Similar situation as OP. My dad started the business (his 3rd overall) 22 years ago and it's been growing steadily since. My dad still does daily scans of our ERP. I run the business with him and we have 40 employees, and I too have had similar conversations with him.
While I'm sure there is a better way to do this (e.g. invest in BI, hire and train a person to do this etc.), the fact of the matter is no one else is as invested in your business as you. So you are wired to find issues (even if none exist). It might just be an old-school small business mentality, but it works.
At the same time, it's tied him to the business in a way that he doesn't know how to get out.
> no one else is as invested in your business as you
This is so important, and I think it's what differentiates small owner operated businesses from multinationals and chains.
Your employees are not going to idly look through logs to see if everything is running smoothly when they are done with their tasks, they'll just go home and call it a day.
I think your mentality is right (as a small business owner myself).
However, to push back a bit, I think sometimes it’s easy to believe that we’re the only ones who can do something because we’re the only ones who have lived and breathe it for 5+ (Pick your number) years. And one might be surprised if they actually tried outsourcing how competent some folks can be.
Coming from the tech world, a lot of my focus has been setting up processes, piece-meal outsourcing and letting employees have more autonomy. Recently we even set up a small team in the Philippines to handle data entry.
However, I've grown to appreciate his view as well over the years.
Can you share what kind of tasks you've successfully outsourced? In my experience it was very hard to outsource task with a vague definition like "look for things that aren't running smoothly".
The low hanging fruit answer is "admin." It's easy to fall into this trap of "only I know how the whole business runs; so I should just keep doing admin stuff." But you'd be shocked at how quickly a competent administrative assistance can handle some of this stuff (including pre-drafting email responses in your "voice").
Next step up is stuff outside of your core-competency. So that's where the CPA comes in to take some financial stuff off your plate. This can be hybrid with an admin assistance.
Then you get into the "core" functions. For a media creator, that might mean editing. Again, it's easy to fall into a trap of thinking some other editor won't be able to match your style or voice. But when you hire someone who sees themself as primarily an editor, and they're good at their job, they're really good at adapting and adopting voice.
With all of these things, often the person you're offloading to can't match your output 1:1. But if they can get you 90% completed rough drafts of the final deliverable, there's immense value there all the same.
While I'm sure there is a better way to do this (e.g. invest in BI, hire and train a person to do this etc.), the fact of the matter is no one else is as invested in your business as you. So you are wired to find issues (even if none exist). It might just be an old-school small business mentality, but it works.
At the same time, it's tied him to the business in a way that he doesn't know how to get out.