How to Prepare for a Meeting with Trump

Finito World

There are meetings, and then there are meetings with Donald Trump.

It is unlikely that many Finito World readers will find themselves summoned to the Oval Office tomorrow morning as Andy Burnham is about to do. But that doesn’t mean there isn’t something to be learned from asking how one would prepare if the invitation arrived.

In fact, it may be the ultimate exercise in preparation. Most important meetings reward the usual virtues. Know your material. Understand what the other person wants. Have your figures to hand. Anticipate the difficult question. Decide what you want to achieve and, if possible, rehearse.

All of that applies to Trump. But it isn’t enough. The peculiar difficulty of preparing for a meeting with the US President is that you are preparing meticulously to meet someone whose own great strength — and, depending on your point of view, weakness — is improvisation.

Trump has long advertised this about himself. Former officials have described extraordinarily abbreviated briefings before meetings with foreign leaders, while accounts of his working methods have consistently emphasised his preference for bullet points, images and conversation over lengthy briefing papers. He has himself written of his preference for keeping his days relatively unstructured.

So what do you do?

The first thing is to understand that you are not really preparing for a meeting. You are preparing for a person – and of course a person with a notoriously high opinion of himself. This distinction matters.

The conventional meeting has an agenda. Trump may have an agenda too, but he also has instincts, memories, irritations, enthusiasms and a strong sense of the atmosphere in the room. The conversation may therefore move suddenly towards something which wasn’t in your briefing document at all. The mistake would be to conclude that because Trump improvises, you should improvise too.

You should do the opposite. Know your three things Before entering the room, decide the three things you absolutely want Trump to remember – not least because it will be a coup if he remembers even that many. They should be capable of being expressed in a sentence each. Better still, they should contain something concrete: a number, a place, a person, a deal, an opportunity.

This isn’t merely a Trump technique. It is good communication. But with Trump it becomes particularly important because the meeting may cease to resemble the meeting you expected. Your beautifully prepared twenty-minute exposition may never occur. If the conversation suddenly turns to Scotland, golf, tariffs or something Trump saw on television that morning, you need to know the route back to your three points.

Think of them as lighthouses rather than railway stations. You may not reach them in the expected order, but you should always know where they are. Know his three things too The second stage is harder.

What does Trump want?

It is tempting to answer this ideologically.  Ask instead: what would constitute a good meeting for him?

Perhaps it is an announcement. Perhaps an investment figure. Perhaps a commitment. Perhaps evidence that something he has previously advocated is working. Perhaps simply the impression of movement. This doesn’t mean agreeing with him – and nor does it necessariy require flattery, although Sir Keir Starmer and others have shown that flattery works with Trump.

It means understanding the transaction from the other side of the table. The disastrous meeting is often the one where two people arrive knowing exactly what they themselves want and neither has spent ten minutes considering what success looks like to the other person.

Prepare for the ambush

This is the part which has become more important during Trump’s second presidency.

In 2025, both Volodymyr Zelensky and Cyril Ramaphosa discovered that an Oval Office encounter could move dramatically away from the anticipated diplomatic script. The Ramaphosa meeting included videos and printed material introduced by Trump during an extended encounter in front of the cameras.

So prepare for the question you hope won’t be asked. Then prepare for the question after that.

Never fight for the last word

Trump is a television personality as well as a politician and businessman. He understands spectacle instinctively – he thinks in images at least as much as he thinks in language. And when he thinks in language, it’s slogans not Obama-esque arguments.

If a meeting becomes combative, there is therefore a temptation to win the exchange. You probably won’t because, as he’ll likely remind, you he’s more powerful than you. He has leverage, and he needs to like you to forget that. The best use of this dynamic has been King Charles III – but he had a kind of leverage himself, by belonging to a tradition Trump instinctively respects.

Have an exit

Finally, know what you want to happen next. A meeting is rarely an achievement in itself. Do you want another meeting? A telephone call between officials? A signed agreement? An introduction? A decision by Friday? Try to leave with something which can be expressed as a verb. Otherwise everybody may emerge declaring the meeting “excellent” without anything in the world having changed.

Most of us will never meet Donald Trump – and many are okay with that. But all of us eventually encounter our own version of the Trump meeting: the intimidating investor, the unpredictable chairman, the brilliant but mercurial client, the interviewer who throws away the prepared questions.

At such moments, preparation doesn’t mean predicting exactly what will happen. It means knowing your subject so well, understanding your purpose so clearly, and controlling yourself so completely that when the unexpected happens you don’t require you to go back to the script.