Sticky Question for Your Boss? Here's How to Ask

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By Robert Half

In your career, there will inevitably come a time when you have awkward or difficult questions to ask your boss. Very few people like uncomfortable interactions, but in order to get ahead at work, you need answers to your questions if you're to do your job well - even the sticky ones. Bringing up delicate subjects requires finesse and diplomacy, not to mention preparation.

Here are some of the top touchy employee-boss topics, along with the right and wrong ways to broach them.

Getting passed over for a promotion
If you're upset or confused about the outcome of a job competition, you should absolutely talk with your boss. However, don't approach the subject by asking, "How come Chris got the promotion and not me?" This confrontational tactic will likely put your boss on the defense, and the resulting exchange will be less productive than it could have been.

The better approach: Focus the conversation on what you can do. Better questions to ask your boss: "I'm interested in advancing in the company. How can I make that happen?" or "I was disappointed that I wasn't promoted. Can we talk about what I need to do in order to reach the next level?"

Asking for a salary increase
Of all of the questions to ask your boss, the ones that involve money can be the trickiest. Before launching into any discussion about salary, research what others in similar positions at other companies are making. Robert Half's "Salary Guides" are good resources. But don't use this information in the wrong way. You can't, for example, just march into your boss's office and demand, "According to my research, I should be making more money!"

The better approach: In addition to showing your manager job market data, you have to make your case. Before you ask for a meeting, make a list of the extra responsibilities you've taken on since your were hired or your last promotion. Don't forget any training or certifications you've received. When discussing your request with your boss, you can approach it this way: "I really enjoy working here. In the past year, I've been asked to lead two new projects and have consistently exceeded my quota. Can we talk about increasing my salary to make it more in line with my performance?"

The promised raise hasn't materialized
If you were led to think you were receiving a raise or bonus and haven't received it yet, don't approach your boss asking, "Where is the raise you promised me?"

The better approach: When you talk to your boss, don't assume any wrongdoing on his or her part. Stay neutral and professional, and - most of all - ask for action. You might say something like, "We discussed the possibility of my getting a raise three months ago. Is there anything I need to do to make that happen?"

Alternative work arrangements
If your company offers some employees the opportunity to telecommute, this can be a very tempting perk. If you want this work flexibility, your approach shouldn't be: "How come half the office gets to work remotely but I don't?"

The better approach: Don't make it about other people. Instead, inquire about what's possible for your own particular situation. Be ready to demonstrate how this would benefit the company, such as how you could be more productive if you could work from home a few days a week. If your boss seems reluctant, propose a trial period. But be ready for pushback: Not every job can or should be done remotely, and many managers are hesitant to allow junior employees to work remotely.

More advice when you have questions to ask your boss
  1. Timing is everything. Don't suggest new work arrangements or spring tough questions on your supervisor when the office is undergoing major changes or is frantically preparing for a deadline. An appropriate time is during your performance review.
  2. Be professional. In all work-related interactions, but especially when you have sensitive questions to ask your boss, mind your business etiquette. This means staying positive, not getting personal and not comparing your situation to that of colleagues.
  3. Focus on action. Managers appreciate workers who suggest solutions and not just dump problems on them. When you approach them about a sticky question, be sure to have a plan in mind - not just a complaint.

Remember: You have every right to bring up tough subjects. Just be sure to ask your questions tactfully. So do your research, gather your courage and request a meeting.

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Robert Half is the world's first and largest specialized staffing firm with a global network of more than 400 staffing and consulting locations worldwide. For more information about our professional services, visit roberthalf.com. For additional career advice, read our blog at blog.roberthalf.com or follow us on social media at roberthalf.com/follow-us.
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