Most organizations investing in executive coaching run into the same wall. They cannot tell which coaches are performing, they cannot share what works across the program, and the information they need to improve is trapped in systems that do not talk to each other. In this working session, Grant Calder draws on two decades of designing and running coaching programs at the Stockholm School of Economics and with corporate partners to name the three gaps that keep coaching programs from getting better over time: the data gap, the methodology gap, and the integration gap. This is a workshop, not a talk. Participants will discuss their own organization's opportunities, challenges, and dilemmas with peers at a similar maturity level, share what is working, and leave with one concrete action they can take in the next two weeks. Grant will also share where AI genuinely earns its place in coaching, not as a replacement for the human coach.