You Can't Win If You Don't Know What Unwinnable Looks Like

Zelensky did just about as well as anyone could do in the same situation. The lesson is to recognize when you're about to face the same situation.

Like the actor playing in the nurse in "Shakespeare in Love" who gives the plot of "Romeo and Juliet" as "It's about this nurse...," I see the start of World War III and think mostly about comms. When I see Zelensky, Trump and Vance hitting the plunger that will blow open all the fissures in the democratic West, all I can think is, “Thank you JD, D and V, for giving me the perfect messaging case study.”

If Zelensky, one of the best communicators of my lifetime could not win this situation, then that’s the lesson. A lot of people fixate on the micro errors they’re convinced they could do better. Almost certainly not.

The lesson is to see what made the situation so hard to win, and recognize it the next time you’re in a crisis. In the end, it's all messaging and the message here — a hard one to learn — is that effective messaging is nothing without context.

How to Prep for Morton’s Fork

There are three critical concepts that help you understand these situations:

• Morton's Fork (where all answers to a question lead to reputational disaster).

• Best Alternative To Negotiated Agreement (your power comes from having alternatives).

• Anticipating neurolinguistic Blitzkreig (situations like Congressional testimony where the point of the questions is humiliation, not information).

Or to put it another way: here’s how to know you can’t win an an interview in a crisis, and here’s how to get the best result from an interview if you don’t have a choice.

BATNA: Why Apple Can Ghost Journalists But You Can't

When your partner asks if their outfit makes them look fat, your leverage in that conversation depends entirely on whether you have a comfortable couch to sleep on. That's BATNA—your Best Alternative To a Negotiated Agreement—and it determines your actual power in any exchange.

Companies like Apple and Amazon maintain radio silence not because they're communication geniuses, but because their massive market positions give them the luxury of walking away. They've cultivated a communications approach based on information scarcity and selective engagement precisely because they can.

Very few startups have this power. And most companies have little to offer the media that actually help the media expand their audience and make money. Always be honest about the cost of not doing the interview: the higher it is, the less control you have. It doesn't mean you should avoid every risky situation, it means you should be clear about the risks.

Zelensky, with Russian troops occupying his country and his military dependent on American support, had no such luxury. His weak BATNA left him vulnerable to every conversational trap laid before him.

Impaled on Morton’s Fork

Zelensky was trapped in what Tudor tax collector John Morton would recognize immediately when he was trying to come up with a reason for Henry VII to pay more taxes. When Morton wanted to squeeze aristocrats for cash, he argued that those living lavishly obviously had money to spare, while those living frugally must be hoarding wealth. Either way, they were getting taxed.

Many companies' worst crises are Morton's Forks. It isn't where they have betrayed one value, it is where two treasured values have come into conflict. I love to teach these moments in my MBA classes, because they force great business minds to see the value of the humanities. A classic case would be tech companies having to pick between privacy and safety (Apple deciding not to track child pornography on device). But also companies being intentional about inclusion will also find that perversely one program to help one group will outrage another. Often the only way through the choice is an old fashioned ethical decision.

John Morton would probably also ask you if this hat made him look fat

In the Oval Office, Zelensky faced his own impossible choice. Vance and Trump had put him in a position where he either said what they wanted or said something that would be devastating to his domestic support: that the war had been pointless. Consciously or not, he picked the message that Ukrainians needed to hear him say, even if it meant forsaking the money they needed.

So, in a crisis, if you’re seeing endless arguments internally, it’s usually due to people who love you and admire you for entirely different reasons. Many of them are your own employees. And to keep the love of one group, you will earn the hatred of another. Child-protection groups will never forgive Apple for shutting down scanning of probably the best platform to share child pornography on the planet. THAT is how far Apple is willing to go for privacy. Like Zelensky, you’re going to have to pick one value from two. At the very least, it shows what you’re willing to give up for that value: something else that you love.

