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The Role of Questioning in Sales Coaching

It happens everywhere – great sales reps rise up the ranks and end up in a management position. Then, for some reason, this sales rockstar that was booking meetings, crushing quota, and having people throw money at them, has a team that can barely attain 70% of their quota.

There are two scary parts to this.

First, it happens more often then we’d like to think.  Second, the skills that made this individual a sales rockstar are the exact same skills that should make them a phenomenal coach, but this is not always the case.

Let’s break this down; what is one action that really great salespeople do?

They ask the hard questions.

This allows them to uncover and peel back the layers of the onion to reach the true pain. This should not be much of a shock to anyone who has spent more than five minutes in sales. One of the first lessons I was taught in sales is if you don’t know what to say, ask a question, and if you can ask a question, make sure it is cutting.

The Value of Questioning

The real value of asking a question is twofold.

As mentioned above, one of the values in asking great questions is that you can peel back the layers and find the root of the issue. The second is far more sinister; it gets the prospect to challenge themselves as to what is at the core of their issue. Further, giving the prospect some space, a good rep can get their prospect to answer their own question.

I would argue one of the most valuable tools in a rep’s arsenal is the ability to get a prospect to answer their own question with your solution. Why? When a prospect answers their own question, your chance of winning has jumped up significantly.

How Does Good Questioning Relate to Coaching?

So this rep who knows how to ask great questions gets their prospects to realize their solution is the cat’s meow, starts managing their team of reps and they fail. Why? They immediately stop doing what they’ve been doing for the last one, five, ten, or even fifteen years; they stop asking questions.

In my role in implementing sales enablement devices, I get to sit in a lot of sales meetings — a lot of them. Time after time I have seen sales leaders wait with bated breath to hear a problem then immediately jump in and tell their reps some old war stories about what they did in (hopefully) a similar situation, how they harpooned the whale, became savior of the world, got keys to the city, yata yata yata.

Shortly after the sales leader starts, all the reps eyes glaze over and even if there was some ambergris in there, it was buried in the blubber.

In this case, the sales leader was dialed into the wrong WII-FM* station. They need to be dialed into their rep’s WII-FM station, not theirs.

How do you dial into the rep’s WII-FM? Easy, ask a hard question.

Similar to the times when that sales rockstar was on the front lines cashing checks and firing the money gun, that former sales rockstar needs to ask their rep some profound questions.


Sales rep: “Hey boss, a prospect said our product was just a nice to have. How do I get around that?”

Sales Leader: “Why do you think that they feel it is a nice to have and not a must-have?”

At that point, the rep should be doing all the talking. Unless the sales leader was on the call or listened to the recording, anything they would be adding is speculative at best.

The sales leader should only be asking a ton of “why’s” and pushing the rep to answer their own question of where they could have dug deeper into the issues and got the prospect from “nice to have” to “must have.”

Wrapping it Up

While asking questions of your reps on how they did seems like a straightforward tactic, it is incredibly difficult to employ.

Most leaders want their teams to succeed; however, feeding reps the right answers is never a winning strategy. Like copying the answers from your neighbor in grade school, you might pass the test, but you will never gain the knowledge.

Only when reps are taught how to dig into a prospect’s issue and become self-aware of the implications of their hard questions will they be effective. If getting a rep to this point is similar to getting a prospect to understand their problems and seeing your solution as beneficial, then isn’t coaching sales reps the same as selling?

*WII-FM: What’s in it for me

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