Working Successfully With a Boss You Hate

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Let’s be honest, bad bosses exist and as an Assistant, you are primed to come up against some of the toughest people in business. Navigating difficult relationships can build resilience and tenacity however dealing with a persistently sour apple is about as demotivating as finding a great parking space, but then realising that you won’t fit.

We reached out to a group of over 200 Assistants who had all spent 15 years+ working across the public and private sector to ask about their experience of supporting a difficult boss. We found that 71% of our Assistants had supported someone that they would never work with again and over half of them left their position because of the behaviour exhibited by that same person.

Fortunately there are many ways to successfully cope and stay motivated if you hate your boss which doesn’t involve you immediately handing in your notice or a daily melt down on social media.

Reality Check

As an Assistant, the expectations others have of you and the definition of the role you take on is to make the lives of Execs around the world more effective and efficient; enabling them and the business to be more profitable via your savvy business brain. The reality? That expectation exists without any caveat regarding the boss being an assh*le.

Our capacity for denial can be astounding and facing a daily struggle with a boss who criticizes every move you make is exhausting. Take a step back and look at the bigger picture. Are you meeting their expectations in the role? Is your day to day sustainable or is there a reason that they are constantly watching your every move? Before you decide to take the bull by the horns and sit them down to address their management style, make sure that you’re not the problem because unfortunately sometimes, it is.

We recently held a panel discussion at our exclusive learning and development events ‘The PA Diaries Live’ with top Executive Assistants from HSBC, Facebook and First State Investments and we were all in agreement that to be a good PA, you don’t need to like the boss. In their experience, working successfully with Execs means being ten steps ahead at all times, developing credibility in the role and demonstrating that you are the most trustworthy, adaptable and reliable person that they interact with daily.

So what should you do if it’s not your problem? In a perfect world, we would all compromise and live harmoniously with each other, the reality of which is as far flung as us becoming best friends with the Queen. Once you have established the genuine cause of the problem and have identified that it does not start with you, it’s time to use your management skills and take control in your next 1:1 meeting…


HR Guru Dan Oswald defines successful communication as H.O.T. – honest, open, and two-way. Utilise your next meeting with this in mind and create an agenda to discuss with your boss the difficulties you are finding within the role (aka how much of a pain in the ass they are).

Advise them ahead of time that you would like to review your performance and the relationship between you both making it clear that this meeting is a priority and that it cannot be rescheduled. If they ignore you and push for an alternative day and time, stay strong, explain that the meeting is important to you and reiterate that it cannot be moved.

Manage the meeting and keep things (and emotions) under control with your agenda in hand spending equal time for you to both discuss how things are going. Move on to your next agenda point and focus on the short and long term plan for your working partnership. Use the H.O.T. method to discuss negatives and positives, areas/key skills to develop and what is important to you both in a successful PA/Exec relationship.

Keep it professional, spend five minutes on a final wrap up, agree on objectives (for you both) and create a pathway to follow going forward. Regular check ins on how your objectives are progressing on both sides will show commitment to the bigger picture and highlight how things are changing slowly but surely.

Draw a line in the sand

Sometimes, no matter how much you try to make things work, getting through to your dragon boss might be harder than you think. After a successful meeting, not much might change and you’re starting to take your frustration out on innocent colleagues and  find yourself becoming more and more demotivated in your job every day.

Before you end up punching a hole in the wall (or your boss) tough love might be your only answer and it could be time to make a change on your CV. Ask yourself this – is it worth it? Do not feel that to be taken seriously as a professional, you need to spend an exact amount of time in a position, especially if you dread leaving the front door every morning.

Power-tripping, badly behaved bosses will always exist, your job description does not cover Therapist or punch bag as well as Assistant.