Have Difficult Conversations with Your Boss

You’re not alone if talking to your boss about tough subjects seems intimidating. You might not know what to say, you might not want to bring up an issue, or you might not know what the outcome will be. Fortunately, there are tried-and-true tactics to go into those difficult talks with confidence. First, we’ll walk you through getting those conversations started. Then, we’ll go over specific templates for common tough workplace conversations so you’ll feel comfortable and get what you want out of the talk with your boss.


Setting Up the Conversation

  1. Define your objective and ideal outcome. Ask yourself “What action do I want my boss to take after we talk?” It’s important to have a clear goal in mind so you can frame the conversation around an objective instead of making it personal. Answer these two questions before you ask to meet:[1]
    • “What do I want to achieve by talking to my boss?”
    • “Is what I’m asking for reasonable/realistic?”
  2. Prepare evidence and facts. Whether you’re asking for a raise, saying no to an assignment, or bringing up a harassment issue, bring documented support for your perspective. That way, you’ll keep the conversation from getting overly emotional and reduce backlash, since you’ll have objective evidence.[2] Evidence can include:
    • Metrics on your performance or workload: sales numbers, emails or surveys documenting client satisfaction, a list of tasks and the timeframe in which you completed them, statistics from past successful projects
    • Written documents: contracts, screenshots, text messages, emails that reflect the problem or need for change
  3. Send an email request to meet in person.[3] Keep the request simple, but ask ahead of time so you don’t blindside your boss.[4] Use email as a way to document that you had the conversation, in case you need to take further action (or even legal action) afterwards. Briefly mention the general subject you’d like to talk about, but wait to jump into the specifics of what you want until you can make your case in person.[5] Here are some examples of ways you can bring up the meeting:
    • To ask about a promotion/raise: ”I’d like to talk with you about taking on more responsibility in my role. Would you have time to talk Friday morning?”
    • To ask for help or bring up issues with management style getting in the way of your work: “I’d like to get your input on how I can streamline my work/boost my efficiency” or “I’d like to hear how you’d approach this roadblock with the Reynolds account.”
    • To talk about workload: “I’d like to talk about managing my workload to better optimize how I’m contributing.”
    • To discuss harassment/an interpersonal issue: “I’d like to get your input on some concerns I had about team dynamics on the Beach Project.” Or, if it’s a serious harassment issue, explicitly state the issue in the email in order to keep written documentation of how the company handles the situation.
  4. Pick a neutral location to talk. Make yourself feel more at ease and even out the power dynamic by having the conversation somewhere that isn’t in your boss’s office. Studies show the “home field advantage” applies to negotiation, so try an empty conference room, or the employee lounge (as long as you won’t be interrupted).[6]
    • Go outside the office and sit on a nearby bench.
    • Have the conversation at a nearby coffee shop.
    • Sit face-to-face for a formal conversation and side-by-side to give a more casual tone.[7]

