I think by "figure out" OP did not mean "learned it to bits" and more like "learned enough to be able hire for that task"

I was bit before by hiring specialists when I did not know what task at hands was, what metrics I should expect, what kind of timeline is reasonable, what potential gotchas are.

And for person with CTO title, I think it must have.

Both points are true:

Don't hire a role you think you need until you're sure you need it. Sometimes startups think "we need an HR person" or "we need a marketing person" before those jobs are actually at the point where they require a full-time person.

But after your first few engineering hires, you will probably know well whether you need, say, a backend engineer. You will have people doing some of that work, and be able to look at your roadmap and estimate correctly.

But for first-of-their-type roles (like my marketing or HR examples), that's harder - often part of it is startup leadership thinking "we could be doing so much XYZ I don't know about", instead of "we're doing 10 hours of XYZ a week and I know we need 40".

Once you've decided you need the hire, you want to get a person as smart as possible.

You have to know enough about the thing to know if the person you are hiring is smarter than you at it.

I see this all the time in hiring and acquiring vendors. Management just wants to fill missing talent, but then can't tell they are getting mediocre work.

If you don't know how to do something yourself, you wont even be able to identify someone who is better than you in that field.

I've seen people who don't know how to market their product go out and try to hire a marketing guy. You might luck out and get someone perfect for you, but I've never seen it.

Usually they just end up wasting a lot of money and learning some hard lessons.

So how do you hire effectively as a CEO? There are too many areas for you to be knowledgeable, yet you need to be able to hire top talent across a variety of areas.

The method I've found is to ask people I respect a lot, "Who is the best X that you know?" Then call/email them, saying, "I'm the CEO of Y, and I'm trying to find out what a good X looks like. So and so said you're the best she knows. Can I have 30 minutes of your time?"

Do 5 of these, and you'll have a good idea of what someone good looks like. (And those 5 may give you some candidates)

This is very difficult though because things like "organizes the team to hit quota every quarter" can come in many different manners.

Didn't Steve Jobs say something about B players should only be hiring A players? Cause we all know if you start hiring C players they will just start hiring D players and so forth. The Bozo Explosion he called it.

There is a balance I guess. You don't need to do all the shooting yourself but you need to know where to point the gun, so to speak.

That isn't reverse. You still need to figure out what you need your self then get person to do your job 10 times better.