Category Archives: leadership

Questions for Connection

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What excellent question have you asked or been asked lately? How did it affect your relationship with the person asked/asking?

Ever since I started working with my life coach in 2005, I have practiced asking more and better questions in any encounter, in all life domains. The returns on this investment of presence and curiosity–idea generation, heightened conversation, and deepening connection, among others–far outweigh the costs of occasional awkward pauses and uncomfortable deflection.

I wonder, however, if I give enough time or energy to answering the interesting quesitons I ask?

Why, for instance, do I behave so differently with people in and out of my family? I feel like the same person in both contexts, and everybody knows the same me; yet I know I show up not the same at home as outside. Fascinating.

Today was Day 190 of my morning pages practice. Looking back, much of the journaling consists of lists, plans, recollections, and reflections. The same questions arise recurrently, mostly centered around behavior and relationships, and I attempt to answer overtly about half the time. Also fascinating! I feel comfortable with this state of things, as the simple act of writing them down and letting them sit on and below my consciousness day to day allows me to consider them slowly. Persistent questions point me to my core values, purpose, and goals. I feel no rush to formally answer these existential, identity-related, philosophical inquiries. I tell the story that simply marking their re/o-ccurrence pins them to some level of awareness where I can return regularly, like periodically adding brushstrokes to paintings that live in various rooms of my mind, heart, and life, when I happen to walk by. These rooms are bright and airy, each equipped with a sturdy easel, thick canvas, rich color palette, and full set of implements to create and revise, ad lib. I feel calm and focused, reassured that whatever is happening on any given day, I have time and energy set aside to process and digest, coming to clarity organically and as needed, all in good time. My morning pages facilitate insights and understanding regularly, and I see this practice sticking for the foreseeable future.

What I really relish, however, is engaging in questions, exploration, and discussion with other people! I wonder if this is how I make friends, actually? It does not matter if I just met you or I’ve known you my whole life; if you’re willing to dive with me like humanities nerds in a submersible to plumb the depths of open and honest questions and wild ideas of possibility–about anything from language to muscle physiology, human nature to politics, phylogeny to music–I might soon profess my undying love for you and chase you for more of that energizing connection. It is most often with friends, in those small, relaxed, meandering, sometimes calorie-laden gatherings, where nascent and novel answers to delightful questions so beautifully emerge and bloom. I carry my journal everywhere, to capture these pearls when they drop, as though gifts from the gods of sentience and relationship.

People crave deeper connection desperately now, in our increasingly chaotic, impersonal, and globalized world. I see references to the 2015 New York Times article “36 Questions That Lead to Love” regularly (that’s probably the algorithm, right?). If you cannot access it, see the original research article by Arthur Aron et al, “The Experimental Generation of Interpersonal Closeness: A Procedure and Some Preliminary Findings” with the questions listed at the end. Organized into three sets of increasing intimacy, the exercise invites us to ask our conversation partners questions such as, “What would constitute a perfect day for you?” “What is your most treasured memory?” and, “Complete this sentence: ‘I wish I had someone with whom I could share …'” From NYT: “The idea is that mutual vulnerability fosters closeness. To quote the study’s authors, ‘One key pattern associated with the development of a close relationship among peers is sustained, escalating, reciprocal, personal self-disclosure.’ Allowing oneself to be vulnerable with another person can be exceedingly difficult, so this exercise forces the issue.” I have the article bookmarked on my phone, and have yet to invite anyone to answer with me–maybe I’ll set an intention to do so on my upcoming friend dates? Part of me thinks I’m doing fine connecting on my own, and you never know, this could be truly next level.

Renowned psychologist Esther Perel created a similar game in 2021, Where Should We Begin, now in its 2nd edition. This query is how she historically initiates therapy sessions with clients. Questions in the game include, “I can’t believe I got away with…” “My latest crush is…” and, “My favorite love story to tell…” The box includes questions that range from lighthearted to serious, to sexual and beyond, which positively tickles me–because it’s all just life. In this age of polarization and easy mutual disdain and disconnection, games like this can help us all recognize our shared humanity.

