Diplomatic Dispatches
The Diplomatic Skill That AI Can't Replace
I once watched my ambassador deliver flawless arguments. Logic, persuasion, charm - textbook diplomacy.
Our host nodded politely… and refused to budge.
Only when I asked, "What would it take to change your mind?" - and listened - did we make progress.
That moment stayed with me.
For years, I've believed diplomacy was about mastering the "big five": Negotiation. Influence. Public speaking. Reporting. Listening.
Get good at these and you're unstoppable. Or so I thought.
But I was wrong. Not totally - these skills absolutely matter. But they're the surface layer.
What really drives outcomes runs much deeper.
When I was asked recently to create a "diplomatic skills" course, I hesitated.
Being truly honest with myself I realised the discomfort lay in questioning what more I could teach about negotiation techniques or persuasion frameworks that you can't already find online.
I was uncomfortable because I knew there was something deeper I was missing. I couldn't shake the feeling I'd be selling people the wrong thing entirely.
And then it clicked: Real diplomatic skill isn't about what you say. It's about how you think.
Most failures I see in diplomacy aren't because someone used the wrong tactic.
They fail because people can't see beyond their own mental models - those invisible cognitive ideologies shaped by culture, history, and bias.
Diplomatic breakdowns aren't tactical failures. They're thinking failures.
Ken Wilber puts it starkly:
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I don't have to agree with everything you say, but I should attempt at least to understand it, for the opposite of mutual understanding is, quite simply, war.
Why Thinking Matters More Than Skills
This is where I stumbled into the concept of second-tier thinking.
Indulge me for a minute. Most people operate at one of three levels:
Premodern - tradition and authority rule. Their thinking is black and white. There is only "one right way," and that usually involves obeying a deity or conforming to what is right and true.
Modern - science, achievement, merit dominate. Usually most prevalent in universities, corporate structures, and self-help teachings. People with a modern worldview are dogmatic about the fact that success should be based on merit and results.
Postmodern - relativism: everyone's truth is valid.
Each level has value. But each also has blind spots. Premodern clings to authority. Modern gets rigid and competitive. Postmodern drowns in "all truths are equal."
The leap comes with second-tier thinking:
Integrating truths from all three prior levels.
Holding contradictions without flinching.
Translating between perspectives.
Thinking in systems, not silos.
F. Scott Fitzgerald captured this perfectly:
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The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.
It isn't "I'm right, you're wrong."
It's: "Authority matters. Merit matters. Equality matters. How do we synthesize the best of each?"
That's where diplomacy truly happens.
Why This Matters Now
AI can memorise tactics. It can regurgitate the "big five." But what it can't (yet) do is integrate perspectives, navigate contradictions, or model humility in real time with another human.
That's our edge. And it's the kind of thinking that future-proofs us.
How to Practice It
Try this before your next tough conversation:
Map assumptions. Write down three you're making and question them.
Flip certainty. Pick one thing you're "sure" about and be open to being wrong.
Dig deeper. Ask yourself:
"What would have to be true for their perspective to make complete sense?"
"Where might we both be right just through different lenses?"
As Malcolm Gladwell puts it:
“
The key to good decision making is not knowledge. It is understanding. We are swimming in the former. We are desperately lacking in the latter.
This isn't about becoming a smoother negotiator. It's about developing the cognitive courage to think alongside others.
The most powerful diplomatic moments aren't when someone proves their expertise. They're when someone makes their thinking visible and provides a window into their perspective.
What's your take? Do you agree, disagree, or see something I've missed?
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