We often have to work with people we are not the biggest fans of.
What if your boss ends up being the person you have the most difficulties with? This can be a huge dilemma if you enjoy every other aspect of your role.
Is it possible to repair a bad situation so you and your boss can have a good working relationship?
A little reflection is the best first step. Ask yourself realistically, can the relationship even be repaired?
There are some major situations that might warrant a "no." For example, if you are being bullied, asked to perform illegal tasks, or if the person you support has unresolved personal issues, then seeking a new healthier work situation might be best.
Identify the causes
If you think the relationship can be repaired, then identify the specific factors that are causing the issues. For example, if there is a common theme of communication breakdowns, perhaps there is another approach that can be attempted? Or if you do not have the resources you need to do your job well, could you ask for that access?
Once you have possible solutions outlined, that's when I advise approaching your boss. I believe in never going to your boss with problems; instead, come to them with solutions.
Either schedule a separate meeting or bring your solutions up in your recurring check-in. (It depends on how many issues you identify.)
In the meeting, be direct but polite. Also, avoid the word “you” if possible; it can cause people to be defensive.
For example, let's say you aren't in the loop on personal engagements (personal travel, personal appointments, etc.) which have created conflicts with items booked on your boss's work calendar. I would say something like, “I want to be the best I can at my job. I noticed that there have been personal calendar bookings that have conflicted with work meetings, so I have thought about some ways to avoid future conflicts. Here are those options: getting personal calendar access, adding me as an attendee on events, or forwarding me emails pertaining to personal scheduling matters. Would any of those solutions work?"
Record your attempts
I recommend documenting your attempts at repair. I would record the date and all details you remember from your meeting. If you work in an office setting, you will need to be prepared in case you ever have to escalate the issues to HR.
Have you made an attempt to repair a working relationship? What was the outcome? Please share in the comments below!