Here’s How To Deal With Difficult Bosses Effectively

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Summer 2014. 

It was a beautiful sunny day in London and I decided to go for a walk in my lunch break. I had had a busy and productive morning at work. Everything was going well. I should have been feeling happy and relaxed during this walk. 

But something just wasn’t right.

I had a meeting planned in the afternoon with a senior executive. I knew my subject and had prepared well. But I knew that, regardless of how well I presented my report, things wouldn’t go well.

See, the person I was meeting was very difficult. There was no way to please them and the focus of the whole meeting would be on tiny errors and insignificant formatting issues.

I wasn’t feeling in control of my emotions. My energy was completely drained as I was spending my lunch hour anxious and stressed about the meeting.

I didn’t know, back then, how to deal with difficult bosses.

The meeting was exactly as expected, a very negative experience and emotionally draining.

But since that day, I have done a lot of learning and personal development in the quest for emotional independence. In particular, I have learned how to deal with difficult bosses through two crucial stages: AWARENESS – your perception of a difficult behaviour or situation – and CONTROL – the conditioning and management of your response.

In this post, I’ll dive into my strategy on how to deal with difficult bosses.

Step 1: Awareness

The first stage is to become aware of the problem. Through awareness, we begin to understand what triggers an emotional response and we are able to approach these triggers with objectivity and empathy.

Focus on the behaviours, not the person

In order to deal with difficult bosses, you need to separate the behaviour from the person. The behaviour is the person’s reaction to their environment. 

By assuming that your boss is difficult, you also make the underlying assumption that they can’t change. 

That’s unfair – we’re all capable of improving.

On the other hand, if you shift your attention to the behaviour, you can isolate what you find specifically difficult. Is it their tendency to undermine you in front of colleagues? Their constant focus on what goes wrong? Or their lack of recognition of a job well done?

Find what you find difficult. Write it down, and note how often the behaviour is occurring before taking action. This is to ensure that you are being objective about the problem, and not blowing something out of proportion.

Put yourself in their shoes

How to deal with difficult bosses

The best way to learn how to deal with difficult bosses is to put their behaviour into perspective – or put yourself in their shoes.

What do you notice about the environment and the events leading to  your interaction? Were they busy reading a report when you engaged? Or back from a stressful meeting? Are they poorly or tired? Were they late this morning? 

Trying to understand where the other person is coming from is half the battle. By being aware that we’re not the only ones in this interaction, we develop empathy and become better equipped to deal with difficult behaviours.

Could you be difficult too?

It’s likely that you are the one being difficult in certain situations. I know, shocking, right?

Now, hopefully for most of us, these situations are rare.

But, in the same way your boss doesn’t realise they are being difficult, perhaps you’re not aware of the impact of your own behaviour?

To know if you are contributing to the problem, you need to do some introspection. Are you feeling angry? Frustrated? Ready for a debate? Do you have a very clear point of view that you refuse to budge from? Something to complain about that means the world to you?

Sometimes, when we’re too stubborn, we forget to consider other people’s perspectives.

In any situation where you face a difficult person, have a quick check-in with yourself to make sure you have an open mind.

Step 2: Control

Once aware of the difficult behaviours and considering various perspectives, you are able to take steps to control your own emotional response.

Although others are being difficult, it is your reaction to their behaviour that causes your problem.

It is important to remember that, although you can influence a person to change, you can only control your emotional response.


How to deal with difficult bosses

When faced with a perceived threat, such as dealing with a difficult boss, our system goes into “fight or fly” mode. 

This physiological reaction causes a surge in adrenaline and cortisol (the stress hormones). Our heart rate increases, digestion slows and blood is diverted towards major muscle groups – maxing out our energy reserves to survive a “life or death situation”.

Only thing is – this is hardly “life or death” (I hope!), and by letting this happen, we tend to lose the ability to think clearly.

The most effective way to counteract the stress response is to relax. Easier said than done in the middle of a difficult interaction with your boss. But there’s one thing you can do to take back control: breathe.

Sounds too simple? It is. 

But most of us forget to breathe when stressed – which in turns makes us more stressed.

