July 7, 2026

How brokers can become ‘AI whisperers’

ATLANTIC CITY, N.J. – A benefits broker can become an “AI whisperer” by giving artificial intelligence tools assignments instead of asking them dumb questions.

Reid Rasmussen, founder and CEO of freshbenies, described how brokers can improve their AI skills during the National Association of Benefits and Insurance Professionals annual convention.

When the ‘magic’ doesn’t happen

Too many brokers ask simple questions of ChatGPT and other AI tools, only to become disappointed when these tools don’t provide brokers with the “magic” they expected, he said.

“It’s not AI’s mistake; it’s that you need to ask it better questions,” he said. “Poor question equals poor result.”

As an example, Rasmussen showed that asking AI to “write an email to a client about a renewal increase” resulted in what he called drivel.

“It’s not AI’s mistake; it’s that I was prompting it like a caveman,” he said.

Rasmussen then provided AI with more details and gave it an assignment instead of simply making a request:

“Write an email to a long-term employer client whose health insurance renewal increased 25%. They’ve already expressed frustration with these costs. I’m their benefits broker. My goal is to maintain trust while explaining the factors driving the increase and setting up a strategic discussion about next steps. Write an email that’s less than 100 words without industry jargon.”

That request generated a more specific response that reflected the broker’s concern for the client’s frustration and set the groundwork for further conversation.

“A better question equals better results,” he said. “Never think about the AI output as the final result. AI is your first draft.”

Answer the questions

Rasmussen called on brokers to be AI whisperers and described WHISPER as standing for “what, how, intent, specificity, persona, examples and requirements.” Brokers must answer the following questions to use AI more effectively:

What do you want AI to do? An example of a weak AI prompt is: “Tell me about level-funded plans. A stronger one is: “Explain level-funded health plans to a small-business owner in plain English.”
How should the answer be structured? “This is the magic,” Rasmussen said. Brokers must ask AI to structure its answer as a brainstorm, table, checklist, email, summary, FAQs, talking points, action plan, or comparison chart.
Why do you need this information? What is your intent in assigning AI a task? Provide context and brief AI better.
What details matter? Who is the audience? What is the situation? What is your tone? What industry is your target? What is the timeline for the information? What is the reading level you want AI to write for? What objections do you want to overcome? Who are the decision-makers you want to reach? What are your fears?

What must be included or avoided in the message? What is the desired length and tone of the message? What compliance considerations must be made?

Give AI a persona

Rasmussen advised giving AI a persona and telling AI who it should act like. For example, a broker could assign AI to act as a benefits communications strategist, a skeptical chief financial officer or a compliance-minded account manager.

“AI’s goal is to get you an answer as fast as possible,” he said. “We can prompt AI to say we don’t want the first answer. Instead, inspire AI with a better prompt. Ask it to give you an answer at a specified level.”

He suggested giving AI examples of something that you think looks good – a great email message, a successful LinkedIn post, a strong proposal or a report in your desired format – and assigning AI to give you its answer mirroring the style that you want.

AI can become a more personalized tool if you provide it with your personal context, Rasmussen said. He advised providing AI with your roles and responsibilities, information about your company, your website, your weekly responsibilities, your top challenges and how AI can help you keep an eye on your calendar, as well as providing it with your tone and preferences.

The result is getting AI to systemize and automate your work, getting your brain to think differently and coaching AI to do better work for you repeatedly.

“AI can help you prepare better, ask better questions and communicate more effectively, but the goal is to create better value,” Rasmussen said. “Your clients aren’t hiring you for your ability to generate words. They’re hiring you for your judgment.”

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