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.

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.

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...