The Leadership Skill That Matters Most

Posted on April 13, 2025 by Catherine Cheng, MD

Photo from my patient who prefers to remain anonymous 🙂

Here’s how:

Whenever you’re about to make a statement or directive, pause. Ask yourself, “What do I not know?” Be honest and humble, or prepare to be humbled. The mark of an excellent leader is the willingness to be schooled from ‘below’ for the sake of mission and team.

Once your ingnorance is identified, formulate a question. As well as you can, make it an open and honest question, the hallmark of which is that you truly do not know the answer and you are not attempting to lead it. Pause again. Is your question truly open, meaning it cannot be answered by yes or no? If so, proceed. If not, revise to a truly open question.

Listen to the answer without interrupting. Do not speak until the other person has stopped talking for at least two seconds. Resist the temptation to issue your previous directive anyway. Follow the thread of curiosity, however thin or faint, to explore what else you don’t know. Done well, one OHQ leads to multiple subsequent OHQs, often branching and diverging to adjacent arenas all interconnected and mutually influential to the central issue.

It can get overwhelming fast, and I suspect many of us do not engage in this kind of query because the emergent morass of complexity feels so daunting. Rabbit holes are to be avoided in leadership think.

If we ask more and better questions, however, we don’t get rabbit holes. We get ecosystem.

I do this every day interviewing patients. Regardless if it’s weight, blood pressure, blood sugar, insomnia, or depression, nothing occurs in a vacuum. Only by exploring the state of every domain of health (work, sleep, exercise, nutrition, stress, and relationships) can I see fully the interconnected origins and impacts of the issue I need to address (often multiple issues at once). Often about thirty minutes into the interview I say, “Wow, that’s a lot.” I sit with my patient a bit stymied at the muddle. Then we talk about their goals, their values, and what lights or dampens their spirit. Reliably, by the end of the day long exam, we get to an action plan that is both brutally realistic and fully aligned with their highest aspirations. It feels inspired an empowered, forward motion already initiated for the coming year.

The best questions help us survey the jungle, its density and pitfalls. It is only after querying the morass and seeing its wholeness that we can know where to act most incisively and effectively. We know we asked excellent questions when the answers provide the map that leads us through the jungle together and with confidence.

Humility. Honesty. Transparency. Safety. Clarity. Accountability. These are the imprints of leaders adept at asking more and better questions. Consider any organization in your experience; I bet these leaders stand out. How would you describe their presence? How do you feel when you’re with them? What effect do they have on the team and its operations?

In case it’s not already obvious, this practice of asking open and honest questions benefits all relationships. In a world of soundbites that continually overgeneralize and oversimplify, stoking judgment and othering, the more we can retain and protect our humility and curiosity, the more we can ask more and better questions that foster understanding and empathy, the better the world will be. We all lead. Let’s do it better, yes?

The Second Mountain

Posted on April 9, 2025 by Catherine Cheng, MD

Ok friends, really quick tonight because I’ gotta get to bed on time!

I had a wonderful conversation with an exec recently who senses himself at a threshold. He has been remarkably successful in his career, not only by societal standards of status and income, but by his own ethical standards of leadership and purpose. Now in his mid-fifties, he looks ahead to closing the conventional corporate chapter of his life and opening the next– he’s just not sure what it will be. It’s not likely to be board work, as so many do. He seeks more meaning, more purpose, a legacy that he can be personally proud of, perhaps? I suggested that he work with a coach to help him think/talk through it, and as I listened more, I thought coaching itself may be his calling. I had an inkling that I knew an inspirational phrase for this life stage, this slow burning fire of positive middle-age transition, but I could not locate it.

As I ended my 100 Pregnancies post asserting that we all have agency to respond to and live life as we choose, I thought of another friend whose work is now a morass of chaotic uncertainty due to the current administration. In reply to the post, she messaged me, “As I start to contemplate retirement and what comes after, I feel almost giddy with possibility. It’s almost like I get a do over of that young adult chapter where all doors where open to me, but I felt so duty-bound and worried about making good choices that I didn’t appreciate it. What a luxury to have another chance to appreciate possibility and to pair it with intention and agency!” She is my people, obviously.

I replied (also giddily), “I (spoke) with someone about this age and exactly what you’re describing–like one more, great opportunity to be and do our best–to fully live into our intentions with the benefit of everything we have lived to date!”

Oh, I should tell you all, I have put down Book for now. After a year of trying fitfully and in earnest, it’s just not happening yet. Instead, I feel called to demonstrate and amplify civil political discourse–Healing Through Connection–through continued short form writing and public speaking. I have connected with a wonderful branding coach to help me expand my audience and innovate my method–anything is possible, and I’m attached to nothing. I’m not giving up my day job; it gets better every year, actually, and new collaborative possibilities shine on the horizon. Still, for ten years now I have cultivated and documented this ‘passion project’–a mission to make our relationships better in every domain, using any and all tools and practices that align with my values of honesty, integrity, curiosity, humility, and kindness. It overlaps with and mutually informs my clinical practice–the most cosmic integration that I built myself and also evolved completely organically.

