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Five Questions To Ask Your Boss

Want a better relationship with your boss? It’s easier than you think to create a great working relationship. The secret is effective communications and a mutual understanding of what you expect from each other.

Some time ago I wrote a short article on Four Questions For Your Direct Reports. Today I wanted to share the corollary to those ideas for managing up.

Ask these questions on a regular basis, ensuring that you and your boss are on the same page. Try inserting one or two of them into your one-on-one meetings with your boss — in the most open-ended way you can. Let your boss surprise you!

  1. How can we best work together? Learning to work together is an iterative process. Ask this question on a quarterly basis. Be prepared with your own answer if your boss turns this around and asks you.
  2. How do you prefer that I communicate with you? People have different communication styles and preferences. This is especially true on the introvert / extravert spectrum. For example, introverts generally prefer email, extraverts generally prefer telephone and face-to-face encounters.
  3. Am I providing the right amount of detail? As you rise higher in an organization you should generally be providing higher level overview information. (Technical organizations, where senior leaders may want more detail, can be the exception to the rule.) 
  4. What are you expecting from me and in what time frame? Maintain a list of your priorities and invite your boss to reset expectations as often as needed. A good list of what you are working on, taken into your one-on-one meetings, can serve as both a way to have this conversation and a template for any status reports you might send your boss. 
  5. What should I do more of?  What should I do less of?  These are particularly useful to invite “coaching in the moment” when you are updating your boss on projects and deliverables. Tell your boss your status and then ask the “What should I do more of / less of?” questions. Your boss will have examples right in front of them that can serve as the basis for feedback. Do this every month or so, and your annual performance review is practically written. 

Good relationships — including those with your boss and your company — don’t just happen. They take effort and deliberate intention to make them great. We often talk about continuous improvement in our processes. Such determination applies to our relationships as well. When you strive for continuous improvement, not just in the way you work, but also in the way you work together, you rise to another level of effectiveness and job satisfaction.

What’s Next

Take a moment to look at the relationship with your boss and pencil in some time during your next one-on-one to ask these questions. Let me know how it goes.

Adapted from Your Next Move by Michael Watkins

Update June 25, 2019. Originally published October 25, 2013.

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About Heather

Heather Hollick has been helping others become better leaders and craft more meaningful careers for more than 25 years. Her experience spans both business and technology, operations and organizational development. Oh, and she was born in Canada, so she can't help but be helpful. 😉

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