Leadership,
Bird by Bird

A field guide for the
thoughtful administrator.

These cards reflect an approach to leadership I've developed over the years. Each one pairs a leadership idea with a bird. Why? Because birds reward the kind of attention that leadership also requires: looking carefully, sitting with uncertainty, noticing what's actually there.

In my Graduate Studies role, I've emphasized communication, collaboration, and continuous improvement. These notes have grown out of the experience of trying things, learning from others, and paying attention along the way. I created them for my colleagues and my team, for the students we serve, and for anyone who wants to lead thoughtfully and keep growing.

I hope you'll find something here that's useful, or that makes you smile, or that sends you outside to look at a bird.

Jon Woon
Pittsburgh, PA

Leadership, Bird by Bird No. 001
What's your why?
A clear sense of purpose keeps you from mistaking motion for progress. Performance isn't meaning. Look to your North Star. Everything else is noise.
Red-tailed Hawk (Buteo jamaicensis) — circles for hours, but never loses sight of the one thing it's after.
Leadership, Bird by Bird No. 002
Ask good questions
Questions let you see around corners. Ask what's working, what isn't, and what you're missing. Then ask why. People know things you don't, but you'll only know if you ask.
Carolina Wren (Thryothorus ludovicianus) — one of the loudest birds in North America relative to its size.
Leadership, Bird by Bird No. 003
Conduct small experiments
You don't need a five-year plan to find out if an idea works. Try the smallest version of it to see what you learn. Then adjust and repeat.
Sanderling (Calidris alba) — runs the tideline, probing dozens of spots in the sand as each wave recedes.
Leadership, Bird by Bird No. 004
Look for the helpers
Who shows up because they care, because the work needs to be done, or because they value serving others? Build your team around them. They're the ones worth listening to.
Pygmy Nuthatch (Sitta pygmaea) — offspring from a previous brood often stay behind to help their parents feed and defend the next clutch.
Leadership, Bird by Bird No. 005
Someone has to do it
Ask the hard questions, explain the difficult decisions, and hold the line when it's unpopular. Rarely thanked. Sometimes resented. Absolutely necessary.
Turkey Vulture (Cathartes aura) — eats what nothing else will, preventing the spread of disease that decomposing carcasses would otherwise cause.
Leadership, Bird by Bird No. 006
Shared sense-making
No single person sees the whole picture. Pooling what different people notice gets you closer to what's actually true. Faculty, staff, students, and deans all see something the others miss.
Tufted Titmouse (Baeolophus bicolor) — joins mixed-species winter flocks.
Leadership, Bird by Bird No. 007
Empower others
Give a person instructions, and they can do one concrete task. Empower them to use their own judgment, and they'll have a career of solving problems no one saw coming.
Osprey (Pandion haliaetus) — parents drop live fish near the nest, forcing the young to practice catching for themselves.
Leadership, Bird by Bird No. 008
Email is my
love language
Some people show care with gifts or quality time. I show it with a thoughtful subject line and the right people in CC.
Rock Pigeon (Columba livia) — domesticated, persistent, shows up daily whether or not you asked it to.
Leadership, Bird by Bird No. 009
It's not about you
Check your ego at the door. Managing optics or protecting your feelings are the wrong reasons. Criticism is inevitable, and yes, some of it will be unfair. The work is for the people you serve.
Killdeer (Charadrius vociferus) — performs a broken-wing display to lure predators away from the nest.
Leadership, Bird by Bird No. 010
Aim to see clearly
Most mistakes aren't failures of effort. They're failures of seeing what's actually happening, not what you expect or hope to see. Clarity comes before judgment, and judgment comes before action.
Peregrine Falcon (Falco peregrinus) — some of the sharpest vision of any animal, and the fastest dive of any bird, reaching over 200 mph. The speed only works because the vision finds the target first.
Leadership, Bird by Bird No. 011
Be unafraid
Say the hard things. Make the hard decisions. Not recklessly, but deliberately. Not because it's comfortable, but because it's necessary.
Eastern Kingbird (Tyrannus tyrannus) — dive-bombs hawks and crows ten times its size without hesitation.
Leadership, Bird by Bird No. 012
Perfect is the enemy
of the good
Getting everything exactly right means never finishing. If it works, it works. Just like the only good dissertation is a done dissertation. You can improve it later.
Black-capped Chickadee (Poecile atricapillus) — small, unglamorous, and everywhere. Gets through winter just fine.
Leadership, Bird by Bird No. 013
Clarity, connection,
and care
Be clear about what you mean. Stay connected to the people you lead and serve. Follow through with care as a practice you show up for daily.
American Robin (Turdus migratorius) — clear song at first light, travels in flocks, never stops feeding the nest.
Leadership, Bird by Bird No. 014
There isn't a secret
pot of gold
Faculty assume a hidden reserve exists and that if you push hard enough, it will suddenly appear. It doesn't exist, and it won't appear. The budget is finite and already spent. Why wouldn't it be?
