You should never hire anyone for something you haven’t first struggled to do on your own. It’ll teach you most of what you need to know to actually interview candidates, it’ll allow you to understand the nature of the work better (do I even need to hire or can we outsource?), and you’ll know exactly what a job well done will look like. It’ll also give you a sense of whether the job is big enough for a full-time hire yet or if you can skimp by on your own (the latter is preferable if possible).

Jason didn’t hire me to help him program Singlefile (now defunct) before he had a sorta-just-barely-working prototype running off his own PHP skills. I didn’t hire Mark to do system administration before I had spent a whole Summer setting up a cluster. Jason didn’t get Sarah on board to do support before he had first done it for years on his own.

The benefits of having done the work yourself before seeking help doesn’t stop at hiring either. You’ll be a much better manager of roles that you’ve already held than when you’re completely in the dark about what it takes to perform. You’ll have empathy available when the going gets tough and it’s not their fault — and a stern voice when it is.

Don’t let big titles scare you off either. What does a business development person do? Find out by trying it on! Call people, make a few deals. Think you need a usability tester? Try a simple session on your own first with friends. No, it won’t be perfect. That’s okay. What you’re paying in initial execution will be repaid many times over by the benefits above.