Lead Like You're Retired (Part 2: Be Curious)

Imagine you are a young woman from Texas trying to convince eight highly independent Venetian gondoliers to work together in a show about their work. Or talking a group of sanitation workers, 96% of whom are male, into letting you choreograph a dance they will perform in front of the entire city.

Most leaders spend a lot of time trying to convince people to follow them, but come on, how many of us have tried to climb a hill that steep. Allison Orr climbed those hills successfully plus a whole lot more. What’s her secret? Well, there are a lot of them in her book Dance Works, but I’ll let you in on one of them: Curiosity. [Too late for the spoiler alert.]

Curiosity, from a place of respect and humility, should guide every project. It can start and ground a project – what you return to when you hit obstacles or aren’t sure where to go next. Curiosity is also at the core of relationship building. When I show up curious, I bring my full self to an interaction. Remind yourself that ‘not knowing’ can be a chance for growth and an opportunity for someone else to shine(1).

There’s a lot to unpack in that paragraph, starting with approaching conversations from a place of respect, humility, and genuine curiosity. In my time as a leader, I thought I approached situations with curiosity and respect. I went into interactions saying that I wanted to hear what people really thought and that I wanted them to disagree with me. I recognized that I didn’t know all the answers and that I needed my team to be engaged.

But if I’m being truly honest with myself, I don’t think that I was authentically curious. I think that I was often too focused on getting the job done as quickly as possible, on crossing off that next item on the to-do list. After all, that list seemed to be endless, and I was too aware that the clock was ticking.

I didn’t use genuine curiosity to create a rock-solid foundation for relationships. I spent more time selling my story than I did keeping myself in the moment, being open to what my teammates were experiencing and deeply considering how they could shape our path forward.

Many people are happy to just follow the leader. They have enough to do in their own lives without taking on more responsibility. It’s likely that, at some point in their working life, they took a chance and stepped out, only to be disparaged for taking the risk. Leaders must work hard to truly create the conditions for people to engage completely and take responsibility. Accountability and initiative don’t come easy, they happen through trusting relationships.

Allison says that we rise above the clutter of our intense lives by building real connections. Everyone has a story about how they ended up where they are. She advises us to seek out that story, show true interest, and remember what they tell you.

In groups, be aware of who is talking and who isn’t. Draw people into the circle. Expect resistance; recognize that you are an outsider and decide to belong no matter how awkward it feels. Handle doubt and hesitation with grace. Have the wisdom to not take things personally. Take pleasure in being with people. Slow down, leave time for unstructured moments, align with the pace of the group. Pay attention to words you don’t understand. Ask about slang and jargon. [See, I told you there were a lot of valuable lessons in her book.]

The slowing down part was particularly hard for me. Retirement has afforded me the opportunity to slow down and focus more on the relationship and the process than the to-do list. The journey truly matters more than the destination. It’s made me a better leader and a better person.

When I was working, I don’t think I recognized and appreciated complex balances in life as deeply as I needed to. Sometimes we talk about these as competing values. Brene Brown calls them paradoxes and opposites. In his book Impact Networks, David Ehrlichman calls them dynamic tensions and says: “they are not problems to be solved; they are polarities to be aware of, integrated and held with care throughout the life cycle.(2)”

This would have been particularly important for me to realize – being an engineer, I was too often in problem solving mode and instead of recognizing a delicate balance of natural tensions.

A couple of the dynamic tensions that Mr. Ehrlichman describes are particularly relevant here: 1) building trust versus taking action; and 2) shared interest versus self-interest.

A couple of paragraphs ago, I could hear you thinking “how in heck do I have time for unstructured moments, let alone to listen to everyone’s story?!” In each interaction we have, we choose how we balance building trust and relationships versus expediency in actions. We decide whether to uncover shared interest and self-interest all around the table before leaping into solutions.

Engagement and accountability don’t happen by accident and they don’t happen with carrots and sticks. Often it comes by focusing on the first part of those dynamic tensions in order to earn the second part. An investment in building trust delivers better action and genuinely exploring shared interest creates opportunities for self.

