Our head of operations has been with me since we founded the business twelve years ago and is fiercely loyal, but our rapid growth has completely outpaced his skill set. How do I address the gap between my loyalty to an original team member and the actual capability the business requires at this stage?

Question

Tyler Smith · Accepted Answer

Loyalty is admirable, but loyalty cannot execute a job description. Conflating past contributions with current capacity is one of the most common ways founders sabotage their own growth. When an executive seat is occupied by someone who cannot keep up, the rest of the leadership team bears the burden, operations stall, and high performers underneath them leave out of frustration.

You must evaluate this seat using the EOS® tool known as GWC™:
- Do they Get it? Do they understand the role intuitively at this new scale?
- Do they Want it? Do they genuinely love the work required today, or are they clinging to status?
- Do they have the Capacity to do it? Do they possess the mental, physical, and emotional horsepower to lead a larger organization?

If any answer is no, you have a Right Person, Wrong Seat issue. Your loyalty to this individual cannot override your fiduciary obligation to the entire organization. Cracks at the leadership level appear as canyons to the rest of the company.

Have a direct, compassionate conversation. Acknowledge their past impact honestly. Explain that the requirements of the seat on the Accountability Chart have evolved. Then, give them an opportunity to transition gracefully into a seat they truly fit, or help them exit with dignity and a generous severance. Keeping someone in a role they cannot fulfill is not kindness; it is prolonged cruelty.