Artist's co-founder found that even the best employees lack the time to seek out learning. Their success comes from a "push-based" model that delivers personalized, timely information via text or Slack, rather than relying on employees to log into a separate learning platform.

To encourage AI adoption, Bitly's marketing team holds a weekly, low-preparation "How I AI" meeting. Team members share personal AI use cases, fostering a safe learning environment, spreading practical knowledge across roles, and helping overcome the common feeling of imposter syndrome around AI.

Mandating AI usage can backfire by creating a threat. A better approach is to create "safe spaces" for exploration. Atlassian runs "AI builders weeks," blocking off synchronous time for cross-functional teams to tinker together. The celebrated outcome is learning, not a finished product, which removes pressure and encourages genuine experimentation.

To drive AI adoption, CMO Laura Kneebush avoids appointing a single expert and instead makes experimentation "everybody's job." She encourages her team to start by simply playing with AI for personal productivity and hobbies, lowering the barrier to entry and fostering organic learning.

When employees are 'too busy' to learn AI, don't just schedule more training. Instead, identify their most time-consuming task and build a specific AI tool (like a custom GPT) to solve it. This proves AI's value by giving them back time, creating the bandwidth and motivation needed for deeper learning.

To avoid chaos in AI exploration, assign roles. Designate one person as the "pilot" to actively drive new tools for a set period. Others act as "passengers"—they are engaged and informed but follow the pilot's lead. This focuses team energy and prevents conflicting efforts.

Moving beyond casual experimentation with AI requires a cultural mandate for frequent, deep integration. Employees should engage with generative AI tools multiple times every hour to ideate, create, or validate work, treating it as an ever-present collaborator rather than an occasional tool.

Webflow drove weekly Cursor adoption from 0% to 30% in its design team after one 'builder day' where every participant was required to demo a project. This combination of hands-on practice, peer support from champions, and clear expectations creates rapid, tangible adoption of new AI tools.

To transform a product organization, first provide universal access to AI tools. Second, support teams with training and 'builder days' led by internal champions. Finally, embed AI proficiency into career ladders to create lasting incentives and institutionalize the change.