How To Tell Your Boss You’re Unhappy at Work

Feeling unhappy, bored, or under-valued at work? It may be time to talk to your boss about it. Don't be afraid! Modern Mentor shares her top strategies for a successful—and totally not awkward—conversation!

Rachel Cooke
5-minute read
Episode #668
The Quick And Dirty

Having a successful conversation with your boss when you're feeling unhappy boils down to these 5 strategies:

  1. Be specific about your unhappiness
  2. Have an outcome in mind
  3. Propose a plan
  4. Listen openly
  5. Commit with clarity
Earlier this year, I was having multiple conversations each week about feeling overwhelmed at work and burnout. It was such a pervasive experience. People were working like crazy to retain customers, to keep supply chains from breaking down, and to just not lose their jobs in scary times.
While burnout remains very present, I’m starting to hear a different storyline. Now that people have a chance to catch their breath and reflect, they’re realizing they just aren’t happy where they are. And they want to do something about it!
If you’re feeling unhappy at work—bored, underwhelmed, underutilized—it may be time to have a chat with your boss. Sound scary? It doesn’t have to be! 
Let’s talk about the critical components of a successful conversation that lets you air your grievances and delivers you a better outcome.

1. Be specific about your unhappiness

In the past few weeks alone, I’ve talked to three different people feeling generally unhappy at work. But when I asked each to articulate the specific source of unhappiness, I got blank stares.
I asked some leading questions and ended up with the following insights:
  • Alex generally enjoys her team and her company’s culture, and she thinks the products they’re selling are pretty cool. But her work has become repetitive, mundane, and a little bit isolating. And she needs a new challenge.
  • James feels challenged and excited by the work he is doing, but he’s feeling underappreciated and not valued for his contributions and thought leadership.
  • Bashir just isn’t passionate about his company’s products, and he wants to feel more connected to a company’s mission and purpose.
There’s almost a pandemic of meh happening. A lot of people are feeling generally underwhelmed or under-excited, or underutilized in some way.  But you can’t solve a general feeling. You need to determine specifically what’s got you down.
Specificity is important because it either helps you know what you need to fix if you choose to stay, or it helps you identify what to look for if you choose to leave and hunt for something new.
So if you’re feeling like a sepia filter has settled over your career, do some reflecting on what specifically is driving that feeling. Telling your boss “I’m not feeling very challenged, and growth and development is a key driver for me” is much more helpful than “I’m feeling blue.”

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2. Have an outcome in mind

What do you want to happen?

Let's go back to my examples:
  • If you’re an Alex, can you identify a specific project you’d like to participate in? A problem you’d like to help solve?
  • If you’re a James, what would appreciation or recognition look like? Would it be a nomination for an internal reward program? An extra day off? A monetary bonus? Public acknowledgement for work well done?
  • And if you’re a Bashir, what would feel meaningful to you? And is that possibly available at your company or is it time to explore other options?
There aren’t right or wrong answers. But you must know what you want before you can effectively ask for it.
Sometimes talking to friends or colleagues can be helpful in getting the clarity you need here. I was able to play that role with Alex, James, and Bashir. Who in your life is positioned to help you find that insight?

3. Propose a plan

Think of your unhappiness as the“you are here” spot on a map, and your ideal outcome as the destination. Now it’s time to build the plan—the turn-by-turn directions to get you from here to there.
As a general rule, leaders respond better to plans than to complaints. A plan shows your proactivity, your creativity, and your ambition to make change.
Here are some key elements to the ideal plan:
  • What do you want to work on—specifically?
  • How do you propose getting it done while still meeting your work requirements?
  • What will you need in terms of resourcing, support, permission, etc.?
  • How will this benefit you, and ideally the company in some way?
Alex knew she needed a new challenge. So she proactively identified a project that felt compelling to her. Her company’s latest class of college interns was due to come in soon, and Alex wanted to play a mentorship role with the cohort. 
She has a passion for leadership and career development and believed an opportunity to practice and showcase these skills would help fill her sense of emptiness.
So, she proposed to her boss that she take on a role. She had mapped out a high-level approach to when and how often she’d meet with them, what topics she’d talk about, how her mentorship would contribute to their success, and critically, how this would contribute to her own satisfaction in her role.
It was a pretty well-thought-out plan!

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4. Listen openly

And now you get to pause, breathe, and receive.
This is, remember, a conversation—not a monologue. Your boss will need an opportunity to react and respond.
Ask for their feedback. How realistic is your proposal? Does it align with your boss’s priorities? Are there different avenues they might prefer to explore with you?
In Alex’s case it turned out her boss was all ears. They listened to her concerns, her desired outcome and her proposed plan. And in the end, they proposed an alternative strategy for meeting Alex’s needs as well as the company’s needs.
Rather than mentoring the collective of interns, Alex’s boss suggested she take on just one intern and would manage him throughout the life of an entire project. 
This felt like a fair compromise, and she agreed. 
It’s essential to remember that your boss has a stake in this, and that their inputs, support, and advice really matter here. So be sure to listen with an open mind and be flexible in what success looks like.

5. Commit with clarity

Be sure to close the conversation with a clear set of next steps.
Alex and her boss agreed to meet again in a week’s time at which point Alex’s intern, and his project, would be identified. From there, she and her boss would establish project goals and identify any support or resources Alex would need.
Too often we leave conversations at work thinking we’re all on the same page… only to realize later that what you heard and what your boss heard were miles apart.
So be clear and tactical on what will happen, by what timeline, and on whose action. Document it, share it via chat or email, but make sure agreements are shared and actionable.
Also, be ready to recognize that not every problem will be solvable. Bashir, in the end, has decided it's time for him to move on and find a new company that truly inspires him.

Now it’s your turn

Are you feeling bored, unhappy, undervalued, or just a little bit meh? Go out and make something wonderful happen for yourself!

About the Author

Rachel Cooke

Rachel Cooke is a leadership and workplace expert who holds her M.A. in Organizational Psychology from Columbia University. Founder of Lead Above Noise, she has been named a top 100 Leadership Speaker by Inc. Magazine and has been featured in Fast Company, The Huffington Post, and many more.