It’s a much bigger problem than this, sadly. The fact that you are even saying “If you want it to continue to work, you also have to be very careful how you com

It’s a much bigger problem than this, sadly. The fact that you are even saying “If you want it to continue to work, you also have to be very careful how you communicate...” is the problem. The problem is that the way we manage things causes engineers and management to be against each other in principle, so that management is pushing one way and engineering is pushing the other way. Your advice is kind of like marital counseling, “let’s agree to not label Tom the person as an inconsiderate asshole but just talk about how he makes you feel,” “OK, well Tom, I am frustrated by your daily behavior that I perceive as assholish and inconsiderate” and I am sure it helps a little but I mean if you think Tom’s feelings aren’t going to be hurt you’re not giving him much credit. In fact if we were being honest with our managers we would be scandalized. We base our estimates on something like an 80% chance of getting something done (which already improves on the 50% chance by roughly doubling our estimate) and then every engineer I know has some informal rule about doubling or tripling the estimate before they hand it off to their manager. Those managers often add their own 20%. Then their managers see that something is up so they slash 50%. More than half of any project—perhaps even three quarters or more—is estimated as safety-factor. You would expect that if we were getting it wrong, we would be getting it wrong the other way, delivering early. The fact that we are late so often is a scandal in its own right. Adding more time buffer is clearly not helping much, since we have such a surfeit of it already. We must have wasted that safety buffer; there is no other explanation for how it disappeared. And once you have set up these luxurious margins of safety it is already too late. Why is the engineer adding that extra factor 4x or whatever it is? It is because management is already at cross-purposes to engineering. That engineer is adding that safety because they do not feel safe without it. Any insufficiently safe ski-lift in active use will see hundreds of buggy ill-specified implementations of safety harnesses: I will go on this ride but I am taking some precautions. The starting assumption has got to be that it is OK to fail on the deadline. This cannot be because of hidden information but must come as a result of trust: “we are eating into the safety buffer, that is totally OK and that is what it is there for, but I want to do whatever I can now to get you out of meetings and approach-planning and to fill out your timesheets for you and heck, even plan an amazing weekend between you and your fiancee to alleviate relationship stresses—and take any other distractions and loads off of your plate so that I can get your single-pointed focus on this feature and we can finish this.” If management makes themselves that safety harness, then there is no cross-purpose.