How to be interesting

(and when to tread carefully)

Have you ever presented something you knew was interesting, but no one seemed to care? This might be why 👇

One of my all-time favorite conversations is between Adam Grant and Malcolm Gladwell on a TED podcast stage (watch here). If you’ve ever read a pop psychology book or listened to business podcasts, you’ve certainly heard their names.

Grant and Gladwell sit down to talk about work life – and the conversation is hilarious (I laughed out loud several times).

At one point, they explore what makes something “interesting.” Gladwell says it’s about specificity. Grant argues it’s about challenging what people assume to be true (jump to minute 18:30 if you’re watching the video).

Not how complex, or important, or actually true something is. Just… unexpected.

Here, Grant is referencing sociologist Murray S. Davis's article "That’s Interesting!" In it, Davis argues ideas feel interesting when they mess with what we thought was true. We’re not drawn to ideas that confirm what we already believe. We’re drawn to the ones that flip our assumptions upside down.

Why this matters

If you work with data, research, or storytelling, this is big.

So often, we lead with what we found.
But if we want our insights to stick, we need to ask:
How does this challenge what the audience thought they knew?

Take this example:

Version A: “90% of employees were satisfied with the program.”

Neat. That’s what we hoped for. Moving on.

Version B: “90% of employees were satisfied with the program, but only 70% would recommend it to a colleague.”

Huh? But if they were satisfied… why wouldn’t they recommend it? That’s interesting.

The catch

Seems simple… but watch out. Not all assumptions are created equal.

As Grant puts it:

"An interesting idea is one that challenges your weakly held assumptions, whereas if you challenge someone's strongly held assumptions they just say 'you're wrong' or 'you're stupid.'"

Presenting data that contradicts a team's casual assumptions about their market demographics might spark productive conversations. However, challenging a founder's core business philosophy – one they've built their career around – is a whole different ballgame.

So how do we be just the right amount of interesting when presenting our insights?

Step 1 - know what type of assumption you are dealing with.
(And if you’re not sure, do some more homework on your audience.)

Step 2 - proceed as follows:

When facing weakly held beliefs:

  • Frame around shared goals first: Begin by emphasizing what you both care about. "I know we both want this feature to land well with customers."

  • Present the surprising data as a pathway to the goal: "I found something unexpected that might give us an advantage in reaching our targets."

  • Use a "yes, and" approach: Acknowledge their existing belief before introducing the new insight. "The initial hypothesis made sense given what we knew, AND I discovered something interesting when I dug deeper into the patterns."

  • Ask clarifying questions: "Does this pattern match what you've observed in other contexts?" This invites them to connect your insight to their experience.

  • Provide concrete next steps: "Based on this finding, we could adjust our approach in these three specific ways..."

When facing strongly held beliefs:

  • Start small and build credibility: Don't challenge their core belief head-on. Find a tiny edge case where they might be open to new information.

  • Make it about external changes: "The market has shifted significantly since this approach was established. Let's examine the current environment."

  • Use storytelling from trusted sources: "I recently came across research from [expert or company they respect] that offers an interesting perspective on this challenge."

  • Present multiple interpretations: "I've analyzed this from three different angles. The first supports the current view. The second and third suggest alternative approaches worth considering."

  • Create low-risk experiments: "What if we tested this new approach with a small sample to measure impact before making broader changes?"

We often think the most important part of our work is the insight itself.
But in practice, it’s just as important how you share it.

See you next week,
Morgan