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.

To overcome resistance and drive genuine enthusiasm for AI, position internal training not as a mandatory requirement, but as a promotional campaign. Focus on showcasing exciting, impactful use cases ("look at the cool things I can do") to create a pull-effect and foster a positive learning culture.

To overcome employee time constraints, Pendo implemented both scheduled, interactive workshops to create dedicated learning time and a Slack channel for asynchronous, "many-to-many" sharing. This dual approach ensures both focused learning and continuous, organic knowledge exchange across the organization.

To effectively learn AI, one must make a conscious mindset shift. This involves consistently attempting to solve problems with AI first, even small ones. This discipline integrates the tool into daily workflows and builds practical expertise faster than sporadic, large-scale projects.

Overcoming teacher reluctance to adopt AI starts with a small, tangible benefit. The simple goal of saving five minutes a day encourages practical, hands-on use, which builds comfort and reveals AI's utility, naturally leading to deeper, more pedagogical exploration.

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.

For large, traditional companies, the most critical first step in AI adoption isn't building tools, but fostering deep understanding. Provide teams sandboxed access to AI models and company data, allowing them to build intuition about capabilities before crafting strategy.

To bridge the AI skills gap where 55% of employees lack proficiency, Dropbox's VP of Engineering suggests a targeted training approach. Instead of generic programs, identify the company's existing high performers, who are likely already using AI effectively, and empower them to train their colleagues.

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.