Discussing Work-Related Gripes With Your Boss Doesn't Have to Be Awkward

If your work life isn’t rewarding you’ve got three possible courses of action:

1. Continue being unfulfilled by your lousy situation

2. Go find another job

3. Try and make things better in your current position

Nobody wins if you pick option #1. Choosing #2 means tearing out your roots and having to start all over again. Choice #3 allots you the best chance to avoid tossing the baby out with the bathwater.

Jennifer Winter has a terrific post up at The Muse all about how to tactfully let your boss know that something’s rotten in the state of Denmark… or just in the office. She starts by suggesting a list-making binge. Tally up all all the reasons you’re unhappy and determine the underlying causes. Unhelpful co-workers? Recent shifts in policy? Whatever it is, you can determine how to treat the symptoms as soon as you come to a complete diagnosis.

The next step is setting up a meeting with your boss and assembling the right vernacular for airing your grievances. As Winter notes, no boss wants to sit through a list of demands or a top 20 “things I hate about my job” countdown. She recommends finding a positive spin that always steers the conversation toward possible improvements. You’re looking to upsell your happiness here — make sure your pitch won’t bring your boss down. Finally, make sure that you either suggest potential solutions or prepare to ask for suggestions. The key is to frame this potentially awkward conversation in a way where the two of you can work together as opposed to making it a confrontation between oppressor and oppressed.

One thing Winter doesn’t go over is how to deal with a situation where your boss is the thing that makes you unhappy at work. You can always try to change your boss (miracles can happen) but if he or she happens to be particularly obstinate and there appears to be little hope for improvement, you might be better off changing jobs.

Take a look at Winter’s article (linked again below) and let us know what you think of her suggested strategies.