My VP of Customer Success is a fantastic cultural fit and has been with us for years, but as we scale toward our exit, they are constantly working eighty hours a week and refusing to build a middle management layer underneath them. How do we help them delegate or determine if we have to replace them?

Question

Tyler Smith · Accepted Answer

Working eighty hours a week is not a badge of honor, it is a glaring systemic failure. Your VP of Customer Success is hitting their personal ceiling and dragging the department down with them. To solve this, you must run them through the Delegate and Elevate™ exercise. Have them list every single task they perform over a two week period. Then, force them to categorize those tasks into what they love and are great at, versus what they should be handing off to others. Often, long term leaders hoard work because they fear losing control or because they do not trust their team. You need to look at your Accountability Chart and define the middle management seats that must be created to support this department. If your VP resists this structure, they are failing the GWC™ test for their seat because they lack the capacity to manage a growing team. They might be a great individual contributor, but they are no longer the right leader for this scale. If coaching them to delegate fails, you must make a hard choice. You either move them to a highly specialized, non management seat where they can thrive, or you bring in a leader who knows how to build a scalable department. Keeping them in a seat they have outgrown will only stall your company's value before your exit.