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Should You Tell Your Boss You're Unhappy?

Whether to tell your boss you're dissatisfied.

Key points

  • Telling your boss you're not happy can seem like a risky proposition, particularly amid layoffs.
  • Many workers today are dissatisfied, but options exist: resigning, biding time, and having "the conversation."
  • Each choice has pros and cons, depending on your situation, and you have productive ways to express yourself.
Motortion/Adobe Stock
Source: Motortion/Adobe Stock

With recent layoffs making headlines, being unhappy at work is an extra burden. You may be pondering whether to approach your boss. The fear of being on the chopping block looms large. Is it worth the risk?

In a recent Resume Builder survey, 40% of companies said they were planning layoffs in 2024. Many of the largest tech companies like Google, IBM, Microsoft, and Tesla have announced job cuts, as have large financial firms, such as Goldman Sachs. It’s a stressful predicament.

That said, if you’re thinking of quitting, you’re in good company:

  • Confidence in job search prospects has reached its highest point in two years, according to a February 2024 ZipRecruiter survey.
  • A widely read LinkedIn and Microsoft study recently shared with Fortune says there are actually more people looking to resign now than during the Great Resignation.

You have options. Let’s consider the pros and cons of each.

1. Keep your situation under wraps, look for a new job, and then resign. If you tend to avoid confrontation and are highly risk-averse, this is likely your inclination, although no one should take this step lightly. You will never need to have that difficult conversation. You can keep your discontentment private and resign when you’re ready because you found a “more suitable position.” You have control over your destiny. If you handle things well, you might even get a good reference.

The downside: First, you’ll ideally need to line up another job and start a job search. You’ll lose the seniority you achieved where you are. If there are any aspects of the job you like, you’ll need to forfeit those. And as with any new job, there are risks—no position is perfect.

2. Bide your time, and maybe things will get better. Sometimes, circumstances can change and surprise you. You might find that the source of your unhappiness can disappear, like a new boss or a departure from a manager or coworker. Other opportunities may arise because of business related changes, such as a new division or client to work on. If you’re underpaid, it’s possible that the company will change its compensation policies for the better.

The downside: It can be stressful to be at the mercy of your boss to help you achieve your goals or to create the environment you seek. Managers are not mind readers and hence, you may be waiting for some time. If you’re dealing with personality conflicts, things are likely to get worse before they get better unless you have established a strong, open communication line. Your work product may suffer in the meantime as you deal with the challenges.

3. Have a tough conversation with your boss to improve your circumstances. Will you always wonder what could’ve happened if you spoke up? Could you be jumping from the frying pan into the fire if this is a pattern? Speaking with your manager about job issues you’re having is never for the faint of heart, especially when layoffs and hiring freezes are happening in corporate America.

But how you package this information is everything. You don’t want to approach your boss in the heat of anger and say I’m thinking of leaving, although it can be tempting. If you use the right techniques, you could salvage an otherwise excellent job.

The downside: Depending on how you present the issues, you may now be more on the radar of your manager, who could question your loyalty. You may feel pressure to perform better after speaking your mind. Your boss may also take it personally. Fortunately, the job market is relatively strong.

So, how do you determine which of these options makes the most sense for your situation? Some questions to consider:

  1. Know your boss. What kind of relationship do you have? Can you be open and honest about your frustrations? Have you tried it before, and if so, what was the result? Have you observed others were able to have a candid conversation with your boss and what was the reaction? What are the possible outcomes?
  2. Looking deeper. Before you run for greener pastures, have you written down the pros and cons of your job? Have you identified the true root cause of your unhappiness? What are the possible solutions your manager could offer to make your life better, and are they reasonable expectations?
  3. Where do you stand? How valuable are you to the company? Do you have unique, hard-to-find skills, solid longevity, or excellent corporate training? Have you received praise for your recent project work in performance reviews or other communication avenues? Are you included in important meetings, and does your boss look to you for help? Do you manage a strong team that has thrived?

How to Have a Tough Conversation

If, after significant thought, you have decided to air your dissatisfaction, here are some tips to consider:

1. Get clarity on the real issues. Be sure you’ve committed to writing the specific challenges you’re facing in advance. It’s easy to let emotions take over when you’re making such a critical decision, especially when personality conflicts exist. The best outcome will occur if you can remain factual, concise and calm.

2. Know the result you’re seeking. Be sure you have identified your objectives beforehand. If you fall prey to using this conversation to vent or teach your boss a lesson, you may be better off leaving. But if you seek a constructive solution, then you’re giving this discussion its best prospects.

3. Listen. Remember, you’re there to gather information that will help you decide your next move. Ask questions and use emotional intelligence to get the answers you need, diplomatically. The bottom line you’re trying to ascertain: Is your boss willing to take the necessary steps to bring you greater job satisfaction? On your part, can you take steps to manage up better?


If you decide to approach your boss, keep in mind that it’s helpful to first weigh the feedback you generally get and also gauge how the conversation is proceeding in real time. As with most sensitive communications, going with your gut instincts is always a wise idea. Remember, this is your career, and you have every right to weigh all your options.

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