The Right Way to Share Problems at Work With Your Boss 

UPDATED: June 2, 2023
PUBLISHED: June 2, 2023
employee talking to boss about problems at work

Not every issue needs to end with rage applying, quiet quitting or other trending exit terms. Instead, an old-fashioned conversation about problems at work might be just what you and your boss need to take the next step forward toward progress together. 

In the present push for improved mental health in the workplace, your own well-being and that of those around you just might depend on your openness. Gallup’s “State of the Global Workplace: 2022 Report” shows “60% of people are emotionally detached at work and 19% are miserable.” There are numerous reasons employees might not speak up at work, from fearing backlash from bosses in charge of their promotions and salary to worrying about how it will impact their reputation.

For example, in the early 2010s, one Ottawa-based employee tried to push back against a concerning payroll system, but was told she “wasn’t being a team player.” One 2021 study found that “voice and silence are independent (Mρ = −.15) and that perceived impact (psychological safety) relates more strongly to voice (silence) than to silence (voice).” Additionally, just because employees speak up doesn’t mean they’re sharing everything. As the study found, “employees largely speak up on issues they believe could be implemented while systematically withholding other issues they do not feel safe raising.” 

“The last three years have been particularly challenging for employees given the dramatic shift in how people work, including shifting to hybrid/virtual environments, the erasing divide between home and work life, financial strain connected to [COVID-19], the economic downturn, many instances of social injustices and so much more,” says Ritu Bhasin, former HR leader, a leadership and diversity, equity and inclusion consultant and expert and author of We’ve Got This. It’s no wonder many people are feeling fatigued and experiencing sleep difficulties. She adds that though the employees can take action, it’s really on the leaders to create a psychologically safe environment for team members to air concerns. 

Her advice for bosses? “Be more mindful and deliberate in how they communicate. Ensure everyone has the opportunity to be heard in meetings. Interrupt their biases. Don’t retaliate when negative feedback is shared. Demonstrate empathy in conversations. And slow down, speak less and listen more.”

How to talk with your boss about problems at work

But let’s be real: Not everyone can just up and leave if the conversation doesn’t go as planned. There are families to support, benefits to consider and a scary up-and-down job market not everyone wants to jump into. Here’s how to know when it’s time and how to have a tough conversation, according to workplace experts.


Your conversation with your boss about an issue shouldn’t be the first time you’ve tried talking about it. Matt Abrahams, a lecturer at Stanford University’s Graduate School of Business, is the author of the forthcoming book, Think Faster, Talk Smarter: How to Speak Successfully When You’re Put on the Spot. “Practicing and role-playing can help you feel more confident. Saying something in your head is one thing, but when it comes time to say it out loud, many people’s nerves get the best of them. Recording yourself and listening to the recording as well as asking trusted others for feedback can be very helpful,” he says.

Pick the right time and format to discuss problems at work

Like any conversation, timing is everything. If you are approaching an already stressed boss with a problem at work, you are unlikely to get the reception and validation you want and deserve.

“Timing and context are important in all communication. You want to make sure that your audience is not rushed and can focus. Checking your boss’ calendar in advance to see what they have before and after your conversation can help you pick an ideal time, and make sure they can devote the appropriate amount of time and focus to the conversation,” Abrahams says. “Similarly, notifying your boss in advance of your planned topic via an email or a conversation can help prepare them.” It’s not a good idea to spring a big point of contention on them without a heads-up. 

Jerry O’Keefe, national director of Kaiser Permanente’s Employee Assistance Program, adds that you can also ask about the best format for bringing up problems at work ahead of time, especially if you aren’t in a psychologically safe workplace with open communication. “Ask how they would like you to bring up concerns, address problems and/or discuss sensitive things. A little communication can go a long way,” he says.

Back it up

If you are presenting a problem at work that might be made stronger with data, bring that to the meeting, recommends Lindsey Paoli, a therapist turned MIND performance coach who helps companies make mental health support an asset for employee performance. “Just as you would negotiate a salary with comparisons, it is important to highlight data that could benefit the implementation of your idea. This takes a suggestion from potentially sounding like a complaint to an evidenced-based idea for improvement,” she says. “A quick google search could be your best friend in these conversations.”

Examples of data you might present include employee or customer feedback, satisfaction surveys or trends within the company happening over time due to a change.

Speak in company-first terms

While you are an important part of the company, your employer is overseeing entire teams and potentially entire locations of your business. So, to pique their interest, speak in terms of what will help the company, not just you. This shows you have a mission-oriented mindset and team mentality.

Paoli says this is an “interesting twist” because in the mental health world, “I-statements” reign. “In a work setting though, we want to keep the company front of mind, highlighting that you are bringing this issue to light as a missed opportunity for the greater good of the whole,” she says. But this doesn’t mean putting your needs last and the company’s first, just changing your approach. 

“This may look like ‘I know it would benefit our employee retention and culture to have mental health training more frequently’ rather than ‘I feel as though I’m burning out and could use more mental health trainings as support,’” she says.

Use the proper chain of command to share problems at work

Put yourself in your boss’ shoes. If their boss comes to them with your complaint, they may become naturally defensive, because now they are potentially in hot water with their own superior. To prevent this adversarial situation, follow the chain of command, Paoli advises. Bring up problems at work with your direct lead, not someone three levels above you.

“Even if you feel your direct supervisor never listens or has something personal against you, always start there first. No one likes to be caught off guard, and going over their head to a higher-up is a great way to risk unnecessary repercussions. Only escalate once you have made your first attempt,” she says.

Start earlier—before the problem at work happens

They say prevention is the best medicine, and that applies in workplaces far beyond healthcare. 

“The biggest thing you can do to have good conversations with your boss about problems is to start having them before anything goes wrong. Without a baseline understanding of how your boss wants to deal with problems when they happen, bringing up your concerns can feel awkward, nerve-racking and weirdly unsatisfying,” says Laura Crandall, an workplace communication and management consultant and the president of Slate Communication, who also teaches workplace communication and intergenerational management at Harvard Extension School. “That’s because problems are often connected to the people we work with. Brian isn’t following through on deadlines, Mae is claiming others’ work as her own or your boss isn’t being clear with expectations and it’s making you nuts. When you have a framework for how to deal with problems, it makes discussing them easier.”

Come in with a plan

Your boss may be more likely to fix a problem at work if you’ve brought a feasible, well thought-out solution. Here’s Crandall’s formula for how employees talking to their bosses can present both the issue and the solution:

  • When you talk with your boss, be direct and succinct.
    • State what you want to address (“I have a concern about Mae’s work and some potential plagiarism.”)
    • Why it’s important to you (“I value the work of the whole team and I’m not sure how to address this. Mae is amazing, and this seems unlike her.”)
    • What you’d like from your boss (“Can you advise me how to proceed?”)
    • What your vision of a solution looks like (“I want to have confidence that we all know the rules about content creation and know how to point it out if there’s a question.”)
  • Ask if your boss wants to know more.
  • Ask when you can follow up on a specific next step and do it.

“Then see what happens,” she adds. “You will learn about your boss by how they respond. In the moment, that can feel harrowing. In the long-term of your working life, having the courage to address problems clearly and directly is worthwhile for your own confidence and character.”

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