MIT researcher shares key lessons from over 100 AI prompt-a-thons

Earlier this year, I spoke with Michael Schrage, a research fellow at MIT Sloan’s Initiative on the Digital Economy, about his prediction that AI will eventually transform the CFO role into that of an AI-powered chief capital officer.

Now, as generative AI and AI agent use become more prolific, Schrage and I reconnected to discuss a tool that’s fast gaining traction in the enterprise: prompt-a-thons. These are structured, sprint-based sessions for developing prompts for large language models (LLMs) like ChatGPT and Gemini. Schrage has led more than 100 of these since 2023, including in executive education, MBA classes, and business settings. “Prompt-a-thons aren’t just workshops; they’re mirrors,” he said. “They reflect not only what people want AI to do—but how they think, what they value, and what they overlook.”

In 60–90-minute sprints, small cross-functional teams design, test, and iterate prompts to improve KPIs, clarify workflows, and challenge assumptions. According to Schrage, most participants discover their initial thinking is “flawed, shallow, or stuck in spreadsheet autopilot.” The prompt-a-thon process reframes prompting as a high-impact diagnostic and design discipline—engineered for fast, actionable insight. “It’s not just about using AI more effectively—it’s about thinking and collaborating more intelligently with it,” he said.

For many finance leaders, the instinct is to upskill people on AI. Schrage suggests flipping the frame: “Let’s prompt your cost centers and forecast failures until something breaks—and gets better.” He points to financial planning and analysis (FP&A) as a particularly powerful starting point. Prompt-a-thons here often surface hidden data, unchallenged assumptions, and areas of organizational ambiguity or resistance. “Prompt-a-thons aren’t about rainbows and unicorns,” he added. “But every so often, one shows up—usually disguised as a counterintuitive insight.”

Why emphasize small teams or collaborative prompting? “A prompt is a hypothesis about how the world works—and the world pushes back,” Schrage explained. “Solo prompting explores. But team prompting evolves and that’s where real learning happens.” Schrage compares the approach to sports analytics: “You’re not just trying to win once. You’re trying to build the kind of team that keeps winning.”

Though he would never position himself as a finance expert, Schrage offers three recurring lessons learned from finance-driven prompt-a-thons:

—Prompts are scaffolds, not shortcuts. Great prompts don’t replace critical thinking—they sharpen and amplify it. One-shot prompts are useful; iterative ones are transformative.

—Avoid trying to automate what you don’t understand. The danger isn’t that LLMs get things wrong—it’s that they confidently reinforce flawed assumptions baked into broken processes.

—Look beyond cost-cutting. Most finance prompts chase efficiencies. The best ones expose strategic blind spots and generate new hypotheses worth testing.

Schrage’s key takeaway is that the quality of a team’s prompts reveals the quality of its decision culture. “People don’t just learn how to prompt; they learn what their organization won’t let them ask,” he said. “That’s when everything changes.”

Prompt-a-thons expose what firms know, want to know, and avoid, he said. By closing these gaps, teams not only boost AI fluency—they get better at asking and answering the questions that matter, Schrage said.

Sheryl Estrada
[email protected]

Leaderboard

Pilar López was appointed CFO designate of Vodafone Group PLC (Nasdaq: VOD), effective Oct. 1. López will succeed Luka Mucic who previously announced he decided to leave Vodafone. López’s formal appointment will begin on Dec. 1, following Mucic’s departure from Vodafone on Nov. 30. López previously held several positions at Microsoft. She also spent 16 years at Telefónica.

Nick Deldon was named CFO of global manufacturer H&V. Before joining H&V, Deldon served as CFO at Home Market Foods. He was also CFO at the Wellness Pet Company, where he was pivotal in growing the company into a $500 million global business.

Big Deal

The 2025 edition of the UBS Global Wealth Report, which analyzed individual wealth across 56 markets, finds that U.S. Wealth grew quickly last year. The U.S. Created more than 379,000 new millionaires in 2024—over 1,000 each day—accounting for more than half of all new millionaires worldwide. This brings the total U.S. Millionaire population to 23.8 million, or about 40% of the global total, according to the report.

This surge was fueled by robust gains in the S&P 500 and Nasdaq, which rose over 23% and nearly 29%, respectively. Wealth growth was tilted strongly toward North America, propelled by a stable U.S. Dollar and upbeat financial markets, according to UBS analysts. The U.S., mainland China, and France had the highest number of millionaires, with the U.S. Accounting for almost 40% of global millionaires.

The report also notes the rise of “everyday millionaires” (those with $1–5 million in assets). Their numbers have more than quadrupled since 2000, reaching around 52 million globally by the end of 2024.

“Wealth is not just an economic measure—it’s a social and political force,” Paul Donovan, chief economist at UBS Global Wealth Management, said in a statement. “As we navigate the fourth industrial revolution and rising public debt, the way wealth is distributed and transferred will shape opportunity, policy, and progress.”

Going deeper

“Oil prices could spike 10% after the U.S. Attack on Iran—‘But don’t be fooled, this may not last’” is a new Coins2Day report by Jason Ma.

From the report: “The U.S. Bombing of Iran’s top nuclear facilities will jolt energy markets as investors brace for the fallout across the region as well as expected retaliation from Tehran. Analytics firm Kpler predicted crude prices should soar as much as 10%, but the spike may not last. That’s because OPEC+ is expected to boost oil output.”

Overheard