Lead to Win X. How to Give and Handle Ultimatums as a Leader or Subordinate
Today we'll learn when and how to give ultimatums as a leader and when to handle them when they're placed on us by our superiors without losing trust, goodwill, and our dignity.
Welcome! The ‘Lead to Win’ section is a companion for The Stoic Manual to equip you with the best strategies and tactics to succeed at leading in your workplace, parenting, relationships, and business—by Dr. Antonius Veritas. Complement this with the ‘Neuroscience-based Tools’ and the Le Monde Élégant social skills section.
“Make the best use of what is in your power, and take the rest as it happens.”
— Epictetus, Enchiridion
She stood in the kitchen, silent, her face unreadable. I’d just blurted the smug words, “If you can’t cook for me, we’ll have to break up.” An ultimatum. The kind that forces a line into a relationship where love, kindness and softness should live.
What I felt next wasn’t power. It was a strange, hollow throb behind the ribs. I told myself I was right. That people need structure. That love without standards is disastrous. But when she nodded, slowly, obediently, and began preparing the meal I had demanded, the triumph I expected never came.
Instead, I felt uneasy. Her affection became distant, her answers short. She didn’t speak her mind anymore, make jokes, and her body language signaled she didn’t feel safe around me. I’d won, but whatever warmth we had was replaced by winter. She wasn’t happy. And neither was I.
I told myself I was refining the relationship, sculpting it toward something better. But I was merely carving out her freedom, piece by piece. Even though I wanted a nurturing and responsible partner, coercion wasn’t the right way to occasion it. I should have treated the woman I loved with more grace and magnanimity.
That’s the theme of today’s entry.
Previously,
See, ultimatums are rarely leadership. They are a collapse of negotiation, persuasion, and influence. A last-ditch decision made not from strength—but from necessity. And yet, there are moments when they are precisely what must be done.
But make no mistake: every ultimatum costs something. A relationship. A career. A team’s cohesion. Your authority. Yourself.
That’s why today’s entry is not here to give moral warnings or tell you never to use them. We’re not children. We are adults—leaders of companies, businesses, families, or at least of our own minds. We know the world is messy. We don’t always get ideal options. So this essay is about knowing when to use ultimatums, how to deliver them, and how to survive them.
We’ll explore three perspectives:
What to do when we’re the ones issuing an ultimatum, especially if we’re in charge.
What to do when we’re the subordinate, tempted to make a demand up the chain.
And what to do when someone places an ultimatum squarely on us, and the deadline is ticking, the consequences agape.
Ultimatums are not bad. They’re dangerous. And as with all dangerous things, their proper use depends on clarity, courage, and control.
Let’s begin…
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