I have purchased yet a different box of questions for connection, How Deep Will You Go? Its creators describe it as “a game of deep conversation without worrying what to ask, to feel closer in a way you never felt before.” Three levels of questions are labeled Ice Breakers (“What motivates you in life?”), Confessions (“Why have you kept going?”), and Getting Deep (“What is something you don’t tell most people?”). Reading the cards, I imagine with whom I’d want to delve. It depends on the question(s), of course, and also context and mood. I can picture a small friend group setting for the playful ones, and core belief/value ones as actual ice breakers for purposeful group work, such as a Braver Angels workshop. For the more intimate questions, though, I picture a one on one meeting, with plenty of preface and mutual agreement to actively engage in deepening personal connection.

Of course, interpersonal closeness is an iterative process: Other than the most superficial queries, the willingness to ‘go deeper’ requires some level of established trust and safety. That can take a while, depending on a multitude of factors. But once that foundational rapport is achieved, subsequent connection facilitated by these questions, one by one, may unfurl like the slow and steady inflation of a hot air balloon from the ground, lifting us gently together to affinity and affection we could never achieve where we started.

Connection decks like Where Should We Begin and How Deep Will You Go? make me so optimistic. I have loved and tried to ask questions like this for years, and now I feel validated. What if we all opened up to one another just a little bit more, just a little more often? What if we held one another’s hopes, joys, struggles, regrets, dreams, and confidences with a little more respect and reverence? What if we approached one another, friends and strangers alike, with the assumption of caring and mutual well wishes, looking to hold one another up, rather than with suspicion and wariness? And what if we rewarded such unearned generosity of spirit with reciprocal kindness?

The practice of mindfully asking deeper, more personal, loving, and intimate questions could go a long way to bridging our seemingly insurmountable differences; we all need this right now. It’s not appropriate in every encounter, of course. We must attune to context and opportunity, and act (ask) with confidence and humility. And that’s also the point, isn’t it?

The more present we are to one another’s vibrations, our moods and energies, the more likely we are to connect in earnest, regardless of what questions we choose to ask or not.

Understanding, validation, belonging, closeness, intimacy–we humans thrive when we feel these often and deeply. I still have hope that we can do it better.


Giving the A

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What grades do we give one another in life?

It seems like a silly question, right?  I don’t often think in these terms.  Maybe we give ourselves and our loved ones A’s, our professional rivals and competitors C’s, and folks in opposing political parties F’s?

I wrote recently that I have gifted The Art of Possibility to multiple friends lately.  I just did it again this week.  One of you, dear readers, started reading it because of that post, and invited me to a self-development book club to discuss!  I am so honored and grateful, thank you!  This post is inspired by you and our ongoing Instagram conversation—thank you again!

I thought I had well and truly integrated this practice already.  As always, there is still room to learn and grow, and I just love how this continuing discovery emerges from sharing the book with people!

Giving the A is:
“an enlivening way of approaching people that promises to transform you as well as them.  It is a shift in attitude that makes it possible for you to speak freely about your own thoughts and feelings while, at the same time, you support others to be all they dream of being… An A can be given to anyone in any walk of life—to a waitress, to your employer, to your mother-in-law, to the members of the opposite team, and to other drivers in traffic.  When you give an A, you find yourself speaking to people not from a place of measuring how they stack up against your standards, but from a place of respect that gives them room to realize themselves.  Your eye is on the statue within the roughness of the uncut stone…  This A is not an expectation to live up to, but a possibility to live into.” (paperback, page 26)

It’s a practice akin to making the most generous assumptions about people—a priori–that we are all here doing our best, that we are not out just for ourselves, that we want one another to do and be well.  And it’s also more than that.  It’s more active, takes more initiative on behalf of the other person.  Giving the A assumes not just that people are doing their best, but also that their best can be something great.  I think of it as approaching people as if the light of the world shines within all of us, and all we must do is uncover it for one another.  It is a way of being together that unlocks the greatest potential for us all to be our best.

New Friend and I compared encounters we had standing in line at a lunch place and checking out at the grocery store.  We shared how we caught ourselves feeling annoyed, defensive, and judgmental (not giving A’s to our respective strangers), and were able to shift our attitudes and put down our judgments and negative assumptions.

Something made me think about those assumptions—the default settings in which we walk mindlessly through life.  If I like you, admire you, and want you to like me, I will likely give you an A automatically.  I am primed to see everything you do as golden.  If I dislike you, then I’m likely to judge any behavior of yours negatively.  Whatever default I automatically set for you, confirmation bias reinforces that original grade I gave you, the label I assigned. So, is the ‘grade’ we give someone (or any given group) simply based on our existing relationship with them?  What if we have no relationship, as with strangers?  I think we grade people then based on heuristics—mental shortcuts that may include stereotypes, prejudices, and other biases.  Consider the risks here, and the harm this can do to us all.

