In the last instalment of The Wire, I shared a personal story about how a single probing question married with careful, deep listening provided key insight to save an important client relationship.  In this edition, I’d like to pivot off that story to consider three key elements to good probing questions.

1. Good Probing Questions Gather Deep Information

The first key to mastering the art of asking good probing questions is revealed in the name itself. We should not seek to merely ask questions. The goal is to ask “probing” questions. When we look to the dictionary, we see that “probing” implies digging into something to explore the breadth of what might be present. Applying this concept to executive-level questions, the goal is not to simply ask questions and most certainly not to ask what is obvious. The purpose of probing questions is to probe – to uncover things that are deep, things that are not easily evident on the surface.

In my training programmes, I talk about a concept I like to call “the leak.” The leak is all that information that comes out in communication which is not expressly stated, perhaps revealing itself through subtle micro-communication of body language, nuance of tone, etc. Putting these two concepts together, an effective probing question essentially provides us more information than only the response to the question. It’s framed in a way that the other party “leaks” something. In the story I shared about the “One Second,” the complexity of the question caused my client to pause. The pause “leaked” critical information.

As such, a good probing question puts you in a position to collect information on multiple levels. There’s the surface-level, black and white answer to the question itself – the “what” of the other party’s response. But there’s also the deep-level information that “leaks” out through their body language, tone, changes in rate of speech, changes in volume, pauses, etc. as they respond – the “how” of the other party’s response. Both sets of data are important.

2. Good Probing Questions Demonstrate Our Competence

Most of the time, when we’re in an executive-level meeting, there’s a good deal of pressure on us to demonstrate our competence. It is easy, under this pressure, to make the foolhardy conclusion that it’s necessary to occupy the air-time to prove our worth. The drawback with that approach is that every minute we spend talking is one minute lost listening. And, by now, we all know that at executive levels, it is the listening which is far more valuable than the talking.

Have you ever seen someone ask a question so brilliant that the question-asker’s competence was no longer in doubt? There is a place for talking. But there’s also a place for listening. A good probing question digs deep and demonstrates competence at the same time.

3. Good Probing Questions Demonstrate Our Class

While not the most important piece of the puzzle, there’s nothing like an articulately framed sentence to subtly convey pedigree. We’re not necessarily talking about indiscriminately or awkwardly flinging uncommon vocabulary. But when our thoughts are articulated and well-framed with precision, we are usually appreciated by our audience.

Putting these three keys together might seem simple on the surface, but we must not forget that in practice we often have to do all three in real-time. Executive audiences are typically highly intelligent which essentially means they have accelerated brain speed. To be able to ask a question, we essentially have to be ahead of them in the conversation, not behind. So, in the real world, asking high-level probing questions means we have to be able to execute all three of these critical factors in what can sometimes feel like an intellectual sprint.

How do you fare in the skill of asking probing questions?

Out of the three factors, in which are you strongest? average? weakest?

What meetings do you have coming up in the near term that you can use to practice?

Trying to work on all three elements at the same time might seem daunting. Could you focus only on developing yourself in one of them first and thereafter progressively move on to the others?