An Answer to a Question that Changed My Entire Career Maybe Yours Too

Jim’s Wisdom #18

February 4, 2021

Perhaps the most powerful tool the trusted strategic advisor creates, uses, and shares with those they advise is insight; special knowledge gained from good and bad experiences, successes and failures, hitting the target, missing the target, and successfully dodging ricochets.
One of the more frequent questions I’ve been asked over the years is, “Just how do you get insight?” Many years ago I was working for a relatively young, first-time, accidental CEO. I say accidental because he got the job being in a room with the previous CEO, who had bungled everything and been fired. Had my client gone to lunch that day, his life would have been entirely different. Instead, he wound up meeting me. His life was so chaotic that he only had time to visit with me after 5:30 PM on Wednesday afternoons.

In so many ways he was far more capable than I. The main difference between us being that I had many times helped others go through what he was going through for the first time. After a number of Wednesdays, I finally asked him why 5:30 PM on Wednesdays was a magical time.

The Answer to My Question Changed the Direction of My Entire Career

He said that Wednesday afternoons were spent by himself thinking about the people he worked for, the people that work for him, what he was doing, what he needed to do and what he had accomplished in the previous week. He had a series of checklists for each of these questions which he shared. Those checklists were the subject matter for our weekly meetings.

From those meetings and conversations, I developed a series of questions for myself to help me pay closer attention. If you work for me, you have a notebook on my desk with those five questions, and you have to answer at least one of them every day, Monday through Friday. They’re on my desk because they form the basis for conversations I can have with employees that are only possible by having this extraordinary question and answer list.

As it turns out, the five questions that evolved formed the basis for how I can focus and learn in-depth quickly. More importantly, when you do this in real time, it turns out that you are ahead of everybody all the time on things that matter. These are the five questions I ask myself routinely as I live the experiences of my life and the lives of others.

5 Crucial Questions that Lead to Insight:

The personal awareness raised by these simple, powerful, helpful, constructive, important, personal questions are the sources of insight; the ability to take a given set of facts or knowledge or experience and extract remarkable, new, often surprising information.

The Real Work of a Trusted Strategic Advisor

This type of thinking is the work of the trusted strategic advisor used for the benefit of others, often and surprisingly more from their own perspective, than mine or yours.

Offering insights about someone else’s situation, problems, or issues can be a risky business. That risk goes with the territory. It also reminds me of my favorite Winston Churchill quote: when asked why he seemed to like war so much, Churchill responded quickly and with his classic enthusiasm, having spent much of his life in wars and stopping, preventing, and mediating wars, “The thing that is most exhilarating about war is being shot at . . . and missed.”

Welcome to the line of fire.

Successfully Injecting Decency into Business Culture and Life

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