the 4 hardest conversations you’ll have in your career

One of the most stressful parts of work life is figuring out how to say something tough, unpleasant, or awkward to a colleague. Most of us aren’t fond of difficult conversations in any setting, but doing it at work can be doubly challenging, because we fear for our professional reputations and relationships.

Here are four of the most difficult conversations you may need to have in your career and the secrets to making them go smoothly.

1. “I’m quitting.” This one might sound easy, and many people fantasize about the day they walk out of a bad job or a poorly managed workplace. But when it comes down to actually doing it, those same people often find it surprisingly hard to let their boss know that they’re leaving. People often feel regret about leaving something familiar, even when they weren’t that happy there, and it can be tougher than expected to say the words “I’m quitting.” That’s especially true when you did like the job and your manager and are moving on for reasons that have little to do with them.

How to approach it: The key to resigning gracefully is to keep it short and direct. For example: “I’ve really appreciated my time here, but I’ve made the difficult decision to move on, and I my last day will be November 17.” And know that it’s normal to feel some regret; bringing any period of your life to a close can be bittersweet.

2. “I’m firing you.” Ask any manager and you’ll hear that firing an employee is one of the hardest things they ever have to do. Even when the employee has been given every chance to succeed, it’s natural to feel terrible about taking someone’s job away. However, taking action when someone isn’t working out is one of a manager’s most basic and crucial responsibilities and can’t be shirked – even though far too frequently, managers err on the side of not letting people go when they should, often because they want to avoid the tough conversations it will entail.

How to approach it: In most cases, a firing should be the final installment of an ongoing conversation. The employee shouldn’t be blindsided, because you’ve already told the person about the problems and what needs to change, warned her if her progress isn’t what it needs to be, and explicitly said that her job will be in jeopardy if you don’t see specific changes. If you handle it that way, then when the actual firing conversation happens, it’s an expected next step, not a surprise. It’s still going to be hard – but it’s far better than firing a shocked employee who didn’t see it coming and had no idea that your concerns were serious ones.

3. “Stop harassing me.” You’ll be lucky if you go your whole career without encountering sexual harassment, racist remarks, or other inappropriate behavior from a coworker. Federal law requires employers to address sexual harassment or behavior that creates a hostile workplace based on race, religion, sex, national origin, age (if you’re over 40), or disability, so you’re very much entitled to tell offenders to knock it off – and to report them to your company if they don’t. But knowing that the law is on your side doesn’t necessarily make it easy to speak up.

How to approach it: First, know that if you’re not comfortable saying something directly, you can go straight to your company’s HR department, which will have a legal obligation to address the situation. However, if you’re willing to say something to the offender on your own, that can be a more efficient and direct method of getting the behavior to stop. (And when you go to HR, they may encourage you to do that if you haven’t already.) The key is to clearly state that the behavior is unwelcome and that you want it to stop. For example: “Please stop asking me out. I’ve told that I’m not interested and I need you to stop asking.”  Or, “I don’t want to hear that kind of comment. Please don’t say those things around me.”

4. “I made a big mistake.” Everyone makes mistakes at work, but if the mess-up is large enough, your job or reputation might be on the line. Coming clean can feel like putting your career at risk, but you’ll look far worse if you don’t say anything and it comes out later. It’s much worse professionally to be someone who makes mistakes and doesn’t own up to it.

How to approach it: Be as straightforward as possible, as soon as possible. Make it clear that you understand the import and seriousness of the mistake, and that you’re mortified that it happened. Explain briefly and without defensiveness where you went wrong and what steps you’re taking to avoid it ever happening again. You might find that this approach makes your manager much less worried than she’d be if you didn’t approach it this way. Or yes, it’s possible that you’ll have a lot of work to do to regain your boss’s trust, or even – in the worst case scenario –  that she has real doubts about your fit for the role. But as tough as that would be, it’s better to talk about that explicitly than to have it happening below the surface without talking openly about it.

I originally published this at U.S. News & World Report.

{ 55 comments… read them below }

  1. afiendishthingy*

    Just had the “I screwed up” conversation with my new supervisor (formerly senior coworker) right before I read this. A year plus of reading AaM, including comments from last week’s open thread, helped me do it just like this column says, so thanks!!! It wasn’t a single mistake as much as “my productivity hasn’t been great in awhile, October was particularly bad. There’s no excuse, but for context I was struggling with depression last month, I’m in treatment, and I want to start sending you weekly updates on my numbers to keep me accountable”. We work in human services and people are pretty open about their own issues, but I was pretty nervous about saying it right out. She was really nice about it, though, asked if I needed anything, gave some more ideas about ways to improve my time management and billable tasks. Phew.

