A recurring pattern of my incorrect communication with bosses

I now realize an obvious mistake I made at GS — I frequently expressed negative attitude when proposing a simpler, easier solution to an otherwise arduous, time-consuming task.

In GS I had daily or weekly interactions with 3 managers — I report to A, who reports to B, who reports to C. The bosses in the examples below include all 3 persons. So my communication issues are fairly wide spread.

Example 1: I once wrote an email to my internal clients on 2 options about a system rollout. These internal clients are the users of the system. I said one of the 2 options would not require the team (potentially including some internal client as well) to stay late in office. I mentioned this stay-late factor as one of the pros and cons. My manager also received this email and she was shocked and even ashamed.

Example 2: My team lead and I each proposed a competing design on a major re-architecture project. I felt so strongly about this design choice that I arranged with team lead to present the 2 designs to my senior manager (who manages about 15 people), me first, team lead 2nd. After a 90 minute presentation and discussion, manager has heard all the facts and analysis. When it came to the final list of advantages/drawbacks, i mentioned that my simpler design has better performance, business logic transparency, auditability, … and can save, very roughly, an estimated 8 days of effort. (I felt it can save 20 days, but couldn't say it in front of manager). Then I said “You all know that long ago I planned a 2-week vacation for this month. The bigger design will be nearly impossible to finish before the deadline. We all know the deadline is not something we can change — many other teams are impacted in this huge project.”

2 months later, this senior manager revealed to me that personal vacation should never be brought up during system design discussions.

Example 3: This happened many times, perhaps 10 times between me and team lead. I often propose a simpler solution, against my team lead's more ambitious design. When discussing (sometimes debating) with him, i often speak about “easier”, “too difficult”, “faster”, “we can change later when we have more time”. These words became such an obvious pattern that team lead wrote in my performance review “seek what's good for the system long term, not what's easy for you… Pushback….Bin often says something is too difficult, but later it turned to be doable… Can-do attitude required.”