Navigating Difficult Conversations …
with your boss
Common challenges
There are approachable bosses and some not-so-approachable bosses. Whichever category your boss is in you might have some concerns about "challenging" her or him.
Even if your boss is approachable and your relationship is a good one, you might be afraid to do anything you think might change that situation.
People have many stories and ideas about why the conversation they are avoiding is going to be difficult. We don't need to list them here. Suffice to say fear of some unwanted consequence is ever-present. It is true many people can point to lived experience of such conversations going badly so the fear is often justified in their mind.
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"Managing up"
We are often asked:
"How do I manage up?"
"How do I give my boss feedback?"
Murray has written a blog post about why the thinking behind those phrases creates problems rather than solving them. Our approach takes a path more likely to be successful for you and your manager.
The fact that you are reading this probably indicates you think there must be a better, more successful way. There is!
How the program can help
So, how does one have a successful conversation without "managing up"?
In summary:
Plan your conversation after thinking about what interpretations and stories your boss might have about the situation (or you).
Think about what your manager really needs. What they need and what you need might appear to be in conflict right now. However, unless you have taken their perspective and can explore that with them your chances of resolving the conflict are very low.
If the issue is your boss is doing something (or not doing something) think about what the potential negative consequences are for them if they continue down that path. Then you have the opportunity to test your story with them and perhaps help them avoid those consequences.
Adopt a curious stance for the conversation - making assumptions about what your boss thinks and what their motivations are is very likely to derail the conversation because it is highly likely you will be subtly or dramatically wrong (no matter how sure you feel you are right).
Check your assumptions with your boss in the conversation rather than with other people. Some people (friends and colleagues) can be trusted "sounding boards" for testing your assumptions but be wary of those who "know what you should do". Be very careful of such "advice". Instead, make notes about other perspectives and remember the only person you can verify that with is your boss.
There are a number of other things you can practice in preparation for these situations to generate a good outcome, despite your fear. The points above list some things you can do but do not detail how to do them. That is because words are not enough here. It's very important to learn and practice new skills in a place you can make mistakes without consequences. We can help in that regard.