A CEO faces three staffing problems: a department head who's hit their ceiling, a VP role to fill, and undocumented tribal knowledge slowing the company down. The conversation weighs practical tradeoffs like coaching versus replacing, internal promotion versus external hire, and whether to pause growth to document processes or hire someone to do it.
A department head you've had since the early days is clearly capped out at this new size of business. Would you coach them hard and give them 90 days to level up, hire above them and let them report up, or move them sideways into a role that fits their ceiling?
I would try to coach them up, but yeah, 90 days is all you can do. Likely B is what's going to happen, and likely if you do hire above them, even though they should stay, they're probably gonna quit at that point. And unfortunately, just everybody's got a ceiling, and the only way you can break through it is to go somewhere else and learn how to break through the ceiling.
You need a VP level higher, but can't tell if you should promote someone within or go outside. Do you A, promote internally, 'cause culture fit outweighs experience gaps, B, hire externally, 'cause you need capability you don't currently have, or C, do both, hire external and pair with an internal co-lead for 90 days?
You're gonna need to bring somebody in externally almost certainly. What you want to do is we want to Actually write a job description for the role that we need, and then we're gonna ask the question, does anybody in the company fit this job description? If the answer is no, hire from the outside. Yep, pair them with somebody internally. Just culture fit alone does not magically make somebody know how to do something they don't know how to do.
You realize your business runs almost entirely on tribal knowledge with almost nothing documented. Do you A, pause growth initiatives to document everything first? B, document only the highest-risk processes and keep moving? Or C, hire someone whose full-time job is building the documentation as you go.
B, you gotta document what you do, but only document the critical. If it's high stakes, so it's really important, if there's a high chance for human error, if it's highly repetitive, document it. This is like a handful of things though, and just have people build the documentation while they do the dang thing. You don't need to hire from the outside to create business and system documentation.
