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How to Solve 4 Sticky Work Dilemmas

Lindsay Olson

Plenty of awkward work situations exist that you'll likely confront at some point in your career. While each situation has its own unique characteristics and there isn't a one-size-fits-all solution, these are some ideas for handling delicate job situations.

[See our list of the 50 Best Careers.]

I Want My Boss' Job

Long before you know your boss wants to leave, you should network to meet people at every level in the company. Coalition building is important. Getting to know the higher-ups and others could give you the chance to participate in interesting projects or develop relationships with people who can help champion your creative ideas and gain you more visibility within the organization.

Many times we feel we could easily do the boss' job, but we also have a very limited view of what our boss does and the challenges that her position entails. It's easy to focus on negative qualities. Study your boss to assess what skills she has that you don't yet and get a better understanding of what she does. Be objective in your observation and work to add those skills to your resume.

Talk to your boss one-on-one about your career track and goal. You don't want to come across as a threat, but you'll want to show her you want a job like hers one day and see how you can work together to gain the skills to get there.

[See 10 Reasons You Don't Want to Be the Boss.]

I'm Pregnant, But I'm Afraid My Boss Will Let Me Go

You just found out you're expecting, but you're worried it might put your future with your company in jeopardy. You know you can't be fired for expanding your family, but you're nervous about how your boss and colleagues will take the news.

It's wise to wait until you're past the first trimester before telling your boss (unless your job imposes risks to the baby). Study your company's parental leave policy to see what you're entitled to take. Think beforehand about whether you want to take off additional time without pay as well as whether you'll be willing to come back at all.

Once you've gotten through those first several weeks, have an in-person discussion with your boss about the news and your future plans. Be open to the possibility that you won't want to work as much or that you'll need to work a modified schedule once the baby has arrived, and brainstorm with your boss about possible solutions. For example, you might suggest a part-time or work-from-home combination as a solution to you wanting to keep your job and also stay home with your baby.

My Boss Leers at Me

Every time you make copies, your boss leans out of his office to get a look. It doesn't feel like full-on sexual harassment, but it still makes you uncomfortable. How can you get him to stop without making a very strained work environment?

Keep a log of when this happens. Documentation is important for when you might need it. Talk to your human resources department about the issue. If your company is small and there isn't an HR department, then talk to that person's boss.

Know your rights. You're entitled to a harassment-free workplace, so rather than quit to avoid it, deal with it head-on and then decide your best course of action.

[See 10 Shattered Myths About Workplace Rights.]

I Want to Work From Home

You're tired of your two-hour each way commute and you want to make your case for working from home. But your boss is old-school, and you fear he'll shut you down.

Make a list of the benefits that you're working from home will provide the company. These include:

--Saving the company money

--Being more productive without office distractions

--Having the flexibility to meet face-to-face when needed

--Taking fewer sick days

Make plans to check in more than usual to reassure your supervisor that you're getting work done. Offer to start telecommuting a few days a week, assess results, and then begin working remotely full-time as the situation proves to be successful.

Lindsay Olson is a founding partner and public relations recruiter with Paradigm Staffing and Hoojobs, a niche job board for public relations, communications, and social media jobs. She blogs at, where she discusses recruiting and job search issues.

Twitter: @PRJobs

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