How To Have A Courageous Conversation With Your Boss?

Jan 11, 2022 5 Min Read
talking with boss

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Empower Yourself To Talk To Your Boss

Your relationship with your boss may be rocketing along successfully, and then it seems to veer off course, or perhaps it’s always been a little rocky and unpredictable. As well, with more people working from home, workplace dynamics are shifting, and you may be finding that the amount of face time you have with your boss has decreased.

Whatever the status, your working relationship is critical for your well-being and career success.

So what do you do if you want to shift the dynamic?

While there are always nuances and context that influence your approach (and it’s never a one-size-fits-all), there are several vital elements to consider.

Flip the lens

Consider how you might approach the situation if you abandoned the assumptions you hold about your boss’s behaviour. Are there conclusions you are drawing or inferences you are making?

Rather than assume bad intent, instead be curious. It is easy to jump to conclusions as to why your boss is acting a certain way when, in fact, it may have nothing to do with you.

Start by flipping the lens you use to view your boss and their actions by metaphorically taking off your glasses, polishing (and in some cases changing) the lenses to ensure you see the world for how it is.

Is their behaviour towards you consistent, or has it changed recently? If it’s changed, be interested in what may have caused the change. It could be that their workload and stress levels have increased, and they are facing surging demands. If that’s the case, seeking to understand and find ways to help is a great place to start.

Avoid the avoidance

The next step is to talk with your boss about how you work together with an open heart and open mind.

Shying away from this type of conversation may – on the surface – appear to be the easy option, but experience shows avoidance doesn’t work.

When you take too long to act, the underlying issue festers and often becomes harder to resolve. By avoiding the conversation, you miss the opportunity to deepen and strengthen the relationship with your boss.

Dr Brené Brown, in her book Dare to Lead, refers to these conversations and actions as your arena moments. These are the moments when you are called to show up, be brave and walk into the arena despite your fears.

Read More: How to Navigate Difficult Conversations

The aim is to enter the conversation with good intent, a genuine interest in your boss’s needs and a desire to achieve a mutually beneficial outcome. This conversation isn’t an ‘I’m right – you’re wrong’ conversation. You want your boss to know you value the relationship and want to bring your best to work every day.

Start the conversation along the lines of ‘I am keen to add as much value as I can to the work I do, and I would love to chat about what else you need from me. Are you open to a conversation about how we best work together?

A good leader isn’t likely to decline that request. If your boss does, you know what type of person you are working with, which means you need to deploy a different strategy.

Focus on the worst case

If the thought of having the conversation feels you with dread, then the Stoic Practice of the ‘Premeditation of Evils’ will help.

It works like this. Think about what it is you want to do. Next, think about the absolute worst possible outcome that could arise if you take that action.

For example:

  • What’s the worst thing that could happen if you ask for a pay rise? They say no.
  • What’s the worst thing that could happen if you have the conversation and your boss disagrees with your perspective? They disagree with you, and the relationship doesn’t improve.

In either situation, if the worst-case eventuates, you know where you stand, and you can then decide what to do next.

The practice gets you thinking about what could go wrong, so if (and when) issues arise, you are prepared and therefore better able to respond. The good thing is what you imagine rarely eventuates, while reflecting on the possibilities often helps you realise that it’s worth taking the risk and having the conversation.

Tap into your power

Stepping into these conversations takes courage.

It’s you drawing on your inner reserves of power and speaking up even when it’s uncomfortable. Having a voice and using your internal energy is essential to having a healthy dynamic with your boss. When you lose your voice and don’t speak up, the power imbalance in the relationship – which already exists because of their positional authority – gets even more out of kilter.

Knowing how and when to use your voice and back yourself helps balance the power that operates in an organisational system. When power is more equally distributed, it is easier to challenge assumptions, act collaboratively, and make more informed and considered decisions.

Throughout my career, I found that it was the times when I dug deep into my inner reserves and moved forward despite my nerves and fears about the outcomes that I got the best result.

As the first female US Secretary of State, Madeleine Albright, said: “It took me quite a long time to develop a voice, and now that I have it, I am not going to be silent“.

Republished with courtesy from

This article is also available in Chinese.

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Michelle Gibbings is a workplace expert and the award-winning author of three books. Her latest book is 'Bad Boss: What to do if you work for one, manage one or are one'.


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