Gather Your Courage and Ask a Transformational Question


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.