10 Questions You Should Never Ask Your Boss – 2019 Edition

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Whether we’re young professionals or mid-way through our career, we all answer to someone higher up, i.e. our bosses. And after a certain point in time, as we interact with them more often, we start to ask questions – questions you should never ask your boss.

For one, they’re unprofessional. But they can also come off as rude, incompetent – and might even cost you your job.

So, to help you avoid such unfortunate scenarios, we’ve rounded up the top 10 questions you should never ask your boss. And we mean never:

1. How much do you make?

We’re all curious. But the question is not only inappropriate – it’ll make your boss feel uncomfortable. And in general, no one who earns a salary every appreciates such a question.

It also suggests that you have a nosy attitude and disregard people’s privacy. This is definitely the one question you should never ask your boss under any circumstances.


2. *Passes bottle* Want some?

Sometime in our career we may find ourselves socialising with our bosses, whether at a corporate dinner or a celebratory event for our clients. But giving a toast and partying are two very different things.

Your relationship with your boss is first and foremost a working one and you should know to never to cross its boundaries. Leave the bottle for Saturday nights – with your real friends.

Instead, try: ‘Do you need a lighter for your cigarette?’ – Of course, this works only if your boss smokes, but it allows you to make small talk without invading personal space.


3. Can I have a raise?

We all want a raise. But asking your boss is no way to negotiate. Like it or not, you must ultimately prove that you are deserving of a raise.

And we’re not saying don’t ask for a raise if you have been bringing additional revenue to the company or have excelled in your performance for a crucial (or several) projects. We’re simply saying that there are other ways.

Instead, try: This 30-step plan to get that raise you think you deserve (with evidence).


4. Are you sure about that?

Openly pointing out your boss’s mistake will certainly get you dismissed from future meetings. Out of all the questions you should never ask your boss, this type of question could jeopardise your career, especially if asked out loud in front of clients.

Instead, try: “I may be mistaken, but based on [insert evidence for reference]…” – This prompts them to reconsider their point and correct the information if necessary without getting on their defensive side.


5. What the #!%$?

While modern sensibilities in the public sphere are becoming more liberal, foul words or questionable language in the workplace is still considered unprofessional – and could get you on HR’s radar.

Swearing suggests that you aren’t able to calmly and maturely deal with certain situations, and may indicate to your boss that you aren’t ready for a promotion.

Instead, try: ‘That’s unbelievable!’ – It sounds much more sensible.


6. Could we get another intern? I’d prefer to do less work.

Interns – or any extra pair of hands in the workplace – are meant to contribute to the company’s capacity to do more with its time. They’re certainly not there to absorb your work so you can laze around.

You should always take a proactive approach at work and be ready to achieve more in order to progress and grow in your profession.


7. How do you not know this?

Many of our bosses are more senior in age and not all of them are Bill Gates and Steve Jobs when it comes to technology and online applications.

Instead, try: ‘Here, let me show you how you can use this’ – It helps to be kind. A professional relationship is a two way street, so you can always teach your boss new things. This also demonstrates your capacity to lead and serve as a mentor to others.


8. Did you hear…?

Don’t be a gossip. The people who succeed and make it to the top of their careers are team players who respect fellow colleagues and cultivate a positive environment.

If you actually do have a problem with a fellow colleague in the office, then you should talk to them face to face and provide constructive, measured feedback.


9. What are you doing for your vacation?

You should respect your boss’s privacy. What he or she does outside of the workspace and after work hours is ultimately none of your business, unless it poses an actual threat to the company – or to you.

Inversely, you have the right to keep what you do on your leave private.


10. Can I join?

You should never ask your boss if you can sit in on a meeting without giving an appropriate reason. Interfacing with clients and stakeholders is a valuable skill every professional should learn to navigate.

Instead, try: ‘I’m wondering if I can sit in on the meeting, as…’ – Justify why you’d like to sit in on a meeting and how that could add value to the discussion or potentially open up new opportunities.

And with that, this last ‘big no’ wraps up our set of questions to never ask your boss. We suggest that you do your very best to keep them to yourselves.


Related: Meet the 10 Highest Paid CEOs in Malaysia (Public Listed Companies)


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