Custom GPT and Projects usage grew 19x in 2025. Teams are building AI teammates—custom GPTs, Copilot Agents, Gemini Gems, Claude Projects—customized with their own data and expertise. But building them is the easy part. Getting them to stick is harder.
One team built 211 AI teammates but only 57 stuck. The rest weren’t all failures. Some were duplicates. Some too narrow for broad use. Some served as productivity tools for specific individuals.
But the 57 that became part of how the team actually works had something in common. Their builders made five design decisions intentionally.
The five decisions:
What relationship are you creating? Tools, sidekicks, and personas set different expectations. Match the name to the job.
What does it need to know? You don’t need perfect internal docs. External research can fill the gaps.
How should it engage? AI that thinks with you, not for you. The difference is in the instructions.
How easy is it to use? If adoption depends on knowing how to prompt well, adoption will stay low. Design for the least expert user.
Does the human still own the decision? Thinking partners surface trade-offs. Answer machines give you one option.
This is Part 1 of a two-part series. Building great AI teammates is step one. Part 2 covers the bigger opportunity: connecting them into workflows. McKinsey found only 21% of organizations are doing this work, yet it drives the biggest impact.
This newsletter features insights from Jim Kruger (CMO, Informatica), Renée Gapen (SVP of Marketing, PointClickCare), and Alexandra Gobbi (CMO, Unanet). Leaders doing the work and sharing what they’re learning. Grateful for each of them.
Prefer audio or video? I created an AI video explainer and AI podcast version (links in comments) using NotebookLM to cater to different learning styles and time constraints. See links in the comments and newsletter.
No one has this all figured out. The more we share what’s working and what’s not, the better off we all are. Which of the five decisions has been hardest for your team? Share in the comments and pass this along if it’s useful.