Clark's Nutcracker (Nucifraga columbiana) — caches up to 30,000 seeds across a mountainside and remembers nearly every one. If anyone has a hidden stash, it's this bird.
Leadership, Bird by Bird No. 015
Test. Update. Repeat.
What makes for good science also makes for good governance. Challenge your assumptions, look for disconfirming evidence, and be willing to change course without ego getting in the way.
Blue Jay (Cyanocitta cristata) — caches food, but relocates it if it suspects it was watched.
Leadership, Bird by Bird No. 016
Take the shot
You miss 100% of the ones you don't take. Don't let fear keep you from trying. You can learn from failure. Don't throw it away.
Belted Kingfisher (Megaceryle alcyon) — has to commit to the dive.
Leadership, Bird by Bird No. 017
Food is cheap.
Morale is priceless.
Pizza isn't a perk — it's the cheapest, highest-yield line item in the whole budget. Food gets people in the same room, relationships get built, and a group becomes a community.
Cedar Waxwing (Bombycilla cedrorum) — passes a single berry down a line of birds before one eats it.
Leadership, Bird by Bird No. 018
Disappointed,
not surprised
Transparency doesn't make hard decisions popular. It makes them legible. If you've explained the reasoning and the constraints, disappointment is expected and acceptable. Surprise means the communication failed.
Common Nighthawk (Chordeiles minor) — appears reliably at dusk, but its flight pattern appears erratic.
Leadership, Bird by Bird No. 019
It's a real job
Faculty set their own hours, choose their own questions. Administration means meetings, email, red tape, and people problems. The calendar keeps filling up, and the inbox is never empty. It's dark because the tunnel has no end.
American Crow (Corvus brachyrhynchos) — commutes to and from a communal roost daily, rain or shine.
Leadership, Bird by Bird No. 020
Give and ask for reasons
A culture of reason is a culture of accountability. Explaining your thinking and inviting challenge makes decisions legible — to others, and to yourself. That's how trust gets built and institutions thrive.
Song Sparrow (Melospiza melodia) — in territorial disputes, one bird sings, and another responds.
Leadership, Bird by Bird No. 021
Risk is probability
and magnitude
Sure, something bad could happen. But how likely is it, and how bad would it actually be? Weigh that against the upside and against your other options.
Great Blue Heron (Ardea herodias) — stands motionless, weighing whether this fish is worth the strike.
Leadership, Bird by Bird No. 022
Patience
It's active, not passive. Not disengaged, not idle — watching. Stay alert. Stay present. Stay disciplined.
Great Horned Owl (Bubo virginianus) — can perch motionless for hours, watching. When it moves, it moves.
Leadership, Bird by Bird No. 023
Mission-focused
The university's purpose is the production and transmission of knowledge. Stay focused on that as our common cause. Don't mistake tasks and rhetoric for the mission.
Arctic Tern (Sterna paradisaea) — migrates pole to pole, roughly 25,000 miles round trip.
Leadership, Bird by Bird No. 024
What's the problem?
Don't skip the most important step. The right answer to the wrong problem is still wrong. Articulate clearly what you're trying to solve.
Barn Owl (Tyto alba) — hunts entirely by sound in complete darkness, homing in on what it cannot see. Knows exactly what it's after.
Leadership, Bird by Bird No. 025
Find joy
It isn't a bonus; it's what makes the grind sustainable. Find the parts that light you up — a student breakthrough, a good conversation, a problem finally solved. If you can't find them, pay attention to that too.
Atlantic Puffin (Fratercula arctica) — recognizes its mate after months apart at sea, with what can only be described as enthusiasm.
Leadership, Bird by Bird No. 026
Know when it's time
Some moments call for departure, others for commitment. The difference isn't always obvious in advance — but missing the window costs you either way.
Ruby-throated Hummingbird (Archilochus colubris) — roughly doubles its body weight before migration, then times departure around weather windows for a nonstop overwater flight.
Leadership, Bird by Bird No. 027
Treat people as ends
People are not merely resources to be managed. Valuing the judgment, experiences, and perspectives they bring to their work honors their dignity and worth. The people are the point.
Trumpeter Swan (Cygnus buccinator) — mates for life, raises young together, and travels in family groups.
Leadership, Bird by Bird No. 028
Make it visible
The hidden curriculum, assumptions that go unexamined, criteria that go unstated, rules that only some people know. Make the implicit explicit. Equity requires it.
Red-winged Blackbird (Agelaius phoeniceus) — the red epaulets are displayed when it matters.
Leadership, Bird by Bird No. 029
Be willing to fail
You don't need certainty. You need enough preparation and judgment to trust your team. Waiting feels like prudence, but it's just anxiety in disguise.
Wood Duck (Aix sponsa) — ducklings leap from the nest cavity on day one, sometimes 50 feet, before they can fly.
Leadership, Bird by Bird No. 030
Always faculty
The best administrators never stop being scholars. Their credibility, their judgment, their sense of what matters — all of it stays grounded in the questions that brought them there in the first place.