The Neurolinguistic Ambush

The transcript reveals a masterclass in communication destabilization techniques:

"Trump, raising his voice: You're in no position to dictate what we're going to feel. We're going to feel very good and very strong."

This wasn't a conversation but a carefully structured ambush featuring:

1. Interruption patterns that made thoughtful response impossible. It makes for great reality TV and audiences don't complain.

2. "Gratitude tests" that functioned as dominance displays. appear grateful enough to satisfy Trump and Vance (implicitly accepting that Ukraine should concede territory) or throw his (and be labeled ungrateful). When Trump demanded, "You're not acting at all thankful," and Vance insisted, "Just say thank you," they weren't requesting politeness—they were demanding submission.

3. Topic switching whenever Zelensky gained traction. If he gave a good answer, they called it disrespectful. If he said he had thanked America, they said he hadn't thanked him enough.

4. Status reinforcement through volume and physical positioning: in this case literally surrounding him with hostile people. There isn't much you can do with this then remind yourself if your own power and be confident. I always like the line from Batman Begins as a mantra: "You don't understand. You think I'm locked up in here with you. But you're all locked up in here with me."

Batman aside, let me share the one skill that is the most useful in this situation: answer the assumption before the question. It's not a natural skill. But it’s the best way to enter into a genuine conversation when you feel attacked by a question. As such, it also happens to be a good skill to answer bullies.

The next time someone at work asks how you think it is OK to take time off when everyone else is crushing it, just pause. They want you to offer an explanation, which will make it seem like you OWE them an explanation. Instead, imagine they had to travel from a position of weakness to a position of strength to ask that question. Then walk them back to their original position by thinking what they needed to even ask it in the first place:

1. The assumption that you need to give an explanation.

2. The assumption that the person asking this has never done something similar either.

3. The assumption that you haven't covered for other people.

4. The assumption that everyone else feels the same way.

5. The assumption that your health is less important than their health.

6. The assumption that their work is harder than your work.
   You then pick the assumptions that are the most ridiculous and answer them: "When other people take time off, I cover for them without asking because I work damn hard. I am back now, so if some people let things slacken while I was away I guess I will pick it up."

Zelensky was doing this throughout the time in the Oval Office: every question assumed he was disrespectful, he had started the war, he was the only one continuing it. My assessment is that had he given ground on any of this, he would have given up more long term: his credibility to his own people, and his ability to bargain for anything with other NATO partners, who are threatened by very similar assumptions.

Your check list

Sometimes the wisest communication strategy is avoiding unwinnable scenarios altogether. As Sun Tzu once put it “Never bring a knife to a fight filled with Morton’s Forks” by following these steps.

1. Identify competing stakeholder expectations before engaging. Zelensky couldn't simultaneously satisfy his domestic audience and his American hosts. When you're serving multiple masters with conflicting demands, recognize the trap before walking into it and at least know which value you're willing to sacrifice to maintain the other.

2. Honestly assess your BATNA. If saying "no comment" or declining an interview isn't genuinely an option, prepare accordingly. Your communication leverage is directly proportional to your ability to walk away.

3. Recognize loaded questions. If both "yes" and "no" lead to disaster, practice third-path responses that reframe rather than directly answer. "That's an interesting question. But it suggests to me you're making a few assumptions that I think can distract us. What I'm focused on is..." can buy precious moments.

4. Counter verbal flooding with simplicity. When facing rapid-fire accusations or interruptions, abandon detailed explanations in favor of repeating simple, memorable phrases. Trump happens to be very good at this himself.

5. Look for the exit ramp. Sometimes the most strategic communicator is the one who recognizes when to say, "I think we've covered enough ground today" and gracefully ends the conversation.

The real wisdom isn't figuring out what Zelensky should have said differently. It's recognizing when you yourself might be walking into a similar trap—and having the foresight to find another path. Because sometimes the only winning move is not to play at all.