The Three Ways to Express Disagreement with a Colleague

On any team of size, there are three constructive ways to express disagreement (or frustration) about a colleague’s behavior / decision / idea:

  1. Disagree publicly in a public Slack channel, email mailing list, or in a group meeting that includes the colleague in question.
  2. Express your disagreement privately and directly with the colleague.
  3. Talk to the colleague’s manager privately about your disagreement. (Rare, but sometimes necessary.)

Here’s what’s not constructive: Talking 1:1 or in a small group with other colleagues about your disagreement (or frustration). If John has a frustration or disagreement with Dan, John should not be talking to Tom, Dick, or Harry about his frustration with Dan, unless one of those people is Dan’s manager.

Commiseration is an extremely common form of social bonding. On teams, it’s tempting bond over shared frustration with someone you both know in common: “Hey. Isn’t it annoying when Dan calls without advance warning and then rambles about his project list?”

Talking about a colleague behind their back, in private, with anyone who’s not their direct manager is extremely destructive culturally.

In Max Levchin’s post about building a meritocracy at Affirm, he says: “Do not allow ‘us and them’ dynamics to foment anywhere at Affirm.” That’s it. When a company transforms from “one team, one mission” to a team composed sub-coalitions and in-groups and out-groups, it’s toast. Rumors build, trust erodes, resentment rises, and team effectiveness plummets.

“Disagree productively and directly” or perhaps just simply “Don’t talk about colleagues behind their backs” are strong candidates for corporate values leaders should codify and enforce.

Remembering Steve Armstrong and His Dhamma Wisdom

I had already meditated a bunch and sat multiple silent retreats by the time I arrived for Steve Armstrong’s silent 10 day retreat at Spirit Rock in 2016. I thought I knew a few things.

I had no idea it would be Steve who would help me realize my own low level of knowledge. Steve helped me connect the teachings of the Buddha to intellectually rigorous modern arguments about the nature of the mind. The clarity of thought with which Steve presented arguments about the “Three Characteristics” of impermanence, unsatisfactoriness, and not-self uniquely transformed my understanding of the connection between evolution/natural selection and the way the Buddha described suffering, its causes, and the path to free oneself from suffering.

In the world of spirituality and self-help, there are many wise and well meaning teachers whose eloquence is lacking; their dharma talks are semi-rambling, their argumentative structure muddied by woo woo platitudes. Steve was different. He was verbally efficient and precise.

Sadly, his wife Kamala Masters (a senior teacher in her own right, whose retreat I sat a couple years ago) announced today that Steve Armstrong passed away over Christmas from a brain tumor. I’m taking the occasion to recall some of my experiences on Steve’s retreat.

First, Steve was a devoted champion of his teacher in Burma, Sayadaw U Tejaniya. Tejaniya, a Burmese meditation master, teaches a version of insight meditation that doesn’t prioritize object-awareness like the breath or a bodily sensation. Tejaniya starts with awareness of any thought or sensation that comes through one of the sense doors (sight, sound, smell, etc.), and the teaching emphasizes the higher level awareness of the fact that you are perceiving an object over focusing on that object itself.

Here’s what Steve asked a thousand times on the retreat, echoing the words of Tejaniya: What does the mind know right now? Are you aware that you’re seeing something with your eyes open? Are you aware that you’re hearing something? Are you aware of a specific thought? To transpose the questioning to this blog post: You, dear reader, are seeing words on the screen right now, but are you meta aware — right now — of the fact that you’re engaged in the act of reading, in addition to processing the words in this sentence to discern meaning? In these moments of awareness, you might sub-vocally tell yourself, “Reading, reading.” If you hear a sound in the background as you read this, you might tell yourself, “Sound, sound.” Eventually you move away from specific noting and try to maintain a continual awareness of any and all sensations, with no concrete focus other than noticing the mind that is doing the observing — which is to say, you maintain a meta awareness of consciousness. (If you’d like to learn more about Tejaniya’s approach, you can read his book When Awareness Becomes Natural.)

This kind of open awareness can be a real breakthrough for beginning meditators who aren’t sure what to “do” during meditation. It can also be a useful practice for very seasoned meditators. At present, when I’m not on retreat, I actually find it more difficult to practice choice-less open awareness than to steady attention on an object of focus like the breath.

Second, Steve explained inner peace as the ultimate aim in a way that stuck. Peace, he said, is not permanent (nothing is) — but it’s always accessible. A life with inner peace is not a grey, neutral, muted life. You can be as energetic as you want, but there’s inner contentment and serenity that you can access, even if it’s frequently interrupted.

Third, Steve’s chant one evening always stuck with me. It’s a popular chant in the pali cannon, I now know, but I heard it from Steve first:

Anicca vata sankhara

Upada va-ya dhammino

Uppajjitva nirujjhanti

Tesam vupasamo sukho

Translation: All conditioned things arise and pass away. They’re impermanent. Understanding this truth deeply brings the highest happiness, which is peace.

