Creative questioning – Why it works and how to do it

Creative questioning – Why it works and how to do it

“How are you today?” should chill your blood and make the hairs on the back of your neck stand up. It presages a low calibre salesperson trying to persuade you to buy something you don’t want. The correct answer is “Thank you but I have made other arrangements”. Move on. Your relationship with “How are you today?” is over. Why is it such a bad opening to a conversation? After all, you may be genuinely interested. Well, if you are, take the trouble to ask a question that is engaging. “How are you today?” is disengaging.

Thoughtless questions turn people off. They show that you want something from them, not that you are interested in them. We all know there is one fascinating subject in the world. It is “ME”. When we discuss ourselves we are happy, even if we are grumbling or complaining. Who we are, why we are, where we are going, are all subjects of legitimate and genuine concern to us. It sounds selfish and it is. But selfishness is a survival system that we employ in order to remain alive and viable. In excess it is bad. In moderation it is essential.

There are many reasons why we want to understand and engage with others. Selling is an obvious one. Good relationships are more than transactional, though. They stimulate our minds, help us to see beyond the little circle in which we live. They are the material of leadership and the basic blocks of friendship. Engagement allows us to prosper and enjoy life. We learn to see our neighbour as someone to work with. When we look in the mirror we see someone worth knowing. To be worthwhile, be worth knowing.

More than half the clients who come to us don’t engage well with others. They often have focus, maybe a clear KPI, even dedication. But they have no idea how to get the other person’s response to address their needs. If the answer to your question isn’t ‘yes’ you have failed. Simple, routine questions don’t work. Creative questions do.

I once coached a lady to handle a particularly difficult job interview. There was no job, she couldn’t have been hired for it even if there was, the interviewers didn’t like ladies, she was an academic – her interviewers didn’t like academics either. Any answer she gave would disqualify her. I taught her how to handle her interviewers by asking imaginative questions. She did so for two and a half hours. They said it was the best interview they had ever had. They created the job on the spot and she held it for the next twelve years.

What was creative about the questions she so successfully asked her interviewers?

First, they were based on excellent perception of the other person. Observation is the basis of engagement. Second, they included creating more about the other person than appeared on the surface. Invention is the way to someone’s imagination. Third, they were flexible about how they discovered what they needed to know. Engagement is about walking together not marching your partner along your chosen path. Fourth, they were curious and interested. True interest is how you show you care.

All communication today starts with a question. All successful engagement today employs creative questioning.

Learn to ask creatively if you want to have effective control.

Terrific Mentors International “Creative questioning wins” is an eight-session role-play programme that works for everyone. Ask about it at