Seven ways to challenge your boss (and stay on their good side)

challenge your boss

Knowing how to cope with conflict in the workplace ‘will catapult your career like no other interpersonal skill’ says workplace expert and author Lynn Taylor — but the stakes are higher if that conflict is with your boss.

So how do you challenge the opinion, direction and instruction of a superior or more senior team member without undermining their leadership? Here are seven ways to get your point across respectfully, confidently and with clarity.



Psychologist Amy Cooper Hakim, an expert on employer-employee relationships, says that the best way to approach any workplace issue is to remove emotion from the discussion. Facts will serve you better.

So make sure you gather reports and research to back-up your thinking. It can also be a lot easier for your boss to accept a new idea if you’ve done the groundwork on how it could be implemented. Build the business case, share your vision, and offer a solution.

Preparation also includes managing your emotional state. Your aim is to be cool, calm and collected and focus on the problem not the personality. If anger or frustration are lurking, leave them outside the meeting room, even if that means taking a walk around the block or venting to a friend outside of work beforehand.

It’s also highly likely you don’t know the full story behind your boss’s decision, so taking some time to put yourself in their shoes may allow you to be more empathetic or understanding of their perspective and decision-making process. 



If you need to talk out an issue with your boss, don’t just ambush them with your objections. Arrange a meeting and give them a heads-up about the subject matter so they can prepare themselves too. They’re more likely to respond positively if you don’t put them at a disadvantage. You don’t have to flag up the disagreement — frame it as a need for further clarity or the desire to share an idea that’s been sparked in your mind.

Lauren Cooney, founder and CEO of Spark Labs suggests ‘bringing hints to the table’ in advance. Share information from reputable sources with your boss ‘that recommend a different path’. If they respond positively, the meeting will involve talking further about this: a more positive place to start.

It may simply be that there’s a course of action that your boss hasn’t considered, in which case, the potential conflict disappears.



Before you launch into a monologue, give your boss the opportunity to share their point of view and ask questions to make sure you’ve genuinely understood. If it’s just the two of you, you’ll have the chance to dig deeper so get curious about what might be going on.

Switch on your listening skills and, rather than sitting there planning how to further your argument or push your own agenda, pay attention to what’s really being said. And beware of entering the conversation with pre-formed judgements. It makes you more prone to confirmation bias — the tendency to see only the evidence that backs-up what you already believe.

Retaining your flexibility and an open mind is key. The solution might lie somewhere between the two of you. As Gabriella Goddard, founder of the Brainsparker Leadership Academy says: ‘Any idea is made up of many parts. Some of them you might not agree with, but other parts might align with your thinking.’



Giving your boss an outright ‘No’ or dismissing their perspective entirely creates a binary of you against them, and in that situation, there’s only one winner. The reality is that you’re both on the same team.

Stay positive and give validity to their idea by acknowledging it, and then using phrases that start with ‘AND’ not ‘BUT’ to introduce your own thoughts.

Think in terms of building on their thinking. This might sound something like: ‘As I understand it, you’re suggesting ABC, and that made wonder whether we might move forwards more quickly by trying XYZ. What do you think?’

Writing for the Harvard Business Review, author Joseph Grenny says, ‘You can be far more candid about your view if you frame it in the context of a mutual purpose that the boss already cares about.’ And being on the same team, this is something that you’re likely to care about too.



Choosing the right moment to raise the issue can have a big impact on how well the conversation goes — and this requires you to tune in to what your boss is doing and how they’re likely to be feeling in that moment.

Career coach Rita Friedman suggests avoiding the time just before lunch ‘when hunger might distort reason’ or at the end of the day when everyone wants to get home. Meanwhile, leadership expert Jacquelyn Smith recommends looking for signs that your boss is relatively stress-free and therefore likely to be calmer, for example if they’ve been for a leisurely lunch or are particularly chatty. 

Where you talk can also make a difference. While you may default to the private meeting room for two, there are alternatives.

‘Are you in a team meeting where everyone is sharing suggestions and ideas with your manager?’ asks writer and employment advisor Kat Boogaard. ‘That could be a perfect opportunity to speak up, without it seeming aggressive, condescending, or accusatory.’ 

However, the flip side of this is that your boss might feel backed into a corner in front of a group that may include their peers as well members of their team. A separate one-to-one meeting might be the wisest strategy. However, there’s no reason why this has to be in the office. Taking your boss out for lunch or for a coffee puts you both in a neutral space and can make it easier to focus on the issue.



While a good leader will welcome your input and may well invite it, reality may bite when a member of their team actually disagrees with them, particularly with bosses who have a more directive ‘Do as a I say’ leadership style.

At stressful times in particular, when they just need to ‘get the job done’, opposition can seem like a serious obstacle that could threaten their ability to deliver. Therefore, dissent may result in their defences going up.

If you’ve not already done so, having a conversation about how to present alternative perspectives can stand you in good stead for the future. Joseph Grenny calls it establishing a ‘contract for candour upfront’.

‘Effective communicators don’t wait for the need to disagree — they hold a separate conversation when the stakes are low and emotions are calm to agree with the boss about how to manage those moments when they disagree,’ he explains.

This could start with an acknowledgement of shared purpose and respect for your superior — perhaps saying how much you’re learning from them or enjoy working with them (if that’s true). Then you could share the importance for you of being able to express any concerns or issues, so you’re able bring yourself fully into the role.



Although a wise boss will listen to their team, they may still decide to follow their original plan. Choosing your battles, knowing when to let go and then getting to work as you’ve been asked to is essential if you’re to be considered a reliable member of the team — and who also has a healthy amount of respect for their manager.

If that feels almost impossible, it’s worth looking at your motivation for pushing the issue. Why does it matter to you so much? Is there something in the chosen solution that bumps up against an important value for you? Do you have doubts around your boss’s competency? Even just understanding where your resistance is coming from can help ease your internal tension and give you a greater insight into yourself, what’s important to you and whether you really need to take things further.