All startups are dysfunctional. To some extent. Some more. Some less. As a founder, one should always be striving to reduce this dysfunction. It is a journey, not a destination. There is no end to it.
Two young fish were swimming in a stream. They see an older fish coming towards them. The older fish passes them, greeting, how is the water, boys? The young fish look at each other and mutter, what the heck is water?1
When people spend time at an organization, they internalize the dysfunctions. They figure out ways around them to get things done. These might be sub-optimal. These might be taking 10x the time. These might be leading to inter-department strife. These might be dragging down the entire company. But, from the surface, it does not appear so. Everything looks hunky-dory. We do not see the obvious.
But, not so to a new hire. To her, these dysfunctions are very apparent She comes with a fresh pair of eyes and perspective. She is not yet indoctrinated. She has not yet internalized the system. The organizational dysfunctions stand out starkly to her.
Use a new hire, especially a leadership new hire, as your surrogate eyes to unearth the dysfunctions within the organization. You might be pleasantly surprised by what you find.