[swatcoder]

I don't know your old founder and can't speak for them, but generally, that kind of phrasing is just idiomatic, and not meant to be parsed literally.

It's just a colloquial way of saying "I've earnestly thought about X, Y, and Z and think it's the most effective way path forward" or "my intuition is telling me X, Y, Z is the best way to go"

It's a way of expressing that they have a strong sense of how to proceed and the "passive-aggressive jab" that you hear is just an artifact of the idiom not being familiar or natural to you.

[lovich]

Or it’s a shitty boss who’s averse to direct conflict and leaves little hints for their employees to interpret like tea leaves.

Can’t really tell which situation it is without more information but both are common

[ryandrake]

Yea, it's hard to convey the non-verbal cues that came along with the phrase. The way he would say it was just dripping with superiority and sarcasm: "If we were -smaaaarrt- [pause to look at the rest of us peasants]... then we would make this so much better..." The unspoken message was really not hard to interpret: "If I was blessed with SMART engineers rather than a bunch of dummies (and I'm looking at you)..."