And boy to the people making the decisions NOT want to hear that. You'll be dismissed as a naysayer being overly conservative. If you're in a position where your words have credibility in the org, then you'll constantly be asked "what can we do to make this NOT a quest to the top of Mt Doom?" when the answer is almost always "very little".
Wrote to my management: "It is, by all means, great when a navigator is able to take over an incapacitated pilot and make an emergency landing, thus averting the fatality. But the conclusion shouldn't be that navigators expected to perform more landings or continue to be backup pilots. Neither it should be that we completely retrain navigators as pilots and vice versa. But if navigators are assigned some extra responsibility, it should be formally acknowledged by giving them appropriate training, tools and recognition. Otherwise many written-off airplanes and hospitalized personnel would ensue."
For all I know the only thing this writing might have contributed to was increased resentment by management.
You are 100% correct. The way I've tried to manage that is to provide info while not appearing to be the naysayer by giving some options. It makes it seem like I'm on board with crazy-ass plan and just trying to find a way to make it successful, like this:
"Ok, there are a few ways we could handle this:
Option 1 is to do ABC first which will take X amount of time and you get some value soon, then come back and do DEF later
Option 2 is to do ABC+DEF at the same time but it's much tougher and slower"
Working teams are good for a project only, then they are destroyed.
I've been managing, designing, building and implementing ERP type software for a long time and in my opinion the issue is typically not the software or tools.
The primary issue I see is lack of qualified people managing large/complex projects because it's a rare skill. To be successful requires lots of experience and the right personality (i.e. low ego, not a person that just enjoys being in charge but rather a problem solver that is constantly seeking a better understanding).
People without the proper experience won't see the landscape in front of them. They will see a nice little walking trail over some hilly terrain that extends for about a few miles.
In reality, it's more like the Fellowship of the Rings trying to make it to Mt Doom, but that realization happens slowly.