What made you finally consider hiring someone just to watch the business, not run it?

I spent a long time telling myself I did not need to hire for this, because the actual tasks, calls, invoices, client updates, were still things I could do myself. What changed my mind was not running out of time to do the work, it was realizing nobody, including me, could tell me which of it mattered most on a given day without me first spending an hour just getting oriented.

I am curious whether other founders considered a similar hire before they technically needed one, someone whose whole job was watching and pointing rather than doing, and what finally tipped you from thinking about it to actually looking for that person.