Crafting Messages That Matter, with Wisdom from a Presidential Pen
Not long ago, I missed something special.
Terry Szuplat, an award-winning author, former senior speechwriter to President Barack Obama, and speaker in his own right, was the featured guest at an IABC Atlanta event. I’d circled the date. Highlighted it. But life had other plans. At a follow-up meeting, I asked Leau Gladu and Katy Griggs, “How’d it go” and “What did I miss?”
Their eyes lit up! Their voices were filled with excitement, “You must read his book!” So, I did. And I’m so glad.
About the Book
Say It Well, a national best seller, isn’t your typical “how-to” on public speaking or storytelling. It’s an invitation to understand the heart and soul of a message, the clarity of intent, the architecture of meaning, and the power of delivery.
Szuplat not only teaches communication; he embodies it. With decades of experience crafting remarks for some of the world’s most influential voices, including President Barack Obama, he brings hard-earned insight, battle-tested experience, and unmatched credibility to every page.
And yet, this book isn’t lofty or unapproachable. It’s honest, transparent, and authentic. It’s also grounded and humble. The author acknowledged that he was among a talented team of speechwriters, praising his colleagues. It’s also chock full of wisdom based on years of real-world experience.
9 Lessons from Behind the Curtain
This author’s greatest gift may be the way he teaches through stories: real, vulnerable, high-stakes moments from behind the scenes. Here are nine timeless lessons he reveals through those stories:
- Words Can Comfort, Reassure, and Heal: In moments of grief or crisis, language has power, not to fix, but to hold. His reflections on national tragedies reveal how well-chosen words can calm and comfort a shaken world.
- Structure Builds Trust: A speech is more than a string of ideas. It takes the audience on a journey. With thoughtful structure, leaders guide listeners toward clarity, even amid confusion or fear.
- Audience First, Always! His central question is simple: What does this audience need—right now? The speaker’s ego steps aside, making room for empathy to lead.
- Clarity Requires Courage: In high-pressure moments, it’s tempting to say more. He shows how brave it is to say less. To speak plainly, truthfully, and from the heart.
- Stories Make Ideas Human: Policy doesn’t move people. People move people! He weaves in personal stories to show how one human story can carry an entire message.
- Moments Create Meaning: The right words, at the right time, can become part of history. He shows how a communicator’s job is to elevate the moment, not overshadow it.
- See If You Can Trim A Little: Just because you can speak for 30 minutes, doesn’t mean you should. Edits make a speech shorter, sharper, better… every time. Even if you can’t shave off 15%, he encourages us to cut more than we thought possible and assures us that our remarks will be better for it.
- Stand and Deliver: Even the best-written speech can fall flat if not delivered with presence, pacing, and authenticity. He shares practical tips to help speakers prepare, manage their nerves, connect with their audience, use silence effectively, and bring their words to life with purpose and confidence.
- The Best Speeches Aren’t About the Speaker: He offers a friendly reminder: it’s not about us. The spotlight belongs to the message and the people it’s meant to serve.
My Top 3 Takeaways
Here are my top three takeaways:
1. Structure Shapes Trust
There are reasons Obama’s speeches were memorable, calming in the face of chaos, and frequently inspiring. They consistently followed a clear, logical arc. Terry outlines how message architecture creates coherence and reassurance.
As someone who’s helped leaders communicate during turbulent times, I’ve seen firsthand how structure can steady the ship. Szuplat reminds us that a speech is more of a performance and having a clear and cohesive “beginning, middle and end” is essential.
2. Connection is Key, but Empathy is the Anchor
While connection is the key, empathy is the anchor. Szuplat shared stories of how he and the team of speechwriters would help President Obama connect with his audience. Then he reminds us that the audience isn’t an obstacle to overcome; it’s the reason we’re speaking in the first place.
Whether you’re drafting a global keynote or delivering an update in the hallway, understanding your audience’s emotional state and worldview is step one. “What’s going on in the world?” and “What do they need to hear right now?” are better questions than “What do I want to say?”
