My father was a successful manufacturing executive who entered the computer industry back in it’s early days. He was also a well-known troubleshooter, sent to take over manufacturing plants in trouble, to set up new plants, and close down nonproductive ones. But I really began to appreciate his knowledge as I watched him in retirement as a consultant for the Small Business and Technology Center at the local university. 
His gift was his low-key, patient approach to less experienced business clients. And the real magic of his consulting was the deceptively simple question. After listening patiently to the client describe their business problem, he’d begin to ask seemingly simple questions about what, how, when, how much and how often. And through that process, you could see understanding begin to dawn on a client as they began to put the pieces together for the first time . . . to reveal a cohesive picture of their business reality.
When I do instructional design, I like to use a similar approach to getting participants out of the rut of their traditional mindset. The art is in crafting the question so that it doesn’t let the participant give the standard answer they’ve heard, or like to use, and it doesn’t scare them off as being too much to think about, or too hard to answer. Generally, that means asking them something about their view, their feelings, their experiences . . . all the things that people like to talk and think about . . . their life.
But if the question is phrased strategically, it will nudge them into a new perspective. Sometimes, the question truly is simple. An example: in a diversity class, I ask the obvious: “Have you ever judged someone on first meeting them? Be honest.” Most of us have, and regularly do make judgement calls within seconds of meeting someone. But it’s the second question (which may appear a little later in the training materials to offset the impact) that carries the real learning experience. “Has anyone ever judged you when they first met you? What did they notice? How did it feel?”
It’s direct, simple— and devastating. We’ve all been judged at some time, by someone for not dressing like others, for a bad hair day, for a lack of knowledge/experience, picking up the wrong fork at a fancy business lunch–or not knowing whether to open a door for someone or not, or being on the receiving end of even well meaning amusement at something we did. No matter how deep we try to hide the hurt, somewhere in our past is a memory of that one time you just didn’t fit in. It’s not to dredge up old wounds. It’s to force a self-reflection and open awareness. Only when we realize we can be judged on anything, meaningful or not, that we can begin to realize the power of our own choices.
But then there are the more direct, personal yet non-threatening questions that are so intriguing people can’t help but delve into them. Like one a friend and I had thought of simultaneously the other day: “If you suddenly were confronted by the very thing you wanted most in life . . . would you recognize it?” Simple, right? But impossible to leave alone because the second part of the question is haunting. It nags at you: what if I didn’t recognize it? What if I MISSED it!? Even the person who says “sure, a Porsche!” will either return to that question later, or will hear someone else say something that suggests the Porsche is just an icon for what someone really wants in life.
So when you are designing questions for discussion or self-reflection or small group interactions, create the ones that can’t be answered easily, that someone can’t glide past with the easy, pat answers. It’s not always about “how did you do this?” or “Have you ever done X, and what happened?” It’s about reaching for the heart . . .and helping people go deeper in understanding their motives, their goals, their hidden biases.
Then, of course, you’ll need to pay close attention to how this gets debriefed. These types of questions don’t need a debrief that forces them to share what is too personal, or to have a black and white answer to a business or life challenge. They are about shifting someone’s perspective far enough that they have opened the door just a crack to allow a new thought, a new approach, a new insight into their normally fixed thinking. The trainer should only validate their self-discovery and make clear how that new insight could be leveraged to produce something meaningful in their other thinking. But that’s a whole ‘nother blog post . . . !
Chanda K. Zimmerman 