You’ve probably never heard of John Pollack before.
And who could blame you? He’s a fairly soft-spoken, unassuming writer from Ann Arbor, Michigan who began his career covering the sewer commission (among other things) in suburban Connecticut.
While an honorable choice of profession, it’s not typically the platform you’d expect from someone who eventually had the largest audience of any content producer on the planet.
But make no mistake about it, you’ve undoubtedly heard his work before.
Free Guide: The Ultimate Inbound Marketing Strategy Playbook 2022
Due to his mastery of linguistics and fascination with its applications, Pollack worked his way from covering local government to writing speeches on Capitol Hill in Washington, eventually becoming the head speechwriter for President Clinton.
Oh, and he never even wrote a speech before heading to Washington. Let alone a presidential one.
So how does one even begin to write for an audience of such magnitude and with such diversity? After reading his newest book, Shortcut, I reached out to Pollack and he graciously agreed to answer those very questions and more.
Q: First off, you probably had the most stressful job interview a person could have. Tell us about that experience.
I was sitting on a couch in the office of Chief Speech Writer Terry Edmonds in the West Wing of the White House. He was flipping through my materials and looking at my resume.
I had applied several times before and had come close but had always been beaten out by another candidate. So this was really my last chance.
He said, “I see you can write well, but what’s this about a cork boat?”
I had put on my resume that I was building this cork boat, so I explained to him that I had this boyhood dream of building this boat entirely of wine corks, and I was planning on taking an epic journey.
I could see he pushed his glasses up to the top of his head and he looked dubious. I mean, he was hiring someone to work for the president in the White House, so he can’t afford to hire a nut job.
At that moment an analogy popped into my head and I said, “well, building a cork boat is a lot like writing a great speech. You take a jumble of small things, whether they’re words or they’re corks, that if they’re not organized properly they’re just a mess. But if you put them in the right order they’ll take you on the most amazing journey.
He got the analogy and I got the job.
A good analogy is a spring loaded argument and if it rings true, it generally wins the day.
Q: You seem to be somewhat of an artist when it comes to linguistics, where did this come from?
I’ve always loved language.
The family lore goes, I was slow to put sentences together. I had individual words and fairly good comprehension but I wasn’t putting together complete sentences.
I was two and I walked into the kitchen and my mom said, “Johnny, go put on some shoes, I don’t want you to walk barefoot in the kitchen.”
I looked up at her and I laughed and I said, “bears go barefoot.”
That was my first complete sentence. And it was a pun.
I had an interest in word play for a long time.
Q: How did this manifest itself as you got older?
I had a freshman English professor who said something profound on first day of class that made a big difference for me.
She said: “Writing is like anything else. If you practice, you’ll get better.”
You get better at things you like doing because you do them a lot. I just kept writing. I got very involved at the Stanford daily. First as a reporter, and then as an editor.
I became interested in storytelling through the journalistic form. I went on to work at the Hartford Courant and shifted into speech writing.
The thing that both speech writing and journalism taught me is that if you’re not keeping it interesting, people have better things to do with their time.
If your lead isn’t good, they’re not going to read the article.
If your next paragraph isn’t interesting, they might not make it to the bottom of the column.
If it’s not interesting there, they won’t make the jump.
The same thing goes for a speech. It can’t be all bran, you’ve got to have some raisins in there to keep it interesting.
Q: Ah, storytelling. That’s one of those buzzwords in business right now so ubiquitous it’s almost lost meaning. How does one get good at it?
Read, read, read.
I remember reading Annie Proulx and thinking, “wow, you can do that?”
She had a very unique style and voice. She came up with fantastic names.
While I don’t write like Annie Proulx or aspire to write like Annie Proulx, knowing that that is a possibility is a wonderful thing. Q: What did you learn about writing great speeches from your time at the White House?
Presidents have it easy in that everyone listens to what they’re saying.
It’s much harder to write a great speech for someone who is not as prominent because then you really have to earn their attention.
I was fortunate in writing for President Clinton in that he cared deeply about the substance and the delivery.
There are speakers who just want to sound good, and there are other speakers who are deeply invested in the policy minutia and don’t get involved with the delivery. President Clinton wanted to do both.
Q: So what are the elements of a great speech that achieves both?
I would say the first rule of a great speech is don’t make it too long. Attention spans are short.
Second, you need to respect your audience. This doesn’t mean you pander to them but ask them what it is they care about and why they care.
Third is tell a good story.
If you tell a specific story you can generalize from it and let people apply the meaning of that story through their own lense.
That’s why fairy tales have such lasting power, because the moral of the story transcends time and culture.
So keep it short, empathize, and tell a great story. Give them something that’s worth their time.
Q: Do you remember the first time you met President Clinton?
