Stephen Krupin still remembers the applause.

It was Memorial Day 2016, and President Barack Obama was speaking at Arlington Cemetery, honoring the memory of three military members who died in combat that year. He spoke about Master Sergeant Joshua Wheeler, an 11-time Bronze Star recipient who was deployed to Iraq and Afghanistan 14 times. He told the story of Wheeler and his Special Ops colleagues rescuing 70 hostages who were about to be executed. He then introduced Wheeler’s widow, Ashley, and their 10-month-old son.

That’s when the applause began.

Stephen, who was senior presidential speechwriter at the time and wrote the remarks President Obama was delivering, told me it felt like the standing ovation went on for hours. He later watched on YouTube to realize it was only 30 seconds — but in that timeframe, he saw firsthand the power of storytelling.

“One of the powers of story, and therefore one of the responsibilities and privileges of a storyteller — whether that’s the speaker or the speechwriter — is to let people know that they are known, to let them know that they’re heard and seen,” Stephen said. “At that moment, they were not clapping because of anything specific that I wrote or anything that President Obama said. They were clapping to say, ‘We see you.'”

Anecdotes and narratives

That story was one of many Stephen crafted for President Obama during his final year in the White House. He thought of stories in two ways: as anecdotes and as larger narratives. The anecdotes allow you to zoom in on a detail of a story, while the narratives provide a zoomed-out perspective.

The ultimate goal is for the anecdotes to serve as an anchor for the larger narrative.

That, Stephen said, is something President Obama excelled at.

“If you listen to State Senator Obama’s speech in Boston in 2004 introducing himself to the country, and you listen to outgoing President Obama’s farewell address in Chicago in 2017, that narrative, that story he was telling about who we are as citizens and who we are together in the country was consistent,” Stephen said. “That consistency creates a sense of community, it creates a sense of credibility, and it helps make everything else he’s hoping to propose possible.”

Prior to his time in the White House, Stephen was policy advisor and chief speechwriter for Secretary of State John Kerry, director of speechwriting for Obama’s re-election campaign, and chief speechwriter for Senate Majority Leader Harry Reid.

In each position, Stephen learned valuable storytelling lessons:

  • For the Secretary of State, Stephen navigated the reality that much of what he wrote would first be heard in a different language. “All of a sudden, idioms and turns of phrase become a lot less important,” he said, “and clarity of the values you’re trying to communicate becomes much more important because it’s got to survive the translation.”
  • For the re-election campaign, Stephen focused on keeping messaging consistent while crafting content for different speakers. “We could be talking about healthcare, and if that person giving the speech is the Secretary of Health and Human Services talking to senior citizens in Arizona, that’s a different speech than a celebrity talking to young, first-time voters in Florida.”
  • For the Senate Majority Leader, Stephen, a former reporter, adopted a journalist’s mindset to learn new topics quickly and effectively. “I was writing a speech every day, often about different things. It’s like coming into a newsroom in the morning and being told that by the end of the day, you’ve got to learn about this thing and then turn around and explain it to other people like you’re an expert.”

Telling a clear story

Today, Stephen is managing director and co-chair of the executive communications practice he founded at SKDK, a national public affairs firm at the intersection of press, politics, and policy. He partners with C-suite executives, elected officials, and nonprofit leaders to help them tell compelling stories through speeches, media training, crisis communication, and advertising.

“Our clients need to tell as clear a story as possible to convey what they do and why it matters right now,” he said. “It’s not that the story needs to be created — it needs to be shaped.”

Stephen also created and teaches a graduate speechwriting course at Harvard’s Kennedy School of Government. There — and with any person he’s ever written for — Stephen reinforces that good storytelling only happens when things are done in the right order.

“You have to understand why you are speaking, what you are trying to communicate, and what you want the audience to do or think or feel when they walk out of the room, relative to how they came into it,” he said. “You have to think through those things first and save how you’re going to do it for the end.”

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3 storytelling tips for you

1) Anchor your story in purpose

Before you write a single word, know why you’re telling the story. Stephen teaches that clarity of purpose is everything. What do you want your audience to think, feel, or do when you’re done? Once you know that, every line you write can serve that goal.

2) Zoom in, then zoom out

Stephen distinguishes between anecdotes and narratives. Anecdotes bring your story to life, while narratives give it meaning and direction. The magic happens when the small story (the anecdote) reinforces the big story (the narrative). Use details to draw people in, then connect those details to a broader truth that sticks.

3) Let clarity carry the emotion

Working with global audiences taught Stephen that a story doesn’t need flowery language to move people. What matters most is the clarity of the values behind it. When you strip away jargon and clever turns of phrase, what remains is the emotional core — the universal truth that connects speaker and listener.