This morning, shortly after I got into the office, I got an IM from a friend I hadn’t heard from in a while.

Mike, can I complain to you for ~15 seconds about something completely unrelated to whatever it is you’re doing right now?

This sounded promising! I said yes please.

So, [the company where this person has worked for several years] is a tough act to follow.
But startup CEOs are really annoying.
Whenever I ask them what they want me to do, they reply by asking, “what do you want to do?”
which is like, duh, if I knew the answer to that, I would go do it
this is why I should have learned a marketable skill- like typing, or how to run an engineering organization.

He sent that string of thoughts to me pretty quickly, so I replied that I thought he might actually go for the typing route after all. Then I said something a bit more serious:

So it’s actually funny you mention that… when I was planning to leave PayPal, I was already working part-time at LinkedIn and was pretty sure I was going to go there.
I did interview with one company, though — just met with the CEO and he kept asking me “what do you want to do”, and I kept saying “what do you need.”
And basically we went back and forth in that form for close to an hour… at the end he told me has was interested in hiring me, but I’d have to tell him what job I wanted. And I felt like I didn’t really understand the company, so there was no way I could tell him what I wanted to do for them.

In other words, I could relate to my friend. But, I continued, I could relate to the other side as well.

Now I’m on the other side, and I can see the crazy CEO perspective. You don’t entirely know what you’re doing or what you need… especially within a realm (e.g., [my friend's area of expertise]) that you may not personally understand.
And you feel like your best bet is to hire people who will figure it out themselves.
Obviously, that takes a lot of trust and belief on both sides.

My friend was intrigued, and told me about how he’d joined his current company:

i sort of wonder if this is [founder of his current company]‘s sort of black art genius gift
b/c he made it very easy for me to leave [big company where he'd worked before] for an ill-defined job at [current company, which was small at the time]
like, there was a broad goal/desire, but not much in the way of details about how it should be accomplished
and i remember feeling, on my first day, that i was basically useless
it really wasn’t obvious exactly what I should do
and I sort of panicked and set to work trying to figure it out

That made sense. Some people rush toward crazy ambiguity and thrive with it. Others hate it and will be crushed by it. I’m in the first camp; my friend is somewhere in the middle. As I explained, what he described was similar to my experiences at PayPal and LinkedIn:

yeah, my guess is that that’s reasonably typical… was pretty much my experience at PayPal and LinkedIn
at PayPal I at least knew what problem I was supposed to solve (find fraudsters); at LinkedIn I didn’t really even have that

Our conversation lasted longer than fifteen seconds, but covered some interesting pieces of startup psychology.