I want a relationship with my supervisor

Caroline Mboijana. PHOTO/FILE 

What you need to know:

In the last six months, my supervisor and I have developed a friendship close to crossing the line between supervisor and supervisee

Dear Caroline,

I have been in my current role for close to two years, and I enjoy what I do and the organisation that I work for. I have made good friends, and many have become friends even outside the workplace. In the last six months, my supervisor and I have developed a friendship close to crossing the line between supervisor and supervisee. We have gone out with the team as part of the team building activities, and many times, we find ourselves talking about our personal lives.  I feel comfortable being around her. I am in a grey area and not sure how I should handle this. What should I do?


Hello Ben, I am glad to hear you are working in an organisation that you enjoy being a part of.  Many people meet their partners through networks and relationships formed at the workplace.  As social beings, we want to build relationships and be around people that make us feel good about ourselves. The last two years of Covid-19 have influenced all aspects of work, including people not shying away from the things that make them happy. While this may be the case, work norms are still in play.  How you manage the supervisor–supervisee relationship that goes beyond work is sensitive. In all organisations, encouraging this relationship is not allowed or discouraged. It can be abused, but sometimes relationships grow and become healthy relationships.

Given the situation you find yourself in, you could consider the following as possible ways of seeking clarification that helps you decide what to do next. You are in a comfortable work relationship and socially outside the workplace.  When you are on a team-building activity, consider probing and asking questions. Is she dating? Is she married? What are her views on work relationships? These questions will give you an insight into her perspective. The critical question you need to ask yourself is whether you want to have a relationship with her. If the answer is no, then maintain the relationship in the workplace and shut down the opportunities where you find yourself “exposed”.

If you want to have the relationship, think through what it will cost you and what adjustments you may have to make. Make sure you recognise the benefits. She is the supervisor, and if you want to have the relationship, you are likely the one to adjust. If you make a move and she is not ready, it may be misconstrued as harassment regardless of your intent. The other extreme is if you do not manage it and she thinks you are good to go, she may make a move and cause you to feel harassed in the workplace. All these scenarios can play out if not managed well. In these cases, there is always a winner and a loser.  Good luck.

Caroline Mboijana,

Managing Director, The Leadership Team (U) [email protected]


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