Surfing the Future: What Leaders Can Learn About Positioning, Storytelling, and Trust in the Age of AI

I had the privilege of joining the Wahine in Tech: Surfing the Future panel put on by Hawaii Women in Tech (with incredible support and hard work to Margaret Schmitt and Cynthia Madden, M.Sc and the whole team!), where we explored not just the “what” of AI, but the “how” of making it matter. It was a great session connecting with Robert Redding , Adam Palmer , and Roseann Freitas to each bring a unique perspective of AI in business today and even more powerful insight to what you can do for an incredible future!

Here’s the truth: AI won’t win you the market. Positioning, storytelling, and emotional connection will.

Too many leaders focus on features and functions. But in today’s noisy world — where every company claims to be “the best” — the organizations that stand out are the ones that make people care.

Key Takeaways for Leaders

Positioning is More Than “We’re the Best”

Your customers have choices — manual workarounds, competing products, or even building their own solutions. Pretending you have “no competition” erodes trust. Acknowledge the alternatives. Educate your customers about the options. Then position yourself clearly in the gap only you can fill.

Know Your Unique Value (and What You Don’t Do)

It’s not enough to say what you are. Leaders build credibility by also naming what they aren’t. Defining what you don’t do helps sharpen your unique value — and opens the door to partnerships instead of endless competition.

Emotional Connection Drives Action

Numbers matter, but they don’t move hearts. People invest careers, budgets, and trust when they feel you understand them. Case studies should sound less like press releases and more like: “I walked into Mark’s office and saw the spreadsheets piled high…he hadn’t been home in days. Here’s how our solution gave him his time and team back.” Stories like that stick.

Be Boldly Different

Safe, “me-too” pitches fade into the background. What do you vehemently disagree with in your market? Take a strong point of view — respectfully, but clearly. Leaders with conviction attract the right customers, talent, and partners.

Multiple Stories, One Core Narrative

Your narrative should align the whole organization, but the storytelling flexes. Leaders need multiple “origin stories” in their back pocket — a pivot story, a moonshot story, a values story — to connect with different audiences while staying true to one core message.

Actions Organizational Leaders Can Take Today

• Identify your vested customers — those who love you, champion you, and see your value without hesitation.
• Map the alternatives they would use if you didn’t exist. That’s your true competition.
• Clarify your unique value in language your customers care about, not just technical features.
• Craft 2–3 customer stories that show the pain, the breakthrough, and the impact — in human terms.
• Decide what you stand against in your industry and let that shape your positioning.
• Align your team around a shared narrative so everyone tells the same story, just in their own authentic voice.

Questions to Spark Team Reflection

1.     What is our unique value proposition, and how does it truly differ from our competitors?

2.     Who is our best-fit customer, and what makes them champion our solution?

3.     What alternatives do our customers have if our solution didn’t exist, and how do we fit into that ecosystem?

4.     What do we vehemently disagree with in our market or industry, and how can we use that conviction to stand out?

5.     How can we craft a narrative that emotionally connects with our customers and makes our message memorable?

6.     What real customer stories can we share that demonstrate the impact of our solution?

7.     Are we transparent about our competitors and alternatives, and do we use this knowledge to build trust?

8.     How do we tailor our message and stories to different audiences or personas?

9.     What are the core values that drive our organization, and how are they reflected in our storytelling?

10.  How can we ensure our team is aligned around a shared story and vision?

Final Thought

AI may be the wave of the future — but without the right positioning and storytelling, it’s just another ripple in the ocean. Your story is the surfboard. Without it, you’re just treading water.

Jamie Champagne, CSP Helping leaders maximize the value of technology investments with clarity, collaboration, and a little bubbly energy 🍾🏄♀️