What should I do in a situation where my manager is well-meaning but incompetent?

This is a very mature question and I like how much context you added. My initial thought was that the manager must be brand new, but this is something that has been happening for 1.5 years. A few ways I've seen other teams deal with potentially bad managers:

• Encourage reports to have a crucial conversation with the manager (but this is, of course, difficult to give criticism to someone who controls your bonus). Sounds like you've already tried this.
• Talk to your skip-level manager. The conversation shouldn't be framed as "I'm ratting out my manager" but more along the lines of "Here are some concerns I have, I'd love your perspective"
• Provide examples where your manager had a poor estimate and unnecessarily caused concern on the engineering side. Try to make this clear and then ask if they agree, and how similar miscommunications may be prevented in the future.

A lot of this is an exercise in communication, so I'd recommend our masterclass in effective communication.

Finally, on the core question of whether to stay or leave, I'm honestly leaning toward leaving. If it's been 1.5 years and you haven't seen marked improvement, it's unlikely things will magically get better without some direction/management change. You don't want to put your career in the hands of someone who doesn't advocate for you / understand you. You're also at Google, so hopefully it's not too difficult to find another team with friends/connections/interesting tech.

As an IC, the reality is that you don't get much ability to shape your environment -- it's generally easier to pick a new environment.

The reality is that you don't get much ability to shape your environment -- it's generally easier to pick a new environment.

- Rahul Pandey

This is why the Star Principle by Richard Koch is my favorite book. Pick better industries, better businesses, better teams: it's much less work to pick great environments than change poor ones.

Thanks for the thoughtful advice, Rahul!

Unfortunately, my manager is an industry veteran (~20 years), but this seems to be part of their style. From what I could tell from another engineer that used to report to them, they were more or less this way for their entire tenure thus far at Google (~3 years). The GoogleGeist hasn't been good for my manager for some time, and I don't anticipate the upcoming one to be much better. So overall, I agree with you and I'm not optimistic that we can see dramatic change in my manager's behavior and competence.

I think I'm going to focus on the following for the upcoming year:

1. Time box my time here on this team (~6 months). Unless the managerial situation changes, I'm changing my team this upcoming year. At this point in my career, I don't feel hindered by my manager - I can get my work done without their assistance - but I think the ceiling on my growth would be much higher with a supportive, competent manager.
2. Use my remaining time on the team here to expand my scope, fill gaps my Manager leaves behind.
   1. Since I'm interested in people management anyway, I'm going to try to lean more into proactively mentoring and coaching my direct teammates. I'm already having 1:1s on a regular basis as the TL, but I'm going to try to make them more structured and more focused on helping their growth.
   2. I'll take more proactive role in managing the projects my team undertakes. Project management and risk assessment isn't my strength, but I'm going to work on it (luckily there is an staff engineer TL adjacent to the team I can rely on). I'm going to try to get ahead of my manager attempting to expedite things and propose more concrete schedules.
   3. I watched effective 1:1 communication series and I'm going to attempt to assert structure in 1:1s w/ my manager, such as agenda/meeting notes, and discuss honestly have about what I believe the team needs. I imagine part of the issue with the lack of focus in my 1:1s with my manger so far has been the fact that I've approached it more passively (since I simply, well, don't enjoy talking to them).

Let me know if you have any further advice for me! I'll keep this thread updated on what I happens so hopefully it will be helpful to those reading this in the future.

Update, 7 months later.

I left the team about 3 months ago, for a similar role within the same organization. I ended up finding my own destination team via word of mouth (there technically were no open headcount), and I held a lot of really honest discussions w/ my skip to make it all happen. I made it clear to them that I was done with my manager, but I have a lot of existing knowledge within the org that I want to continue to use for the benefit of the org. The whole thing took about 3 months to complete. The current economic environment also meant my skip lost a HC and wasn't able to backfill so that made it more challenging. I did discuss the same feedback w/ my manager and they were very receptive; however, I'm not entirely sure they would be able to absorb them.

While the new work is more demanding, I feel much better because I am no longer coming home everyday frustrated!

For those in similar situations, here's what helped me through the last 6 months:

1. Deciding for myself that I am going to leave. The timeline might not be in my control, but making that decision in my mind and sticking with it through it all was very helpful. The answers here were helpful to me finalizing my decision!
2. Putting in exceptional work while searching. This earned me extra credibility with my skip who facilitate the move - if you know your manager is a problem, so do they.
3. To find job openings in the org where none exist publicly, I looked for new initiatives, teams that are undergoing churn or some sort of change. Additionally, the thing that I think mattered was that the target team (a) was more important than my current team, such that the org will be willing to reallocate resourcing (b) needs people of my specific background to bridge some sort of gap.

Overall, I learned that doing the hard work myself of setting up the transition such that the people in power can simply "approve it" made it more likely to happen. Bonus points if executing your plan enables the same people to do a favor to a peer or boss (e.g. support an P0 initiative within the org).