How to navigate tricky situations with your boss

Concept of difficult choices in business
By Robert Half International
In an ideal world, you’d always know the right thing to say to your boss and the perfect time to say it. Unfortunately, things aren’t usually so clear-cut in the real world. Tricky situations with your manager are bound to pop up, and how you handle them counts.

Here are four potentially difficult scenarios you may find yourself in and strategies to help you decide if, when and how to speak up.

1. Your boss promised to look into the raise and promotion you asked for, but it’s been three weeks, and you still haven’t heard back.
Money and titles are delicate subjects. So for starters, choose your moment wisely. Instead of blindsiding your boss in the hall, schedule a quick meeting when things are relatively relaxed — not the week the whole team is scrambling to finish a big project. Let your boss know what you want to talk about when you schedule the meeting. Then, be prepared to quickly reiterate your case for a raise or promotion and politely ask for an update.
Whatever what your manager says, remain calm and professional. Don’t raise your voice or say something you’ll regret later.
If your request is rejected, turn the conversation to your future career path. Ask your boss where she sees you going in the company and what skills or accomplishments you need to take those next steps.
Just be careful not to push too hard. If your supervisor remains noncommittal, keep in mind that silence can sometimes be a polite way to say no.
2. You’re convinced your manager’s latest strategy is a bad one, but you don’t know if it’s wise to speak up. 
Is your supervisor generally open to feedback? Or does he often seem annoyed at being questioned? Use this as a litmus test to weigh the costs and benefits of speaking up.
Then, think about whether you’re picking the right battle. If top management has already signed off on the strategy, for instance, you might be wasting your breath and social capital on something that’s set in stone.
If you decide to speak up, do background research first and realize that your boss might have information you don’t. Approach your manager in private rather than contradicting her in a meeting.
Remember to keep the discussion positive. Focus on introducing new ideas and solutions, not telling your boss she’s wrong. For example: “I’m excited about the sales team reorganization. I wanted to share this case study on another company that has gone through similar changes so we can be aware of challenges that might arise.”
3. You need to make a complaint about your boss’s unprofessional behavior, but you don’t know who to tell or how to bring it up.
Before making a formal complaint, do a gut check. Is this a personality clash or something truly serious? If you’re the only one at the office who struggles with your manager, different working styles might be the real culprit.
More serious issues may warrant an official complaint, but tread carefully. Document the behavior and approach HR in a calm, professional way. Ask for help and advice rather than making demands, such as saying that your boss should be fired.
If your company is so small that it does not have an HR department, look for someone at your boss’s level or above who might be open to offering support if you approached the person privately.
4. You’re unhappy in your job and want to look for a new one, but you’re thinking about talking to your manager first.
There’s almost never an upside to telling your boss that you’ve been sprucing up your résumé. Even hinting that you might start exploring other job options usually backfires. It calls your loyalty into question and places you directly in your boss’s crosshairs. Why should he offer support if you already have one foot out the door?
Instead of walking down this risky path, give some thought as to why you’re unhappy in the first place. Is the company culture a bad fit? Are you looking for more challenging work? Identify the key things you need to stick around long term.
Then, set up a meeting to talk with your manager about your position with the company. Tell her about changes you feel would be beneficial — stressing how these changes would benefit the company — but skip any job-hunting talk altogether.
No matter what tricky situation you’re facing, your goal should be to get through it while keeping your relationship with your manager intact. After all, it’s the most important one for your career.

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