American Goldfinch (Spinus tristis) — trades its bright breeding plumage for a more subdued winter coat - different colors, same bird.
Leadership, Bird by Bird No. 031
Do unto others
Be as transparent with others as you expect them to be with you. Explain your reasoning, not just your conclusions. Accountability runs in both directions.
Northern Cardinal (Cardinalis cardinalis) — attacks its own reflection for weeks, certain it's defending territory from a rival that was never there.
Leadership, Bird by Bird No. 032
Think outside the box
Some problems can't be solved from inside the frame. Nine dots. Four lines. The answer is outside the convex hull.
Burrowing Owl (Athene cunicularia) — most owls nest in tree cavities - this one digs underground.
Leadership, Bird by Bird No. 033
Beware career concerns
Some build, others climb. Advancing mission may require the kind of sacrifice and honesty that supports others in the long run. The ladder often rewards saying the right things in the moment. Don't confuse the two. Do what the institution needs.
Brown-headed Cowbird (Molothrus ater) — lays its eggs in nests built and defended by other species, who then raise the cowbird's chick, often at real cost to their own.
Leadership, Bird by Bird No. 034
Reason together
Share ideas, then challenge and build on them. Each idea invites a response. Each response opens something new. The back-and-forth is genuine deliberation, and it generates something no individual can reach alone.
European Starling (Sturnus vulgaris) — a murmuration has no leader, with each bird responding to its nearest neighbors.
Leadership, Bird by Bird No. 035
You are not alone
No one leads, learns, or succeeds alone. Lean on colleagues, mentors, and communities of practice - they are sources of strength. Build a culture so others can do the same.
Common Raven (Corvus corax) — calls in others so that a group can defend a large food source from a rival pair.
Leadership, Bird by Bird No. 036
Metric isn't mission
Imperfect proxies for what actually matters shouldn't be optimized as if they were the real thing. Metrics are information, not a substitute. Don't let the dashboard become the destination.
Piping Plover (Charadrius melodus) — the threatened shorebirds are among the most studied, with extensive data, yet the population is still declining.
Leadership, Bird by Bird No. 037
No surprises
Keep people informed, even when something seems straightforward and the details feel unimportant. A quick "FYI — no action needed" builds trust and alignment.
Canada Goose (Branta canadensis) — they're loud and they poop everywhere.
Leadership, Bird by Bird No. 038
The goal is flourishing
People thrive when they grow into their potential, find meaning in their work, and contribute to something larger than themselves. Keep that in view. Build the community and conditions that enable it.
Bald Eagle (Haliaeetus leucocephalus) — nearly gone from the lower 48 by the 1960s. Brought back not by chance, but by deliberate effort.
Leadership, Bird by Bird No. 039
Everyone belongs
Everyone who is here belongs here. Not tolerated, not accommodated — fully included. Make that true in practice.
African Penguin (Spheniscus demersus) — breeds in dense colonies where individuals recognize each other by voice. No penguin is anonymous; no penguin is alone.
Leadership, Bird by Bird No. 040
Keep flowing
When something gets in the way, don't force your way through it. Stay calm, stay steady. Move gently, but keep moving. The rock will become sand.
American Dipper (Cinclus mexicanus) — lives in fast-moving streams, constantly bobbing, never still.
Leadership, Bird by Bird No. 041
\ \ \ \ \ \ \ \ \
Distribute authority
The chain of command is not about following orders. Each level is trusted to exercise judgment suited to the conditions on the ground. When responsibility and authority match, the mission succeeds.
Sandhill Crane (Antigone canadensis) — migrates in formation; the lead position rotates to whoever's best positioned, not a fixed rank.
Leadership, Bird by Bird No. 042
Less is more, sometimes
Restraint might be the right call. So might firmness, or visibility. Read the room, and match the approach to the audience and the situation. Consistency in values, flexibility in approach.
Mallard (Anas platyrhynchos) — males bright and showy, females drab and camouflaged.
Leadership, Bird by Bird No. 043
Complexity
requires resilience
Optimizing for efficiency in complex environments optimizes for fragility. Redundancy, flexibility, and distributed risk prevent a single point of failure from becoming a catastrophe.
Northern Mockingbird (Mimus polyglottos) — never stops expanding its repertoire.
Leadership, Bird by Bird No. 044
Stop and think
Most things feel urgent. Fewer things actually are. Not everything that demands an immediate response deserves one. What can, and should, wait?
American Kestrel (Falco sparverius) — hovers motionless against the wind before striking.
Leadership, Bird by Bird No. 045
Leave it better than
you found it
Your greatest accomplishment is what you leave behind: documented decisions, people ready to lead, systems that don't depend on any individual. That's the difference between filling a role and having real impact.
Pileated Woodpecker (Dryocopus pileatus) — excavates a cavity, uses it for one season, leaves it for other species to use.
Leadership, Bird by Bird