I also think the grades we give can be fluid.  I messaged New Friend that they depend on “so many things–intersecting variables—our baseline relationship, its context, the circumstances of any given encounter, our mind state at the time… So mindfulness, as it so often does, comes back to me over and over as the practice on which to center myself. If I’m present in the moment, I’m more likely to notice what grade I’m giving the other person, and to myself as well.”

Aaah, the grade(s) I give myself–my default self-beliefs and -talk!  Off the top of my head:
As parent: B, maybe B+ overall… but in my high stress moments, C-… Or maybe it varies between certain aspects of parenting? I blame myself for many of the kids’ struggles–F! I have written that my greatest regrets in life are all relational; if I’m honest, they all occur in my closest relationships.  When I think of my ‘grade’, it’s a judgment.  And that is not the point of the practice.

The ‘grades’ we give, both to ourselves and others, are limbic, subconscious, automatic, and context driven.  But what do they really mean; how do they affect our relationships?  I think of them now as markers of possibility—ceilings of potential connection.  The letter ‘grade’ simply expresses concretely the abstract, insidious limitations we unconsciously put on one another’s potential as fellow humans.  It’s not that we go around actually assigning grades to people we know and meet.  ‘Giving the A’ is a mindfulness practice—an intentional way of being that honors maximal relational connection potential in and among all people, ourselves included.  So, when I think of myself as parent, giving myself an A does not mean I think I’m perfect or infallible.  It is not meant as a judgment of performance.  It means I give myself the grace to continually attend, assess, adjust, and show up by best; it holds loving space for my aspirational self to emerge and blossom, without pressure, obligation, or requirement.  I feel physical relief just realizing this distinction. 
Where do you need to give yourself an A?

Why practice Giving the A?  I do it to live in peace with myself and other humans–to see us as we all wish to be seen–with kindness, compassion, acceptance, and love.

When I give myself the A, I show up to you differently, and I’m more willing to give you the A. My energy is light, open, welcoming, inviting, accepting, validating, encouraging, and connecting.  When you feel that from me (and it is a feeling–intuitive, subconscious, non-rational), it affects how you show up to me, also.  It is both subtle and profound, incidental and transformative.  Our interaction and dynamic goes a certain way, any one of myriad possibilities, depending on what we each bring in the moment.  And it can change in a heartbeat–hard left, deep dive, instant bond or severance–if we’re not paying attention.  Maybe the hard times and disconnect happen more when we’re mindless, and the loving, connecting times when we are mindful?  Or maybe it’s just that we see the potholes coming and can navigate around them more easily in the latter.

Imagine if we saw one another as loving works in progress, every one of us, no matter what our circumstances, past experiences, and fears?   What if we held mutual possibility for all of us to step into our own full potential in any domain?  That’s a world I’d like to inhabit, and practicing Giving the A makes it a lot more likely.

Me with Ben Zander, 2009

The Expert and the Student

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What do you take for granted that you know and do?
How do your conversations with colleagues differ from those with ‘laypeople’?
How does your specific expertise emerge and manifest outside of its own domain?

Friend recently told me about the time his friend offered their Adderall (a stimulant used to treat attention deficit and hyperactivity disorder) for his full body, multi-system allergic reaction to food (which technically constitutes anaphylaxis and should be treated with epinephrine, or at least a strong antihistamine like cetirazine [Zyrtec] or diphenhydramine [Benadryl]). I had immediate, strong, and mixed feelings and thoughts: What? Oh, your friend was trying to be helpful.. and that is absolutely not the right thing.. and omg, what badness could have happened? ANTIHISTAMINES FOR ALLERGIES! And this is why everybody needs an accessible primary care doctor, FFS. Okay, okay, self-regulate. Friend has lived with his allergies for however long, he has apparently handled it fine thus far; this is not my business. Unsolicited medical advice is not often welcome, Chenger, so zip it! And GAAAAAAH, my dear friend, the next time you have an exposure, I pray please for you to have more knowledgeable folks around you! OH that self-restraint really challenges me sometimes.
I share this story as an example of how my doctor mind is always present, always assessing. I felt caring, protective, and concerned when Friend told me, and not at all dismissive or condescending, so I hope that is not how it comes across. All I want is for Friend to be well, to have all he needs for that, and to help if I can, within appropriate boundaries. I hope I respected his boundaries well that day, while still conveying how much I care.

