What Writing 3,477 Speeches Taught Obama’s Speechwriter

Andrea Pacini —

Andrea Pacini and Terry Szuplat

In this special event, Terry Szuplat – former White House speechwriter for President Barack Obama and author of Say It Well – shared practical lessons on how to prepare, structure and deliver speeches that connect. From focusing on one core idea to owning your words, his insights showed how any leader can speak with more clarity and impact.

At our recent special event, we had the chance to hear directly from Terry Szuplat, one of President Barack Obama’s longest-serving speechwriters and the author of Say It Well. More than 250 people registered to join the live conversation, where Terry shared stories from his time at the White House and practical lessons on how anyone can speak with greater clarity and impact.

Writing and Speaking as a Skill

Terry reminded us that powerful communication is a skill. He told the story of a young Barack Obama who once tried to give a speech without preparation. The result was a struggle: he lost his train of thought, stammered and felt embarrassed. Years later, that same man became known worldwide as one of the most effective speakers of his generation. The difference was practice.

Preparation Shapes Success

A strong speech starts long before the delivery. Terry emphasised the importance of writing things out. “If you haven’t written it out, you haven’t thought it out,” he said. Writing forces you to confront your arguments, test their strength and decide what really matters. 

Focus on One Core Idea

One of Obama’s guiding questions before any major speech was simple: What’s the story we’re trying to tell? Terry encouraged us to ask the same. An audience cannot remember everything, but they can remember one clear message. Distilling your talk to a single core idea makes it easier to prepare, easier to deliver and more likely to resonate.

Connection Comes First

Terry explained that great presentations are meant to be experienced. As a speechwriter, he often watched audiences rather than the speaker, looking for signs of engagement – smiles, nods or moments of stillness. That reaction mattered more than the words on the page. He also spoke of writing for one person at a time, focusing on how to connect with a specific listener rather than trying to please everyone.

Taking Ownership as a Speaker

Perhaps the most important lesson Terry shared is that leaders must own their voice. A speech is the speaker’s message and responsibility. Obama showed this by staying involved, editing drafts himself, and sometimes writing entire sections in longhand. For any leader, this kind of engagement is what gives a speech authenticity and power.

This event was a rare glimpse into the craft of speechwriting at the highest level, but the lessons apply to every speaker: prepare with care, focus on one clear message, connect with your audience and take ownership of your words.

If you couldn’t join us live, you can watch the full recording below. And keep an eye out for future events where you can continue building your public speaking skills.

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