It mystifies me that a fairly unambiguous, direct decision made by the CEO (managers have regular 1:1s with their reports) can be interpreted as somehow optional or negotiable. If you're going to have a diva moment and quit because someone threatened to fire you for not doing your damn job (for the manager, holding the 1:1's--for the VP supervising that manager, holding the manager to the expectation of holding 1:1's), the company can go without you.
Viewed in isolation, your point makes sense. But in most start-ups (at least the ones I've worked for) there are multiple unambiguous decisions from the CEO along with a good number of ambiguous ones that are all deemed to be "top priority". You can't do them all and you don't know the weights that are assigned to each of the "top priorities" so you duck out on things that seem like lower priorities. In a typical chaotic startup company it wouldn't surprise me at all that something like regular 1:1 meetings with your manager could fall by the wayside.
I think that's the OP's point, though. Sometimes you have to clarify which decisions are unambiguous, not presently open to negotiation, and absolutely mandatory. If a decision has been perceived as something less than that, you need to clarify it. "This is your job, this is why it's important, and like everyone else in the world who doesn't have a damn good union, a sinecure, or serious blackmail on their boss, if you don't do your job you get fired."
There are many, many ways to clarify that this is important without threatening the man. If you jump straight to "blah blah blah in 24 hours or you're fired", that's just awful management. It is possible that Ben did not jump straight there, but that's certainly the way he tells it.
The 24 hours bit is a little harsh, but let's be honest here--saying "do this or be fired" is brutally honest, nothing worse. Any other way of putting it would just be a euphemism for "do this or be fired", and euphemisms are bullshit.
Just because a way of expressing is not the absolute rudest thing you could think of doesn't make it a euphemism. If anything, under normal circumstances, "Do this or be fired" is a dysphemism for just telling somebody to do something.
I mean, we're talking about a situation where clearly people hadn't been doing something they'd already been told to do, and somehow expected not to be fired over it.
It's actually not clear that they'd been told to do it (at least, not clearly) based on Ben's description of the situation. Nowhere does he say anything like "I'd talked to this guy about this before" — instead, he talks about how he leads by example and throws out lots of suggestions that he doesn't really expect to be followed.
So the job of a manager is just ensure that CEO's orders, no matter how stupid they may be are executed without any shadow of doubt, and no questions asked? By highly intelligent employees?
That's some lame management and some lame company to be in.
It's also every employee's job to honestly and openly argue with anything that he finds stupid or unnecessary. If he doesn't speak up, or if he loses that argument, then yes, he is supposed to commit to the decision that's been made and execute it to the best of his ability.
Conversely, it's every senior employee's job to listen to these arguments in good faith and countermand his own bad decisions once they've been pointed out as such.
What isn't anyone's job, ever, is to receive instructions from above and silently ignore them. Especially in this particular example, a manager who hasn't had a 1:1 with any of his reports in half a year probably isn't some brave conscientious objector trying to hide from the oppression of the CEO, he's more likely a shitty manager and the people working for him would probably be glad to see him summarily fired in the first place.
