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One Question That Will Help You Pivot with Confidence

"Tell me about the first time you realized you needed X"

Photo by Ravi Pinisetti on Unsplash

We're in a moment of extremely high change in our organizations. There is a lot of talk about pivoting, innovating, and making bold changes. And I agree. We've been trying to make them too.

But "bold change" is easy to say and hard to do, because we're uncertain. How can we increase our confidence that we're making good bold changes and not just swinging wildly for the fences?

Here's the secret: Ask five customers (or your ideal prospects) this question: 

"Tell me about the first time you realized you needed X..."

Highland President Jon Berbaum shares his perspective on how pivot with confidence. Watch the video above or read his advice below.


Warning, people will tell you their story in 30 seconds, and you want them to tell it in 30 minutes so you really get the detail of what they did and why. To do that, you need to get curious about the story they start telling. Why did they do X? What were they thinking during Y? How did Z make them feel?

It all starts with this one magic question, "Tell me about the first time you realized you needed X"

Why this question?

Because it gets past a persons opinion and gets to their experience. You want experiences, not their opinions. What they actually did, not what they think.

Let me give an example. During the last two months one of Highland's pivots has been to launch an online training academy to teach our research, design, and innovation methods.

First, we asked a few customers and ideal prospects their opinion on this kind of training. Their opinions? Their teams were already high skill, and the training space was crowded with folks like IDEO and Luma Institute.

Then we asked them for their experiences. They did go to trainings with IDEO, Luma and others, but they walked away feeling the training was always surface level, providing concepts but not nearly enough depth to actually master any of the methods and practice.

Opinions would have caused us to walk away. Experiences led us to created an offering focused on deep dives, using our most experienced practitioners to teach people how to actually do customer research and product and service design.

We spun up a rough website, opened a cohort, and filled it up in 5 days. That's how you pivot with confidence.

If you have an idea for a pivot, use this question on 5 people: "Tell me about the first time you realized you needed X".

If you want to join the next cohort of Highland Academy that teaches this entire research method, you can learn more here.