Musings on Leadership

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I subscribed, a couple of weeks ago, to a product marketed to “leaders”, or those who hope to be leaders. The content looked interesting, and it has indeed been well worth the investment of time and treasure–but I’m also reminded of my deep ambivalence about “leadership”.

Niccolo Machiavelli, in the 15th and 16th century, had some powerful insights about how to exercise a kind of leadership. My memory of The Prince is vague, but one bit of advice surfaces (likely imperfectly) from memory as particularly wise counsel. A prince, he said, should not harm potential opponents in ways from which they can recover. Either leave them in peace, or destroy them; don’t leave them hurt, insulted, and able to avenge themselves. It’s wise advice, effective for the prince who wishes to retain power, and quite possibly good for his kingdom, in the stability it provides. It’s also quite “cold”, and the negative associations of Machiavelli’s name today are not entirely without reason.

Jim Jones was a highly successful leader, if one looks at the depths of his followers’ commitment. Demagogues, from the ancient world to the present, have often been successful, building broad, passionate support and stamping the world deeply with their imprints. Preachers wealthy from “shearing” their flocks are, by some standards, successful influencers. The captain and the chaplain behind the massacre at Mystic were quite effective in leading others to fulfill their objectives.

The thing is, leadership isn’t inherently positive. Influence, vision, motivation, strategy, changemaking, persuasion, and efficacy can all be horrible things.

A lot of leaders shouldn’t be leading. Many are leading toward harmful goals. Many are “leading” for the side benefits: the prestige, the identity validation, the economic gain. And some lead with positive goals, but lead poorly, negating the value they might offer to humanity.

Could it be that leadership would benefit from being a profession, with gated admission, a code of ethics, and competency requirements? “Mr. Smith, after reviewing your objectives and actions and surveying your colleagues, the review board has imposed a mandatory suspension of your leadership responsibilities and influence. An application for resumption will be considered if submitted within three months. The application should include both a demonstration of the social good of your objectives and a specific plan for remediation of the issues addressed in the attachment.”

A “leadership profession” is hardly likely, to be sure, and probably a bad idea. But how might things change if each of us established a “review board” inside their head? This “board” would enforce a basic set of leadership standards on ourselves, and coach us through improvement when we fail. When others “betray the leadership profession”, we’d help them redirect, or work to de-legitimize them as leaders if they reject such standards? How would we keep that ethos from turning into a circular firing squad?

What would a foundational set of leadership standards look like? Is a shared set of standards even possible?

I don’t know. I do think, though, that a story about Jesus sheds light for me. The story goes that his apprentices were with him, and jockeying among themselves for status. And Jesus sees this happening (they were all together), and he gets up, grabs a towel, and starts washing the besandaled, road-dirty feet of every one of his apprentices who were with him. The teacher, stooping in front of each apprentice and scrubbing his polluted feet! They were, of course, appalled, even shamed, that he was doing this to them. And then he told them: “You know that those who lead ‘out there’ can do whatever they want, and other people call them great and good. But among you–someone who is ‘great’ will be a servant to others.”

What does a foundational set of leadership standards look like? What distinguishes a good leader from one who shouldn’t lead? How might we, collectively, increase the prevalence of beneficial, competent leadership?

Three-Minute Thought: The Skills of Miners and Mongols

One pattern of learning is to delve deep into a subject, going far beneath the surface to find the treasures that no one else sees. These mines hold treasures, and they’re unassailable–but it’s easy to block the entrance to the “surface” world.

Another pattern is that of the Mongol hordes. Their pattern was to move fast, spend a bit of time securing the territory, and then sweep onward, taking with them a harvest of intellectuals and craftsmen from the conquered cities. They were formidable…and as they went, their culture changed to something new.

The Mandelbrot set, a fractal, is infinite in detail, yet it fits in a constrained space. Yeast also grows in fractal fashion, yet in expansionary mode.

The empire of the mind needs to produce its own treasure. The empire needs intellectual raiders.

A Basket of Books

As a kid, I brought home library books by the laundry-basket-full. My books-per-week rate has gone down substantially as other responsibilities have grown, but I still love reading.

