Is It OK To Tell Your Boss That You're Unhappy At Work?

This is a tricky career conversation that is high risk, high reward, so tread carefully. Your job is at stake.
Sharing your true feelings to your boss can be dicey. That's why it's important to weigh whether sharing how you feel can lead to real change.
calvindexter via Getty Images
Sharing your true feelings to your boss can be dicey. That's why it's important to weigh whether sharing how you feel can lead to real change.

Feeling unhappy at work is an unfortunately common frustration many of us deal with in our jobs. The harder thing to decide is what to do about it.

Telling your boss that you are frustrated or unfulfilled is a tricky conversation. A good boss wants to help you grow and be engaged with your role, but their job is not to be your therapist or close friend, either. Being too candid about job dissatisfaction can backfire.

“Working as a coach for women of color in tech, I’ve seen being honest about being unhappy or unfulfilled go many ways, from a boss retaliating or suddenly going cold and less open, to a boss being kind and understanding even if they weren’t particularly helpful, to a boss really stepping up to help with learning and development trainings or championing for a promotion and raise,” said Nadia De Ala, founder of Real You Leadership, a group coaching program for women of color.

The risk with being too honest about your unhappiness is that your job may become even more miserable than it currently is. But sharing your truth can also be a turning point in your relationship to your boss and to your work.

A good manager would want this conversation to happen before you hand in your resignation notice.

“It’s not only okay to tell your boss that you are unhappy with your job, it’s preferable,” said Gorick Ng, a career adviser at Harvard University and the author of “The Unspoken Rules: Secrets to Starting Your Career Off Right.

“Put yourself in the shoes of your manager: Would you rather your employee come to you with their challenges —and give you the chance to address them — or hide them from you and quit out of the blue? Chances are, you’d rather have a chance to fix the problem.”

So how can you ensure that bringing up your feelings is going to be helpful? Here are four critical factors to weigh before you wade into this delicate conversation with your boss:

1. Are you in a good place emotionally to share how you are feeling with your supervisor?

Talking about your unhappiness can bring up anger, frustration and anxiety, so it’s best to process those emotions within yourself before you share them in a high-stakes conversation with someone in charge of your development.

“If you are at your breaking point, take a breath before you have it,” said Lawrese Brown, the founder of C-Track Training, a workplace education company.

Brown said that if you are in a too-intense mindset, “it’s not going to come out as a brainstorming conversation. It’s going to come out more as a final negotiation.”

2. Is your manager receptive to hearing this information?

Unfortunately, some bosses may take your unhappiness as a personal betrayal and retaliate. Gather intel by asking people who have worked with your manager to see how they handle bad news, Brown suggested.

De Ala said to consider how much psychological safety you feel with your boss and how good the communication and support is between the two of you.

“Nuance matters here, and if you don’t feel safe to say this, you don’t feel safe,” she said.

3. Have you reflected on the specific source of your unhappiness?

If you are not specific about the work-related stressor that is causing your unhappiness, your boss will not know how they can help you, and revealing your feelings will not move the conversation into action.

“It has to be a very specific conversation that you can bring to your boss, or else the rebuttal will be, ‘That’s your job,’ or they will even put it back on you: ‘I want you let me know how I can support you,’” Brown said.

Only you can know yourself best. Ng said he finds that workplace challenges come down to three things: people problems involving co-workers, position problems in which people are frustrated by low pay or lack of benefits, or place problems in which issues are more about where an organization is going, how it is run, or what it cares about.

Some problems may be out of your boss’s control to fix.

“If you are in an organization where there isn’t any opportunity for you to do more of what energizes you or focus on something new and different that you see as part of your long-term path, then that is the information, basically, to look elsewhere,” Brown said.

If sharing vulnerable feelings with your boss makes you anxious, it can help to reframe the conversation as an opportunity to gather information from your boss about whether the organization can help you address your issue. “When we come from a space of ′I have information on myself, but you can tell me about the organization,’ that’s a much stronger conversation,” Brown said.

Having a proposed solution can help, but you don’t have to have all the answers. You simply need to have an idea of what your manager could help you with. De Ala said it can be as simple as communicating, “I’m grateful for this role and unhappy because I’m burnt out and I want to find ways to do more fulfilling work. I appreciate your guidance and advice. What’s possible with learning a new skill set/getting a new role/etc.?”

4. Do your needs align with what your boss can offer? If not, you can start looking elsewhere.

Lara Hogan, author of “Resilient Management,” said there are four questions you should ask yourself to determine whether a conversation with your manager could help change how you are feeling:

  • What’s the No. 1 thing you need right now, such as rest, support or clarity?
  • If you could wave a magic wand and change one thing about your work, what would it be?
  • What’s the No. 1 thing your manager cares or worries about, such as attrition or deadlines?
  • Where’s the overlap between what your manager cares about and what you need?

That way, if you do see an area where you and your manager align, you can frame your conversation around that positive direction with language like, “I’m looking at my next steps here. And I would like to learn more about this,” Brown said.

If there is no area of overlap between your boss’s needs and your own, then that’s valuable information, too. “If you don’t see a way to connect what your manager cares about to what you need, then it might be time to find a new role or job,” Hogan said.

Sometimes, it takes having the conversation with your boss to figure out this answer, too. De Ala shared herself as an example. When she worked as an account manager in tech sales, she found the courage to tell her boss candidly that she hated sales.

“I explained even as a top quota-hitter, I’ve been unfulfilled for awhile and I could keep doing it, but not for long,” De Ala said. “I focused on stating my truth and my experience of the work, and then I shared my ask for my boss to help me stay with the company and nurturing a new career path because I still wanted to be there, just not doing what I was doing.”

Once her manager was in the loop, he used his resources to help her figure out her next step, which in De Ala’s case turned out to be quitting and switching to a new career.

“I felt relieved to be honest and stop putting up a front that I was happy there,” she said. “My boss was able to receive this and supported me in any way he could, even as I eventually transitioned out, as an advocate and available mentor for me should I need it.”


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