We’ve already told you about the value of asking smart questions during the discovery phase of an enterprise sale (more than once, in fact). And with good reason—you need to listen more than you talk, and you’ve got to dig into a prospect’s pain points, priorities, and long-term plans if you’re going to navigate your way to closed-won. But can you ask too many questions?

According to new data from conversation intelligence (yes that’s a thing) firm Gong.io, the answer is “absolutely.”

Know your audience

Last year, Gong released a study of over 500,000 recorded discovery calls and concluded that the most successful sales calls were those in which the seller asked between 11-14 questions. Seems like a lot to us, but hey, they did the math. But this week, Gong published data gleaned from “39,105 deals made on web conferencing platforms” and concluded that after four questions, a seller’s chance of a successful close began to plummet rapidly.

So what gives? Bad math? Squishy data? Did decision-makers suddenly get a lot more impatient over last year?

As it turns out, the answer is “none of the above.” In fact, the key difference in these two studies was whether or not the person fielding the questions was a senior stakeholder or a more junior staffer. That’s because senior execs have, as Gong puts it, “discovery fatigue.” They’re continually taking sales meetings and having seller after seller asking the same basic questions is wearisome, especially when they’ve got a million other things on their plates.

Gong’s findings should make it clear that you’ve got to know the key things we mentioned above before meeting with a senior stakeholder. But we’d take that a step farther and suggest that you need to know that stuff before you meet with any stakeholder.

Here’s why.

Proper planning prevents poor performance

Folks who ride motorcycles have a saying: “Dress for the slide, not the ride.” That means you wear long pants, a jacket (ideally leather), and a helmet when riding in any weather. It might not always be convenient or even comfortable, but in the event that you find yourself skidding face-first down 30 yards of asphalt, you’re going to be glad you took the time to prep properly. The same is true when it comes to prepping for a sales call.

There are two reasons for this. First, even if you’re not conducting your discovery call with a decision-maker, knowing key information ahead of time will not only help you prepare a more customized, effective pitch, it’ll impress the heck out of whoever’s on the other end of the call. Second, you never know when your point of contact might call an audible and invite a senior stakeholder to the call without alerting you. Trust us—it happens.

So use your sales intelligence tools wisely and well ahead of time. Leverage insider info whenever and wherever you can. Start the sales process with an informed perspective, and you’ll be in better shape to get to a close easier, faster, and with a lot less frustration.

And whatever you do, don’t call on an SVP or C-suite decision-maker with bush-league questions like “What’s your tech stack?” or “Who are your primary competitors?” They’re going to laugh you out of the room—and you won’t get a second shot at their business.

Executive Insights

Questions are key, but you can ask too many questions during discovery, especially when senior leadership’s involved. By leveraging sales intelligence solutions and insider insights, you can arrive to the discovery call prepared for any eventuality and armed with a customized deck that’s sure to impress. Otherwise, the sale will remain firmly out of reach. Forever.