How a Whoop Product Leader Made AI a Habit for Her Team

Most tech leaders promote AI adoption through training sessions or performance metrics. A product leader at Whoop is more focused on creating habits.

Hilary Gridley, the head of core product at the wearables company, said on an episode of “Lenny’s Podcast” published Sunday that her goal is to make AI feel like a natural part of daily work, not a mandate.

To do that, she relies on a three-part framework: consistency, friction reduction, and a strong reward loop.

Consistency means building an everyday relationship with AI — and that starts small, said Gridley.

“It has to start super easy. You have to give them things that take no more than a minute or two to do,” she said.

To help her team form the habit, she created “30 Days of GPT” — a list of daily micro-tasks designed to ingrain AI use. The list begins with simple prompts, like uploading your calendar into ChatGPT and asking for meeting talking points. It eventually moves into more complex tasks like “reverse-engineer prompts to make LLMs think like you.”

Grindley said she avoids frontloading real, complex work into the process. She’s focused on forming habits, not on education.

“Work is hard,” she said. “I start with things that are just fun, simple use cases.”

“I don’t know anyone who has gone through this and not come out the other side feeling a hundred times more confident in their skills,” she added.

Create a reward loop

Another key to her strategy is designing a reward loop — a crucial but often overlooked part of behavior change.

It needs to be powerful, immediate, and emotional, Gridley said. “When this person does the thing that you want them to do, they feel like a million bucks,” she added.

One way she makes that happen is through Custom GPTs. Team members can upload a document and get immediate feedback or an improved version — no advanced prompting needed.

“They get the joy of, ‘Oh, this helps me, this was cool’ without any of the despair of, ‘Oh, I’m not very good at prompting,” she said.

Gridley also said giving shout-outs in team meetings and encouraging demos when someone uses AI to solve a real problem are effective ways to recognize and reward adoption.

“If I’m trying to build any kind of habit on my team,” she said, “it’s less about the accountability of how I’m enforcing this, and more about how I make it so rewarding for people to do it that they do it naturally.”

Gridley did not respond to a request for comment from Business Insider.

Her comments come as the corporate rush to adopt AI is shifting into high gear.

More than three-quarters of business people surveyed by McKinsey said their companies used AI for at least one business task as of July 2024, up from 55% since late 2023, according to a March report. The consultancy surveyed nearly 1,500 participants online across various industries, company sizes, tenures, and regions, including 42% who said they work at organizations with over $500 million in annual revenue.