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Working with difficult Executives

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When we talk to candidates about why they are looking to leave their current role, we often hear it’s because they have a “difficult boss”. They don’t really want to leave the organisation or their role, but they feel unsure about how they can better manage the relationship.

Here are some tips:

  • Understand that your boss’s work load and stress levels may be high sometimes. Appreciate the fact that part of the challenge of your role is to figure out how to best support them at these times. Are they the type that becomes unapproachable and closes their door needing some thinking time? Do everything you can to give that to them, pick up some lunch and drop it in to them. Field calls that are unimportant and act as a gatekeeper protecting them from others whilst they focus. Free up their calendar and be the Executive Assistant that takes a step up rather than a step back. When they realise you want to be an ally, genuinely wanting to make a difference and support them when they are under pressure, they are more likely to open up and be more communicative with you when ‘having a bad day’.
  • A difficult boss is often one that is a micro-manager. Working with someone that micro manages makes you feel incompetent and has you second guessing yourself even when you know you are right. The best thing to do when working with this style is to learn their patterns and anticipate their needs. Prove to them that you are reliable, diligent and resourceful without needing to be prompted. Don’t just meet deadlines, deliver completed tasks early and ask for additional responsibilities to show that you are handling your workload. Prove that you are on top of things as much as they believe that they are!
  • Always maintain your professionalism! It’s not about making your boss your friend, it’s about making them realise that you are a highly capable professional whose prime objective is to support them in achieving their goals in the best way possible. So if you remain non-emotive, professional and diligent when they perhaps are not, it will be likely that they will think twice before taking out their frustrations on you next time.
  • One thing that many successful Executives do really well is leave their work at work. They find a way to switch off so that they are fresh and capable of tackling things head on each day. If you are working with a particularly challenging Manager you need to do the same. Sometimes this is difficult as part of your role can be to support your boss ‘out of hours’. But if things come up when you are away from the office you need to attend to them quickly and then switch off again as soon as possible. Gym classes, cooking classes, exercise, study, a good movie or book, mid-week dinner plans with friends – it doesn’t matter what it is, as long as it takes your focus away from thinking about the office and your Manager.
  • Timing is the key! Approaching a difficult boss is all about timing. If your boss is making you feel uncertain about your performance, wait for a good time to bring up the subject and ask for some guidance on how to improve. On a quieter day, ask if you can buy them a coffee and get them in an even more relaxed mode, giving you the opportunity to open up even more if they are responding well. Some questions that you might like to ask – “Tell me about the best PA you have had? What did they do to enhance your days?” “Can you give me some feedback on my performance, I would really like to know how I can better support you?” “Last week was extremely challenging, can you tell me what I could have done better to help you?”

Often a challenging or ‘difficult to please’ Manager with really specific expectations will end up being the one that enhances your career and develops your capabilities. If you persist, learn how to approach them at the right time and provide them with the right forum to give you constructive criticism and advice on your performance, you can learn a lot from the challenge of supporting them.

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