I have come to the realisation that I do a much better at hiring for positions that I've tried to execute before.
- hire a Product Manager after you've owned the roadmap for 6 months.
- hire a Sales Manager after you've sold your product to at least 10 users.
- hire an HR manager after hiring and managing 10 people for yourself, after doing 1-on-1s.
Before you proceed with that new hire you've been thinking about or others have been asking for, try that job for a while. This will help you understand the challenges of the position and appreciate how hard it is to get results.
As a result, you will design a Job Description that is more realistic and will conduct more relevant and interesting interviews for yourself and the candidates.
The same is true for activities other than hiring. Before you automate a certain action with a program, its best to try and do it manually a bunch of times.