Whether you’re asking the classic discovery question of “What’s keeping you up at night?”, or the more updated Consultative Selling query of “How can we partner together on this?”, the questioning techniques used by salespeople are informed by the evolution of sales as an industry.

Challenger Selling understands the importance of investigation as well but shifts the focus onto different types of questions, ones that cut to the heart of the customer issue and lead to a true value-add conversation. These are the 4 types of powerful questions you’ll frequently see Challengers asking their prospective customers:

1. Mobilizer Identification 

In our latest publication, The Challenger Customer, we dive into customer buying profiles. We found that stakeholders generally fall into one of three categories:

  1. Mobilizers (customers more able to drive the purchase decision)
  2. Talkers (customers more apt to waste your time)
  3. Blockers (customers who prefer the status quo)

As a salesperson’s time is much better spent with a Mobilizer, it’s important to diagnose each stakeholder as quickly as possible and the easiest way to do so is to ask yourself two questions:

  1. Does this individual display healthy skepticism?
  2. Do they demonstrate interest in the greater good of the organization?

The first question helps to understand whether this individual is engaged and paying attention. Challenger selling revolves around educating customers with commercially insightful, often counter-intuitive information, and a customer pushing back with skeptical questions is a great indicator of a mobilizer.

The second question helps to determine whether this stakeholder is looking to genuinely help their company or bolster their own position within the organization. How a stakeholder responds to these questions will give you a better idea of what category they fall into, and allows you to adjust your plan accordingly.

2. Commercially Insightful Verifiers 

Challenger selling relies heavily on developing a Commercial Insight; an impactful customer message designed specifically for the stakeholder you’re meeting with. These messages are built on  problems, called reframes, which the stakeholder may or may not be aware of.

As the salesperson delivering the Commercial Insight, it’s important to verify that the insight is reflective of their reality throughout the pitch. However, it’s not useful to do this via closed questions, e.g. yes or no. Instead, you want to give the stakeholder the chance to confirm what their version of that reframe looks like.

Here’s an example from our Grainger case study below:

Grainger’s commercial insight was built for Operations Managers, based on a reframe that the average Operations Managers is spending more than they think on one-off, unplanned purchases. A Challenger seller delivering this message needs to verify that the Operations Manager they’re speaking with is feeling some version of this pain.

Rather than ask “Do you experience issues with the way you currently go about one-off purchases?”, which would give the stakeholder room to say “no”, you should tweak it a bit and ask “How do you currently deal with one-off purchases within the context of your annual budget?” Asking the question almost as an assumption encourages the customer to share their unique pain points, rather than shutting down the conversation with a simple “yes” or “no” answer.

3. Buying Journey Verifiers

 A different kind of verifier, the buying journey, helps sellers understand where in the process the customer is, rather than where they are as a salesperson.

Asking questions such as “What are you currently doing about this issue” or “What other internal stakeholders have you included to solve this problem” can give you an understanding of how far along in the buying process the customer is. This will help you better position your sales tactics to ensure a successful close.

4. Powerful Requests 

Powerful Requests are one of the Challenger seller’s most useful tools. Because we’re delivering impactful, tailored messages with our Commercial Insights, it’s important to understand how engaged our prospect or customer is.

Some stakeholders may talk a big game in the moment, or appear as though they’re ready to move forward, but afterwards can end up stalling or slipping through the cracks.

In order to avoid wasting their time, Challengers combat this dynamic by using Powerful Requests: asks of the customer that will indicate to the seller whether they’re serious about moving forward or not.

For example, a salesperson asking for internal data or figures to provide a more accurate estimate of the pain points caused by the status quo. An engaged, serious customer will either provide you with that info, or work with you to get what you need. These are highly useful in determining whether a prospect is ready to take the next step.

Start asking better questions

As we’ve seen, the types of questions that Challengers ask focus more on understanding the customer’s unique circumstance to better communicate the value in their language.

Challenger, Inc.

Challenger is the global leader in training, technology, and consulting to win today’s complex sale. Our sales transformation and training programs are supported by ongoing research and backed by our best-selling books, The Challenger Sale, The Challenger Customer, and The Effortless Experience.