Not all bosses appreciate employees who dare to express conflicting views, particularly in more conservative cultures such as in Asia. Unlike the Western individualist culture where people are strongly encouraged to speak up and assert their personalities, the Asian culture typically frowns on questioning authority and expressing opposing views. Seniority prevails over everything and to disagree with your boss means going against the culture's norms.
That being said, we've seen a gradual shift towards a more open and empowering Asian work culture, fueled in part by social media and the open sharing of values and ideas between people in different parts of the world. So while there are still conservative organisations that expect employees to keep their heads down and do as they're told, the good news is that there are a growing number of progressive and liberal companies in Asia now, particularly those in the start-up and tech space.
It's healthy to disagree with your boss, and he or she might even appreciate a different perspective - as long as you do it for the right reasons, in the right way.
Don't just disagree for the sake of disagreeing. Back up your perspective with relevant facts, and offer a viable solution to the problem. Being critical without offering any helpful suggestions to resolve the issue will just annoy your boss. Make sure you have something constructive to contribute, and your boss will have incentive to consider your views.
In order to ensure your views are relevant, ask yourself whether you are looking at the situation from the company's perspective. Do your ideas help the company achieve its goals more efficiently? Are your views aligned with the company's best interests? Disagreeing simply because you don't personally agree with your boss's point of view doesn't make it a relevant reason, and will probably aggravate your boss.
The way you express your views often determine the reaction you get to it. While expressing your perspective, acknowledge that it's just your point of view. Assure your boss that you still respect his or her views even though you might not necessarily agree with it, and keep the conversation open and positive. Don't come across as a know-it-all - that's a surefire way to get in your boss's bad side.
As the saying goes, there's a time and place for everything. If you're going to disagree with your boss, don't do it when he or she is having a bad day. Pick a moment when your boss is relaxed and not rushing to meet deadlines or struggling to manage a work crisis.
On the other hand, if you have a conflicting view during an internal meeting, put it across in a respectful manner so your boss doesn't feel embarrassed. If it's a meeting with outsiders, you should wait until you have a chance to speak to your boss in private. Disagreeing with your boss in the presence of third parties will make you (and your organisation) look unprofessional.
Often when we're pitching ideas, the way we "sell it" affects how the idea is perceived. Instead of just stating your point of view, sell the benefits of the idea to your boss. This means highlighting the value proposition behind the idea - i.e. the specific advantages it offers and how it will deliver better results than your boss's original idea. Put yourself in your boss's shoes. Would you buy what you're selling?
As a side note, let's take a look at how different cultures express disagreement, particularly in business settings: