Obama Speechwriter Terry Szuplat Wants to Change Your Next All-Hands Presentation [Full Q&A]

Is a State of the Union address basically a high-stakes pitch deck presentation? Terry Szuplat, who wrote many of President Barack Obama’s speeches from 2009 to 2017, thinks business leaders could benefit from studying the rhetorical flourishes of political leaders.

In his new book, Say It Well: Find Your Voice, Speak Your Mind, Inspire Any Audience (Harper Business, 2024), Szuplat explores how to keep speeches authentic, cut through corporate jargon and ensure words translate into action. He spoke with b. about how leaders can succeed in persuading audiences.

b.: What inspired you to write this book?

Szuplat: I actually struggled with public speaking myself. I spent most of my life behind the scenes — in my case, writing speeches for other people. Then, suddenly, you find yourself having to speak publicly, and it can be nerve-wracking, even anxiety-inducing.

One of the ways I got better was by trying to remember the lessons I learned from one of the world’s great speakers: Barack Obama. Here I was, helping him communicate, but I couldn’t always communicate effectively myself. So I had to sit down, reverse engineer and think deeply about what I learned from [Obama], what he was doing all those years, and then try to distill it in a way that would be useful to others.

I think I’m better than I used to be. I’m still working on it, but there was a point where I would look for reasons not to do it. It was just too scary. Why do things that are scary, right? But now I like doing it. I actually enjoy it, and it’s taken me a while to get there. I’m not perfect; I still make mistakes and am still working to get better, but I’m not so afraid that I turn down opportunities anymore.

I think a lot of people do that, though. Imagine how many voices we haven’t heard over the years because we self-censor and don’t put ourselves out there. We hear inspiring speeches from people in business, politics and advocacy all the time, but for every one of them, there are probably tons of people who are too nervous to speak up. One of my hopes is that folks will read this book and realize, “OK, I may not be perfect either, but I can put myself out there. I have something to say. I can make a contribution to my company, to my community.” I’m still working at it.

b.: What did the process of “reverse engineering” President Obama’s delivery look like?

Szuplat: The way I learned it was by listening. We’re called speechwriters. Writing is an important skill, obviously, but one of the most important skills is listening.

When we were working for President Obama, one of the things we were lucky to do was go up to the Oval Office. We’d sit there, ask him questions, and listen — let him talk out what he wanted to get done in the speech. We weren’t allowed to record those conversations, but we took notes.

Listening is how you capture somebody else’s voice. One of the things I would do, too, is put on my headphones and just listen to his speeches, listen to him talking. We all have our own way of speaking, and I think it’s your job in corporate communications and elsewhere to really make sure you’re channeling the voice of the person you’re working for.

b.: Why do you recommend the “50-25-25 rule” (spend 50 percent of your time on planning, 25 percent on writing, and 25 percent on practicing and editing)?

Szuplat: One of the mistakes a lot of leaders make, especially in business, is, when they find out they have to give a presentation or make a pitch, they immediately demand a draft on their desk by the end of the day. That’s mistake number one. No one has had the opportunity to think through it. They’re just on the clock, producing immediately, without even bothering to ask the CEO or executive what they actually want to say.

I see this over and over again. [The bosses] get their draft by the end of the day and are furious because it’s not what they wanted. Well, how could the team possibly know what the leader wants to say when they haven’t been told? 

I teach my students and encourage all my clients to use the 50-25-25 rule to use time wisely. You don’t have to start rushing in and producing content immediately. The important first step is to think through what you want to say before you try to write it. However much time you have to prepare — whether it’s a month, a week or a few days — set aside the first 50 percent of your time to think, research, outline and plan. Don’t start writing immediately. If you write before thinking, it’s going to end badly.

I tell CEOs that they need to make time for their team. Speechwriters and comms teams are not mind readers. They don’t know what you want to say unless you tell them. Barack Obama would always build in time to speak with us before an important speech, and I tell people that if the president of the United States had time to do that, then any CEO or business leader can make that time, too.

So 50 percent of your time should be spent thinking, planning, talking and brainstorming. Only then do you start writing, which should take about 25 percent of your time because you’ve already thought so deeply about it. The final 25 percent should be spent practicing and editing.

Another big mistake I see, particularly in the business world, is not building in time to practice and edit. If you’ve got to speak at 6 p.m. on a Friday night, don’t be working on your draft until 4 p.m. and then suddenly share it with your organization, asking for feedback. There’s no time for constructive feedback or for people to feel comfortable giving honest input.

Having a clear structure and process takes the fear out of it — 50 percent of your time thinking and researching, 25 percent writing, and 25 percent practicing and editing.

b.: Artificial intelligence (AI) tools like ChatGPT can be useful when used correctly, but many people — especially nonwriters — use it for speeches or LinkedIn posts. How do you feel about this trend?

Szuplat: I do talk about it in the book because ChatGPT exploded right in the middle of me writing this. My basic thought on that is, there are two main uses of it. The first is to have it write your speech, presentation or pitch for you, and I would encourage people to never do that.

