Leadership lessons from Widow’s Bay and the Bay of Pigs.
Of course a scene from a comedy-horror show got me thinking about leadership; specifically on how faking it leads to fear, and fear leads to self-protection, and self-protection leads to a culture of compliance1. From there it was just a short hop, skip, and a jump to thinking about President Kennedy and the Bay of Pigs.
“Really?”, you say. Yep. Read on and let me know what you think.
Heads up! I mention “non-fragility” in this post without much of an explanation. If you want more, read Brian Klaas’s essay “What is Resilience”. For the reader to whom I made a half-arsed commitment to writing about resilience, this essay is better than anything I could have attempted.
Ding-Dong-Ditch
I just started watching the comedy-horror show Widow’s Bay and was quite taken with an exchange between the not-really-of-the-island Mayor and the delightfully stereotypical crotchety-superstition-believing old timer Wyck. It seems that the Mayor was a regular visitor to the island in his youth and would join in with other lads in that annoying and very-not-cool prank of ringing door bells and running away. But Wyck calls the Mayor out on this piece of personal history in the following exchange.
Mayor: Why won’t you let me lead this town?
Wyck: I don’t think you can lead.
Mayor: Will you be able to forgive yourself if you’re wrong, and you have ruined this town’s chances?
Wyck: Will you be able to forgive yourself if I’m right?
Mayor: You cannot stand someone else being in charge, can you?
Wyck: Nah.I just know people,
Mayor: Wyck, I have done nothing to deserve this lack of trust.
Wyck: You remember when you and your little buddies used to take turns doorbell ditching my house during your little summer visits?
Mayor: That is what this is about? Oh, for @*% sake. Wyck I … Look, okay. I am sorry I doorbell ditched your house when I was 11. Please do not destroy the @*%town over it.
Wyck: But you never actually did it, did you?
Mayor: What?
Wyck: Nah, see, I was watching. I’d see you sneak up to my door and pretend to ring the doorbell. Then you’d run back to impress the local kids, laughing, and take all the glory. And that’s how I know you’re not a leader. Because you’ve always been a goddamn coward.
A small aside: This scene reminded me of Simon Sinek’s Leaders Eat Last. The title of the book comes from a US Marine Corp tradition (I know, two posts in a row where I refer to leadership lessons from the Marines, my 20 year old self is gob smacked) where officers go to the back of the food line indicating that when things get risky in battle, they will put the needs of their teams first. In other words, a Marine officer doesn’t fake and run.
Anyhow, back to the Mayor of Widow’s Bay and fearful leadership. A leader that is performative (you know, fakes door-bell ringing) will become fearful of being found out2. They will shape a culture of compliance in which they, and oftentimes their leadership team, shield their fearfulness from questions, differences of opinion, and feedback. They are never stress-tested, pushed to do their best, learn, and grow and the organization ends up short on ideas, problem solving, innovation, and genuine success.
Eventually what looks like stability (it’s neat and tidy when no one asks questions or has ideas or opinions) will reveal itself to be mediocrity and fragility on the way to failure.
“In hiring, we no longer should be looking for conformists and rule followers but problem-solvers and experimenters.”
- Harvey Schachter, Teaming is Today’s Essential Workplace Skill, The Globe and Mail, May 18, 2026.
Telling it Like it Is
There are two big problems with a culture of compliance. One is that people don’t comply and the other is that they do. In neither case does the leader have the trust-based relationships in which people will tell it like it is.
A culture of compliance is why President Kennedy was told what his advisors thought he wanted to hear about the planned invasion for the Bay of Pigs, rather than what he needed to hear (Hey Jack, the coordinates are a little iffy, the CIA isn’t telling us everything, and if this goes sideways we’re going to look like fools, the rest of Latin America will be more difficult to control, Castro will be an anti-imperialist hero, and Che Geuvara’s face will be on the t-shirts of left-leaning university students for decades to come).
The story goes that when this all did go quickly sideways, Kennedy pulled the plug by withholding critical air support, bringing the invasion on day three to an ignoble end (for the US; it was glorious for Castro) and was livid (like really, really, livid) with his political advisors for not telling him like it was.
But give the guy credit, he learned that being surrounded by compliant sycophants was not the road to success and when the Cuban Missile Crisis rolled around the following year he sought out advisors to tell it like it was, even if it wasn’t what he wanted to hear, and a dangerous conflict involving nuclear warheads was averted. (Quick nod to the Soviet officer, Vasily Aleksandrovich Arkhipov, who during the crisis did NOT hit the nuclear torpedo launch button despite pressure to do so.)
I know I’ve given an overly simplified take on a complex geopolitical situation that continues to play out today just to make my point that leaders need to seek out and be open to difference of opinions, uncomfortable truths, and a telling like it is to make credible, strategic, and impactful decisions. They need to lead, by example, a culture of non-fragility, not compliance for success. (Like that? See A Bit of Finnish Sisu for Your Workday and some thoughts on less talking and more doing of psychological safety.)
Prompts for Reflection
- How might you, out of self-protection or fear, be creating a culture of compliance?
- How is this diminishing your and the organization’s trust-worthiness, anti-fragility, and success?
- How do you ask for feedback or different opinions or ideas?
- How does this build trust-worthiness, anti-fragility, and success for you and the organization?
- How do you respond, including body language, to a difference of opinion or outright disagreement?
- How do you view, repair, and learn from a mistake or an intelligent failure (different from moral or foolish failure)?
- How do you respond to a mistake or an intelligent failure of those around you?
- What is next in your learning and growth? Why? How? Who will support you?
“Well, I’ll tell you one thing that I know
You don’t face your demons down
You gotta grapple ’em, Jack
And pin ’em to the ground.”
- Joe Strummer and the Mescaleros
Let’s book a chat to explore how I might support your courageous leadership. You and the work you are doing are worth it.
Babs
PS: As always, reflect in your own way, be kind and truthful, consider getting away from the screen and using paper and pen, and if so moved get creative, dance it out, sing it to the stars, or write a poem to your cat.
Photo by Andrea Lightfoot on Unsplash.
- I know there is at least one Star Wars fan out there reading this. And yes, this sentence made me think of you and Yoda. For the rest of you, the famous Yoda quote is “Fear is the path to the dark side. Fear leads to anger. Anger leads to hate. Hate leads to suffering.” ↩︎
- I’ve only seen episode one and so I’m hoping for the Mayor to have leadership growth through honest reflection, smart risk taking, learning, and some funny-scary haunting type stuff. ↩︎