2025 may go down as the end of an era in retail. This was the year that the longtime CEOs at two of the largest chains decided to hand the reins over to their corporate proteges. The retirements of Walmart's Doug McMillon and Target's Brian Cornell come as the industry is facing an array of new (and long-term) challenges in the form of a global trade rebalancing, accelerated adoption of AI, and increasingly stretched US household budgets.
Leadership transitions are pivotal moments. A CEO's first 100 days in a role are exhaustively studied; the last 100 days far less so, despite the steep costs of poor exits and the compounding benefits of good ones. For organizations, mishandled transitions can erode shareholder value, destabilize strategy, and undermine trust. For individuals, they can unsettle identity, strain relationships, and tarnish reputations.
These numbers reflect the critical need for effective support during leadership transitions. If this sounds familiar, here's how leaders can coach someone up to replace them. COACH THEIR MINDSET AND NOT JUST THEIR SKILL SET When we hand off a role, we often default to knowledge transfer. We overemphasize tools, systems, and processes. But that is not where most leaders struggle. The deeper fear for most new leaders is internal: Will I ever be as good as you?