My current “basket” is relatively small, though it holds more than the books below. A few of the books I’m currently excited about/intrigued by:

  • Questions Are the Answer, by Hal Gregerson. I’m several chapters in. Interesting discussion of the power, uses, and abuses of questions.
  • The Effective Executive, by Peter Drucker. This was a magical book when I first read it 20(ish) years ago; it still is, partway through my current re-read. Drucker was a prophet of business, lucidly describing the effective “knowledge worker” long before most others. Actually, his whole corpus is wonderful. Also pick up The Daily Drucker for a daily, one-page nugget of (frequently) transformative thought.
  • Range: Why Generalists Triumph in a Specialized World, by David Epstein,  is a book I haven’t yet read, hadn’t even heard of till recently, but am very excited about starting soon. It sounds like he interacts with a lot of other interesting ideas: Gladwell/Coyle/Syed/Dweck on the development of talent and growth mindset, the tension between “deep dive” and “broad survey” approaches to knowledge (and the magic that happens at the intersections of fields), and in general, something approaching the “latticework of mental models” that Charlie Munger uses for evaluation of ideas through diverse frameworks. (See Poor Charlie’s Almanack, Shane Parrish’s Farnam Street, or a simple Google search for more on Munger and models.)
  • The Great Escape: Health, Wealth, and the Origins of Inequality I’m barely past the introduction. My initial sense is that it will be an interesting, and non-simplistic, examination of how economic growth moves the “average” upward, how it causes inequality…and how inequality can, in turn, contribute to economic growth. The author starts with a story of his father’s “great escape” from mining…and a reflection on the many in similar circumstances whom his father’s “escape” left behind, then uses this as an example of the many “escapes” that happen. I’m looking forward to seeing how the author interacts with the ethics of the issues.

Other books will wait for another day.

Three-Minute Thought: 100:1 ideas

A great roadmap I stumbled across for generating and exploring ideas for action, and actually moving to implementation (rather than just having a cloud of circulating ideas):

  • Generate 100 ideas.
  • Choose the top ten and dig deeper into them.
  • Drive one of the ten to full implementation.

More info via Charles Chu and Nick Bentley, though I encountered the idea somewhere else (but can’t remember where).

All Intellectuals Are Wannabes

I’m a wannabe intellectual. I always have been. I love the life of the mind, admire those who’ve done the work and come up with original insights–but I haven’t put in the hard work, and have no Revelation From The Deep Well of Reality to share.

But it occurs to me: maybe all intellectuals are wannabes. Not one knows everything there is to know, even in his particular field. And despite the occasional originality, most intellectual advancement comes from remixing the thoughts of others. Remixes happen under the influence of a particular person’s experience and cultural context; even if they aren’t “original”, they may bring new insight. And ideas don’t flow instantaneously and freely throughout humanity. So, if the group of which I’m a part would otherwise never encounter the ideas of a “great intellectual”, to translate and bridge her ideas into my context is not arrogance, is not redundant effort, but is service to those around me and to the world.

All true intellectuals “wanna be” better, and want the world to be better, and invest mental and (probably?) communicative energy in that. “Better” is a moving target, individually and corporately, and we won’t ever declare complete success–but perhaps even one who isn’t a “real”, qualified, worthy intellectual of the highest caliber can add value in this effort.

I am anything but an accomplished intellectual. But maybe it’s OK to be a wannabe.

Related:

  • The Loving Intellect”, a worth-reading article (focused on a “Christian intellectual”) in First Things, a publication I often regard with some skepticism. I found to be helpful the idea of deconstruction as a tool for use in a larger effort.

A few of the many sources I love for “remixing”:

  • Farnam Street: impressively wide and deep consideration of how to live, learn, and think well; introductions to many other thinkers.
  • Brain Pickings: wide-ranging reflection; introductions to many others. 
  • New Scientist: somewhat “popular” science magazine 
  • Aeon Magazine: just check it out. 
  • Oh. And the book Worldchanging, by Alex Steffen, was lovely when I read its first edition. It’s probably somewhat dated by now, but inspiring.
  • Related to that: check out the Ashoka Foundation, with its focus on social entrepreneurship around the world.

Three-minute thought: analogies and treasure stores

“Three-minute thoughts” are quickly written, minimally fleshed out, possibly wrong, certainly non-comprehensive, and may or may not become a regular feature in some form.

We learn through analogies (“this is like that, except for…”), and most of our useful thinking is done through analogies. The boundaries of our thought are, generally, constrained by what we can mentally access for analogy. Being mostly a “surfer” of the intellectual world is not inherently deficient, as long as you maintain velocity–the more ideas and models of the world you encounter, the more you can organize your intellectual library of curiosities, the more likely you are to recognize the value (or lack thereof) of an idea, and the richer will be your treasure store of material for use in analogy.

Offhand questions: How does this connect with the ideas of spaced repetition for retention of important knowledge, the value of forgetting in maintaining a functional mind, or the ideal of T-shaped knowledge?