Tackling Common Conversations

  1. “I’ve made a mistake.” It’s not easy to come clean when you’ve messed up at work, but having the conversation will show your boss you can take responsibility and use the situation as a chance to grow. Break the conversation down into three simple parts:[8]
    • State the facts of what happened: “I missed the meeting with our new client on Friday and as a result, they told me they went with a different vendor.”
    • Take responsibility without making excuses: “It was totally my mistake.”
    • Address how you’ll fix the problem: “I’ve reached out to five similar companies who’ll be at the event to see if they’re interested in our products. I’m meeting with one of them this afternoon.”
    • Describe what you’ll do differently in the future: “This won’t happen again. I’ve set up a new system for calendar bookings and notifications.”
  2. “My boss’s management style doesn’t work for me.” Stick to the facts in this conversation, since you want to avoid it seeming like a personal attack. Whether your boss is micromanaging you, preventing you from finishing a task, or simply making your life at work more difficult, try this approach:[9]
    • Avoid telling your boss exactly what to do (“you should”) or using phrases like “unprofessional” and “wrong.”[10]
    • State the situation and the actions you’ve observed: “I noticed you’ve been monitoring the spreadsheet edits with the team every week and providing me with a lot of great feedback while I’m working.”
    • Describe the impact the actions have: “We turn around that data really fast, and so it’s hard for me to flag and implement all your suggestions and finish the task under that tight deadline. Plus, I feel more stressed when you’re checking every line.”
    • Suggest a solution: “Could we separate feedback sessions from data processing sessions? For instance, I’d love to hear your thoughts before I start processing the data so I can really focus on your suggestions before I go to implement them.”
  3. “My workload is too heavy.” You might feel worried about looking like a complainer, but feeling stressed and burnt out won’t help you get work done! Approach this conversation by setting boundaries and providing alternative solutions.[11] Here’s the breakdown for tackling this tough conversation:[12]
    • Describe the goals you and your boss share: “I know as a company we’re really committed to customer satisfaction.” By describing common goals, you set a team-effort atmosphere and show you understand how you’re contributing to the bigger picture.[13][14]
    • Discuss the reasons your workload is unreasonable: “Now that I’m in charge of processing online orders, it’s much harder for me to meet with customers in-person.” If necessary, provide evidence of the projects you’re working on and how long they take.
    • Suggest a solution: “How would it sound if I do online orders in the morning and train Arthur to process them in the afternoon, so I have time to meet with customers?”
    • If you can’t propose solutions, ask for input on priorities and try to brainstorm alternative options together:[15] “Between online orders and in-person orders, which should I prioritize this week? I’m finding online orders take up a lot of time now that our website’s growing.”
    • Say no to more work and/or offer to help in a smaller way: “I won’t be able to take on that project and put my maximum effort into it with the other two projects I’m working on. But I’m available to be a second set of eyes on it and help out whoever ends up spearheading that.”
  4. “My boss is being overly critical.” A negative performance review or bit of negative feedback can leave you feeling surprised, underappreciated, and even angry. First, take a step back and try to see the situation from your boss’s perspective. If you reassess the situation and still believe the feedback was unfair, look at objective measures of your performance. Then, break down the conversation like this:[16]
    • Describe the situation you want to talk about: “I was hoping to talk about my latest performance review, since it took me a bit by surprise.”
    • Continue with your shared objectives: “I know we’re looking to strengthen the sales team all around, and I’m looking to boost my skills as part of that effort.”
    • Acknowledge the other perspective: “I really value your feedback, and the notes you gave me about how I can improve my pitches were really helpful.”
    • If the review was based on bad data, speak up without using the words “you’re wrong," for example: “I noticed you listed my customer satisfaction rating as 54, but on my end, it comes up as an 84.”
    • If the review or feedback is subjective, ask for your bosses’ input on concrete steps you can take to improve: “What are three measurable ways I can contribute more to the team?” Asking for concrete feedback allows both you and your boss to look at the situation from a more objective perspective to hopefully clear up some unfairness.[17]
  5. “I want a raise.” Prepare a list of your achievements at work and note any areas where you particularly excelled. Have you taken on additional responsibilities? Research company policies on when you typically negotiate raises (ex. at the start of the fiscal year). Do a quick online search to find comparable salaries for the industry you’re in as well as average pay for your position at the company. Practice the conversation with a friend and then bring it to your boss like this:[18]
    • Start the conversation casually: “How’s your day going?”
    • Lead into what you want: “I’m hoping to talk to you about my compensation/my role.”
    • Describe 3-4 of your top accomplishments: “I’ve had a good quarter/year, and I was able to achieve…”
    • Ask for the raise simply: “Based on those accomplishments and the new responsibilities I have, I’m looking for a comparable increase in salary this year. I’d like a 10 percent bump in my base compensation.”
    • If your boss says no, highlight other opportunities (if you have them): “Recently, a few recruiters have reached out to me. I’d really love to stay at this job, but it’d be easier for me to turn down those opportunities if I were making more money here.”
    • If your boss talks about tough financial times at the company say: “I understand the company’s going through a rough patch, but I wanted to raise this now that I've taken on extra projects. I hope we can reassess a few months down the line.”
  6. “I’m being harassed at work.” If you feel comfortable, first ask the harasser to stop. Before speaking to your boss, check your company’s harassment policy and follow the steps listed—especially if your boss is the one harassing you. If your company doesn’t have a policy, then bring the issue to your supervisor (or your boss’s supervisor). Go into the conversation knowing that you legally have the right to report harassment without punishment.[19] Here’s one way to start the conversation:
    • Describe the situation and provide evidence (if you have it): “For the last week, Kendra has been using racial slurs in the company group chat. I have the screenshots here.”
    • Bring up the impact of the situation: “As a person of color, it makes me deeply uncomfortable and unable to properly do my job. Other members of the team have also been affected.”
    • Ask about next steps: “How can I report this?”

Following Up

  1. Paraphrase your boss’s responses. It is important to listen your boss' point of view.[20] Show them you’re listening and avoid misunderstandings by rephrasing the solution you agree on. Ask clarifying questions if you’re not sure why your boss is responding in a certain way or what the next steps look like.[21]
    • For example, if you asked about a raise: “To confirm, you’ll check with your supervisor and get back to me on Monday?”
    • If you asked about workload: “So it sounds like Arthur will help me out with online orders. But you’d like me to still spend about 50% of my time with in-person customers?”
    • If you asked about resolving a harassment issue: “To clarify, will you file the complaint or is there more action I need to take on my end?”
  2. Document the main points of the conversation in writing. Cover the gist of what you discussed as well as the next steps you’ll need to take. That way, you’ll both be on the same page about future actions (and you’ll document the conversation in case your boss fails to follow through).[22]
    • Start by thanking your boss and recapping the meeting: “Hi Kendra, thanks for meeting with me today to discuss my compensation."
    • Describe the next steps: "I’m looking forward to hearing back from you on Monday after you talk to your supervisor."
    • Attach any documentation and restate your request: "I’ve attached the documents I showed you to this email for your consideration as you ask Tim about the 10% salary increase I’m requesting.”
  3. File a formal complaint if the situation gets worse. Go to HR or your boss’s supervisor if you’re dealing with a situation that violates your legal rights or creates an unsafe work environment. Use your documentation to demonstrate the issues and how the company has failed to resolve them promptly.[23]


  1. https://www.fairwork.gov.au/ArticleDocuments/712/managers-guide-to-difficult-conversations-in-the-workplace.pdf.aspx
  2. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3835442/
  3. [v161953_b01]. 28 September 2021.
  4. https://www.fairwork.gov.au/ArticleDocuments/712/managers-guide-to-difficult-conversations-in-the-workplace.pdf.aspx
  5. [v161953_b01]. 28 September 2021.
  6. https://www.researchgate.net/publication/227419124_Location_in_negotiation_Is_there_a_home_field_advantage
  7. https://www.fairwork.gov.au/ArticleDocuments/712/managers-guide-to-difficult-conversations-in-the-workplace.pdf.aspx
  8. https://hbr.org/2019/02/what-to-do-when-you-realize-youve-made-a-mistake
  9. https://gbr.pepperdine.edu/2011/02/the-abcs-of-effective-feedback/
  10. https://hbr.org/2021/06/words-and-phrases-to-avoid-in-a-difficult-conversation
  11. [v161953_b01]. 28 September 2021.
  12. https://hbr.org/2017/01/how-to-tell-your-boss-you-have-too-much-work
  13. https://www.sagepub.com/sites/default/files/upm-binaries/54195_Chapter_7.pdf
  14. [v161953_b01]. 28 September 2021.
  15. [v161953_b01]. 28 September 2021.
  16. https://www.sagepub.com/sites/default/files/upm-binaries/54195_Chapter_7.pdf
  17. https://www.fastcompany.com/3002460/thick-skin-thinking-how-use-negative-feedback-your-advantage-work
  18. https://www.npr.org/2020/12/08/944307129/how-to-ask-for-a-raise-know-your-value-and-bring-the-evidence
  19. https://www.eeoc.gov/laws/guidance/what-you-should-know-what-do-if-you-believe-you-have-been-harassed-work
  20. [v161953_b01]. 28 September 2021.
  21. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3835442/
  22. https://www.fairwork.gov.au/ArticleDocuments/712/managers-guide-to-difficult-conversations-in-the-workplace.pdf.aspx
  23. https://www.eeoc.gov/laws/guidance/what-you-should-know-what-do-if-you-believe-you-have-been-harassed-work