There’s a good chance that you have a great working relationship with your boss. It makes the office that much more comfortable to be at and the job itself more fun! You get along well, there’s synergy and you generally enjoy each other’s company. It’s safe to assume then that based on this positive connection you’re able to talk about anything with your boss. Well most things, at least. Actually, when you think about it, there may just be some things that you’re not comfortable to discuss but really should tell your boss.

It’s only natural that you feel this way – after all, they are the boss! Irrespective of how well your working relationship with your boss really is, there’re always some things you hesitate to talk about. You probably contemplate bringing it up, but it’s hard to gather the courage and say it.

Here are 5 things you probably find hard to articulate but you really should tell your boss.

1. “I Don’t Agree With You”

It’s never an easy path to take when you’re about to go head on with your boss. Bosses tend to make decisions based on their vast years of experience and knowledge, which in most situations is usually more than their team members. Hence, generally speaking, their decisions are backed by rational thinking making it all the more intimidating to challenge. However, it’s possible that they’re overlooking some detail – an insight that you may be able to provide. That’s why it’s all the more important for you to build the courage to speak up. Make sure you do your homework before you red flag them!

2. “I’d Like A Raise”

One of the hardest thing to ask for is a raise. You probably get very nervous when you even think about bringing it up! Don’t worry, your boss won’t fire you for asking for a raise. But to make that statement easier for your boss to swallow, try a different approach. Talk about your responsibilities and how you’ve been working hard to groom and enhance your skills. Highlight what initiatives you’ve taken to step up your game and how you’re ready to expand your job scope. Once you’ve shown your boss how interested you are in the next career boost, bring up your desire to be compensated accordingly. Asking for a raise is your prerogative – it’s how carefully you craft the message that’s key to ensure a positive outcome.

3. “I Messed Up”

Covering up your mistakes is probably the first reaction you’ll have. It’s only natural that you don’t want your boss to find out you had a slip-up because you fear the repercussions. Agreed that the outcome could possibly be against you, however, covering up one mistake could lead to a chain of events that’ll end up being overbearing to manage. Besides, you can’t hid it forever! By facing your fear and owning up to the error you may upset your boss for a while, however, you’ll earn something far greater – their respect! Being honest earns you much more mileage that’ll be rewarding in the long run.

4. “I Don’t Know How To Do This”

It starts at the time when you’re being interviewed when you present yourself as someone who’s capable, competent and skilled. Later, when you’re employed, you do your best to back that belief and deliver on the promise that you know your profession. But, and let’s be honest here, you can’t possibly know everything there is to the job. Particularly when there’s a request for something that’s new and innovative. You may put on that confident front that spells out “I know this”, but in reality you probably have no clue about it. Of course you don’t want your boss to ever see your weaknesses and shortcomings. Again, honesty should be your top priority in such situations. Come clean with your boss and admit that you don’t know how to execute the task. However, make sure to back that statement with a willingness to learn and give it a shot.

5. “Could You Stop Doing That”

Probably the hardest thing to ever say to your boss is to stop doing something. It’s high on the list of things you’ll probably never want to say to your boss. But think of it this way – your boss often tells you when to stop doing something and supports their intervention with reasons. The same applies to your boss, who may possibly be doing something that’s hampering your ability to perform, negatively impacting the team or the company, or even preventing growth. As a member of the team and someone your boss trusts you should be able to voice your concern and counsel them on how to alter their behavior. It’s definitely not going to be easy, but support your observation with evidence and reason with them. Make sure to highlight the best interests of the team and company and I’m certain your boss will be quite receptive to your opinions.

Are there other things you’re afraid to discuss but really should tell your boss? I’d love to hear some from you.

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