Opioids, anti-inflammatories, corticosteroids, Tylenol–they all address pain, and by different mechanisms, with different side effects, and can be combined and not in certain ways–I know these things. Blood count, chemistries, lipid profiles, iron, B12, CRP, sed rate, TSH–I have ordered and interpreted these and other ‘routine’ blood tests for almost thirty years now. I see patterns for fluctuations, correlates to behaviors, and advise accordingly. Pain, headache, dizziness, nausea, rash, shortness of breath, diarrhea, and myriad other things–I know what’s common and how to treat. I know what to do when I don’t know what’s happening. I know who to call for help. I know how to sit with you, my patient, when things are uncertain and you feel acute distress. I know how to listen beyond the objective answers to my questions. I see you, or at least I do my best. And the longer we know each other, the better I know how to help you, no matter what’s going on. I am an expert at primary care internal medicine.

“Routine,” Orthopod said to me before my knee surgery. I imagine he saw me as a fellow physician and assumed I understood the technical aspects of procedure risk and outcome expectations–which I did. And I was the patient in that scenario, anxious despite my expert medical knowledge, and possibly in part due to it, because I also know how things can go unexpectedly sideways in any operating room. “Routine for you,” I replied. I trusted him, the surgical expert, with my knee and my health. No longer a medical student, and still a learner in a different role, I felt vulnerable and safe. I think we both had a little a-ha moment then.

“Jacob, watch, please? Where does the movement start, again? What is the difference doing it this way versus that way?” In the gym, I am absolutely still a student, though I have been an athlete since adolescence. I have passed the prerequisites of anatomy and physiology. I understand force, mass, and acceleration. And every session, there is still no shortage of new knowledge, experience, and practice to acquire. This is what brings me back so enthusiastically–the more I learn, the more confident I get, and the better I can perform. I make steady progress because my teachers are both knowledgeable and approachable, generous and creative with their instruction.
I wonder what/where/how I might be more willing to study if I had such teachers?
How lucky that throughout my life, I have benefited from so many amazing guides, mentors, and coaches.

In preparation for this post, I listed things at which I am expert, proficient, and novice. Obviously the novice list is longest–humbling and inviting! The proficiency list is gratifying, actually, as I can stand justifiably confident in a variety of diverse skill domains–yay! And when I’m honest, the expert list is remarkably short, which is as it should be.

So it makes me think: How wonderful to be a student of everything, including in my own areas of expertise! Medical knowledge has doubled at least twice since I started training 29 years ago, and that rate continues to accelerate. There is simply too much for any generalist to know, even though we still know a lot and continue to learn about everything. Every time I connect with a specialist colleague, I walk away or hang up smarter and a better doctor for my patients. Bless my colleagues, all!

When I describe my interest in leadership to people, I say that I ‘study’ it. To some, I may seem like an expert. And though I do consider myself advanced in my leadership education, I will always consider myself a student, because every leadership role is unique and fluid. I will never be in a position to not learn and improve. I value humility; when I see it in experts and leaders, I trust them more immediately and implicitly. That is the kind of leader I aspire to be. Learner-leaders cultivate other learner-leaders by example. What an excellent, virtuous cycle!

Student mindset is growth mindset, a beginner’s mind. Maintaining it helps me connect more easily with others with whom I may mutually teach and learn from in loving and organic, natural and synergistic reciprocity. It keeps me open and improves, hones my overlapping, intersecting skillsets. It deepens all of my life experiences, inviting contribution from anyone I meet, anything I do. Everything blooms in brighter, more vivid color and texture; every day holds infinite possibility!

I meet experts in multiple domains every day, and I wish I had time to pick all their brains. My morning pages and brain dumps help me process and integrate all of these encounters and more. So much to gain, so many people to meet and love, so much connection in the offing, oh my goodness, it’s just too good!

My wishes for you, dear readers:
May you meet experts who enrich your life by kindly sharing their wealth of knowledge.
May you stand ready to receive their offerings with openness and curiosity.
May you share your treasures of life experience with generosity and humility.
May all of these encounters nourish you, mind, soul, and being.
And may it all make us better for ourselves and one another.

Onward!