Audiences connect more with speakers who are personal, speak from their heart, bring their own experiences to bear, and share why they care about their company, product or service. The best speeches are personal speeches, and a bot will never give that to you. The only way to get that from a bot is to go through about 30 rounds of prompts. At that point, you’re basically writing your own speech.

So, I would say, never use AI when you want to write a presentation or pitch that is personal and from the heart. You really want to connect with your audience on a human level. A bot will never know what’s in your heart, and you should never give your voice over to a bot.

The second use is as a wonderful co-pilot — a partner for research, finding quotes, coming up with case studies, or maybe playing around with an outline or brainstorming 10 potential topics. Of course, you have to check all your research, but it’s useful. Sometimes I use it this way — take 1,000 words, drop it in, and ask it to cut half. I never use that [version] because it’s too choppy, ugly and messy, but it helps me see what might be cut. Then I go in and edit it myself. So, yeah, never as a writer, but often as a fellow researcher and thought partner.

b.: Sometimes it’s not accurate, and sometimes it gives you material that’s worse than what you put in.

Szuplat: I suspect it’s different for copy editors who create content for products where no one’s expecting a human voice or connection. But so much of what I write about in the book is these human moments — when a person has to get up in front of a group of other people — at work, in your community or on Zoom — and you need to forge an emotional, human connection.

b.: Do you think the rise of AI will make human speeches more distinguishable?

Szuplat: I really don’t want people getting up and reading content generated by a machine. If we get to the point where that’s common, we will have lost something profound about humanity. When we get up to honor our loved ones in a eulogy, give a toast at a retirement ceremony, or inspire our company to work harder toward a goal — if we start handing those moments over to bots, we’ll lose something about ourselves.

There have been a few occasions where politicians or preachers have tried this, almost as a joke, and usually, the audience can tell something’s off. It feels too generic; there’s nothing personal in it. I’m sure people will use AI, but my fear is that they’ll miss these wonderful opportunities. Imagine a best man getting up at a wedding and saying, “I used ChatGPT to write this.” What a sad moment — being asked to speak on one of the most important days of your best friend’s life and delivering something that’s rote.

Vanderbilt’s Peabody College put out a statement after a mass shooting, and at the bottom, it said it was prepared with the help of ChatGPT. Everyone was furious because, in that moment, people were looking for reassurance from a human being, and they got a machine. That university took a PR hit, as they should have. It wasn’t even a long statement, just a few paragraphs — that’s what you have a PR or corporate communications team for.

I’m sure AI will take over copy editing and tasks like product manuals, where we don’t expect to interact with a human. In those spaces, who cares? We were never looking for a human connection anyway. But if we want that human connection in a news article or anything where we’re seeking a human voice, I hope we don’t lose that.

I have a chapter called “Talk Like a Human” where I go on a tirade against jargon and corporate buzzwords. Those are the kinds of things that AI and chatbots are spitting out because they pull phrases like “catalyzing innovation for synergistic outcomes” from the internet and regurgitate them. But you can also tell AI not to use any jargon or buzzwords. I hope that, five to 10 years from now, it becomes obvious what you shouldn’t use a bot for.

b.: With that in mind, what helps you set a speech apart from the rest?

Szuplat: Don’t be generic, especially if you’re in the business world and one of several speakers or panelists. Don’t just say what everyone else is saying. Infuse your presentations and speeches with stories that no one else has: why you chose this line of work, why you’re involved in this company, or stories you hear from your customers. Personalize it as much as you can.

Many business leaders struggle with that. They tend to think they’re just there to give a presentation about the product or service, and while that’s important, research shows that the real way to connect with your audience is on a human level.

Number two is to appeal to values, which is covered in Chapter 7. There’s a section on how to wrap your business and product in a larger set of values. I wrote that deliberately because there’s a lot of debate, particularly about companies pushing political agendas. … I include various examples of businesses effectively integrating their work with a larger set of values.

Different companies do it different ways, but you have to be smart about it. If you care about it, it’s there, but it’s not in your face if you don’t. If there are two companies offering the same product, research shows that customers and employees will often choose the one that aligns with their value system. That’s not a left or right thing; it’s just how people make decisions.

b.: How can leaders make their message stick?

You’ve got to talk like a human. … Many business leaders fall victim to corporate buzzwords and jargon, thinking it makes them sound smart — but it actually confuses the audience. If your audience is confused, they won’t buy your product or sign up for your service. I call it the “barbecue rule” — think about how you would talk at a barbecue with your family. You wouldn’t use all that jargon, but we do it when we come to work.

Lastly, you’ve got to turn your words into deeds. It’s not enough to give a speech about a product. The real measure of a speech is what your audience does afterward. If they go back to work and keep doing the same thing the same way, you’ve missed an opportunity. When you bring an audience together, you’re taking their valuable time, so be clear. … If you’re asking employees to work extra hours, you should be doing the same. If you’re asking for donations or commitments, you should be doing that, too. This is the true measure of an effective leader and presentation.

Say It Well is available now.

This Q&A first appeared in the b. newsletter. Subscribe now!