Selling to the C-suite: Asking Better Questions in Sales Calls

As I sat down to continue my series on selling to the C-suite, I challenged myself to identify a gap that both senior executives and new salespeople share.

Now, you might think I racked my brain for hours staring down a blank Word document. In reality, the answer is straightforward: Many people, from early-career salespeople to executives, don’t believe that strategic questioning is a skill that can be improved.

Part of the problem is undoubtedly formal training. The other half, I’ll put down to misunderstanding the true role of questions. Questions are more than tools forgathering information. Extraordinary questions have the power to build trust and rapport, uncover hidden pitfalls, spur innovation and create organization-wide value. What executive wouldn’t be interested in those benefits? With that in mind, let’s look at how salespeople can ask impactful questions in their executive sales calls.

C-suite Sales Call Prep: Identifying Areas of Impact

By this point, everyone should be using AI-based tools to make research and call prep more efficient—their ability to synthesize information is unparalleled.

There’s no need to spend 45 minutes listening to an earnings call or 30 minutes reading the transcript when AI can pull out highlights from the C-suite’s remarks and a summary of key business drivers and analyst questions in mere seconds. The only question is: Now what?

Now, it’s time for the human component—time to leverage your creativity and prediction skills. Look at the list of key business drivers and ask yourself: What’s getting in the way of those business drivers? and which areas can my solution uniquely impact? From there, imagine the component parts, workflows and tech behind those business drivers. Based on this exercise and any additional light shed by the analyst questions, you’ll be able to predict business issues that you can solve. The final step is to develop open-ended questions appropriate for the role and the situation.

How to Ask Respectful, Impactful Sales Questions

Let’s start with a hypothetical:


You’re an AE for a MarTech company that’s become a dominant player in ad automation. You typically sell to marketing VPs in companies where subscription-based revenue is top of mind.

TheTarget Company

Acme Computing is focused on new customer acquisition. Despite this focus for the past two quarters, its forecast for customer acquisition remains conservative—a point that came up during that last earnings call.

TheSales Questions

Open-ended Questions

As always, you’ll use the research you’ve done to get the prospect talking:

●     I understand that new customer acquisition is top of mind for Acme this year, how does this affect your role?

●     As I was listening to your latest earnings call, I was struck by the conservative forecast for new customer acquisition. Can you tell me more about this approach?


Here, you’ll dive deeper for more information and uncover problems worth solving—and ensure that a problem your company can uniquely solve is at the top of the list:

●     You mentioned building the demand-gen infrastructure to improve market penetration. Is the pace and scale of this project affecting your customer acquisition projections?

●     If you had a partner to provide proven ad infrastructure, would this speed up your time to launch?


Remember to always use these questions at natural junctions in the conversation to mirror the prospect’s language and build rapport.

●     From your perspective, it’s not the strategy or delivery workflows that are getting in the way, but the demand-gen infrastructureis that right?

As always, these are merely examples. The overarching insight I want you to take away is to always look for that pressing business driver and imagine how itmight impact your prospect and what business/personal value you can bring to the table.

C-suite Sales Call Practice

The classic conundrum: sales leaders want to maximize selling time and believe salespeople don’t get enough practice. All too often, these two realities create an environment where sellers practice on real-world prospects. I’m sure you’ve seen the aftermath of that!

           To build confidence in the right selling behaviors, it takes practice. Yes, you should always prepare for executive-level sales calls by formulating a list of open-ended and probing questions based on your research. You should also find opportunities to role-play the scenario. Thankfully, AI-powered tech can act as your teammate. This will enable you to role-play sales calls informed by your sales process, ICPs, products and competitors—and even get as granular as simulating individual prospects based on their LinkedIn profile. If you’re not using similar tech, you can always work with your manager to role-play calls based on your target personas—then internalize their feedback by running through the critical points on your own time and refining your questions further.


Remember, revenue-tech will be your teammate—helping you to increase efficiency, build confidence and open the door to more creative tactics. Then, you’ll use proven techniques to forge human-to-human connections. After all, can you imagine a machine seller asking an anxiety question to a no-nonsense CRO and getting a good response? Of course, not. Questions like that only work after you’ve used the process above to demonstrate sincere curiosity and build trust. In the end, it all comes down to building the selling behaviors that build buyer confidence.


For more selling advice, check out:

● My latest in Selling PowerMagazine: “How AI Modernizes Sales Coaching for Managers.”

 “Empower Sales Team with a Strategic Enablement Function,” in Highspot.

● An exclusive preview of my latest book, The Power of Value Selling: The GoldStandard to Drive Revenue and Create Customers for Life.

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