Make or Break: The Dynamics of the Assistant to Boss Relationship

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It is a truth universally under-acknowledged, that sometimes, people just don’t like you. And it’s not always an easy truth to accept. This can happen in your personal life – a friend of a friend you just don’t get on with, or a family member’s partner who doesn’t seem to approve of you. It can be even more devastating when it occurs in your working life – a colleague who just won’t warm to you or perhaps you feel excluded from the office camaraderie when you are a new starter. But what happens when it’s someone you work closely with, and someone who has more power and status than you – someone who is your boss?

The Interview

Let’s start at the beginning. Ideally, when you are interviewing for a new role, you will meet the boss. Will it be a good fit? Do you share the same values? Is this something you can see working long term? Interviewing is like professional dating, two people trying to work out if there is a future partnership between them however, there are several potential barriers you may come up against deeming your experience less sweet and more sour.

What if you’re unable to meet your future boss during the interview process? Maybe you do meet them but then you can’t gauge a true sense of their personality due to the nerves of your first meeting. Or maybe you didn’t ask the questions you needed to help you understand the role and the expectations of the business in more detail.

The Solution

Questions like ‘how do you handle pressure?’, ‘are you an introvert or extrovert?’, and ‘what are your trigger points?’ are good to ask during an interview to the person you are potentially supporting. It’s just as important for you to get to know them, as it is for them to find out about you. Interviews should be a two-way conversation, not an interrogation meant to scare you into submission.

While In Your Role

So what if you like the boss, but you get the sense they are just not warming to you? You feel that you’ve tried everything to charm your way into good favour, but the more you try, the more it feels like they are pulling away. It’s a horrible feeling to dedicate your attention and energy to creating a good relationship with someone, and to feel that they are not as invested. Let’s be honest, if this was a romantic relationship, this might be the point where you choose to walk away.

It’s important to add a caveat here; if you know that this working relationship is never going to improve and you have given it your all, then you have a couple of options. If the relationship is in any way aggressive, undermining or verbally abusive in the workplace, then HR must be involved, and you need to make the decision if you want to continue to be in a toxic environment.  Assuming the relationship isn’t toxic, but just ‘underwhelming’ at this point, then there are a few ways of approaching it.

The Solution

Open and honest conversation is your strongest option. Book some time in the diary for an informal chat over coffee to give feedback on how you feel  your relationship is developing. They may be surprised that you have any concerns and from their point of view, everything might be fine. Or they might agree that things can be improved, in which case you can ask them for their ideas and suggest a few of your own. Until you have that discussion, you will never know. If both parties agree that the relationship can be improved, try to encourage them to be proactive in their own efforts of making a positive impact going forward. Maybe they take a long time to trust, or they are not wanting to overwhelm you with information, or perhaps they are a more withdrawn personality type. Explain to them what kind of relationship you are looking for. It may not be that you will ever talk about your personal lives, but you can still develop strong working relationships. Or perhaps they are happy to share personal information with you, but may not proactively ask about your life, for fear of prying.

It’s important to remember that you can have a perfectly good working relationship with someone whilst not liking them, you don’t have to be friends with your boss, after all. As long as there aren’t negative reasons for disliking them (they are rude, or undermining, or belittling, for example) then you can still create a good partnership. Opinions and feelings about people can also change over time and it is likely that your relationship with your boss will ebb and flow, just like any other relationship. It’s easy to forget, and expect perfection 5 days a week, for 8 hours a day but honestly, is that realistic?

The Extras…

Time and patience is key in any relationship and not everyone develops strong relationships automatically. It can take months of trust being incrementally built upon, and for others, the connection is there immediately. Neither way is right, and neither way is wrong – all relationships are different in the same way that all people are different.

Acknowledging people’s differences will help you grow and develop your own skill set. You can learn from the best on how to create great working partnerships, and you can learn how to do things differently when you see it going wrong. Developing relationships is something you will have to consistently work on throughout your life, both in and out of the working environment.

Written by Abigail Jones, multi award winning Executive Assistant at Facebook, ambassador at The Assistant Room and qualified coach and mentor to assistants around the world.