Workplaces are no more places where you can have your own way. With so much diversity within organisations and with conflicting individual values and egos, there are times when dealing with your colleagues at work can evoke a mixture of complex emotions inside of you.
While challenging your equals is relatively easy for you, it’s another thing entirely to challenge those who are above you. But there are times when you have to challenge your boss. Unless you have the courage to challenge, you will be a Yes Man who will never progress in career life.
Challenging your boss at work is something that might cause weaker employees to crumble at their knees. The very idea of arguing or disagreeing with higher management might very well be the thing that could cause you to lose your job.
However, people shouldn’t be afraid of standing up to their superiors at work, especially if the argument revolves around an important issue directly related to business matters.
Despite what kind of professional relationship you might have with your superior, there’s nothing for you to fear about engaging in some sort of debate with your boss if you are thinking about the wellbeing of the company you are working for. You need to challenge your boss in a constructive manner and end up being respected for your actions at the end of it.
It is tricky when you have a beef with your boss. How do you disagree with a person who most likely hired you — and has the power to potentially fire you? Say something, and you run the risk of being seen as difficult or even adversarial. Stay silent, and you could seem ambivalent or complacent.
But your boss wants you to be successful. Your company hired you because they think you are an asset, so bring your experience and point of view to the table — but do it strategically.
Time it right
Bringing something up at an inopportune time can spell doom for whatever issue you are trying to address.
Choose the right moment — likely a private chat — to discuss things.
Key in any negotiation is understanding what the other side values. The best way to get them to listen is to be able to reflect back to them that you understand what’s important to them and to the organisation.
This might take some detective work on your part.
It may be that you have to ask some good questions, because you may not understand what’s behind the decision or action that you’re disagreeing with. So before you state an opposing view, “You have to understand what it is you are disagreeing with at the root & how it kills value. You can use this information to frame your suggestion as something that’s different from theirs—but that still serves your boss’s ultimate purpose or priority.
Make it their idea
If you present information in the right way, you might change your boss’s mind about things — and let her come to her own conclusion.
This approach will usually take more than one discussion, so don’t give up. Plan on having a few conversations over time to make this happen.
Help them look good
When managers and bosses are dealing with their team, they get a lot of the brunt of what’s not working and the complaints. Remember that your boss is trying to look good, just like everyone else, and if you can help her do that, you have got a greater chance of success.
You may not agree with them, and you may have some constructive feedback, but if they feel like you are trying to help them shine, they will be more open to your ideas.
Don’t wait until the last minute
Sometimes people will bring up a dissenting point of view after the fact, when no one can do anything about it, and that’s just not productive. No matter what, make your thoughts known while there’s still a potential opportunity to take action.
Be prepared to lose
There is never any guarantee whether you will emerge as the victor of an argument with your boss, and if the end result paints you as the loser, then you need to be gracious about the outcome and move on.
Even though you put up a good fight and managed to remain poised under pressure, you should still respect the decision of the aftermath and walk away from it knowing that you have said what you needed to say to your supervisor.When your boss sees that you are gracious in accepting the loss and emerges from the conflict with no hard feelings, then it helps them see that you are someone who understands the value of professionalism.
Your gracious demeanor will allow them to raise their level of respect towards you, not to mention strengthening the level of trust, which just goes to show that you can survive a fight with your boss and live to tell it. There’s always a chance that you will speak your mind and nothing will change. And you have to mentally prepare for that possibility.
Your point may be taken, but it may not be taken well, in that it’s not going to change anything. It doesn’t mean losing your job, it just means you may have to comply with something that your boss feels is the best approach.
Know what is at stake
Another thing that you need to take into serious consideration when picking a fight with your boss at work is that you should know exactly the reason why you are disagreeing with your immediate superior, and the possible consequences that could come out of that argument if your challenge was proved to be unsubstantiated and not objectively driven but personal.
This is of the absolute importance because you need to see the bigger picture in any debate so that you will know exactly where you will stand once the issue is laid to rest.