Ask The Experts Special: Tackling Five of Work’s Most Difficult Conversations

Our advice column has tackled all sorts of uncomfortable workplace situations, but these five conversations top awkward charts.

For the past year our experts have been tackling every perplexing work-life challenge you throw at them, so in honor of Difficult Conversations week, we’ve compiled five conversations that will likely come up at some point during your career, along with expert advice on how to handle the situation without embarrassing yourself.


1. How Do I Ask For A Raise?

Probably the biggest and most nerve-wracking question that all of us face at several points in our working life: you think you do your job reasonably well, and you certainly think you deserve more money, but how do you know when it’s the right time to ask for a raise, and how do you go about it?

Leadership coach Lolly Daskal advises that you should ask for a pay increase when one or more of the following has happened:

  • Your job description has changed and your responsibilities have grown.
  • You’re frequently praised for a job well done.
  • You’ve nailed down a big accomplishment or innovation.
  • You can demonstrate that you’ve made a specific positive contribution above just doing your job.
  • You can point to a track record of consistent performance.

See the rest of her advice on just how to broach the subject here.

2. How Can I Tell My Micromanaging Boss to Back Off?

Unfortunately this is another one that many of us have to deal with at one point or another–a manager that checks up on every.single.thing. you do. It’s a delicate situation to tell your boss to back off, but feeling micromanaged can leave you feeling like you aren’t trusted. Daskal addresses this one by first establishing why bosses mircomanage, then offering a step-by-step approach to address it:


Make a List of Specific Examples: Make a list of circumstances where your work could have been more productive with no one standing over your shoulder. Let your boss know that your goal is to increase productivity and save time for both of you. Describe the issue as one of refining processes.

Ask What You Can Do: Ask if there is anything you can do to develop your professional skill set. Allow your boss to give you some suggestions. Making improvements benefits you both.

Give Updates and Build Trust: Commit to keep your boss informed at their preferred level throughout the process so they remain in the loop without constantly checking in. Tell your boss that you wish to show them that you can be trusted to deliver the work on your own.

Click here to read the full article.

3. How Can I Get My Boss To Give Me More Critical Feedback?

The opposite of a micromanaging boss is an absentee one. How can you improve at your job or advance in your career when your manager never gives you any feedback? Asking your boss to “please criticize me!” is an awkward conversation, but here are a few pieces of Daskal’s advice for asking for guidance:


State the issue. Tell your manager that you see how hard she works, and that you would like to make her life easier by doing well at your work. Tell her you have an idea that might work for both of you. A little investment each week can be a big investment in the future—yours and her own.

Set up weekly meetings. Ask your manager if you can set up a regular time each week to meet to go over progress on your work, talk about new issues that might have come up, and get her input on questions you’ve encountered. Thirty minutes is ideal, but if all you can get is 15 minutes take it. If she is unwilling to doing it weekly, suggesting doing it every two weeks. Try to make the meetings casual and friendly—maybe even go out for lunch or take a walk.

Take charge of the meeting for her. Write an agenda ahead of time and email it to her. Include the status of important projects; your top priorities for the next week or two, your progress against your broader goals if you have them, and any question you are struggling with. You can also use this time to ask for feedback on particular projects and even just generally (“How do you think things are going overall? Is there anything I could be doing differently?”).

For the rest of the plan, click here.

4. How Do I Tell My Boss I’m Pregnant?

All working women planning a family will have to have this difficult conversation with their bosses at some point. While it might help to explain why you’re throwing up after every morning meeting, it also comes with sticky discussions about who will cover for you while your on leave. business and leadership professor Evelyn Williams advises this reader to frame the talk around how she will still meet her employer’s needs rather than what her employer will need to do to accommodate her. Here’s a little of her advice:


Before you enter into the conversation, go talk to other seasoned managers in your network that are outside the company to get a fresh perspective. How will your employer fill your very capable shoes for three months? And how will your employees manage without their stellar boss at the helm? And are you definitely planning on coming back to work after your three month leave or are you undecided?

Click here for the full article

5. Should I Accept My Coworker’s Facebook Friend Request?

A workplace etiquette question question for our time: what should you do when you like your coworkers but you don’t want to let them into your social media world? Psychologist Art Markman helps us navigate this potential social minefield. His answer may surprise you. The best thing to do? Just ignore it. Here’s why:


Someone who sent you a friend request on Facebook might just be expanding their Facebook network without thinking that the connection has any deeper implications. Individuals like this will not be offended if you don’t accept their invitation. In fact, a week after making a friend request, they might not even remember they sent one. So, there is a good chance that if you ignore someone’s friend request, they will never even notice.

The other reason it is useful to do nothing is that it helps you maintain some of the ambiguity in your social relationships with coworkers. While you may not want to have close friends in the workplace, there is no reason to explicitly tell people that. You run the risk of creating feelings of rejection by creating a fine boundary between people who are “friends” and those who are “coworkers.”

Read the rest of his reasoning here.

If you have a dilemma you’d like our panel of experts to answer, send your questions to or tweet us a question using #AskFC.



About the author

Kathleen Davis is Deputy Editor at Previously, she has worked as an editor at, and Popular Photography magazine.