Managing Upwards: How To Deal With A Difficult Boss

Managing Upwards: How To Deal With A Difficult Boss workplace toxicity

Everyone has had to deal with a demanding boss at some point in their career, and it’s something that can make your working life miserable.

The key to dealing with a difficult boss is to shift your focus towards your own personal development and success. By doing this, not only will you improve your day to day working life, but your future career prospects. 

Understand where they’re coming from

You may not feel like doing this if you’re unhappy with their behaviour, but taking some time to understand your boss’s point of view will put you in a much better position to improve the circumstances. 

Think about their key concerns; what are their deliverables, and what are they likely to be worrying about?

If you can understand this, you can start to anticipate their behaviour and manage expectations, which will help you deliver the results they are looking for. More than this, you can begin to frame your communications with them around what they feel is important, which will create better results.

Leadership training

A great way to learn to manage upwards is by participating in leadership training, even if you aren’t yet in a leadership position. Leadership training is designed both for current leaders and future leaders to prepare for their roles.

Practical management training will help you develop effective communication methods and build relationships based on your unique skills and traits. This is a valuable skill set for your future career, and you can use this knowledge to communicate with your boss and cultivate a better relationship with them, which will help improve your working situation.

Communicate effectively

Your boss might not be aware that they are making your working life miserable so it’s worth speaking about. 

Although honesty is essential, it’s also crucial to be mindful about how you approach the conversation. For example, try not to criticise your boss personally or directly. Instead, try to approach them in a more results-orientated way, which means focusing the conversation around work and how you can achieve your goals.

Taking this approach demonstrates a proactive and helpful attitude on your behalf and is also more likely to yield the results you are hoping for.

It’s important that you take responsibility for any areas where you may need to improve and show that you are willing to take steps to do so.



You might not feel like empathising with someone who is treating you poorly, but it will help you.

By being empathetic towards your boss, you will move from being a victim of their behaviour to being an observer of their difficulties. This shift will help you build resilience because it puts you in a stronger position.

This switch in power will help you deal with the situation with a clearer head.

Remember your ‘personal brand.’

No matter how difficult the situation is, you must remember the image that you want to portray in the workplace. 

The most professional approach is to not ‘bad-mouth’ your boss to co-workers. You never know what might get back to who, and it’s not worth risking your reputation over.

Instead, reach out to sympathetic friends outside of work or to family members if you need to vent (as we all do at times!) but at work, try your best to keep a cool head.

Look after your wellbeing.

Looking after your wellbeing is essential all of the time, even more so when dealing with a difficult situation at work.

An excellent place to start is by taking care of your physical health. Numerous studies have shown that people who exercise have lower stress levels and higher contentment levels overall. 

Amodigo offers several sessions focused on health and wellbeing, where you can engage in stress busting activities such as boxing or pilates, take part in a boot camp, or learn a bit more about nutrition and the role it has to play in your health.

Another good way to look after your wellbeing is by clearly managing your time and your work effectively to not feel stressed because you know that you have everything under control.

Doing small things like making an effort to get a consistently good night’s sleep will significantly impact your overall mood and well-being, which will mean that you are much better equipped to face the challenges of the day.

Finally, we do believe that the struggle of overcoming difficult challenges can result in you becoming a stronger, more resilient leader in the future. But remember, there are some situations that are unmanageable because unfortunately in life, some people are unreasonable. In these cases, you must put your wellbeing and long term development first. You don’t have to suffer in silence.

*If you are struggling or having a hard time, you can call the Samaritans 116 123.

*You should also consider speaking to your workplace HR team if you are encountering discrimination, bullying or harassment.