Lead Like You're Retired (Part 3.5: Life in Questioning Mode)

Hi there! Sorry I’m a little late. My goal is to post every other month, but life got in the way this time (actually, I should say that death got in the way, which we’ll get to later).

In Part 3, we talked about how important it is to ask questions. At the end of that post, I promised that I would spend some time practicing what I preached. And I found a few moments of life’s magnificence as I spent more time in Questioning Mode.

I made use of James Ryan’s essential questions from his book Wait, What? I can’t count how many times his “I wonder…” kept me from interrupting the flow of conversation with an intrusive suggestion for what my conversational counterpart should do. I did this so automatically and so often, that it led me to reflect on why I did that.

Without fail, “I wonder” helped me refocus on the person I’m talking to and avoid my need to feel smart, helpful, and valuable. In other words, it helped me put the focus on the other person instead of me. If you want to be a great conversationalist, this is the golden rule. [My wife is a Jedi master at this which is why everyone loves to talk to her.]

As I reflected on 2023, “What truly matters?” helped me gain confidence that I’m on the right path and identify adjustments for the road ahead. In mentoring, it helped ensure the best use of our limited time by coming back to what’s important and avoid being consumed by sidetracks and details. In retirement, I often feel the tide of the trivial threatening to drag me away from the shores of joy to instead drown in a sea of ‘meh’.

I discovered some wonderful new questions in Kristin Neff’s excellent book Self-Compassion that were especially helpful during my 2023 reflection. This reminded me that: 1) Finding great questions is a lifelong journey; and 2) As I said in Part 3, the questions we ask ourselves might just be the most important questions we ask.

Asking ourselves great questions is a cornerstone of great leadership. At the very least, each of us is the CEO of Me, Inc. I might branch out to lead my family, group, or organization, but it all starts with how I manage myself. The stronger that foundation is, the better I will be when leading others. As they say in the pre-flight safety talk, put your mask on first.

Kristin’s book is full of practical help for shoring up Me, Inc. Right off the bat, I was drawn in by: How do you typically react to yourself? How do you react to life’s difficulties?

This led me to ask: What if I gave myself a little grace? Instead of mercilessly berating myself when I messed up, what if I told myself the same thing that I would tell a friend if they messed up?

As Brene Brown says on the cover of this book, it is a transformative read, and I found it to be especially so for a perfectionist. In the short time since finishing this book, it’s already helped me consider better questions, actions, and reactions. Just giving myself a bit of grace when I make a mistake leaves me more in the tank to be there for others.

Because I was in questioning mode, my curiosity was elevated, and this resulted in a little moment of life’s magnificence. I walked into a store that I’ve been to many times before. When I’m there, I’m typically trying to get in and out as quickly as possible. I’m the opposite of curious.

That day, I made it a point to stop and look around a little more. For the first time, I noticed that there were bottles of bourbon on a shelf near the register. This is not a liquor store or a bar. I looked up a little higher on the shelf and saw a giant pyramid of tiny red Solo plastic cups with writing on them.

As an expert questioner, I asked the woman behind the counter, ‘Um, WTF?’. [No, I did not actually ask that distant unwelcome relative of Wait, What?]. The nice woman called her manager Kelly over to explain.

Kelly told me that last year, a customer came in looking like he’d had a horrible day. Kelly said to him, “You look like you could use a drink” and proceeded to pour him a shot of bourbon. [At this point I was too stunned to ask why there was a bottle of bourbon handy for such an occasion.]

The customer was so appreciative that he came back the following week and dropped off a bottle. Word started to get around and it eventually happened so often that the back of the manager’s business card now says, “A whiskey selection is available upon request.”

Following that story, I asked the obvious question: May I have a shot of whiskey? This proves I’m smarter than I look. We shared a shot, which I used to toast a dear departed friend. I signed and dated my plastic shot ‘glass’ to be added to the pyramid. I left with a warm sense of appreciation for being curious.

