This in-depth article delves into the limitations and potential reinvention of the executive coaching industry in preparing leaders for future challenges. It identifies four flaws in the traditional coaching model and proposes solutions. One cited flaw is the oversimplification of “effective leadership” within executive coaching, neglecting unique contextual factors in each organization. Addressing contextual questions, such as the particular problem sets leaders need to tackle within a company and the varying stakeholder and cultural considerations, is paramount for providing relevant and practical executive coaching. Additionally, the article stresses the need for coaching engagements that cultivate “collective leadership capabilities” essential throughout an organization’s leadership ecosystem, rather than solely focusing the engagement on individual needs. My 2016 article, “Identifying Leadership Capabilities That Drive Business Performance,” discussed the importance of building collective leadership capability. Given the escalating demands on organizational leaders, pinpointing the required leadership capabilities and leveraging them as a competitive edge will be critical.