I was walking into the Oval Office and he steps through into his secretary’s office, and they said, “Mr. President, this is your new speechwriter, John Pollack.”
And I said, “good to meet you sir.”
He said, “wow, that’s a great bow tie.”
That was our first exchange.
Q: What was it like working for him?
He was super smart, he always had good ideas, and if he had a question, it was generally a well-informed one.
Working in the White House is a great experience. It’s a front row seat to history.
There’s a lot of texture to the work there that is never on camera. It’s the talking with the calligraphers who do the official invitations in the East Wing, or talking with the cooks who are working on a steak dinner, or talking to the tux service people who tend to the fireplace in the Roosevelt Room.
So there’s just a great texture to it. I loved it.
Q: How good a writer is President Clinton?
Sometimes I would write a speech and it would be used word-for-word and sometimes he’d change a lot.
When the Supreme Court voted to stop Florida from tallying up ballots in Bush vs. Gore and hand Bush the victory, President Clinton was in the United Kingdom and we put together a draft regarding the Supreme Court decision and we sent it off via the situation room.
We’re waiting for a response and it comes back all marked up. He marks it up with a sharpie and sometimes it’s hard to read his writing.
There were three pages and only three words survived: Vice President Gore.
Q: How do you even approach writing for over 300 million Americans?
Whenever you’re writing for the public, there’s a possibility that people will pay attention, but many people tune out politics much to their detriment and the country’s detriment.
When you have a third of the people voting, you get bad results.
I think about the ideas we’re trying to get across and what’s a compelling way to frame them in human terms.
Why does this matter and why should you care?
In a public arena you might not be trying to sell products, you might be trying to inspire behavior. Get people engaged in their community. To make change and help people live up to their full potential.
While people often think of politics as a dirty business, there’s 300 million people, there’s 535 representatives all representing competing interests and finding the common ground is a messy business.
That’s the nature of democracy.
You really have to approach it from a sense of possibility. Often people approach it from a cynical viewpoint and that’s too bad. It’s easy to understand why many people are cynical, I’m not saying the results of Washington are uplifting, but they have that possibility. The more people that tune this out, the worse the results are.
This is why what people say and do in their speeches is important. Q: What does your writing process look like?
My writing process is always about finding the right story.
The last state Clinton visited as president was Nebraska. He was giving a speech at the University of Nebraska Kearney.
I was asked to do the local color at the beginning and come up with a good introduction. So I called the Kearney Public Library and talked to the librarian and got some history.
There was this fantastic anecdote that I learned about how after the Civil War there was a lot of talk about moving the United State Capital to a more central location.
There was a real estate speculator in Nebraska who was pitching Kearney. It had the advantage of being safe from invasion. It was in the middle of the country, and it was halfway between the two coasts.
People wanted to know how they’d pay for all the monuments and buildings, and he said that there would be a land rush and speculation and as for the old building, they’d turn it into an asylum.
I thought that was perfect.
The president used it and as he was speaking ad-libbed another line that made it even funnier. He told the story about turning it into an asylum and people laughed and then he said having worked in Washington for the last eight years, it is an asylum.
He made a really funny add on the spot and it went over well.
I’m looking for the story. You don’t always know what you’re looking for, so you’ve just got to put your feelers out and see what sticks.
Q: Do you remember the first time the president read a speech you had written?
It was exciting.
I was in a colleague's office and he was on the road somewhere. I don’t remember where.
I mean, there was the president and you know what words are coming next.
Q: Over a decade has past since you wrote for the president. Why publish Shortcutnow?
I think the world faces bigger challenges than ever and we need defined, fresh solutions and common ground.
To do that, we’re going to need some creative thinking. Analogies are vital catalysts in achieving that.
Q: Is this same sort of transformation taking place in business as well?
Businesses are trying to come up with new things and sell them.
Analogies help us invent and they help us persuade.
In an era when people are so busy and so bombarded by information, the person, company, or cause that can make their argument in the shortest amount of time, most effectively, is going to come out ahead.
The way that do that is through analogy. Analogies come in a lot of different disguises and those who master them come out ahead.
They’re not always easy to come up with, but the analogical instinct is something that everyone has and everyone can hone.
Once you start paying attention to the analogies around you, and start taking them apart, you are more able to start making them. But first, you need to recognize their presence and their influence.
Q: Tell us something about President Clinton that we don’t know.
He has the most beautiful pair of cuff links I’ve ever seen in my entire life.
They are a pair of presidential eagles cast in gold.
They were finely cast. They were extraordinary in what they symbolized and the attention to detail was amazing.
I loved those cuff links.
For more on the art of analogies and how they influence and sell ideas, check out Pollack's book Shortcut.