All you need to do is consciously slow down your breath, even count during each inhale and exhale. I tend to switch to box breathing when I start losing my cool – works like a charm!

Focusing on the breath will help you (1) reduce your heart rate and shift from reactive to proactive, and (2) anchor you in the present moment, giving you awareness and help you realise that the situation is manageable.

RELATED: 8 Healthy Habits to Radically Boost Your Energy


In my experience, the best way to deal with difficult bosses is to set clear expectations from the get go. 

By that, I mean clarify what your boss is expecting from you (in terms of actions, deliverables, deadlines etc…) and vice-versa what you are expecting from your boss (in terms of support, flexibility, ownership etc…).

By focusing on clarity and expectations, you shift towards a more objective relationship. This will help you move past difficult behaviours and emotional responses.

That being said, sometimes the difficult behaviour is indeed the lack of clarity from a boss. I’ve recently had to deal with this: an hour-long phone call with a senior exec and absolutely no clue as to what was expected of me. 

The call ended up being a rant about pretty much everything and a complete waste of time for both of us.

When clarity is the issue, make sure you keep on top of the action points. Keep rephrasing what your boss is saying: “so just to confirm, you want me to contact X to get an update on Y?”. 

Write it all down, and gently move the conversation along to the next point. Before you close, go back to your action points and confirm again. Then send an email to your boss with a recap of what was agreed. 

Overkill? Maybe, but people easily forget and can tweak the facts to their advantages, especially difficult people. Don’t give them the option!

Make A Plan

How to deal with difficult bosses

Sometimes, trying to be rational with a difficult person just won’t work. Most of the time, difficult behaviours can be dealt with through self-control and managing expectations. 

But in some instances, you will be dealing with irrational individuals and toxic behaviours. No matter what you do or say, it just isn’t good enough.

As always, go back to objectivity. Take a breather, and write down what the difficulties are. Be mindful to remove emotions out of this analysis.

Once you have clarity over the problems you’re dealing with, you can start forming a plan:

  1. Can you confront your boss about their difficult behaviours? This is not always a possible course of action. But if you think you can have a genuine conversation, try it. Remain objective and inclusive (using “we” instead of “you”). Focus on the behaviours, not the person.
  2. Does this need to be escalated to a third-party? If you are genuinely dealing with an irrational boss, engaging directly might not yield great results. Instead, consider seeking help. Talk to your HR contact and they will know what steps to take, specific to your company. Do you have an employee assistance program? Opening up to someone you don’t know can have tremendous benefits and help you see the wood from the trees.
  3. Do you need to step away from this relationship? Sadly, you might come to a point where you feel helpless and no-one is able to help diffuse the tensions. What options do you have to end the toxic relationship with your boss? Can you ask for a different line manager? Move to a different team? Or is it worth considering leaving your job all together?

RELATED: How To Quit Your Job Like A Pro

Throughout your resolution process, remember to behave like a professional. No gossiping, no attacking the personality of your boss or losing control of your emotions, being angry etc… Think long-term. What do you want people to remember you for?

Always Respond With Kindness

Regardless of what decision you take, what plan you make and whether or not you can solve the problems caused by a difficult boss, always respond with kindness and have it in you to forgive.

Being kind and compassionate is ALWAYS the most effective reaction you can ever have. And forgiveness cures everything. 

It doesn’t matter if your boss’s behaviour changes in response to your kindness. It’s not about them, it’s about you.

Being kind to others works like magic. In fact, it is key to emotional independence. You take responsibility for your own emotions, treating your environment objectively and adhering to your core values no matter what. Difficult people cannot get to you. You are in charge.

In Conclusion…

The big takeaway when learning how to deal with difficult bosses is that YOU are in the driver seat when it comes to your emotions. 

Once you become aware of a difficult situation or behaviour – be it a one-off or a regular pattern – you can take steps to control your response and manage the relationship effectively.

Focus your efforts inwards, finding your centre, and through grounding you will develop the strength to tackle any difficult boss you ever encounter.

And you’ll always come out stronger on the other side…

Have you had to deal with difficult bosses in your career? How have you approached it? Please share below, I’d love to know!

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