S2E06: Terry Szuplat, Former Obama Speechwriter, Communication Coach, and Author of Say It Well

How Terry Became a Presidential Speechwriter

Terry’s path into speechwriting is refreshingly human. He jokes that his “true story” is applying to law school, not getting in, and then finding another route. That route led him into speechwriting roles at the Pentagon, in consulting, and alongside elected officials.

But the seed was planted much earlier: as a 22-year-old intern, Terry watched White House speechwriters help President Bill Clinton communicate on the world stage. It was, in his words, an “awesome job” that fused history, poetry and policy into one message. Fourteen years later, he became a foreign policy speechwriter in the White House himself.

His route to Obama was also a reminder that careers are built through community. The speechwriting world in Washington, DC is small. Terry volunteered at the 2004 Democratic convention when an unknown keynote speaker from Illinois “blew everybody’s minds.” He volunteered again four years later during Obama’s campaign, got to know the team, and when they won, he was invited to apply.

Then came the writing test. “The most terrifying week” of his life. One shot at the dream job. He cleared the calendar, put everything into it, and got the call. :

Why Obama’s 2004 Speech Still Matters

When Terry describes Obama’s 2004 convention speech, the lesson is not “sound like Obama.” It’s the opposite.

Two things struck him:

• Obama led with personal story. He said what only he could say, in a way nobody else could replace. :contentReference[oaicite:6]{index=6}
• He connected the personal story to a bigger story. He used it to paint a vision of what the future could be, rather than delivering a dry list of policies.

This is the same trap I see in business pitching all the time. Teams default to generic presentations because it feels “safe.” But generic is invisible. If your pitch could be delivered by anyone in your company, you have missed the point.

Terry makes a powerful point for leaders who hesitate to bring themselves into the room: it’s not all about you, but it is partly about you. People are not only buying the product or service; they’re buying belief in the people delivering it. If your audience has no sense of who you are, that is a missed opportunity.

Speech, Presentation, Pitch: It’s the Same Job

One of my favourite lines from Terry is that he doesn’t separate speeches from presentations. Whether you call it a keynote, a pitch, a toast, or a team update, the job is the same:

Human to human, you are there to create connection and move people.

If all you are doing is delivering information, you could send a memo.

But if you are standing in front of other human beings, your opportunity is bigger than information. It is influence.

The 50–25–25 Rule (And Why Most Leaders Get It Backwards)

Terry shares a simple framework from his book that instantly makes preparation less chaotic: the 50–25–25 rule.

• 50% thinking: plan, research, interview people, collect stories, gather examples, understand the audience and your purpose.
• 25% writing: draft once you have material and clarity.
• 25% practising: read it out loud, rehearse, refine, and make sure it works as an auditory experience.

He describes what happens when organisations skip the thinking: people build decks and scripts fast, feel productive, and then can’t answer the most important question.

What is this presentation actually about?

This part is painfully familiar in enterprise deals. Everyone adds their “ornament” to the Christmas tree. The deck becomes 150 slides. The story becomes fog. And the audience walks away remembering nothing. Terry’s antidote is relentlessly simple: decide the core objective and the one message you want remembered, then protect it.

Pressure Is Real: Crisis Speeches in Two Hours

Because Terry worked on national security and foreign policy, speed mattered. Tragedies, attacks, disasters: sometimes the President would need to speak within two or three hours.

Even then, Terry says the fundamentals stayed the same. The process just condensed.

And in high-stakes moments, one principle becomes non-negotiable: panic does not help. Panic freezes thinking. His job became staying calm so he could listen, process feedback, and do the work.

If you have ever had a CEO pitch with a 24-hour turnaround and the entire company watching, you will recognise this energy immediately.

Leadership Lesson: “We Have Four Days to Make It Better”

Terry describes Obama’s feedback style in a way that every leader should study.

For the biggest speeches, the team might sit with the President a week or two out, before the policy machine swarmed the message. Obama would ask:

“What’s the story we’re trying to tell here?”

“What’s the one big message we want people to remember?”

And when a draft didn’t hit the mark, Obama didn’t tear people down. He’d say something like: “I could give this speech today… but I don’t have to give it for four days. So we have four days to make it better.”

That is what high standards look like without demoralising the people doing the work.

Ask the Driver: The Aussie Chant Story

This is the perfect example of “ideas can come from anywhere.”

Terry tells a brilliant story about being in Australia, in a motorcade, with a speech that still didn’t have the right opening. The audience would be Australian troops, waiting in a hot hangar, and Terry wanted a first line that would create instant connection.

So he asked the driver.

The driver suggested: “Aussie, Aussie, Aussie”, which the crowd would shout back: “Oi, oi, oi.” It didn’t “mean” anything. It was pride. It was belonging. It was human connection.

Obama delivered it within the first 15 seconds and the roof came off. And it set the emotional tone for the rest of the event.

The leadership lesson is subtle but important: we often only ask senior voices for input. But the people around the edges of our organisations see things we don’t. Ask them.

Create an Experience, Not a Data Dump

As you might imagine, I loved the moment where we connected speechwriting to experiential pitching.

Terry’s view is simple: you can tell people what to think, but most people don’t like being told. It is more effective to lay out the problem, offer paths, and help the audience come towards the idea on their own.

He also reduces persuasion down to a timeless structure:

• Problem
• Solution
• Change or benefit

Thousands of speeches. Same bones. Different clothes.

And yes, music matters. Not while the President was speaking, but before and after, to shape the energy of the room. Terry even shares his own hype songs (including House of Pain and ACDC’s “Thunderstruck”), plus the famous footage of Obama listening to “Lose Yourself” backstage.

Final Words: Say What Only You Can Say

Terry’s closing advice is the heartbeat of the episode:

Don’t fall back on generic presentations.

Your audience wants to know who you are, why you care, and what you bring.

Say what only you can say.

If you lead pitches, write keynotes, sell ideas, or want to communicate like a leader, this conversation is packed with practical wisdom from the highest-stakes communication environment imaginable.

Find Terry

Terry shares his workshops, training, and resources at terryzuplat.com.

He is also active on LinkedIn (search “Terry Szuplat”).

And his book is Say It Well, filled with the stories and lessons behind world-class speeches.

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Danny’s book: Pitch: How to Captivate and Convince Any Audience on the Planet is available now, and it’s the complete playbook for building pitches people actually feel.