How to Talk to Your Boss If You’re Unhappy at Work

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You love the company you work for. Its values and mission statement align closely with yours, and your boss is fantastic. So, why are you battling a lingering feeling of dissatisfaction?

Could it be that you feel like you’re always on the clock and your work-life balance is out of whack? Or, is the reason for your unhappiness less apparent?

Whatever the reason, consider if there’s potential to improve your satisfaction with your current job. It might be as simple as launching a productive dialogue with your boss about your feelings.

If you haven’t tried that yet, it’s time to make some notes, get your ducks in a row, and schedule a sit-down.

Lay the Groundwork for a Productive Discussion

Man working from remote office on laptop
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Before you meet with your boss, take a moment to acknowledge that successfully discussing anything work-related often depends on how you present the information.

Try to approach the discussion from a place of problem-solving, rather than simply complaining.

Remember, your boss likely wants you to be happy, so they’ll generally be receptive to helping you find a positive way forward. But first, you should analyze why you’re feeling unhappy at work.

1. Understand Your Discontent

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Where do you start when you’re unsure why you’re feeling unhappy? Well, you can use many methods to determine your best job fit.

You can try popular personality tests or a career aptitude survey, but you might find your answers with a simple pen-and-paper exercise.

Create a list of pros and cons or brainstorm freely to identify your feelings and concerns about your role.

Don’t censor your thoughts; look for patterns in the cons column. Ask yourself if these issues are short-term or point to a more profound unhappiness in your role.

If they’re related to a specific project you’re working on, you might decide just to push through.

On the other hand, if they’re connected to something ongoing, don’t let them fester. It’s time to move forward with your meeting.

2. Assess the Scope

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Next up, determine if the issues you’ve highlighted are personal, role-related, or tied to poor work-life balance. Once you’ve analyzed your feelings, you might need to do some digging to identify the root cause of your unhappiness.

Are you feeling isolated? Could that be an adjustment to remote work?

Or, do you constantly juggle intense anxiety? Are you struggling with last-minute meetings and ambiguous work expectations?

When you start categorizing the causes, you can create an actionable plan to improve your happiness at work.

3. Document Your Concerns

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Your boss is busy. They’ll likely get frustrated if you give them a vague sense of unhappiness. It’s going to be hard for them to solve that. And honestly, that’s not generally their job.

Instead, set yourself up for a successful conversation with your manager by preparing talking points. Create an outline or list of talking points that provide substance to your feelings.

Consider if any of the following apply to your situation and what specific examples you can use:

  • If you feel like you’re constantly on the clock, you could note specific instances where work infringed upon your time. That might sound like, “I often find myself answering work emails and calls during family time, weekends, or late in the evening.”
  • Are you consistently overwhelmed by your workload? You could explain that you’re feeling stressed or burnt out. You might say, “I have been managing five projects simultaneously, which is more than I usually handle.”
  • Perhaps you feel like you need more career opportunities. Bring that to light with details, such as, “I have expressed my interest in learning new skills or taking on new roles, but I have not been given those opportunities.”

Clearly outlining specific concerns will give your manager context and open the floor for potential solutions.

4. Identify Potential Solutions

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Before reaching out to your boss, prepare some potential solutions incorporating your career goals and primary duties. What changes could make things better?

Offering solutions demonstrates your proactive approach to resolving your unhappiness and moves the conversation to solution-oriented, rather than problem-focused.

5. Choose the Right Time

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Timing is crucial in how receptive your boss will be. Avoid Monday mornings, when the week’s workload is being sorted, and Friday afternoons, when everyone’s winding down.

Even if they genuinely want to support you, it’s unlikely they’ll have the time or focus to give you their full attention during those times.

Instead, select a relatively calm day and time to converse with your boss, and send a polite request for a meeting. Schedule the meeting with ample time, rather than springing it on them last-minute.

And don’t treat the issues with urgency when they’re not critical. While they’re important, you don’t want to give the impression that they will make or break your ability to complete your work for the day.

Structure the Conversation With Your Boss

Human resources, interview and resume with a woman manager and candidate meeting at work. – Yuri A /

Once you’re clear on what you want to discuss, it’s time to create a foundation for your meeting.

1. Set the Scene

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It can feel awkward to discuss your unhappiness at work. But your boss can’t fix anything if they don’t realize it’s broken.

Begin the conversation by expressing your appreciation for your boss’s time. Then, briefly state the purpose of your meeting.

Stay focused and try not to let your nerves cause you to chatter or wander off-topic. Bullet points and notes can help immensely with staying on topic and having a productive conversation.

2. Communicate Clearly

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When expressing discontent, aim for a balance of assertiveness and understanding. Speak clearly about your issues, but avoid coming off as overly negative.

Remember, your boss can’t tell you that your feelings are wrong. They’re yours. So, use “I” statements, such as “I feel” or “I believe,” instead of “You never” or “You always.”

Also, remember to monitor your tone so you don’t appear aggressive or accusatory.

3. Foster Collaboration

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Be open to feedback and keep an open mind. After you’ve stated your concerns, allow your boss to respond.

This part of the conversation is about understanding their perspective. Hopefully, you both have a goal to work together to find a solution.

Be receptive to your boss’s perspective. They might offer insights or solutions that haven’t occurred to you.

If you don’t like the feedback you’re getting, ask for time to consider what they’re sharing with you and schedule a follow-up.

Take time to digest what they’ve said and then continue the conversation.

4. Propose Your Solution

Young woman in an online meeting
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Following your boss’s response, propose your solutions if they haven’t already offered a workable one. Be clear and specific, showing how these changes could benefit you and the team or the company.

The solutions you propose will depend on your particular issues, but here are some general suggestions:

  • Flexible work hours: If you’re struggling with a lack of work-life balance, flexible work hours might be the solution.
  • More meaningful projects: If you don’t feel challenged or engaged, request more meaningful or diverse projects.
  • Professional development: When your career is stagnating, discuss opportunities for professional development.
  • Changes to your work environment: If your concerns relate to your work environment, consider discussing potential adjustments, like a quieter workspace or the possibility of remote work.

If appropriate, ask to schedule a follow-up because a single conversation may not change everything to the extent you need. Be your own advocate and keep the conversation going until you see the positive changes you require.

If the Conversation Doesn’t Go Well

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The unfortunate reality is that sometimes these conversations might not lead to sufficient changes, or your boss might not be receptive.

In that case, your follow-up should look quite different and will depend on your commitment to your company and your unique situation.

Here are a few options for your next steps:

  • Seek mediation: Consider working with your human resources department. They can often provide objective advice and assistance in addressing workplace issues.
  • Document everything: Depending on the severity of your unhappiness or the root cause, consider whether or not you should maintain a record of your conversations and any actions followed. You’ll be thankful for the documentation if you need to escalate your concerns further.
  • Set boundaries: Regardless of the feedback you get, it’s crucial to set boundaries that protect your time and prevent burnout. For instance, you can avoid answering work-related emails or calls outside of work hours. If you’re assigned work during off-hours, communicate when you’re unavailable.
  • Evaluate your options: If you can’t find a resolution, it’s time to reassess. Are there other roles within the organization that might be a better fit? Or, is it time to consider a new job or career?

Creating Positive Change

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Remember, the goal in discussing your unhappiness at work is to improve your job satisfaction and work-life balance. Be patient with the process, but be prepared to make changes to achieve career happiness.

A single conversation might not fix everything, but it can launch a dialogue that leads to a happier, healthier work-life balance in a thriving career.

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