Allison advises us to think about what’s in it for the other person. Listen closely for need and think about how the pursuit of your goal truly and meaningfully helps the person you need help from. I practiced this the other day and was surprised at how much better the conversation went compared with my usual approach of drilling into what I need and how you can help.

It’s easier for me to do that now because my needs are more often focused on what others need. That’s part of my retirement contract: work is primarily about making the world a little better for others. I wonder how much more effective I would have been if I had led like I was retired. And I think that, just maybe, that’s the way we should always deal with other humans.

I’m part of a family business and I read something interesting the other day:

Family businesses that last incorporate curiosity. They seek to learn from others through conversations with other families. “They use those conversations not to find the answers, but to help them ask better questions…We never find the complete ‘answer’ from one conversation. Rather, we find specific approaches and practices that make us question how and why we do things.(3)”

And that leads me to Edgar Schein’s landmark book, Humble Inquiry.

“Humble Inquiry is the fine art of drawing someone out, of asking questions to which you do not already know the answer, of building a relationship based on curiosity and interest in the other person.(4)”

Schein echoes what keeps us from doing this more often: we cram as many tasks as possible into each unit of time without bothering with relationship building because that takes too much time(5).

The key is ‘you don’t already know the answer’ and the problem is that often I won’t know unless I learn to ask the right questions. Not knowing has been known to lead to disaster. Leaders are particularly susceptible to this ailment because many people don’t want to offer up information and the leader often isn’t looking for it.

Cue Ted Lasso and one of the best scenes in the series when he pointedly delivers advice to Rupert to “be curious, not judgmental”. Oh dang, that hits the bullseye for me. Along with being in too much of a rush, I am too often judgmental. I’m working on breaking this habit which is another misbehavior I attribute to my New York upbringing.

Humble inquiry maximizes my curiosity and interest in the other person and minimizes bias and preconceptions about the other person. I need to access my ignorance and ask for information in the least biased and threatening way. I don’t want to lead the other person or put her into a position of having to give an acceptable response. Schein’s book has lots of practical help to do this well.

And so does Brene Brown. In Dare to Lead, she explains that we are incredibly uncomfortable with not knowing the answer – especially in leadership. Our egos want us to beat everyone in the room with an answer even if it doesn’t address the real issue. We’re impatient and controlling. Instead, we need to be more curious, let go of control and dig deeper into the problem before focusing on solutions.

“Curiosity says: No worries. I love a wild ride. I’m up for wherever this goes. I’m in for however long it takes to get to the heart of the problem. I just have to keep listening and questioning.(6)”

She offers some great starters for getting deeper into an issue, including:

• I’m curious about…

• Tell me more, walk me through, I’m wondering…

• That’s not my experience (versus you’re wrong)

• What problem are we really trying to solve?

Curiosity, humble inquiry and Brene Brown rumbling are important tools for any leader.

In a recent article in The New York Times, David Brooks says: “In any collection of humans, there are diminishers and there are illuminators, Diminishers are so into themselves, they make others feel insignificant…Illuminators, on the other hand, have a persistent curiosity about other people.(7)” In retirement, I’m finding it just a little easier to work on being an illuminator.

I don’t know about you, but I’m curious about what else I’m going to learn in retirement. Spoiler alert: it might have something to do with asking good questions.

(1) Allison Orr, Dance Works: Stories of Creative Collaboration, (Middletown, CT, Wesleyan, 2023), 148-149.

(2) David Ehrlichman, Impact Networks: Create Connection, Spark Collaboration and Catalyze Systemic Change, (CA, Berrett-Koehler, 2021), 72.

(3) Family Business Magazine, https://www.familybusinessmagazine.com/culture-continuity-key-family-business-longevity.

(4) Edgar H. Schein, Humble Inquiry: The Gentle Art of Asking Instead of Telling, (CA, Berrett-Koehler, 2013), 2.

(5) Ibid, 58.

(6) Brene Brown, Dare to Lead, (NY, Penguin Random House, 2018), 172.

(7) David Brooks, Give the Gift of Your Attention, (The New York Times, Sunday, October 21, 2023), 6.