Deep Knowledge: A Pure White Stone (Part 4 of 4, unfinished)

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This series reaches its climax with a resounding…lack of resolution. We’ve covered the dream of a firm “place to stand”, something that can be known and proved. We’ve looked at the idea that we see “through a glass, darkly”. We’ve visited my chamber of “sticky notes”, a place filled with provisional models of the world and my subjective assessment of their quality–along with a few un-provable things I’ve chosen simply to hold as true. (Visit that post for an interesting interchange in the comments. It reveals my status as a near-complete layperson in the realm of philosophy, but includes some helpful insight from my conversation partner.)

I initially intended this post to be the end of a four-part series, shading substantially into the “religious”–as, I think, do most attempts to explore the nature of knowledge and of the world. As I tried to write it, though, I discovered that, at the moment, I can’t really write the intended post. The ideas, I think, were sound–but just aren’t coming together in useful, fleshed-out form. As a sketch, though, consider with the previous three posts that:

  • One’s model of reality is ultimately based on at least one, and probably many, unprovable assumptions.
  • One therefore must act without the comfort of provably “knowing” that one is acting correctly.
  • I make the huge jump of assuming that a supreme god, who is powerful, good, and loving, and who created physical reality, exists and actively builds channels of relationship with humanity–and that that God self-revealed as YHWH and as the first-century Jewish man Jesus. At this point, Dawkins thinks my “flying teapot” assumption is foolish and Marx thinks I’m turning toward numbness rather than addressing the real problem–and I can’t prove the validity of my assumptions, though they’re no more poorly warranted than strict materialist assumptions.
  • If such an assumption is actually true, then “loopholes” to the impenetrable veil of uncertainty may be possible, by the action of the One who transcends physical reality. It would be possible to “know”, not by sheer deduction but by revelation. And yet–even pure, divine revelation comes to finite, biased, flawed, humans in biased and flawed societies, and the Venn diagrams of mystical revelations, mental illness, and chemical journeys aren’t simple. I cannot know, with provable certainty, that my faith is in something “real”.
  • The early writers of my faith tradition beat me to this realization: “faith is the assurance of things hoped for, the conviction of things not seen” (Heb 11:1). In another letter, the Apostle Paul wrote that “hope that is seen is no hope at all. Who hopes for what they already have?” (Rom 8:24).
  • Faith is trust. Faith is not “knowing” or even deeply understanding; what is known is no longer a subject of faith. Faith is lack of knowing, but acting in reliance on a truth or a person despite being unable to make certain that you’re “right” in your trust.
  • Even “knowing” is a complex term. I “know” my wife and I love her, despite being unable to prove that she actually exists! And yet, while I think I know her well, there’s much of her essence that I know I don’t know, and much that I don’t yet know I don’t know. I “know” the language I use to develop software: not in terms of what it “truly is”, but in terms of how I interact with it.
  • …and somewhere in all of that is where the “pure white stone” comes in. In the strange, glorious and beautiful, horrifying and bloody, confusing apocalyptic vision of John (according to church tradition, the John who was Jesus’ companion), a transcendent Jesus promises that “To the one who is victorious, I will give some of the hidden manna. I will also give that person a white stone with a new name written on it, known only to the one who receives it” (Rev. 2:17). And somewhere, deep in my psyche, I “know” that John, and other prophets and mystics, encountered something real, something that my materialist reflexes can’t deal well with, something that needs to be woven with the rationalist threads of my being to make a rich, paradoxical, whole. The “what is it” and the “secret name”, that powerful, effectual symbol of my essence, are gifts from one who embodies power, gentleness, and paradox.

To use my mind is essential for perceiving truth. To use my mind leads to the conclusion that the mind cannot, with certainty, perceive truth. We sapiens are built for knowledge, and to find it fatal. We “level up” our understandings of the physical world and the world beside or behind it–and we do violence to both as we vivisect them.

I’m a skeptic. I’m a mystic. I’m a stoic, and a believer that real men do cry. I’m a superstitious materialist, and a doubting believer. Pick a category, and I’ll disappoint your expectations. But, if my faith is indeed in something real, I’m loved. And one could do a lot worse as a philosophical north star.

(Note: you should really visit the comments to the previous post. Those comments make very clear my status as a philosophical naïf; it’s been a long time since Philosophy 101, and, it was Philosophy 101. But it’s clear that I’m addressing myself to subjects that minds far sharper and more experienced than mine have also addressed over the centuries, and would do well to orient myself again to the topics and prior work–and I’m intrigued by the prospect!)

Deep Knowledge is a four-part series in progress, in which I ramble concerning the nature of knowledge, our capacity to handle it, and our orientation to it. Parts include:

Deep Knowledge: The Chamber of Sticky Notes (Part 3 of 4)

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I’ve been looking for the solid truths of the world, things I can know without a doubt. And yet, I’ve discovered that–though I don’t doubt the existence of the truly real–to say that the real exists is a very different thing than to say I understand the real.

