My manager and I don't see eye-to-eye. How can I improve this relationship?

Before I give any concrete advice, I just want to say that it's critical to push for empathy in these scenarios and not see the other party as an enemy. Change is hard, and if you're used to doing things a certain way for many years at your previous job and then you come into a new one that's all different, it can be a culture shock.

In a nutshell, your mentality should be more like "I want to work better with my manager, so I can be a more effective report and we can achieve more together." as opposed to "My manager doesn't do things the right way, and I need to change that."

That being said, here are some tactics:

Do Your Homework, Have Clear Examples

• At the end of the day, everybody understands and is worried about impact. "Is the team able to ship projects and hit its goals?"
• Find instances where this misalignment hurt the team and your manager was a key player, whether its paralysis settling on projects to prioritize or project execution.
• Show that the problem areas are scenarios where the manager is pushing for something and the clear majority of the team is pushing for something else.

Understand Your Teammates, Build Alliances

• Build relationships with your teammates, especially the other senior engineers on your team. This is something you should be doing no matter what as a senior engineer.
• Once you get to a point where you feel comfortable with them, you can bring up this manager topic and get their feedback.
• It's possible your teammates don't agree or have come up with methods on how to work more effectively with your manager. Whatever it may be, it's useful to learn.
• If your teammates agree with you completely that this situation just isn't great all around, then this makes your case far more compelling, particularly when talking to your skip manager.

Let Your Skip Know

• As your manager's manager, the skip is the key player towards delivering constructive feedback and getting it to land.
• Talk to them about this, ideally in a 1:1 setting. If possible, have a monthly 1:1 with them, so you can build up this relationship and make it more fluid in situations like these.
• If your skip is reasonable and you've done the above 2 things, I feel good about your chances of genuinely creating positive change here.

Sharpening The 1:1s

• Write a clear agenda for your 1:1s before they happen and let your manager know beforehand. You can say something like, "Here's what I want to talk about in our upcoming meeting - It's really important to me that I get your input on all of these." This clarity makes it harder for the meeting to go off-topic.
• It's natural for people to go off-track in meetings. In these scenarios, just politely get them back on track. "It makes sense to me what you're saying, but I would really like to talk about XYZ in the agenda for ABC reason - Can we switch gears?"

Related resources:

• How To Effectively Leverage Skip Level 1:1s
• Voicing Your Problems And Frustrations Productively

As fate has it, I’ve been in this situation a few times. Here’s how I dealt with it - It really helps to ground everything with empathy and data.

Empathy:

• I would like to learn what concerns my manager is facing. You never know the pressure they might be under or the objective they want to drive and if they think a particular concern is not being addressed by the team/or you.
• Once establishing the concerns, evaluate it objectively, use data, other team members to establish if concerns are not being addressed. For example, say your manager’s concern was that the team is having too many sev2/3 incidents from the services owned by the team and that it’s not being taken seriously by the team to address the tech debt, evaluate with them if this is actually the case.
• Explain how their behavior/actions are affecting you and the team. Continuing on the previous example - the misalignment is due to too many sev incidents, but his actions/behavior are not helping to resolve this issue instead demotivating you/team, no one wants their actions to misfire. It’s in the manager’s interest to have a well functioning team and no one really goes to work thinking “let me do a bad job today”
• The principle here is to try to translate feelings to data, then you can actually evaluate and move forward

Data

• The second way I learned to deal with these situations is by data. Say, you/team tried to learn what the manager's concerns are and given feedback on how their actions/misalignment is impacting the team. It’s time to involve a third party/escalate, for this you need solid data.

• Here’s how I would talk to my skip level -Causes of friction - Situation, manager’s reaction on the situation, your feedback to them, their reaction to your feedback, what are the next situations followed etc.

• By keeping everything organized in facts rather than feelings, you are giving your skip level an opportunity to coach your manager

My template is more or less like

• Here’s the situation
• Here was the discussion i had with my manager
• Here was his response
• Here was his action post feedback (either improved or the same)
• Here is how I feel about it
• Here is how I think the team feels about it (maybe guage how the team feels in any retrospective meetings, one-on-one, etc.)
• Here is how that is translating into productivity for the team.

Once you provided the feedback to your skip level, move on. If this is a systemic problem within the company, time to find different company - as one person can never change the whole top down management chain. Usually, most things like this are misunderstandings of situations rather than top down toxic behavior.

+1 to everything Alex Chiou suggested :)

(lot more articulate than I was )