From a manipulative boss, that sounds like "convince me I'm right."

I try to flip it around and say "here are my assumptions, what information or understanding am I missing? why is this is a bad idea?"

We all miss things due to our own biases, lack of understanding or information, experiences, or even just not being on that email thread. I think my questions have worked because it plays towards people who want to demonstrate how smart or well-informed we are... and we're all there at some point. :)

I just straight up say, here's a bad naive way to do this. How can we improve on it or do it differently? It's unlikely I've come up with the best solution in the world and the people on my team, who are probably smarter than I am, together will be able to get a lot closer

> I make sure to preface my suggestions to the team with, "Now, this is probably another terrible manager-idea, but how about we…".

Does this work for you? I mean, do you get more constructive criticism using this? I tend to think in real life we are programmed to agree with our managers most of the time. Have you received more sincere feedback when you start saying this?

Yeah, it makes it easier for people to push back, disagree, or propose alternatives. Part of it is that, as a manager, I really shouldn't be making suggestions for engineering approaches, and I try to defuse the feeling of "my boss told me to do this" by explicitly pointing out that I'm usually wrong.

Just indicating that you are okay with being incorrect is enough to garner at least SOME contrary opinions.

Probably if is a trend, instead of a single remark here and there..

The thing is, when the team ask "is this really the simplest way...?" what they're really saying is "we're not convinced, can we talk about this?" They're trying to open a dialogue. Replying with a stock, amorphous phrase like "kill several birds with one stone" is a conversation stopper.

It's not about whether the idea is really a good or bad idea. It's that the team feel that the proposed course of action doesn't make sense, or that a better one is apparent, but that the leader ignores their concerns. That's going to destroy morale. If, as the leader, you can't even convince your own team that your idea is good, it's probably not good.

To go one step more the team is also acting on their intuition -- they haven't fully used deductive reasoning to come up with their own solution to the problem, it just "smells bad", and now they're coming up with rationalizations (weird that OP calls it strategic reasoning) why it's not a good way.