You may have seen the movie version of a command center: panels of screens, some with scrolling data, others with plots of missile trajectories or disease outbreaks, and yet others awaiting instructions (authenticated by iris scan or voice-print, of course) from the Very Important People. They know what they need to know. They have eyes in the sky, NSA taps into Internet chokepoints, radar, real-time data feeds. They know how to respond, and they do so decisively. It’s a very satisfying story.

The command center of my psyche is a bit different. Behind a sliding bookcase, at the end of a tunnel that glows with candlelight and smells of incense, is a windowless room. It’s anything but gloomy, with warm wood walls and abundant cushions for reclining. There’s a desk and a comfortable chair…and on every wall, a chaos of sticky notes.

“I should eat more protein; p=0.6.”. “Cycling even in horrible air is still a net positive for health; p=.55”. “John is generally trustworthy; p=.95”. “Killing a person without provocation is morally wrong; p=.999”. “I should not give to beggars by default; p=.5”.

You might know the story of Erwin Schrödinger’s hypothesized cat, who lived (or died) in a box with a flask of poison and a switch to open the flask (or not) based on the randomness of radioactive decay. Until the box is opened, says Schrödinger’s interpretation of quantum theory, the cat is both dead and alive. Aside from the flask-of-poison thing, the cat has a wonderful life. It will not, it cannot, commit to so simple a thing as being either alive or dead!

Unlike the cat, I’m often forced to decide. I’m often forced to act. And those decisions are never perfect ones, based on a perfectly clear view of reality. I’m forced to make a provisional decision, a guess, and then move forward from it. But the guess might be wrong!

Some guesses “feel” more confidently right than others. I really don’t think I’ll conclude anytime soon that, well, execution by flaying is after all an appropriate action in some cases; my opinion on the subject is really rather firm. But my sense that “it will probably take about an hour to go across town” has much less confidence attached–neither half an hour nor an hour and a half would be completely shocking. Both of these have subjective probabilities of being right; the “no gruesome killings rule” with near certainty, the travel-time expectation with about 50% confidence. And yet, I sometimes have to act on an assumption that’s as likely to be wrong as right–or even, sometimes, on a “best out there, but probably wrong” one.

The problem is, the inability to see perfectly inheres in being human. In other words, flawed perception and flawed reasoning is guaranteed. (If you haven’t had your fill of umlauts, go check out Kurt Gödel for one lens on this.) In such a situation, the question is not whether you’re wrong, it’s a question of how wrong you are. And then, to act in the way that seems least wrong, with no guarantees that it is indeed the least-wrong way. And so, my sticky-noted beliefs have probabilities attached. They might be wrong. Even the probabilities might be wrong. But life often demands answers, and the sticky notes provide them–acknowledging that they’re imperfect, that I’m imperfect, and that I can truly, indubitably, know almost nothing at all. To claim otherwise is to assert my perfection, which I’m far from ready to do.

“Sticky notes” aren’t just for insignificant issues. Often, the “wishy-washiness” of a sticky-note isn’t because its subject doesn’t matter; it’s because it does, and the issues are far too important and too complex to risk “locking into” a wrong position. And yet, since many situations demand “answers”, the sticky notes are there: acknowledgments that my understanding is certainly incorrect and incomplete to some degree, and that each of my “answers” is provisional, and subject to change if I find a better one.

Among the sticky notes, there is one small cluster of metal etchings. That’s a cluster of things I simply choose, completely indefensibly, to hold as true. (I don’t pretend to have moved beyond the smallest foothills of understanding it, but Michael Polanyi’s work on “personal knowledge”, as filtered through the first part of Lesslie Newbigin’s Proper Confidence, was nevertheless a game-changer for me on this, an argument that a set of some such indefensible commitments is essential to communicating about any kind of knowledge.)

Each of my sticky notes helps me engage the world without collapsing into indecision. Each one reflects the reality of my cognition: three pounds of soft tissue trying to grasp something far vaster than itself, with the guarantee that its perceptions will be incomplete and incorrect, and that their processing will be influenced greatly by the “noise” within and without.

Sometimes, in the windowless comfort of the Chamber, there’s an inexplicable whisper of wind. The notes on the wall rustle; occasionally, one falls to the floor and I can’t quite figure out where to reattach it. And I rest, and I read, and I sort, and I update my scribbled portals to the world.

Deep Knowledge is a four-part series in progress, in which I ramble concerning the nature of knowledge, our capacity to handle it, and our orientation to it. Parts include: