Like we were handed a solution to implement that architects and product folks had been talking about for most of this year. But they didn't include anyone that was day in day out hands on with the systems they wanted to change. To do that and then ask the people implementing if we can speed things up would be quite annoying.
It's asking them to contradict the design decisions that people 1-3 levels above them made. Risky business for sure. Even moreso for technical folks that in general aren't as adept at sussing out the difference between someone really asking and someone looking for a rubber stamp on a decision already made.
The point of these questions should be to encourage really creative thinking to break out of "normal" operating modes (take on tech debt, etc) and if that's not well understood, or perceived to be an instruction to crunch, then you haven't set the context appropriately and will burn people out.
> Can we re-frame this in terms of the customer’s problem?
> What’s the soonest we could get this done?
> What would you need to get this done tomorrow instead of next week?
Well, that sounds like a recipe for high turnover. I know few engineers who would want to work for this kind of low trust boss and they are all bottom of the barrel consultant types. I thought Stripe was doing better than that.