How to Handle Sticky Situations at Work

Tips on navigating five difficult work scenarios with your manager.

Working in corporate America, you're bound to encounter a difficult communication situation or two with your manager -- from asking for vacation time during a busy month to letting him know that you're considering jumping ship. Whether you're an entry-level worker or in a more senior position, having to address these types of issues is an inescapable part of office life.

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Here are five common scenarios with advice on how to approach them without burning any bridges.

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You're Being Recruited By Another Department Head

The situation: You like your current job, but it would be remiss of you not to keep your eyes and ears open for new opportunities that allow you to grow and learn new skills. A manager in another department has taken note of your stellar performance and makes it clear that she'd be more than happy to have you on her team. However, your boss isn't in the loop, and you don't want to offend or anger him. A week goes by, and the pursuing supervisor steps up the pressure: "I'd hire you tomorrow. Shall we talk specifics?" You're interested in listening to what she has to say, but you don't want to burn any bridges. How do you proceed?

What you should do: First, let the manager who's courting you know that you're flattered she's taken note of your work. Next, if you're seriously considering making the move, be very clear in letting this person know that you have an obligation to your current boss. Ask her how she wants to proceed with bringing your manager into the loop. They are peers, and it would be much better for the person pursuing one of his top performers to initiate the conversation.

You're Expecting a Child

The situation: It would be nice if it weren't a big deal to tell your boss, "Good news! I'm having a baby." Unfortunately, there are lots of situations where that just isn't the case. If you're new on the job, have recently returned from a leave of absence or have taken on a new assignment, the long walk to your manager's office to say "Guess what? I'm having a baby and will need to go on maternity leave for at least three months" can be stressful.

What you should do: Wait a few days after learning the news to think about how and when you plan to tell your boss. For example, during a one-on-one catch-up meeting where your manager is already in planning mode may be best. Doing this will allow the two of you to talk candidly and begin preliminary discussions about how to divvy up your workload among the other team members while you're away. Don't feel pressured to lay out your entire life's plan during that initial conversation. In the months to come, be sure to give your boss ample notice of whether you plan to return after the baby is born or if you'd like to transition into a partial telework schedule once your maternity leave is over.

Your Teammate Isn't Pulling Her Weight

The situation: When it comes to meeting deadlines on important team projects, a colleague isn't doing her share. No one wants to be known as the office tattletale, but the problem co-worker needs to be put on notice sooner rather than later.

What you should do: If a co-worker's lack of productivity is holding the team back and making everyone else look bad in front of clients, first pull that person aside privately to share your concerns. Then, if the problem co-worker continues underperforming, take it to your direct manager. He or she has a number of options in deciding how to deal with the issue, including replacing the person on the project. You can say something like:

"Josh, can we chat privately for a second? I hate to be somebody who talks about other people, but I need to let you know that Sally is having trouble keeping up with the incoming client calls on the Web development project. I don't know how to support her in that, but you need to be aware of it because by the time I finally get their messages and call back, they're furious. We shoot for a 24-hour turnaround. I'm not getting the messages until nearly two weeks later, in some cases. Again, I'm not trying to throw anyone under the bus, but it's a process breakdown that has ramifications way beyond Sally's desk."

You're No Longer Challenged in Your Current Role

The situation: One of the toughest conversations to start with a boss is the one that delivers the message that you don't like your job. You can feel very exposed when the topic of discussion is your job satisfaction because there’s the fear that your boss may say, "Well, quit."

What you should do: If you feel that you can no longer stand the monotony of your current position, tell your boss but proceed with caution. The ideal time to initiate such a conversation would be during your quarterly or annual review. In sharing with him how you've grown out of your current role, be sure to include suggestions about how you think it can be improved. If you want to get more involved in sales training, say so, and make it clear to your manager how that would benefit the team.

If you're at the breaking point where you're ready to leave the company if things don't change, you can say that without giving your manager an ultimatum. For example, you could say something like:

"George, you've got your hands full. I don't expect to be one of your highest priorities, and I want to support your goals. However, I need to do more digital design work to help keep my skills current. It doesn't look like you're going to need much of that type of work from me. I understand if you can't move things around to give me what I’m looking for. And if that’s the case, that’s totally fine, but I’d want to start putting my resume out there. If I do that and end up finding another position, I'll be sure to give you plenty of notice."

You Want a Raise

The situation: You have suffered through a couple of years without a bump up in pay -- and have the lackluster savings account to prove it. If you're a top performer and get no complaints about your work, you're well within your right to bring up the issue with your boss.

What you should do: Before you storm into your manager's office demanding a raise, try to understand his objectives and highest priorities. You're much more likely to get traction with your request for a pay increase if your accomplishments relate directly to the company's core business goals. Next, research the market, using sites such as and, so you know where you stand in relation to other professionals in your field. If your pay is below the market wage, you've got a shot at an increase even if the company has a general salary freeze in place. Write up these points and then ask your boss for a sit-down meeting to discuss them. You can say:

"Tom, when you have some time, can we sit down and do some planning together? I want to get your thoughts on my job goals for the year and also discuss my salary level."

Giving your boss some time between your request and the actual meeting may give him the opportunity to go to bat on your behalf with the powers that be.

Liz Ryan
Contributing Columnist,