What’s your favorite question? Do you have a ‘go to’ list of 2-3 questions for various scenarios?

I’ve been thinking a bunch about asking questions lately. Questions that get to the heart of a matter.

After all, it’s business review season, assessment season, budget season—what I call ‘question season’ for senior leadership.

My thoughts around asking questions are compounded by my son, who is 7. He is consistently asking questions. Great questions.

And it’s easy to get in the habit of just answering them. A lazy habit really for a parent. A lazy habit for a senior company leader too.

The harder thing to do, but better for growth, is to turn the question into a “what do you think” question back. Listening, and where needed, asking follow-up and clarifying questions.

I had the pleasure of working with a brilliant consultant, Dr. Roger Hendrix, several years back. He started nearly every seminar the same way.

He would choose someone in the group, call them by name, and say, “Ask me a question?”

Not only was this an awesome icebreaker and way to get the team’s creative juices flowing, but it always seemed to set a productive tone for the off-site meeting ahead.

He allowed it to play out until one of us asked something relevant to the reason for our time together.

Opening up with such a simple query always seemed to drive home an interesting point about the importance of asking questions in business.

Similarly, my friend, media leader (and now winemaker) Jim Moroney, believed in and practiced the Socratic method of learning. He did it overtly with great success.

Another mentor of mine, Kathy Clements, also practiced it. The difference … it wasn’t a formal method of learning to her, rather a natural state … to ask questions.

Both made their direct reports, and the companies they led, better by asking thoughtful questions.

Asking questions is an empowering experience. It allows the questioner more control over conversation flow. And can even help a conversation going south get back on track.

Rather than telling someone something, try asking a question. It is among the most provocative forms of communication available, especially in business.

With two caveats:

Don’t forget to ask yourself tough questions.

And the most important component in asking questions … listening for the answer.

P.S. My favorites? “Can you tell me more?” “What is the upside, what is the downside?”


At JDA, we’re having fruitful conversations with senior media leaders across the country around driving revenue, sales leadership and marketing best practices. If I can be a sounding board for you or your company, please reach out to Angela@jimdoyle.com

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