This series of interactions and reflections on my way to the treadmill tonight finally unlocked that inspirational phrase in my memory–The Second Mountain! I listened to this book by David Brooks when it released in 2019:

“Every so often, you meet people who radiate joy—who seem to know why they were put on this earth, who glow with a kind of inner light. Life, for these people, has often followed what we might think of as a two-mountain shape. They get out of school, they start a career, and they begin climbing the mountain they thought they were meant to climb. Their goals on this first mountain are the ones our culture endorses: to be a success, to make your mark, to experience personal happiness. But when they get to the top of that mountain, something happens. They look around and find the view . . . unsatisfying. They realize: This wasn’t my mountain after all. There’s another, bigger mountain out there that is actually my mountain.

“And so they embark on a new journey. On the second mountain, life moves from self-centered to other-centered. They want the things that are truly worth wanting, not the things other people tell them to want. They embrace a life of interdependence, not independence. They surrender to a life of commitment.

“In The Second Mountain, David Brooks explores the four commitments that define a life of meaning and purpose: to a spouse and family, to a vocation, to a philosophy or faith, and to a community. Our personal fulfillment depends on how well we choose and execute these commitments. Brooks looks at a range of people who have lived joyous, committed lives, and who have embraced the necessity and beauty of dependence. He gathers their wisdom on how to choose a partner, how to pick a vocation, how to live out a philosophy, and how we can begin to integrate our commitments into one overriding purpose.

“In short, this book is meant to help us all lead more meaningful lives. But it’s also a provocative social commentary. We live in a society, Brooks argues, that celebrates freedom, that tells us to be true to ourselves, at the expense of surrendering to a cause, rooting ourselves in a neighborhood, binding ourselves to others by social solidarity and love. We have taken individualism to the extreme—and in the process we have torn the social fabric in a thousand different ways. The path to repair is through making deeper commitments. In The Second Mountain, Brooks shows what can happen when we put commitment-making at the center of our lives.”

I’m starting to think this blog, Book (eventually), and my commitment to relational leadership have all been my Second Mountain. Duh-HA! I also feel myself at another threshold now–empty nest and potential for even more personal expansion. Daughter is not the only one getting ready to launch! So might I live yet a Third Mountain?

What precipice meets you right now? How do you feel about it? Where do the feelings manifest in your body? Who else knows and can hold the space, un/certainty, excitement, trepidation, and giddiness with you?

Two more books come to mind, both that I also listened to years ago:
Changing on the Job by Jennifer Garvey Berger and
The Infinite Game by Simon Sinek

So let’s see where and what this all goes, eh? Very exciting!

Breathing Through It

Posted on April 5, 2025 by Catherine Cheng, MD

From my Insta tonight (@chenger91):

Happy Weekend, friends!

Wishing us all an energetic balance of rest, fun, productivity, and connection. All I want to do is write jar smiles!! 🤪🥰😂

Thanks to Coach Eric and (guru) Pierre at Ethos who led the elite human performance class today—I didn’t die, YAY HOOEY!! 😁

Our current government sows chaos in practically every domain of socioeconomic systems, and the fallout may take years to realize. Morbidity and mortality could be staggering. And yet, here we are. We stepped into it together and we’ gotta figure out together how to get out. It will take all of us doing differently from what we have done to date—I think we have proven much of that isn’t working, yes? 🤨🙄

This is an opportunity. We get to re-invent and co-create. Unlike those in charge now, we can ‘A5R it’—take a thoughtful, critical, and wise look at things, keep what’s working well and revise the rest. All good change requires iteration. It’s an infinite game. We start by bringing our best, most creative and compassionate selves to the front. Easier said than done in distress. So we do what we can.

Like Pierre taught us today:
1. Control our breath, and expand laterally.
2. Focus on microgoals (like the next breath).
3. Speak positively to ourselves (AND ONE ANOTHER!).
4. Envision the successful future.

It’s not rocket science. But it is humanity, so it’s messy. Still, we’ got this. 👊🏼👍🏼💪🏼👏🏼

@eric.koetting
@debarpierre
@ethostrainingchi

ODOMOBaaT: One Day, One Moment, One Breath at a Time.

The Insta post included the photos below, all notes written for friends in distress.
We could all do a better job recognizing, validating, empathizing with, and exploring one another’s distress, no matter what the geopolitical circumstances and environment. Most people don’t lash out for no reason. We have all spent too long ignoring others’ distress. This has to change.