The Art of Questions

Whether we are mentoring, coaching, or facilitating a small group discussion, we use questions to draw the BEST out of people. Questions come in many shapes and sizes, each designed for a particular outcome and used with a specific agenda.

There are some people who seem to ask just the right questions. If you haven’t yet met that kind of person, then perhaps you can become that person. In truth, this effect is a combination of listening skills and an toolbox of strategic questions. We’ll get to the listening skills in a later post, but for now, here are three three types of strategic questions that we can use in both individual and group settings to draw the best out of people.

1. Must-Select Questions

Must-select questions are very powerful, particularly at the beginning of a conversation, or with a person who is being guarded, as it forces a person to both think and respond, while presenting itself under the guise of simplicity. An example might be:

•  “On a scale of one to ten, how courageous do you think you are?”

Must-select questions like this are neither classically ‘open’ nor ‘closed’ (see below), but rather provide options within boundaries, priming the person for a follow-up question based on the information they have already given you.

This can either occur:

• Straight after an individual response, where follow-up questions could be “Was there a particular memory that triggered that number?” or “So you said 4, what do you think would take that to a 5 or 6?”
• Or if in a group setting, after all group members have responded, “I noticed that several of you chose 8, what do you think has made you so courageous?”

You can use a combination of both, but it is important to memorise people’s responses.

Note: In a group setting, must-select questions are best prepared by saying, “We are all going to respond to this question. But before anyone shares, we’re going to take a moment to settle on our number in advance, because this isn’t about what others say, this is just a gut-instinct response from you.”

2. Open Questions

Open questions are probably the most widely used form of strategic question whether in an individual or group setting, and while some people instinctively ask them (particularly if this has been modeled to them) others need to strategically shift their style from closed questions in order to draw the best out of people.

Put simply, in contrast to a closed question, an open question is any question that cannot be adequately answered using a single word. There are infinite possibilities, but an example might be:

•  “Why do you think some people are more courageous than others?” or
• “What is an example from your own life where you demonstrated courage?”

“Why?” and “What?” questions most often present as open, and even if someone tries to respond with a single word response, a gentle, interested prompt of “Tell me more” will usually open them up. It takes a certain level of courage to ask open questions simply because the person asking the question cannot fully anticipate what the response may be, which is why listening skills are so critical.

3. Follow-Up Questions

The third type of strategic question is the hardest to master, but the most important to practice. The reason follow-up questions are difficult is because they require you to simultaneously listen, while also thinking more broadly about where a conversation may be heading.

Where an open or must-select question can stand alone, a follow-up question is utilised to draw more out, needing to be crafted in the moment, in response to what has previously been shared.

It’s important to recognise that we don’t ask these questions because we are gluttons for information, but rather to help the person or group get greater clarity around an idea or situation. Follow-up questions are what give a conversation depth, a denial of superficiality that helps draw the best out of people, leading them to see things they never knew they had within them. Some examples might be:

• “Have you experienced this before?”
• “How did that make you feel?”
• “Did you recognise God in that?” or simply,
• “Why?” 

Replacing “this” or “that” with specifics of what was shared shape these questions for even greater impact. Follow-up questions can take both open and closed forms, because the power doesn’t lie in the potential of the question itself, but rather in the fact that you have listened and understood what has already been shared.

One more thing. (Don’t miss this.)

Before, during and after a conversation, always test your heart. Be wary of pride. Sometimes being equipped with tools and knowing how to wield them can develop in you a false superiority. Remember, it is all for them, drawing the BEST out of a person, to build THEM up; never for strengthening your own position or the need to affirm your own value.

Sometimes you will see something, a connection, an insight, before they do. Hold it loosely and consider it a gift. In humility allow it to shape your questions, but always be a learner and a listener, in this way you will truly lead.