5 Questions You Shouldn’t Be Afraid to Ask Your Boss

There is a fine line between being too permissive and being too demanding – and this is especially true in the workplace.

On the one hand, if you simply accept the status quo without questioning anything, you might skate past everyone’s notice. Your contributions, concerns, desires, and ambitions could go unrecognized, especially in the corporate environments that often reward demanding, assertive behavior.

You need to be at least a little demanding if you want to get ahead – but not too demanding, or you may come across as a high-maintenance and self-important.

To strike the perfect balance between self-centeredness and passivity in the workplace, you need to know how and when to ask the right kinds of questions. Here are five such questions that a career-minded individual should never be afraid to ask their boss – just don’t be too aggressive about them:

1. Can I Have a Raise?

You shouldn’t fear this question, but you should be judicious about when you ask it. You want to make sure the timing is right, for maximum positive effect.

If you have any of the following information on hand when you ask this question, you’ll be setting yourself up for success – and you won’t come across as demanding or unrealistic:

1. Examples of additional responsibility you’ve taken on since your last raise.
2. Evidence that you are outperforming your peers or going above and beyond the call of duty regularly.
3. Evidence that your peers who you are performing comparably are earning more than you are.
4. A higher salary offer from a prospective employer.

This information won’t guarantee you a raise, but it will ensure that you appear justified in your approach. Management won’t think you’re totally off-base, and that’s a good thing.

2. Can I Have More Responsibility?

You might worry that, if you ask this question, you’ll be given additional work that is either overwhelming or beyond your capabilities. If that’s the case, just remember that you are the one making the advance. As a result, you have the chance to propose additional duties that you feel comfortable with.

If your manager does offer duties outside of your comfort zone, consider asking for additional support in terms of training and or development before taking the responsibilities on.

Now, why, exactly, should you ask for more responsibility? Because doing so will show your boss that you’re a team player. Demonstrate your commitment to the company, and you may earn yourself a promotion and/or a pay raise in no time.

3. Can I Have Some Help?

You may be the type to soldier on without help even when you feel overwhelmed, but that can be a foolish decision. If you don’t ask for help and then fail to meet your targets, do you think your boss will accept “I didn’t want to wound my pride” as an excuse?

If you feel overwhelmed by your workload, take a cold, hard look at what’s on your plate. Determine what sort of additional resources you may need in order to meet your targets, and then make a quantified request for help from your boss. That way, you’ll be bringing your boss the solution, and not the problem – and that’s always the best way to get the help you need.

4. What Are My Goals?

Many companies are so busy fighting fires that important things like goal assignment can go neglected. Don’t suffer in silence, working aimlessly without any clear goals or objectives. Doing so will only result in more pain for you and your manager down the line.

It is your manager’s basic duty to assign you clear goals. If you don’t have them, how can you be expected to meet or exceed performance expectations?

If you don’t have goals, ask your manager. If the goals still fail to surface, prepare your own set of goals and propose them to your manager.

5. Can I Have Tool X to Work More Efficiently?

In resource-starved, cash-strapped environments, it can seem futile or even greedy to ask for better tools to increase your efficiency. However, you should never fear asking for performance-boosting resources – as long as you do it the right way, of course.

Show your boss your current productivity rate, and then forecast your future productivity rate with the new tool. As long as you can demonstrate a significant ROI to your boss, you should never be afraid to ask for more resources, no matter what the environment is like.

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For some people, asking for things comes quite easily; for others, it’s a major challenge. If you want to get ahead in your career, though, you need to be ready to push for what you need when it comes down to it. Be prepared to ask the right questions, in the right way, at the right time, and you’ll set yourself up for career success.