Further Reading

  • Bazerman, M. H., & Moore, D. A. (2012). Judgment in Managerial Decision Making (8th ed.). Wiley.
  • Bolman, L. G., & Gallos, J. V. (2011). Reframing Academic Leadership. Jossey-Bass. (2nd ed. as Gallos & Bolman, 2021.)
  • Buller, J. L. (2013). Positive Academic Leadership. Jossey-Bass.
  • Burkeman, O. (2024). Meditations for Mortals. Farrar, Straus and Giroux.
  • Greenleaf, R. K. (1977/2002). Servant Leadership: A Journey into the Nature of Legitimate Power and Greatness. Paulist Press.
  • Lamott, A. (1994). Bird by Bird: Some Instructions on Writing and Life. Pantheon.
  • Newport, C. (2024). Slow Productivity. Portfolio.
  • Ostrom, E. (1990). Governing the Commons. Cambridge UP.
  • Patterson, K., Grenny, J., McMillan, R., & Switzler, A. (2002). Crucial Conversations. McGraw-Hill.
Leadership, Bird by Bird
  • Scott, K. (2017). Radical Candor. St. Martin's Press.
  • Aristotle. Nicomachean Ethics. → Card 38
  • Brandom, R. B. (1994). Making It Explicit: Reasoning, Representing, and Discursive Commitment. Harvard UP. → Cards 20, 31, 34
  • Habermas, J. (1984). The Theory of Communicative Action, Vol. 1. (T. McCarthy, Trans.). Beacon. → Card 34
  • Kahneman, D. (2011). Thinking, Fast and Slow. Farrar, Straus and Giroux. → Card 44
  • Kant, I. (1785/1998). Groundwork of the Metaphysics of Morals. Cambridge UP. → Cards 27, 31
  • Muller, J. Z. (2018). The Tyranny of Metrics. Princeton UP. → Card 36
  • Nussbaum, M. C. (2011). Creating Capabilities: The Human Development Approach. Harvard UP. → Cards 7, 39, 38
Leadership, Bird by Bird
  • Perrow, C. (1984). Normal Accidents: Living with High-Risk Technologies. Basic Books. → Card 43
  • Rogers, F. (2003). The World According to Mister Rogers: Important Things to Remember. Hyperion. → Card 4
  • Sen, A. (1999). Development as Freedom. Knopf. → Cards 39, 38
  • Simon, H. A. (1947). Administrative Behavior. Macmillan. → Cards 24, 41
  • Sinek, S. (2009). Start With Why. Portfolio/Penguin. → Card 1
  • Voltaire. (1772). La Bégueule. → Card 12
  • Weick, K. E., Sutcliffe, K. M., & Obstfeld, D. (2005). Organizing and the process of sensemaking. Organization Science, 16(4), 409–421. → Card 6
swipe the card, use arrows, or ← → keys

© 2026 Jonathan Woon