How to Ask Your Boss for Management Advice

One of the isolating aspects of becoming a manager is that you feel like you can't ask for help without looking like you aren't qualified to be a manager.  Too many managers just struggle alone because they are used to being successful and don't want their boss to question the wisdom of hiring/promoting them into this management role.  

There's a way to approach your boss that will make you look, not just not incompetent but actually quite capable, and will probably leave your boss feeling like they're smarter than they realized, too.  The key is to do your homework before you go to your boss so that you can have a focused conversation. You probably did this all the time with technical problems when you were an individual contributor.  It's the same idea.  

When to use this approach:
You're stuck and need your boss's input to move forward on a problem, but you want to do it in a way that conveys your capabilities.

When not to use this approach:
The situation is urgent, completely beyond your capability to handle, or your boss has demonstrated a bad management philosophy that you wouldn't want to emulate.

Questions to ask yourself before meeting with your boss

  • What is the situation/problem?  See how succinctly you can frame it.  
  • What would an ideal solution look like?
  • What seems to be the best possible realistic solution, given the constraints as you see them?
  • What have you tried already?  What were the results?
  • What have you ruled out, and why?
  • What would be most helpful to you to make progress on this issue?
  • What information or action would help you to move forward?


In considering these questions, you may realize there are some possibilities you haven't tried yet.  It might make sense to try those first before going to your boss, or you might include it as part of the conversation: "It seems like I should try X next - what are your thoughts?" or "Do you see any pitfalls with trying X and seeing if that helps?"

Once you've clarified your thoughts, you can go to your boss.  The key is to avoid throwing the problem into their lap and then expecting them to magically fix it.  He or she might, but it doesn't make you a critical part of the process and make lead to questions about why you're there. 

How to ask your boss for help

Succinctly lay out the situation/issue. 
"It became clear in the senior management meeting that Jean thinks we are still working on project A in addition to the B initiative we took on last week, whereas we thought that A would be on hold until B was taken care of."

State the question to be resolved.
"I am trying to determine whether we should try to do both or go back to Jean and see if we can get an extension on the deadline for A."

List key options you've considered.
"I know that several other projects have missed their deadlines, so Jean might not be keen on adding A to the list.  At the same time, getting B done while also handling A, not to mention our usual client support work, will burn out the team."

State what options you think could work.
"It seems like the options are to meet with Jean to request an extension, or use some of the surplus from last quarter to hire two temps to cover the recurring client support work.  Of the two, it seems like hiring the temps would be better because meeting the deadlines for both projects would be bigger wins than coming under budget."

Ask for their reaction and input.
"This affects your ability to use that surplus for other projects, though.  Are there other options you would add?"

Agree on next steps and when/how you will follow up.
"Okay, so I'll talk with the team to see which of their tasks can be handled by a temp, and we'll hire one person on a trial basis for two weeks to see if that gives the team enough breathing room.  If not, we'll revisit this and consider asking for the extension."

This way, all your boss has to do is react to what you're presenting.  That's much easier than coming up with ideas out of the blue, and you're likely to get far better answers this way.  Even if they come up with something totally different, you are likely to walk out of this meeting with an action plan.  If you had just shown up with a crisis, they would probably have asked for time to think about it, and the options might become more limited by the delay. 

Related resources

"Management time: who's got the monkey" article in Harvard Business Review by William Oncken, Jr. and Donald L. Wass
This is my all-time favorite article on delegation, and it applies to managing up as well.

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