3. Simplicity isn’t a Sacrifice
Simple doesn’t mean ‘easy.’ Far from it! It means thoughtfully pared down and impactful. That’s something I’ve long believed, but Szuplat articulates it better than I ever have. Stripping away the extra isn’t about dumbing down; it’s about crystalizing the message and elevating what matters most.
He shared anecdotes that indicated President Obama was known to ask, often at the eleventh hour, for his speeches to be tighter, clearer, more distilled, even removing whole paragraphs (sometimes an entire page) to increase their impact.
Think you're done with the draft of your presentation? Cut 15%. Because you can always make it shorter.
— Terry Szuplat
He shared one vivid behind-the-scenes moment, “Suddenly, the president was standing over me, holding the draft in his hand. ‘This is a good six-page speech,’ he (Obama) said. ‘It would be a great five-page speech.’ I thought he was messing with me. We’d already begun our descent into Santiago, and his speech was just a few hours away. ‘See if you can shave a page off,’ he added.”
He thought the president was messing with him because the speech was just a few hours away. He explained how he typically made cuts to copy like a surgeon. This time he needed a machete. The result: the speech was about 15% shorter. And, it turned out… it was fine. Nobody screamed. Nobody complained.
He coined this “The 15 Percent Rule”: the idea that trimming roughly 15% of even a well-crafted speech will almost always sharpen its clarity and effectiveness.
A Quiet Whisper, Reignited
I chose to listen to Say It Well instead of reading it. Something about listening to what Szuplat had to say in appealed to me. The book also stirred something in me, something familiar: that quiet voice I wrote about in The Whisper that Yearns to be a Roar.
The urge to share something meaningful with the world came roaring back. This book reminded me that the messages that matter most don’t shout. At first, they connect. Then they reach. Finally, they resonate. And that kind of message is personal and its origins start from deep within.
His work gave me both the encouragement and the tools to continue the work to craft and refine a message worth sharing. While I may never become a Ted Talker, I’m excited to begin putting Szuplat’s wisdom to work.
A Surprising Discovery
After finishing the book, I searched for more. I watched a video of him speaking at another event (see video). Then I looked him up on LinkedIn.
That’s when I saw it! He has been quietly following me since 2022.
I paused. Smiled. Naturally, I was thrilled. Then, I felt genuinely grateful.
I’ve worked with some remarkable leaders. But this man has worked closely with the President of the United States! President Barack Obama is arguably one of the best orators of our time. That’s next level! And yet here he was… following me! A quiet reminder that even those we admire from afar might be closer than we think.
Dig Deeper: Wendy Wollner, CEO of Balancing Life’s Issues, sits down with Terry Szuplat, former senior speechwriter for President Obama, to explore the art of communication, leadership, and storytelling. (Playtime: ~1:13)
I reached out to thank him. To let him know his stories and insights will make a difference in the way I’ll guide future leaders to craft their speeches, as well as my own when the time comes. Now I’m not only following him on LinkedIn, we’re also connected!
Parting Thoughts
After hearing him in my ear for several hours and having learned that he’s been following me for a few years, I hope it’s not too bold to now refer to the author by his first name. True to form, Terry knows his audience. I see some of myself in him, someone who was always a person behind the scenes (until recently). More comfortable behind the curtain than on the podium, just like me.
Terry’s work is proof that the best communicators aren’t always the loudest. They are the clearest, the most empathetic, the most intentional and authentic.
On a personal note, I plan to listen to the audio book again, more slowly the next time. Perhaps a chapter a week. That way I can really digest his insights, internalize the lessons learned, and put those lessons into practice with a specific project in mind.
If you’re someone who leads, teaches, persuades, inspires (or aspires to), Say It Well is more than a good read. It’s a guide for how to prepare, show up, speak up, and communicate with impact.
Say it well. Say it with purpose. Say it so others feel seen.
Terry, you’re an inspiration to speechwriters and communicators everywhere. And I wish you continued success sharing your message around the world! Thank you for the reminders, the fresh insights, the incredible stories and, most of all, for the inspiration. Inspire on!
Lead with Light!
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Love this, Al! Great takeaways from an excellent book.