The Free Do-Over

Guest Post by Bob Mac Leod

In the movie Groundhog DayPhil Conners relives the same day over and over again. This gives him the opportunity to practice the best lines for any given conversation. In my real life, my most excellent, compelling answers, and most powerful, dynamic questions usually come after I have left the conversation. Sometimes five minutes later, other times much later when I am replaying the conversation in my mind… or laying down to go to sleep. So many times I have wished for a second chance at a conversation!

Recently my email system gave me a second chance.

I am a financial guy both in my work and personality. A co-worker forwarded an article to me about the financial challenges the Social Security system faces in funding retirement costs. This is generally known information and not an earth-shattering revelation, but it was news to her. The article was fairly one-sided in its presentation. Not technically inaccurate, but not telling the whole picture and definitely designed to leave the reader with angst. Social Security is, after all, an extremely complex financial situation for our country and not easy to unpack in a short article.

She asked me, “Bob, I wanted you to read this article and tell me what you think about what they are saying about Social Security. I wondered if you know more from other sources like the Wall Street Journal.”

She’s a good friend and I wanted to allay her concerns, so I typed out a quick response to her.

That is, I expected it to be quick. Before I realized it, my response was longer than the original article and a whole hour of my evening had trickled away as I shared my depth of wisdom on the subject. As I saw my response I realized it was way too long and heavy. So I re-read it, took out a bunch of stuff, lightened the tone, and hit Send. Then I closed my computer and five minutes later I was in bed.

But I didn’t fall asleep right away. Once my mind relaxed and went to work, I realized I had bungled the entire opportunity!

First, I was only guessing at what she was actually asking me for. Her question was, “What do you think about this?” But I could not know whether she was alarmed at the contents, frustrated at the writer’s tone, agreeing or disagreeing with him, etc. As a result, I had then given an hour to a one-sided conversation I was not looking for, and that had an opportunity cost because I gave up other activities.

As I lay there, about to drift into sleep, I thought to myself that I could have invested just sixty seconds by asking her two simple questions:

  1. What is your concern upon reading this?
  2. What are looking for from me?

Asking those questions could help me discern the real reason behind her email, and help me then answer those questions… and likely much more quickly.

Although this conversation was not a heavy relationship make-it-or-break it conversation, and my email did not contain any angry or embarrassing content I would regret come daylight, I was frustrated with myself for how I handled it. Like so many times before, I wished for a second chance at that conversation.

The next day when I opened my computer to start my work day, I discovered the email still sitting in my Drafts folder! Apparently, I had closed the computer too soon after pressing the Send button, and it never completed the send!

I deleted the contents of the draft and replaced it with the two simple questions written above. In 60 seconds I had the new response on its way.

It goes without saying that years of reading Leading With Questions is beginning to sink in. (I just wish it would sink in five minutes sooner!) Instead of seeking to have all the answers, I’m seeking to have the right questions. This situation was a reminder that my first stop should be to ask questions. Simply stopping before answering can give me a pause, and—frankly—prevent me from actually answering the wrong question.

Bob Mac Leod


Bob Mac Leod has served with Cru since 1992, all of them in ministry finance. His first 14 years were in the US finance office, and last 15 in the international office where he is currently serving as the Financial Controller.  Bob and his wife Kathy have been married for 24 years and have two sons in college.


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