We are making our first external executive hire to lead our operations, but we are terrified they will bring big-company bureaucracy that kills our entrepreneurial speed. How do we structure their first ninety days on our leadership team?

Question

Tyler Smith · Accepted Answer

Bringing an outside executive into an entrepreneurial leadership team is a high risk move. To prevent cultural rejection, you must design a strict, structured onboarding process that focuses on learning before executing. During their first thirty days, your new hire should have one job, which is to observe and learn. They must shadow team members, talk to customers, and understand how your operations actually function. They should not be allowed to make major structural changes or implement new processes during this initial phase. This prevents them from introducing unnecessary, complex big company bureaucracy before they understand your unique entrepreneurial culture. In their second thirty days, they should start identifying operational gaps using your existing EOS® tools. Have them participate fully in your Level 10 Meetings and contribute to your IDS sessions. Their focus should be on building relationships with their peers on the leadership team and understanding the core values of the business. By day ninety, they should own their seat completely. At this point, they should take on their first set of quarterly Rocks and be fully accountable for their departmental metrics on the scorecard. By structuring their integration this way, you ensure they adapt to your operating system rather than trying to force their old corporate habits onto your team. If they resist this learning phase and immediately try to build empires or write massive policy manuals, you will know early on that they are not a fit.