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How to win an argument with your boss

Pictured: Meryl Streep plays nasty boss Miranda Priestly in hit film The Devil Wears Prada. Image:  20th Century Fox
Do you feel like your boss is Miranda Priestly? Image: 20th Century Fox

Some people love their boss, others hate them. But most will find their relationship lies somewhere in between, dotted by moments of both camaraderie and sheer irritation.

And while few will find themselves in an outright argument with their boss, it’s important to know how to handle the situation, and walk away with a resolution.

According to workplace expert Michelle Gibbings, the first thing to remember in an argument, is that no one wants to - or should - be having arguments with their boss.


“Try to never get into an argument with your boss because as soon as the conversation starts to get heated, both sides are no longer in a good place to continue the conversation,” she told Yahoo Finance.

“So if you can feel the heat or the intensity rising in the conversation and you can see it veering off course, often it's worth disengaging in the conversation at that point and going back at a later date when you're feeling calmer to continue the conversation.”

The big danger is that words said in an argument can be incredibly difficult to recover from, and you’re just generally not your best self.

Well-reasoned criticisms get twisted into barbs, and space for reflection is lost.

So, the first step is to avoid an argument at all costs.

But if you do have issues that need addressing, Gibbings has several tips.


Pictured: female officeworker closes her eyes at her desk. Image: Getty
Just breathe. Image: Getty

“Firstly - and this will sound like a ridiculous suggestion - remember to breathe.

“What happens when we get stressed or anxious or overly passionate about the conversation is we don't breathe deeply and when we don't breathe deeply, it's almost as though the emotional part of the brain is now running the show.”

Without breathing, the cool, logical part of the brain is left in the dust and emotions can continue to rise.

Ask questions

The second step is to ask questions.

“Seek to understand where your boss is coming from, because the more you understand where they're coming from, the more you might learn.”

This way, you can shift the way you’re pitching your part of the conversation to better meet the ends your boss is trying to achieve.

Seek common ground

The key in “winning an argument” is to never approach an important discussion with a goal of winning.

Instead, constructive discussions are built around a desire to find common ground so you can both move forward positively.

“If you go in with the attitude of, ‘This is about me winning’, then you will often end up in a position where you may win the outcome of that conversation, but what you've done in the process is destroy your relationship with your boss,” Gibbings said.

“So always think long-term. You want to be in a position where you speak up, you put forward your point of view, but you need to do it in a way that's respectful and a way that protects the relationship that you have with your boss.”

Got it. How honest should I be?

This depends on your relationship with your boss. If you have a trusting relationship, then you can probably be more honest about your thoughts. But if you’re struggling with a fractured relationship, it’s critical that you’re careful about damaging the relationship further with tactless words.

“It's like any relationship, even a relationship with a partner. People would say honesty is the best policy and absolutely, you want to be honest, but you also need to be considerate of their feelings.”

You should ask yourself: “I might be being honest, but am I being nice?”

“Consider the impact that the comments you make are going to have on the other person and is it going to help you in the long run.”

Additionally, pick your time and place.

“There may be things which you wouldn’t say in a public forum, but you'd say to them one-on-one, so pick your time, pick your place and be deliberate about what you say.”

I’m unsatisfied with the outcome

If you’ve reached the end of the discussion and feel unsatisfied with the outcome, there are two main options:

  1. Let it go; or

  2. Escalate it.

Deciding which way you go is a judgment call with no hard-and-fast rule.

Instead, you’ll likely only decide the next step after reflecting on the discussion.

“You need to go away and reflect, work out, ‘What was I trying to achieve? Where is this landing me? How much does this really matter to me? And what are going to be the outcomes if I pursue this further?”

It’s important to consider those questions before making any more moves, but ultimately your choice will also come down to your values, Gibbings added.

“You need to stay true to who you are and true to your values,” she said.

“If you step over your values, then you run the risk of damaging your reputation and your integrity and that's not good, so stay true to who you are and what you stand for.”

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