you have the information needed to pitch the appropriate product or service offerings.

Understand Your Prospect’s End Goal 

Most prospects aren’t going to spell out what their deepest pains are or what exactly achieving their goals would mean to their businesses on their own. It’s up to you to pull this information out of them using the probing questions that’ll help you refine your understanding of what prospects are trying to achieve with your solution.

In your discovery calls, start by asking, “What problem are you trying to solve?” If you need to dig deeper, follow up the question with something like, “How important is it for you to solve that problem?” or “What would you gain by solving that problem?”

A few other sample questions that may be helpful in this process include:

  • “What would happen to your company if you don’t solve that problem?”
  • “What have you tried already to solve that problem?”
  • “What obstacles have you previously encountered when trying to solve that problem?”
  • “Who in your company benefits most from solving that problem?”

Once you know what prospects are trying to accomplish or what challenges they’re facing, tailor your sales process to their overarching business goals by communicating how exactly your product or service will meet their specific needs.

Use Positive Words 

Finally, this should go without saying, but remember that the way you ask probing questions is just as important as asking them in the first place.

Sales calls aren’t fun for most people. Remember, you’re interrupting your prospects’ day with an unexpected – or unwanted – sales pitch. Communicating your respect for their time through positive words and an enthusiastic delivery makes a difference according to David Campbell from Right Inbox

Try to think of your call as opening up a conversation with your prospect, rather than simply asking questions and seeking answers. Focus on building a relationship – not just making a sale. Making your appreciation for your prospects’ time and the opportunity to connect clear will ensure this relationship starts off on the right foot.

Be Human When Using Probing Sales Questions

Ultimately, the goal of using probing sales questions isn’t to fire one after another at your prospects until you’ve uncovered all the information you need. It’s about creating a dialogue that helps you better personalize your pitch and establishes the foundation of a strong relationship.

Keep lists of probing sales questions in your back pocket, but deploy them sensitively and back them up with a positive tone and active listening. With time and practice, you’ll discover a balance to using them that allows you to build rapport while still moving the sale forward.

What are your favorite probing questions to ask in a sales conversation? Leave a note below sharing the questions that have worked best for you in the past ↓

Sujan Patel is a partner at Ramp Ventures & co-founder Mailshake . He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit and many other Fortune 500 caliber companies.

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