If you want to be a bad product manager, don’t escalate any issues to your boss. You don’t want to show that you’re incapable of doing your job, so don’t ask for help unless you really need it. If you do need help, make sure your boss knows all of the ins and outs of the problem, including the whole backstory, and don’t specifically ask for help — just communicate the story and see what he/she says. You don’t want to actually “ask,” you want to just explain what’s going on and see what the response is.
If you want to be a good product manager, escalate issues appropriately. While there are many decisions for which you as a product manager are responsible and accountable, there will always be some issues that require escalation. Part of managing your relationship with your boss and managing issues and risks is knowing when and how to escalate issues. Escalating too many issues is just as bad as not escalating any. Escalate too frequently, and it will appear as though you are not competent in your job. Escalate too rarely, and others may have to help clean up problems that could have been avoided had they been informed of them earlier.
First, understand when issues should be escalated. This may be easiest done with an honest conversation with your boss to understand what types of issues he/she expects you to manage on your own, and what types of issues he/she expects you to discuss or escalate. Different managers have different approaches and want different levels of involvement.
You can also ask yourself if you have the knowledge to make the decision or accomplish the task, and if your boss has more knowledge in this area, whether that additional knowledge would change the outcome. Alternatively, you can ask yourself whether you have truly reached a point where you can do nothing more — have you tried everything you can possible think of and you still are not able to resolve the issue?
If other stakeholders need to be consulted, think about whether traditionally you have involved them directly or whether you have gone through others. Are they your peers or are they at a much more senior level?
Once you have identified whether the issue needs to be escalated, you need to clearly and concisely explain the issue and your expectations. Provide enough context without delving into unnecessary detail. Make sure to highlight the different possible solutions and the benefits / detriments of each. Outline any known implications on customers, sales, operations, cost, or any other aspects of the product or the business. Provide any relevant competitive information that may aid in resolving the issue.
Last, and most importantly, clearly state what you are looking for your boss to do. Do you need a yes/no answer? Does he/she need to discuss the issue with someone else? Is there a specific action that you need your boss to take? Is there a specific date by which you need an answer or resolution? Or, are you escalating just so your boss is aware of potential future issues? It may sound basic, but if you are providing your boss with information, you need to make it clear why.
Raising issues to your boss can help you be a more productive and successful product manager, provided you know when and why to raise issues, how to raise them, and what you are looking for your boss to do in response.