How to Challenge Your Boss & Be Loved for it

Challenge your boss

The boss is not always right but all too often people fear that they might be ridiculed or even risk losing their job if they challenge their boss and speak forthright. You might have come up with an efficient solution to an ongoing problem, or an idea for a viable project, but you need to be able to approach your boss before these can be implemented.

People learn how to effectively communicate with the general public everyday in jobs; however, very little time and effort is spent learning how to open up the lines of communication with the boss.

Develop Trust

A key aspect to developing a healthy employee-boss relationship is trust. This works both ways. You will earn trust and respect from your boss if you keep to your project deadlines, are a reliable member of the work team, and are prepared to go that extra mile.

Regard your boss as a fellow human being with feelings, and not as the ‘enemy’.

Avoid Trivial Matters and Gain Respect

Do not approach your boss with trivial matters. He is most likely a very busy man that will feel that you should iron out these issues by yourself. Running to your boss with the slightest of problems will also lead to a lower regard towards you and the notion that you lack drive, independence and initiative.

Exercise Tact

Sometimes it reaches the crunch point, whereby you know that you need to speak out. If done correctly you will not only keep your job, but also, possibly, earn some extra respect from your boss.

It’s essential that you exercise tact and adopt an appropriate tone of voice. Someone that is too simpering will be readily dismissed just as will one that comes across as arrogant. Be firm and sure of yourself.

In some situations, it might be that your boss has made a mistake. Don’t embarrass him in front of others, and don’t make demands. The right way to deal with this would be to show sensitivity towards his feelings and try to have a casual chat with him in a private setting about the matter in hand.

Timing Is Crucial

Some bosses have a confrontational nature, and don’t take kindly to what they regard as a criticism or a challenge to ‘their’ authority. It’s important to exercise a good judgement of appropriate timing for that all-important challenge with your boss.

If you ‘catch’ your boss at a bad moment, such as when his schedule is fully booked up or is clearly in a bad mood, then wait until a more suitable opportunity arises.

In a very busy working environment, it may be worthwhile scheduling a meeting with your boss in advance. This also prepares him for the idea of something new, rather than being taken by surprise.

Research Your Ideas Thoroughly

When preparing for a confrontation with your boss, remember to do your homework! This involves considering every aspect that you can possibly think of, and ensuring that there are no apparent flaws in your ideas.

Consider what type of questions might be asked of you, and mentally prepare for your answers. Back up your ideas with several sources of evidence, facts, and figures.

Be Sensitive

Remember that your boss will be more accommodating when he realizes that you are not attempting to threaten his position or authority.

Make it clear to him that you will not press this matter any further if it does not succeed within a reasonable and realistic deadline.

Your Duty

For those that find specific situations within their work environment unacceptable to the point that they are considering handing in their notice, you have a duty to yourself and other employees to speak out.

If your boss doesn’t listen – well, at least you know that you attempted to resolve matters.


A company will thrive when communication channels are open, and a break down in communications can spell disaster. It’s important that the boss is able to take in new ideas; ultimately, if the company fails, it will be his actions and in-actions that will be brought to account.

It is important that you feel comfortable in your work place and are able to open up to your boss, and let him know your thoughts on a particular matter.

Understand the Issue

Keep a clear head, be rational, professional, and have a good understanding of what it is you’re challenging.

There is nothing worse than an opinionated employee who has clearly misunderstood the issues at hand. Do not allow the situation to become a heated argument.

Compliment Your Boss

From the outset, be friendly towards your boss. Pay him a few compliments about something that he has done that you appreciate.

Relax and reassure him, so that he understands that your intentions are well meaning.

Know When to Back Down

When fresh ideas are being taken on board, a company grows and evolves with the times. Remember, there are a time and a place for everything. Once you have made your challenge, it’s essential to back down and respect your boss’s final decision on the matter – unless you come up with further evidence for your cause.

If you fail to do this, you risk the chance of creating dissent within the work environment. It is reasonable and responsible to support your boss in order to create a sense of unity, and a harmonious atmosphere.


There might be aspects of your cause that you haven’t considered. When making your challenge, be prepared to listen to your boss’s reasoning, explanations and logic too.

Remember that your challenge is not about winning a ‘fight’ but about negotiating and understanding. Do not be overly defensive nor on the attack – exercise diplomacy.

While remaining true to your disagreement, it’s a good move to agree with your boss’s valid points, and this will further your own cause. Your boss will appreciate that you are a reasonable person, rather than an upstart.

Be Willing to Compromise

It’s important to walk away from your challenge and feel that you have accomplished something as opposed to being manipulated by the boss into backing down.

You may need to be willing to come to a compromise in order to reach an agreement that is acceptable to you and in the company’s best interests as a whole and not just a benefit to those with accounting jobs in the finance department!

Your Boss’s Preferences

Pay attention to the particular aspects of your plans and ideas that your boss has issues with, and take these factors into consideration when making revisions, and for future ideas.

Observe your boss, and take note of his preferred methods and routines. When you challenge your boss, ensure that you make him feel that he is in the driving seat, and ask him for his opinions, feedback, and any other comments.


If you are able to challenge your boss successfully without gloating, he will feel more comfortable to approach you for feedback and further ideas. Your future opinions will be highly valued, and you might discover that your boss will go out of his way to seek you out specifically.

A sign of trust and respect from your boss will also help to further your career prospects, and he may be more inclined to recommend you highly for future jobs. This is a positive sign of a healthy relationship between the boss and his employee.

How do you challenge your boss? Share your tips int he comments!

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Darren is a professional writer who produces content on a wide range of topics, including on finance jobs.


  1. Cecilia Harry on the 10th May

    My favorite question to ask my boss is, “What do you think?” It engages him, lets him know I want his opinion, and he gets to freely share, which I have observed is something that energizes him.

    I think the key is to really observe and get to know your boss so you can understand his/her preferences when it comes to communication.

  2. Bobbi on the 10th May

    What if your boss is a woman? Not asking that question legitimately but I really find it disturbing that the author of this article assumes all persons in a position of power are men….

    • Millie Tante on the 21st May

      What a stupid comment.

      Obviously the advice is equally applicable.

      Obviously writing ‘he or she’ throughout would make for an inelegant article, sacrificing readability to appease some rabid bra-burning lesbians.


  3. Jane on the 17th May

    I’m with Bobbi on this one. I was all ears up until ‘Do not approach your boss with trivial matters. He is most likely a very busy man…’

  4. gardencat on the 11th November

    “Make it clear to him that you will not press this matter any further if it does not succeed within a reasonable and realistic deadline.”

    Really! What if the matter being discussed is fraud and illegal behavior on the part of the boss?

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