It’s the complex dance of people who lead from the middle of the organization:

Getting what we need and want from our boss, while serving the needs and wants of our staff team, all while helping the boss address her unique priorities.

To support this dance, I came up with 12-ish questions to help you understand your boss, help your boss understand you and your team, and negotiate priorities and information-sharing between you.

If you want to try out these questions, be considerate. At the wrong time, even a generous question like “How can I help?”, even with a generous boss, may backfire or seem like complaining. A busy boss might think, “I already have 18 things waiting on my input. Do I have to figure all this out, too?”

Three thoughts for how to deal with a boss’s busy-ness and possible (likely) decision fatigue:

Pick the right time. Ask for a separate meeting if you need one.
Do NOT ask your boss all these questions at once. That’s too much to deal with. (Unless it’s part of a larger strategy and teamwork discussion and you have a generous amount of time.)
Do some of the thinking for the boss. Think ahead about the answers you want to hear. Be ready with ideas and options for the boss’s likely responses and follow-up questions. Not to put words in their mouth, or assume what they are thinking, but to help them answer your questions sooner. A way of helping your boss help you and your team.

Sound promising? Hope so. With that mindset in mind, here are questions to learn what matters most to your boss at any one time and to help her help you and your team.

Priorities for the boss, for you, and for your team

What are your top priorities for the next 30 days?
How can I and my team help with these priorities?
What are your top priorities specific to me and my team, over the next 30 days?

Preparedness for change and problem-solving

I’m working with my team to think ahead and handle change well. What are the top two changes (opportunities, challenges) you see coming up for me and my team?
When do you think planning and workflow changes can or should begin?
The biggest challenge facing my team right now is X. How do you want to be involved as we work on that? (Directing us? As a thought partner? Just updates as we go?)

Improvement, learning and development

What feedback do you have for me on my individual work these days?
What feedback do you have for me on the work of my team?
I have been thinking about staff learning and development. Do you have ideas on how to improve performance in our capacity and performance measures (KPIs)?
What training needs do you have in mind for me and for us?
May I share with you my thoughts on my own training and coaching needs, and my ideas for where to get this support?
May I share with you my thoughts and plans to meet the training and coaching needs of my team members?

Let me know if you try these out. Let me know if you have any other questions or discussion prompts you use to get what you need and give your boss what she needs.

Managing Up: 12-ish Questions to Ask Your Boss to Help Her, and Help Her Help You