There is an AI teammate living inside our product (OctoAgent), but AI’s real transformative effect starts with the team using it every day. The question for us was never “should we use AI?” It was always this: “How do we make learning to work well with AI systematic for everyone?” Our answer came down to three habits.
1. The weekly AI hour
Every Wednesday, one hour blocked on everyone’s calendar: Teams show each other what they tried with AI that week, what worked and what didn’t. The format is deliberately informal: Share your screen, try it, break it, discuss it. A prompt from operations that summarizes cancellation rules inspires the finance team’s reconciliation check the following week.
2. Prompt clinics
Twice a month we work in small groups on real business scenarios: “Summarize this contract’s cancellation terms”, “Draft a stop-sale notice for August”, “Find bookings with a missing transfer”. The goal in a clinic isn’t writing an elegant prompt; it’s learning to ask the right question, verify the output, and know where to stop. The best examples go into our internal playbook, open to everyone.
3. OctoAgent pilot teams
Before a new AI capability ships, a small volunteer pilot team uses it in their real work for a few weeks. What comes out of a pilot isn’t only a bug report; it’s a description of a new way of working, the point where we can say “this is how we do that task now”. Pilots also give the team natural AI ambassadors: They become the first stop for questions.
Our principles
Three principles sit underneath this learning setup: Transparency (work produced with AI is shared in a way that makes clear it was produced with AI), verification (critical output always passes through a human check, and our four-eyes culture applies to AI output too), and rewarding curiosity (the team member who experiments, shares, and can say “I don’t know” is the one carrying this culture).
In closing
We treat AI as a skill rather than a toolset, and skills only develop with regular practice. The weekly AI hour, prompt clinics and pilot teams: Together, they’re the gears that turn curiosity into daily practice.