Want to Be a Better Storyteller? Get Better Impact Stories With “Garlic Press Questions”

Senior learning leaders know that stories move people, win executive buy-in, inspire teams, and even shape culture. But stories of learning impact don’t appear out of thin air—they require careful planning. And “starting with the end in mind” begins much earlier than most people realize. Over nearly 18 years of helping talent teams capture impact for award applications, I’ve found that success often hinges on that very first stakeholder conversation. If you want to win a learning award—or deliver a solution that drives business results—you need to better prepare for, conduct, and extract key insights from that initial dialogue. “Garlic press questions” can help.

Consultative Selling, Kitchenware Edition

Years ago, I was a holiday sales associate at Sur la Table in Seattle’s Pike Place Market. My favorite item to sell? The garlic press. This efficient little tool ranged in price from around $8 to $35. Talking with would-be buyers exemplified consultative selling: Understand the problem, then guide the customer to the right solution.

My first question was always, “Is this for you or a gift?” If it was for the customer, the next was, “Do you cook a lot with garlic?” One couple said they rarely used garlic but needed a replacement for a broken press. Easy call: basic Zyliss model. Another couple said they used garlic constantly and kept breaking cheap presses. They walked out with a top-tier RÖSLE.

For gift-givers, simple questions revealed clues about the recipient’s tastes and garlic habits. Trying to impress a foodie sister-in-law? RÖSLE. Office gift swap under $10? Zyliss.

But never did I ask, “What kind of garlic press would you like?” That would earn me a blank stare—and make the customer do my job for me by solving their own problem.

Yet too often in L&D, that’s exactly what we do.

Knowing What Isn’t Asked in the Room Where It Happened

When I ask some aspiring award applicants about their impact metrics—what business problem they were solving, what KPIs they aimed to move, how they measured skill gaps—I get blank stares. That reveals what wasn’t asked in the original stakeholder meeting: what I call “garlic press questions.”

These simple, nonintimidating prompts ease business leaders into supplying the right information without putting them on the spot, which could inadvertently prompt them to make up an answer rather than look uninformed. That’s why even queries that seem innocuous can be surprisingly unhelpful.

In fact, here’s the number 1 question to avoid: “What would success look like for this training?”

Yep, it’s a trap.

A seasoned L&D pro I know once asked that exact question to a seasoned executive. The answer? “Completions and great survey results.” Jaw-dropping, right? But what could this L&D leader say—“Wrong answer”? He was now stuck designing for low expectations.

If you want to create programs that will drive real impact, be accountable for business results, and protect your team from budget cuts, you’ll need to guide that conversation differently.

Start With the Relationship

To get practical guidance, I turned to four award-winning chief learning officers. Their first order of business? Not business at all.

Lou Tedrick, who just retired after a storied career including nearly 25 years at Verizon, where she served as vice president of global L&D, advised: “Always start on the human side. If it's a stakeholder you know, ask about their family, favorite sports team, hobbies, or recent travel. It shows you care for them as a person.”

If you don’t know them well, Lou advised, do your homework. “Get information from peers, team members, LinkedIn, your leader, etcetera. Find out their likes and dislikes. See if you can learn something about them personally that you may have in common or that could be a good conversation starter.”

Kimo Kippen, founder of Aloha Learning Advisors and former CLO of Hilton Worldwide, agreed: “There’s huge work on the front end. Profile the executive to understand them personally. Always focus on building the relationship so you can earn the right to advance the conversation.”

Strengthen Your Foundations

Kimo also stressed the need to be a “businessperson first, learning enabler second.” Dan Pontefract, founder of the Pontefract Group and former CLO of TELUS, echoed: “Approach stakeholders as business partners first—partners in crime—so we can first unlock clarity that then drives meaningful, measurable L&D impact. It’s not learning first—it’s business outcomes (fueled by relationship building) first.”

Being a business-first partner requires more front-end work. Come to the conversation ready:

• Build your business acumen. These four CLO contributors have at least one business degree each (13 total). If you're not yet comfortable with fundamentals (like reading an income statement), now’s the time to learn.

• Know your company. Understand how it makes money, its market position, and its competitors. If it’s public, attend earnings calls with your team and host discussions after on key insights and potential L&D implications.

• Understand their function. Research the stakeholder’s division—its goals, challenges, and public wins. Find publicly available info, from mainstream news to LinkedIn posts, and ask trusted insiders.

As Lou puts it: “Be a student of the business and your stakeholders’ business and know how your offering can support their success.”

There’s Still More Context to Gather

All four CLOs advised learning your stakeholder’s other pressures and priorities, including their stakeholders, with a question like, “What business metrics or KPIs are you accountable for that we should know about?” In other words, counseled Jenny Dearborn, chief people strategy officer at BTS and former CLO at SAP, “Start with their scorecard and work backwards.”

Jenny also advised pinpointing which KPIs matter to your stakeholder’s boss and boss’s boss, which Dan also recommended, calling it, “opening up the political Pandora’s Box.” Jenny suggested questions like, “What problems does your boss come to you and ask you to fix?”, “What are the most pressing business issues discussed in your boss’s staff meetings?”, and “How do your projects align with corporate business strategy?”

Kimo suggested asking what personal success looks like, so you can help your stakeholder achieve recognition, status, a promotion, or whatever may be motivating them.

“Is This for You, or a Gift?”

Now that you’ve done the prep, here are four time-tested garlic press questions to steer your stakeholder to real business needs:

• “Forget about learning for a moment—what’s getting in the way of your business results?” (Dan Pontefract)

• “What is the business problem or opportunity you're solving for?” (Lou Tedrick)

• “What metrics on your dashboard are blinking red that you’d like to turn green?” (Jenny Dearborn)

• “What’s keeping you up at night?” (Kimo Kippen)

Then, define measurable success with Dan’s closer: “A year from now, what specific result will tell you we’ve nailed it?”

Conclusion

Capturing L&D impact isn’t easy, but these three steps can transform your stakeholder conversations and help you surface the essential data you need to design for, and track, measurable L&D success:

• Prepare through focused research and business learning.

• Build trust-based stakeholder relationships.

• Uncover real business needs with “garlic press questions.”

That’s how you get impact stories worth telling—and results worth sharing.