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No. 101 – How do I ask my boss to stop joking about my tough living situation?

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5 April 2023

I have had to move twice in the past year after my rent increased beyond what I can afford. I am currently looking for somewhere new to live, and I am really struggling to make ends meet. Each time I change address I need to let work know, and my boss has made jokes about how I never seem to settle in the one place long enough to have a fixed address. I know he is joking, but it is really upsetting because I am so stressed about my living arrangements. I would prefer not to make a formal complaint. Do you have any advice for how to raise this with him?

Your boss sounds like he has no understanding of empathy and seems so convinced everyone else has the same lived experience he does, he cannot comprehend anyone might be finding times tough right now. The rental crisis and spiralling rents mean your situation is one, sadly, which is not uncommon. We need leaders who are on the lookout for people who might be struggling, so they can check in to make sure you have the support you need.

See if you can meet with your boss, one on one, and explain your situation so that he has a better understanding of what you are experiencing. That may at least stop the jokes. If he fails to respect your situation after that, I would encourage you to speak to someone else about what is happening to ensure your workplace is not one where you feel you are being belittled or bullied. In addition, please be sure to access any EAP support your organisation may offer.

I work remotely for a company and have regular one-on-one meetings with my manager on Zoom. We are on different sides of the world, so the time we have to catch up is precious. Unfortunately, my manager takes up a lot of our time by repeating topics we have already discussed in depth, or goes off on tangents. I usually have a list of items to discuss with her, and I don’t always get through it. She has also told me she has received feedback that she needs to be more focused on meetings, so she’s aware it’s a problem. Regardless, she will spend a lot of time in our calls talking about other matters, and I feel like I’m unable to interrupt without being rude.

My first suggestion is to start preparing an agenda for the meeting with a clear set of topics you want to make sure you get through. The second is to agree with her on how you will work together and for that, you may need a separate, stand-alone meeting.

Do you ever have one-on-one meetings that are not about your long list of tasks but are about your performance or about how things are going generally? If not, suggest to your boss you would like to schedule a one-on-one purely to talk about how things are going from her perspective (and yours) as well as ways you can improve your work together, every month or two. This will give you the opportunity to ask your manager for any feedback on how you are doing which – hopefully – will lead her to ask you for any feedback you may have too. I would then take the opportunity to talk about how you can best work together, given the limited time you have to catch up, and make some specific suggestions about how the meetings can work in future.

I’m in my thirties and currently manage a large team at a job that I love. Prioritising my spare time, however, is a challenge. Is there anything specific I should be casting my focus on outside my current role? For example, should I be striving to one day join a board or am I better off volunteering my time on panels and podcasts. I suspect doing a bit of everything is the ideal?

This is a very hard question to answer without knowing what your long-term goals might be given both the ideas you have asked about are quite different. If you would like to build a public profile that may open up opportunities down the track, then public speaking, podcasts and being available to comment in the media could be just where to start. If you are interested in building a board career, more focused networking with current company directors and making sure you complete things like the AICD Company Director Course could be a good place to start. Either way, have a clear sense of where you want to end up and then work backwards from there.

Send your questions about work, careers and leadership to Your name and any identifying information will not be used. Letters may be edited.

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