This is the audio of his evening closing remarks near the conclusion of the retreat, where that chant comes at the end. He’s riffing with no notes. I’ve returned to it often in my sits as I find it a good 15 minute overview of the goals of a retreat and the basic argument of mindfulness meditation. 

Fourth, one of the claims of mindfulness meditation practice is you can notice and eventually uproot negative habits of mind. Steve told a story on the retreat about self-pity, from his five years living in Burma. When he was a monk, his “job” was meditating from 3 AM to 11 PM every day. He said that in the early years of his practice he would feel a lot of self-pity. “It’s so noisy in Burma and it’s making it hard to concentrate” or “I’m so sleep deprived, how could I possibly meditate” or “I’m too white and western to really understand meditation.” He noticed that when these feelings of self-pity arose in the mind, his body would feel drained of energy. He spent years observing the seeds of self-pity. He’d try to catch the very early fragments of the feeling, and when he did, he’d say to himself, “I see you self-pity!” He did not invite the thought to tea; he kept it at the doorway to the mind but did not let it enter. He could “catch” the thought while it was still in formation. And he watched the feeling pass away. Over time, he said, you become better and better at noticing and catching unconstructive thought patterns like this, and eventually you can uproot the tendency altogether.

Self-pity is indeed noxious. While gratitude practice would seem to be the right counter-habit, I’ve actually found “agency practice” — reminding myself, “I chose this, I have agency, I made a choice that led me to this experience” — is actually a better combatant to self-pity.

A few other closing thoughts, which I’m writing in haste on a Sunday night before the world goes back to work and 2026 begins:

  • On Steve’s retreat I met Franz Moeckl who taught Qi Gong. It was my first experience with movement meditation and the martial arts. Franz himself was a fascinating character, living a very spiritual life in the mountains of India, and he was a great complement to Steve on the retreat. Franz once told us, to encourage folks to do Qi Gong with him, that your best meditation sits come after movement/exercise. It made the determined meditator group very keen on qi gong and very keen on sitting the optional sitting session afterwards. Steve got a kick out of how Franz motivated people. This is a video of Franz’s qi gong movements, which are the exact movements we learned. I think back wistfully to standing barefoot in the beating sun practicing these movements…pushing the ocean waves, gathering the qi. All the things. I haven’t seen Franz teach a retreat in many years. I wonder if he’s still teaching, if he’s still alive.
  • A couple years ago, when I asked a senior teacher from Insight Meditation Society about Steve’s cancer, she said, “He can’t talk much anymore, but the dharma is so in him, that you can still feel his energy.” Some people radiate their ideas energetically, in addition to verbally.
  • There’s a cohort of the original Western dharma teachers who all studied in Asia, brought their insights back home, and formed the early meditation communities in epicenters like Barre, Massachusetts and Woodacre, California. They will soon die. Teachers who I have learned from and admire in this cohort include Joseph Goldstein himself (the OG), along with Phillip Moffitt, Kamala Masters, Carol Wilson and James Baraz. There’s a real passing of the torch that’s happening right now in the Buddhist insight meditation world.
  • Lastly: Steve said on retreat 10 years ago that your spiritual life begins the moment you deeply understand that everyone you love will die and everything you love will go away.

Goodbye, Steve. Thank you for teaching thousands of students how to see the world through dhamma eyes.

What I’ve Been Reading

Books, books, books.

The Money Trap: Lost Illusions Inside the Tech Bubble by Alok Sama

Fun stories from the Softbank era from a Softbank insider. Masa is such a fascinating character.

All Fours by Miranda July

The book causing women everywhere to divorce their husbands. It’s a compelling quasi-erotic romp through the mind of a mid-life woman rediscovering her sexuality.

But how skilled was he? An overly skilled lover was kind of icky—desire should make you clumsy. I always imagined us tripping all over ourselves with hunger. …

“Everyone thinks doggy style is so vulnerable,” Jordi said, “but it’s actually the most stable position. Like a table. It’s hard to be knocked down when you’re on all fours.” …

My friends are always obliging me with ephemera like this—screenshots of sexts, emails to their mothers—because I’m forever wanting to know what it feels like to be other people. What were we all doing? What the hell was going on here on Earth? Of course none of these artifacts really amounted to anything; it was like trying to grab smoke by its handle. What handle?

Mouth to Mouth: A Novel by Antoine Wilson

A fun novel about a oceanside rescue of an art dealer. The lives of rescuer and art dealer and others intertwine in compelling ways.

Read, Write, Own by Chris Dixon

A terrific argument for the power and potential of blockchain networks. Chris lays out the case for why we should not celebrate big tech’s control of our communication and social network platforms (Fb, Google, Apple, MSFT, etc). At this point, only email has open protocols free of any one big tech provider. Some excerpts (out of order):

What if you couldn’t resell or reinvest in your house or car? Or what if you had to change your name wherever you went? This is the digital world of corporate networks. ….

Think about it in terms of the infrastructure of a city, an analogy to which I’ll continually return. Roads should perform basic functions, but you don’t need them to be hotbeds of innovation. There isn’t that much creativity required; they just need to convey cars. On the other hand, you do want lots of creative entrepreneurs building around the roads: creating new shops and restaurants, constructing new buildings, expanding neighborhoods, and so forth. Roads should be thin, and their surroundings should be thick. …

Cost savings are nice, but wouldn’t it be nicer if companies let users, not just shareholders, participate in their financial success? The market cap of Big Tech companies totals in the trillions of dollars. Users, especially early ones, contribute much to this success. They sell products on Amazon, publish videos on YouTube, share content on Twitter, and so on. Users make early bets, just as founders and investors do. And yet in most corporate networks, users are treated as second-class citizens at best, or as a product to be served up to real customers, like advertisers, at worst. …

The design of the dominant social networks explains what went wrong. Powerful network effects locked users into Big Tech’s clutches, and that lock-in led to high take rates. It’s hard to know precisely what take rates many major corporate networks charge, because their terms can be opaque and noncommittal, but it’s reasonable to estimate they charge around 99 percent. …

The corporate model is like a highly managed theme park that builds the whole experience end to end. The blockchain network is like a city that starts with core building blocks and encourages bottom-up entrepreneurship.

The Decadent Society by Ross Douthat

I try not to miss anything Ross writes.

The Safekeep by Yael van der Wouden

Wonderful plot. One sentence: “Outside, the snow kept on falling. She took off her coat, lit a fire in the kitchen, and made herself small before it.”

The Score Takes Care of Itself: My Philosophy of Leadership by Bill Walsh, Steve Jamison, and Craig Walsh

I didn’t get a lot out of this book. There were some good sentences, though, on the costs of intensity:

When I give a speech at a corporate event, I often ask those in attendance, “Do you know how to tell if you’re doing the job?” As heads start whispering back and forth, I provide these clues: “If you’re up at 3 A.M. every night talking into a tape recorder and writing notes on scraps of paper, have a knot in your stomach and a rash on your skin, are losing sleep and losing touch with your wife and kids, have no appetite or sense of humor, and feel that everything might turn out wrong, then you’re probably doing the job.” This always gets a laugh, but not a very big one. Those executives in the audience recognize there is a significant price to pay to be the best. That price is not something they laugh at.

Who Is Government?: The Untold Story of Public Service by Michael Lewis

Michael Lewis is one of the GOATs but I didn’t find much that was gripping here. Lewis’s premise that government workers are deeply under appreciated is an extraordinary claim.

Lessons from Village Global

Seven and a half years ago, we founded Village Global. Since then: 300+ companies backed, $500M+ AUM, and dozens of lessons learned about how venture firms work.

I just published “30,000 Hours with Village Global” – a smattering and sprawling set of reflections and questions on what’s happening in early stage VC, the art and science of venture, and the hard questions about firm moats.

If you’re a founder, GP, or LP in the ecosystem, I’d love to hear your thoughts.

Book Notes: Good Material by Dolly Alderton

The British author Dolly Alderton writes charmingly about the woman’s perspective on love. Good Material is a fun one.  I stayed with the plot the whole way and did much highlighting on its extensive wisdom about men vs. women and its sharp observations on 30-something life. Bolding is my own.

We shifted from overfamiliarity to inquisitiveness from sentence to sentence; alternating from feeling like old friends to strangers. We gave too much information about ourselves, then we pulled back. We got a kick out of the novelty of each other, heightening ourselves for the other one’s enjoyment…

“Reverse break-up schedules,” he explains. “When men and women break up, men hate everything about their ex-girlfriend for three months, and then they miss her, and then they think they love her, and that’s when they text her. Meanwhile, she has spent three months loving him and then she hates his guts forever,” he says, leaning in for emphasis, his breath hot and tangy with gin. “We were never meant to be with each other. Men and women are not compatible.”

“Hey mate, saw what’s happening online. Hope you’re ok.” I have no idea what he’s talking about, but there is no scenario in which this text is not one of the worst texts you can wake up to other than being informed of a death.

Complaints about people on first dates:

  • Talked too much and too smugly about coming from a big family, as if it was her decision to have three siblings.
  • Somehow managed to relate the plot of every film we watched back to her own life.
  • Was too connected to dogs and spoke to them as if they were people.
  • Too nostalgic. Couldn’t live in the present. Will always think that yesterday was better than right now. He genuinely believes the peak of his life was when he was in his early twenties and doesn’t understand that he has the power to make the best moment of his life the moment he’s living in.

She was the one with all the power. Because the person who is in charge in a relationship is the one who loves the least.

[Getting over a breakup] “You don’t let go once. That’s your first mistake. You say goodbye over a lifetime. You might not have thought about her for ten years, then you’ll hear a song or you’ll walk past somewhere you once went together—something will come to the surface that you’d totally forgotten about. And you say another goodbye. You have to be prepared to let go and let go and let go a thousand times.”

…which led to an argument, and he said: “I would love you no matter what your opinions were.” And I know he was telling the truth. He would have loved me unquestioningly and stubbornly forever. And I don’t know if I want to be loved like that.