> I'm skeptical of this statement. It seems to rest on many unreliable assumptions (e.g. at a busy company, it seems that a team lead may know better than the CEO when his team needs additional resources to deliver).

As a team lead at Automattic, pretty much all of us have regular chats with Matt -- some on bi-weekly group hangouts, others casual private conversations in Slack -- but we all communicate our personnel needs and concerns to him, and sometimes the solution isn't "Hire a new person for X squad" -- it may be take someone looking for a team switch and shift them around internally.

Having actually experienced this in practice, Matt really is stellar at making sure we have the people we need.