The Second Showdown in the Oval
Earlier this year, Volodymyr Zelenskyy’s international reputation as an expert communicator became a casualty of Trump 2.0.
The current administration has used the bully pulpit to berate and dominate other international leaders.
In February, JD Vance lectured the Munich Security Conference about their approaches to migration, election integrity, and political inclusivity.
In May, Donald Trump surprised South African President Cyril Ramaphosa with a provocative video about “white genocide” against farmers.
In July, Trump lectured the Brazilians about their prosecution of former president Jair Bolsonaro, who tried to stage his own January 6-esque coup after losing his reelection bid, and levied tariffs (even though we already have a trade surplus).
It should be no surprise that Trump, a consummate New Yorker who came out of a mob-dominated construction sector, separates the world into “loyal” and “disloyal” segments (there’s a loyalty list).
I was watching nervously during Zelenskyy’s August 2025 meeting in the Oval Office. Would lightning strike twice?
Good news! As one Ukrainian Jew to another, Volodymyr — you did great.
You Focused On the Right Audience
Here’s Zelenskyy’s opening statement:
Thank you so much, Mr. President. If I can, first of all, thank you for your invitation, and thank you very much for your efforts, personal efforts to stop killings and stop this war. Thank you. And using this opportunity, many thanks to your wife, the first lady of the United States. She sent a letter to Putin about our children, abducted children, and my wife, she’s a first lady of Ukraine. She gave the letter. It’s not to you, to your wife. I won’t. I won’t. Yeah, yeah. Yeah, yeah. So we are saying this is a sensitive topic, yes, please. And thanks to our partners, and that you supported this format, and after our meeting, we can have leaders who are around us, U.K., France, Germany, Italy, Finland, even Asia. I mean, all partners around Ukraine supporting us. Thanks to them, and thank you very much for the invitation.
Donald Trump likes to be praised. He likes to be thanked. JD Vance has been turned into a meme for claiming Zelenskyy did not thank them the first time around (not true), but Zelenskyy left no opportunity for that critique on try #2. He says “thanks” eight times in roughly as many sentences.
It is odd that world leaders tend to die right after Vance visits them.
Former press secretary Sean Spicer claims that Trump has a soft spot for images of hurt children. This may be true — allegedly, it was one of the drivers of his decision to drop the M.O.A.B. (mother of all bombs) during his first administration. Zelenskyy plays into this by sharing a letter about abducted Ukrainian children — and framing it in a selfless, humble way as if it were just his wife’s independent idea.
I should also note Zelenskyy’s really fantastic-looking suit. Trump, who often makes decisions based on media appearances, was critical of Zelenskyy’s combat fatigues. Zelenskyy did not want to dress like a traditional politician during wartime, but needed to show deference to Trump without compromising on his domestic image.
This is a great middle ground.
You Said “Yes And” To Trump’s Worldview
A reporter asks about Trump’s willingness to “give” money to Ukraine. Trump says that they’re selling weapons, not donating them. Zelenskyy completely agrees, saying, “We have the ability now to buy weapons from the United States. We are thankful for this program and this opportunity.”
Is this true? Technically, yes, even though they had and used that ability under the Biden administration, but Zelenskyy knows that Trump wants to differentiate his approach from his predecessor. Zelenskyy knows his audience and subtly adjusts his language accordingly.
You Framed Trump As the Protagonist
When asked, “What security guarantees do you need for President Trump to be able to make a deal with American troops, intelligence, equipment? What is it?”
Zelenskyy replied, “Everything. Everything. Really, it includes two parts. First, strong Ukrainian army. That’s what I began to discuss with your colleagues. And it’s a lot about weapon and people and training missions and intelligence. And second, we will discuss with our partners. It depends on the big countries, on the United States, on a lot of our friends.”
Simple. Easy to understand. Many are saying that this plays into Trump’s consistent rhetorical use of bandwagoning (because everyone is moving in a direction, that’s the right direction)!
And You Kept It Concise
Zelenskyy’s longest answer is 166 words:
Thank you so much. First of all, we have the ability now to buy weapons from the United States. We are thankful for this program and this opportunity. We are thankful for Europe. They pay for this. And through NATO program, for example, and et cetera, we have some programs where we can have some money to finance this. And this is a part, I think, it’s not a part for the war and to defend us. It also will be a part for security guarantees, to strengthen our army, to rearm Ukrainian army. This is very, very important.
And it depends how much money we need to rearm. For example, the question of air defense, we spoke about it with President Trump. And I’m happy that we have now bilateral decisions and we’ll work on it with production, American production. Nobody in Europe has so many air defense, like Patriots, for example. We need it very much. And this is also about defending.
You might say—wait, that wasn’t even that long. You’re right. It’s exactly as long as it needed to be.
How Did He Do It?
I wasn’t in the room with him, but I have some reasonable guesses.
Great media training from his years of comedy.
Great mindset from his advisors to not be distracted or frustrated with the sometimes erratic ramblings of the American president (Trump’s longest answer goes on for over 600 words).
A great amount of effort was dedicated to studying the most successful Oval Office meetings of this administration.
Like when Mark Carney framed Trump’s trolling of Canada in real estate terms.
Or when Kier Starmer gave Trump gifts, like Buckingham Palace hours.
Or NATO Secretary General Mark Rutte’s consistent “flattery diplomacy.”
What Should You Do?
Whether you're briefing your boss or pitching to a boardroom, Zelenskyy’s performance offers a few lessons worth internalizing:
Know who you’re really talking to. Zelenskyy aimed squarely at the man whose support (or sabotage) could make or break his country’s future.
Speak their language without losing your voice. He didn’t try to “out-Trump” Trump. He just adapted — reframing existing programs to align with Trump’s worldview.
Don’t over-talk the room. You don’t get points for exhausting every talking point. Zelenskyy kept his answers tidy and memorable.
If the rules of the game change, change your play. The wardrobe shifted. The tone calibrated. Adaptation is maturity under pressure.
It’s easy to romanticize public speaking as a performance art, or reduce it to a list of checkboxes (credibility, conciseness, pathos, blah blah blah).
But moments like this one remind us that the most effective communication is less about "what feels good" and more about what works.
