Obama’s speechwriter on how to nail your holiday toast

Obama’s speechwriter on how to nail your holiday toast | Soho House

Cody Keenan, the man behind the former President’s famous speeches, gives Soho House West Hollywood the ultimate masterclass

Thursday 8 December 2022   By Cody Keenan

Congratulations, you’ve been asked to deliver a toast. 

The first thing I hope you feel is pride. Whether it’s for a wedding, a reunion, a party to celebrate a business deal, Christmas, or whatever – someone has chosen you to come up with the words to commemorate friendship and teamwork, sum up a person’s life, or kick off a couple’s journey together. It’s a big honour – a captive audience is a gift that not everyone in life receives. After pride, though, comes the panic. What do you say?

Well, before you say anything, you should write something. That’s not surprising advice from a speechwriter, I know. But the simple act of taking the time to collect your thoughts, put them on paper and practise will not only remove stress from the equation – it will make for a better, more thoughtful, more memorable toast that adds something special to the occasion. 

Really, write it. A toast is nothing more than a bite-size speech. It should have a beginning, a middle, and an end. It should tell a story. It should make people laugh and applaud – and you get to decide when they do that. Your audience is your orchestra, and you get to conduct them.

Once you’ve written your toast, rewrite it again and again, and use paragraphs. This will separate the different components of the speech in your mind. It will build in places for you to take a breath. Both are important for memorising the toast, which you should do – more on that later.

As you’re writing, though, there are four simple rules you should follow. 

Obama’s speechwriter on how to nail your holiday toast | Soho House

'A toast is nothing more than a bite-size speech. It should have a beginning, a middle, and an end. It should tell a story'

1. Make it short

A groom’s father once offered the most uncomfortable wedding toast I’ve ever witnessed. Not because of the content, which was endearing – but because it was 28 minutes long. (We all checked.) The sun was setting as he began, and it was fully dark by the time he finished. 

If a guest gets up to go to the bar in the middle of your toast – which will open the floodgates for several more to follow – it’s well past time to wrap it up. Whatever the event at which you’re speaking, keep your toast to two minutes. If you’re the best man or the maid of honour, give yourself four. People haven’t assembled to see you, which brings me to my second rule…

2. Keep it focused

Your host has chosen you, of all people, to speak. That doesn’t mean your toast should be about you. It shouldn’t. Your hosts trust you to add to their event by contributing a thoughtful moment that will stick with the audience long after it’s over, not annex it. 

Begin your two minutes with gratitude, thanking your hosts and remarking on what a gift it is for everyone to be together. 

Follow that with a joke if you can. Self-deprecating is always good. Self-indulgent is not. Inside jokes are only funny for the people on the inside. A joke that everyone can understand immediately brings the entire audience inside, which puts them on your side. (This should go without saying, but jokes that are racist, sexist, or involve the most humiliating thing your host has ever done will not.)

Then tell a story. Just one is best. Choose one that lends itself to a larger truth, some lesson or quality about the person, the couple, or the organisation that gets heads nodding. 

Through it all, a generosity of spirit – with the opener, with the joke, with the story, with the lesson – should be your tone.

Obama’s speechwriter on how to nail your holiday toast | Soho House
Obama’s speechwriter on how to nail your holiday toast | Soho House
Obama’s speechwriter on how to nail your holiday toast | Soho House

Above: Keenan joined Pod Save America’s Tommy Vietor at Soho House West Hollywood to discuss his new memoir, 'Grace: President Obama And Ten Days In The Battle For America' 

3. Keep it real

Your toast should be something that only you can say, not something that a ringer could come in and deliver without edits.

A simple tip here is that it should come from your heart, and not from Google. If President Obama was hosting or attending a state dinner that would be covered by the media in another country, we might search for some appropriate poetry or literature from that country’s culture as a sign of respect. Shakespeare for the Brits, de Tocqueville for the French, Heaney for the Irish. But always, per rule number two, in service of a larger truth about the relationship.

You, however, don’t have to do this. At a White House reception with the Irish Taoiseach, President Trump once offered what he said was an Irish proverb. It was not. It was a Nigerian proverb his speechwriters found on a zombie GeoCities website, and he managed to embarrass himself in front of a foreign leader. 

If your hosts are universally known, say, for their Taylor Swift stanhood, then go for a lyric from Midnights. Otherwise, don’t. At best, finding a quote on the internet is cliche. At worst, it shows you’re uncreative and suggests that maybe you don’t know your host that well at all. They asked you to say something, not Bartlett’s. Take the time to come up with something original. 

4. End with a strong clink

I mean this literally and metaphorically. After you’ve told your story, and spoken to its larger meaning, raise your glass and offer one simple line to the targets of your tribute, a line that underscores the larger truth of your story.

‘To Jack and Diane – who prove that for all life throws at us, the thrill of living is never really gone.’

 
Obama’s speechwriter on how to nail your holiday toast | Soho House

A note on delivery

It’s natural to be nervous when speaking in public. Everybody is. But think of it this way: have you ever rooted for a speaker to fail? Of course not. Your audience is rooting for you. They want to be entertained. They want to know what you know about their hosts.

Reading your toast suggests that you’re nervous. Memorising it suggests that you’re confident. Taking the time to write and rewrite gives you a head start here. Keeping it to two minutes makes it easier. Practising a few times beforehand locks it in. Then, on game day, deliver it one last time in front of a mirror, give yourself a wink, and leave your script behind.

Have a drink first if it calms your nerves. Only one. I’ll have a bourbon neat. But no more than that. The audience may laugh at a drunk speaker, but it’s not the kind of laughter you want. Worse, it’s not the kind of laughter your hosts want.

One last thing. This is a performance. Your body language alone can tell an audience how to feel about your toast. Speak slowly. Smile. That suggests confidence more than anything else can – and you’ve won over your audience by the end of your first carefully crafted sentence.

And now you can hit the bar.

Obama’s speechwriter on how to nail your holiday toast | Soho House

Cody Keenan wrote alongside Barack Obama for 14 years, most recently as White House chief speechwriter and as his post-presidential collaborator. His new book, ‘GRACE: President Obama And Ten Days In The Battle For America’, recently became an instant New York Times Bestseller.