The biggest barrier to delegating is not trust, it is documentation. Founders assume handing off a task means writing a detailed manual, so they never start. There is a far faster way.
Record, do not write
Open a screen recorder like Loom, hit record, and do the task exactly as you normally would while narrating what you are doing and why. A process that would take an hour to write up takes ten minutes to record. You talk faster than you type, and the video captures the small judgment calls a written doc usually misses.
Narrate the why, not just the what
As you work, explain the reasoning behind the steps that are not obvious: why you tag a client a certain way, what you check before sending, where the common mistakes hide. That context is what turns a VA from someone who follows steps into someone who handles the task the way you would.
Build a library over time
Drop each recording into a shared folder organized by task. Within a month or two of normal work, you will have a training library that lets you onboard support fast and hand off new work without reinventing the explanation each time.
The first time you record a process it feels slow. By the third, you will wonder why you spent years explaining the same tasks over and over in real time.