Manage your boss by not screwing up their OODA loop. Open your mouth at the Observe stage no matter if they want you to or not, don't distract them at the O and D stages, and make the best as fast as possible of their Act stage. Slowing down or sabotaging their O,D, or worst of all, A, makes you look like a problem and slows the loop cycle time making the likelihood of future bad O or D even higher while also pushing the correct A out while possibly cutting into future Observe stage available time, a quadruple lose-lose-lose-lose situation, which is impressive in its own way.

That model may work for fighter aces but it doesn't work for the office. In any project that takes more than a day you spend most of your time in the 'Act' stage and get a ton of new information before you finish executing.

Technical managers have to be sensitive to new information, * especially * when it ruins their spec.

I don't think he wants great people. That's the point.

I think he wants cheap people. Everything he is looking for is hinting at cheap.

Not necessarily. He says he operates in NY, so he can't pay too cheap. Even the most loyal employee will jump ship if the competing offer is 2x what he's currently making, especially with NY cost of living.

What he wants is stability. You'd be surprised how many very smart people put a premium on that sort of thing, especially when they get older.

They won't get 2x offers if they don't have a pedigree and can't handle hard tech interviews. (Which is what he's filtering for).

An employee with limited options = A more stable employee

Humbly disagree. 2x offers depends on how little he's paying them to begin with vs how easy it is to switch jobs. You don't need a pedigree or be able to handle hard tech interviews to switch jobs in NYC. You just need to go on a lot of interviews. Eventually, one will say yes.

NYC isn't exactly a place where you have limited options. You want limited options? Try to find a job upstate.

In this situation the employer has stable option, you'll stick around no matter the crap.

From perspective the employee it isn't stable. Sounds like he'd get rid of you, if you disagree with anything.