Another moment demonstrating the power of questioning came on a Delta flight to Detroit. In January. Usually, I have my noise cancelling headphones on before buckling my seatbelt. I’m not curious about my seat mate. But it’s Questioning January, so here goes nothing.

After helping my seatmate get her bag into the bin, I take the plunge and say hello to a stranger on a plane. I default to the proven but boring “So, what do you do for a living?” and she says that she is in the healthcare industry and has a doctorate in cancer research with a specialty in Non-Hodgkins Lymphoma. As it so happens, someone close to me has just told me that she has NHL and doesn’t know what to do.

Even a blind conversational squirrel like me can find a nut if I’m in Questioning Mode.

Since we last ‘spoke’, I had the opportunity to be on two different panels, answering questions from students at The University of Michigan. In both panels, the moderators asked participants to write down questions on index cards. This was a good way to practice “How can I help?”: Rather than guessing what people want to know about, let’s just ask them. We got some difficult questions, so I guess they are teaching the right things in business school these days.

In the second panel, the moderators did something that I hadn’t seen before. After answering questions, they asked each of the panelists to pose a question back to the audience: What’s an important issue that you are dealing with and what the audience do to help?

No pressure, right? We had to think quickly and deliver a great question, just like the audience did. Then they had a few minutes to discuss at their tables before offering help to us.

In every Q&A, there’s a bit of a dynamic where the panelists are elevated to the front of the room and asked to deliver their incredible wisdom. I loved how turning the tables at the end brought us all back into the room as ‘fellow travelers’ on the road of life.

And, in another little moment of life’s magnificence, the panelists got some genuinely valuable wisdom back from the audience.

As a board member, I’ve been trying to do a better job at asking great questions. I’m in the room because the gray hair I have is supposed to be covering a box full of wisdom. If I’m asking whether you misspelled a word on slide 22, I’m not sure I’m earning my keep. If I want to be great at this, I better figure out how to ask amazing questions.

I figured that a good way to do this might be to volunteer to do some mentoring. I’ve felt a lot of pressure to ask great questions in those settings – especially when someone is looking for me to help on a difficult issue. They lay out the whole enchilada for me in all its glory and then look at me like, “okay sensei, what have you got?”.

That moment has a lot of pressure and excitement in it. It’s a real test of whether I’ve been truly focused on the other person and whether I’m wise enough to know just what to say in that moment. I think if you have a good major league batting average in this setting, meaning you nail about 30% of them, you’re damn good. It’s terrifying and exciting at the same time, like I imagine it is shooting a free-throw in the last seconds of a close game.

In the past, I didn’t think about that moment of terror, because I was the one pointedly asking for wisdom. Then I read a story told by a mentor who gets a call from a young man asking for help with a very difficult business situation. There was a lot riding on this for the young man, his family, and the world. He described that moment of sheer terror when the young man stopped talking and he was expected to offer up his wisdom.

As I read that story, I realized that I was the young man he was talking about. I came to him in desperation. I laid out the story and I waited. After a very long pause, he asked me the last question I expected him to ask me.

And it turned out to be an incredibly helpful question. It caused me to think about the situation in a very different way. It didn’t solve the problem, but wisdom isn’t meant to – it’s meant to provide you with the tool you need in that moment to help you help yourself. Great questions are meant to get the brain cooking – whether answering your own questions or someone else’s.

Over the last few months, I found myself facing my biggest challenge, as I walked with a friend who was suddenly stricken with cancer. I’ve never been more focused on another person, and I’ve never felt more pressure to be of service to another human. He passed away last week. I pray that I was helpful, I pray for him and his family, and I will miss the future we thought we had.

I’ll wrap up with one last story of listening, questioning, and guiding someone through a difficult decision. Our 18-year-old dog Sparky was not doing well, so I took him to our veterinarian.

She listened carefully and asked great questions. She focused completely on me and Sparky. She didn’t tell me what to do – even as the expert, it wasn’t her place to do that. Instead, she helped me come to the crossroads and think about both directions. In the end, I realized that letting him go was the right thing for him even though it was painful for me. I miss him very much and I’m grateful for the life we shared. I love you little buddy!