If I'm having a serious problem with my manager should I bring it up to their manager? I work at a startup and we don't have an HR department.

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This is a hard one to respond to without knowing what the problem is. If you feel comfortable sharing more detail, I think you could get some more actionable advice here, but in general, I would suggest:
1. Discussing your concerns with your manager directly first, if you haven't already. If you skip this step, you run the risk of them crying foul given that you didn't give them an opportunity to address the issue themselves first.
2. If the above doesn't yield favorable results, then yes, bring it up with your manager's manager, but warn your immediate manager first, so that they're not blind-sighted.

I agree with V1.

You’ll definitely want to make the attempt at point 1. Most likely I would assume this would happen over a phone call, but if you’re able then I would also get it in writing.

I was struggling with processes that were being set or owned by my manager. We had a professional and candid conversation which broke up into:
1. Why is this an issue for me
2. What am I suggesting to make the issue better
3. Collaborating on what next steps my manager could do (aka action items) based off of my suggested solutions

After the call, I recapped everything in an email which was presented more as “notes from our call” but also served as a written record of my concerns and holding my manager accountable.

This will make you look more favorable if you do ever get to point 2 of going to your managers superior. I think overall; you don’t want to go to your manager or their manager will problems. You want to go to them with solutions.

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