Gather Your Courage and Ask a Transformational Question

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Note:  This was originally published in June, 2015

10 of my law school classmates made it to sandy, sunny Lake Michigan for a weekend gathering, truncated into 36 hours, due to widespread workaholism and our cross-country flights. As if the decompression time wasn’t short enough, I ate into it by foisting a “group exercise” on my acquiescent friends.

In three short paragraphs I propose three lessons from that experience together.

First, win the inner battle to ask a fruitful question. It wasn’t easy for me to do so. I was fighting a part of me that said, “Do NOT make yourself the center of attention, and ‘bother’ your friends in this way.” But, I had some basis for my intervention. I am one of 7 siblings, and I have spent many a Christmas, Thanksgiving, or a 2-day getaway with them, answering the same questions 6 times over, and in turn getting a thimbleful of information as I asked about each of their lives. I have experienced the same thing at firm gatherings, executive team meetings and retreats, where I could have gotten more information and connection from exchanging emails. And, if I’ve learned anything from my work it’s this: A good question, shared among a group can lead to deep information sharing and much stronger relationships. Especially as peers or “underlings,” we naturally shy away from taking charge of a group – asking a big question — and instead we allow it to be catch-as-catch-can. And we predictably catch very little. So, summon your courage. Ask the question that gets to the heart of the matter — whether that’s business, life, or business-life).

Second, it behooves us to spend more time on the questions we ask of our key people, than all the answers that we have for, rehearse and share with them. Most great leaders are great speakers. All great leaders are great listeners. Thus, among our weekend friends were world-class criminal prosecutors, career public defenders, a cabinet secretary, and that former governor friend of mine. They get paid to speak and speak well, but what struck me most was how each one of them listens. Listens and learns. Listens and deepens trust. I could see they were doing that thirty years ago when I first met them.  And they were now, as I asked this simple question:  “Would you share two things that have given you joy in the last five years?” (If you were to do this, you could instead ask about pride, concerns, hopes, etc., but without getting into a long digression on positive leadership, I’d recommend a question like “What’s giving you joy…or gratitude or appreciation?”)

The third lesson comes from one friend’s answer to my question about joy. (He’s probably the most accomplished and over-taxed of our motley crew. He had gone to irrational extremes to spend 15 hours with us. Next week he is going to even greater lengths to make his 40th year grade school reunion (a poignant time of friendship, for his father had died during that time). He said to us, “We act like what matters is the transactional stuff we do every day at work and even at home; we say, ‘I’ll do this; will you do that? I’ll charge you this for doing that for you; I don’t have an hour, but I’ll give you 15 minutes.’” Fighting back tears, he talked about how life gains value when you will drop anything and everything to be there for someone who is part of you, or someone who needs you – family, friend, or total stranger. Such moments, as we experienced at that picnic table at the beach, are not transactional but transformational. Seldom does joy emanate from transactions. Instead, it comes from simple questions, honestly offered, answered authentically, and heard with an open heart and open mind. In a business setting, this is where trust, mission, and inspiration are born — in simple questions, authentic answers, and powerful listening.

Gather your courage, formulate the truly important questions, and listen attentively to the replies, as you

Lead with your best self.

7 responses to “Gather Your Courage and Ask a Transformational Question

  1. As one of the others sitting around that table Saturday night, I could not agree more with each of Dan’s points. We had all spent time during the previous 24 hours catching up — one-to-one, in small groups, etc. — but Dan’s willingness to create a forum for each to answer the same very simple question was unbelievably rewarding. We all were focused on the same question — listening intently, mentally scrambling to be ready for our turn, exchanging our reactions in a heartfelt manner, learning so much from people we deeply care about, and growing as a result.

    Transformational is the right word, especially when it comes to the third lesson in Dan’s email. The point was simple, yet easily overlooked. The people who really mean the most to us in life — whether family, friends, co-workers, you name it — are those who do not view the relationship as a series of transactions. It’s easy to fall into the trap of “I will do this for you because you will do something in return (now, soon, some day).” It’s quite another thing to have a person in your life (let alone 9 or more such persons) who says the right thing or does the right thing, yet you know they say or do it without even the implicit understanding that you are required or even expected to reciprocate.

    May everyone have the kind of experience that Dan made possible, and the kinds of friends that the ten of us have been blessed with!

  2. In reading this week’s post, I am sure it was better that you did not become a Catholic priest. While Jesus was a teacher, and one could easily argue that was his core skill, he was many other things, and so priests have many other duties. Here we see you as the Socratic teacher, which is a spot you appear made for. Even at a social gathering you are doing the Socratic thing.

  3. Just wanted to say how much I enjoyed this article – it really hits home on many levels (and I’m glad you came back to Michigan to enjoy that beautiful lake view, too!). Appreciate the tips – especially this week’s. Thanks – and keep up the great work, leading with YOUR best self!

  4. I’m on vacation in California but took a minute to read this week’s entry. How moving. How inspiring. How i hope/plan to do this!

  5. I have hopes of putting my creations (inventions) on the market. Being a victim of repeated abuse, I decided to use my pain, along with my love of art and my creativity talent and create a new item. I think it is great. Which I now also have diagrams for two other items completed. I am hoping to put them on the market to sell and to make life better for 7 or 8 young people; Inc my son, and my 6 nephews/nieces. To me that is joy. You teach business, Dan, and is very Intelleigent, maybe you know something about patents? Or putting something on the market even w/o a patent? I have contacted a couple and they have contacted me back but I’m not a business person to know really what I’m doing. I would love to hear your thoughts, Dan.

  6. Very helpful as I sit in my office doing my job knowing one of my best friends is getting news whether her cancer is back for the third time. I told her on the phone today that I should have been with her when she went to the doctor. She is single and dealing with this alone today. She is so anxious she told me she was shaking. So, I am leaving the office to be with her if it is bad news, and I almost think I should leave if it is good news and celebrate with her!! Your message made me come to this conclusion.

    Love your writing, Dan!

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