I just wrapped up a roundtable discussion hosted by CIO Mastermind. Members of our groups participated, as did several other technology leaders from around the country. 

At the end, one of the guests asked me, “That was an outstanding discussion. Is that how your groups often look?” 

I said, “Yes. We have sharp leaders, and sharp leaders ask sharp questions.” 

Have you ever been in a meeting that went off the rails because someone asked a question that sent the discussion in a different direction? Have you ever walked away from a conversation and wish you had been clearer in what you were wanting?

The Questions You Ask Determine The Influence You Have

I meet too many leaders who believe that they are good at asking questions. They are not.

Here are questions I have heard leaders ask:

• Questions that mask their own agenda. They are driven by self-interest.
• Questions that manipulate. They elicit answers that merely set up the answer the questioner wants to give.
• Questions that are off-topic
• Two or more questions asked at the same time
• Vague questions that get the hideous, avoid-at-all-cost response, “What are you really asking me?” or “I don’t know what you are asking.”
• Questions that come with a set-up or explanation

We are all guilty of the poorly asked question. We are also guilty of underestimating how damaging it is to our leadership.

Training Beats Trying

You have heard me say this repeatedly: If something is important, it’s not enough to try. You must train for it.

There are five exercises that will sharpen your ability to ask questions.

First, listen longer than is comfortable for you. I have a tendency to jump in too quickly. To listen longer doesn’t mean that you lose control of a conversation or permit rambling; it does mean that you discipline yourself to speak at the right time, not before time. 

Second, ask follow-up questions. (Please do this in your personal relationships. The sense that you really care is worth the effort to train for this). The best question is the next best question. People have more to say. They don’t necessarily believe that you want to hear more.

Third, ask deeper questions. There are four types of questions, from shallowest to deepest:

• Closed questions. These are questions that elicit a yes or no answer or facts. They aren’t bad; they are just best when used rarely.
• Open ended questions. These are questions that cause a person to reflect. They will often respond with, “That’s a good question.” Round the bases when you hear that, because you just hit it out of the park with that question.
• Expansive questions. These are questions that expand a person’s perspective, and take context into account. “How would your CEO respond to this?” “What is your team going to feel?” 
• Personal questions. These are questions that connect the inner person to the mental exercise you have been putting them through. They are feeling questions, but they are more than that. They are questions that engage the person’s self. “What excites you about this?” “What is your fear?”

Fourth, ask short questions. Seven to eight words max. This takes practice. You will find that the shorter the question the greater the impact. The longest question in my samples above were seven words.

Fifth, start your questions with the word How as often as possible. 

All five exercises are measurable. Don’t try it. Train. 

Habits of the Hearer

Get into the habit of asking questions that will increase your influence:

• Questions that are focused on the need of the person you are speaking with.
• Questions that are driven by discovery. Help a person expand their thinking and broaden their options.
• Questions that result in discernment. Help a person clarify their thinking and narrow their choices.
• Questions that create movement. Help a person identify a goal, a plan and/or a first step.

My life, career and influence changed for the better when I learned the art of the question. I discovered that the smartest person in the room wasn’t the one who poured out the most but  the one who drew out the most. 

People want to know what you think. They might even remember what you said. But they will never forget that you were the one who showed them how to think. 

I have taught leaders how to speak. I have taught leaders how to ask questions. Without doubt, asking questions was the harder of the two for leaders to master.

But you can do it. And I can help you do it

Sharp leaders ask sharp questions. The rest comes easily.