    1. nofelix*

      Well done for having the conversation. Most people would just hide, especially while dealing with depression.

      Be careful with depression and goal setting. Weekly updates might be stressful if they’re just serving to underline that you’re still missing targets. If you start dreading sending over your numbers, the arrangement might not be right for you, especially if there’s fear of failure or anxiety mixed in with your depression. It may be better to focus on areas you’re being successful in at the same time, to avoid creating a narrative in your head that you’re a bad employee. Good luck.

      1. Afiendishthingy*

        Ohh there’s moderate to severe chronic anxiety + ADHD also, depression was a fun bonus! But the way things currently stand supervisor sees my numbers at the beginning to middle of the next month when it’s too late to do anything about it. So this way it’s the same goals as before just with shorter deadlines, which works better for me.

    2. SophiaB*

      Well done you!

      This is one of the things I find really hard, but I tend to find there’s a reward from ‘fessing up in terms of mental unburdening.

      I’m glad your boss was so supportive about it too, and is willing to help you.

    3. Lily Rowan*

      Man, good for you. I should have had that conversation last spring, but never quite did, just looked like a fuckup for a while.

  2. Allison*

    I agree 100% that the firing shouldn’t be a surprise. It baffles me how many employers will smile and act like someone’s performance is just fine and cracker jack riiiight up to the point where they can’t stand the employee and have to show them the door. Because telling an employee their job is in jeopardy is bad for morale, but for some reason no one thinks blindsiding people, and making it seem like you could be fired any day for a problem you weren’t even aware of, could also be bad for morale.

    I get that firing is tough, just like breaking up with someone is hard, because even if they know it’s coming you know they’ll be upset, and it’s pretty final – you know there’s very little chance of being able to change your mind once the conversation is over.

    1. I'm Not Phyllis*

      YES! Just like you shouldn’t be hearing about your shortcomings for the first time at your performance review. I’ve even had a (great) manager who kept hinting to me that I should be looking even though she loved working with me – she knew what I didn’t, which was that my department was about to be restructured and there was nothing she could do to save my job. It should never come as a surprise.

      1. Lamington*

        One of my former managers waa notorious for this. She waited one year to let one coworkee know that he had some complaints about a project. He was let go few months after. He never heard from the other team they were having issues with him. We just suspected the manager didn’t like him and use this as a excuse to fire him.

      2. AnonPi*

        “Just like you shouldn’t be hearing about your shortcomings for the first time at your performance review. ”

        This a 1000X. It frustrates me to no end how much that is done where I work, especially with new people and students (undergrad, grad, postdocs etc). Instead they fume and comment behind the person’s back (and to other people), rather than just sit down and have a discussion with the person about their poor performance, what they did wrong, etc. We had one student that was never taken to task, and they were just going to “quietly” not renew him w/o telling him until the day his contact ran out – thankfully someone let it slip and he quickly found another job about a wk before this happened. They did him no favors by never holding him accountable, and it wasn’t really fair they were going to just let him go with no warning, when they knew they weren’t planning on keeping him for a good month+ before hand. While he was a poor worker and I didn’t really like him all that much, I still don’t agree with how they handled it.

      3. AdAgencyChick*

        I think your manager was doing the best she could for you under the circumstances — most likely she was forbidden from disclosing an impending layoff, and was trying to help you in any way she could without jeopardizing her own job by giving out confidential information.

      4. AnotherHRPro*

        With pending layoffs, it is tricky. Managers are not allowed to “give a heads up” on layoffs. It sounds like your manager was trying to give you hints about it but that is as far as she could go.

        I’m sorry that your job was eliminated. I think that is almost always a surprise.

    2. Winter is Coming*

      To offer some insight from the employer’s side, I’ve had to terminate a few people for cause — two of the most recent ones come to mind. Both were coached, counseled, warned (both verbally and a few times in writing – with their signature acknowledging receipt of the warning), following our company’s progressive discipline policy (which is outlined very clearly in the company handbook) very closely, and given every chance to improve (and told EXACTLY how to improve). Both were still shocked! So, the employer can do everything within their power to prepare someone/help them improve, and it can still go in one ear and out the other. Side note, it still doesn’t make it any easier to let them go.

      1. Not So NewReader*

        Some people think if they are not fired immediately for a transgression that means they are safe and will not be fired. In their minds it’s an all or nothing, so no immediate firing equals no firing ever.

      2. Windchime*

        This happened at my work, too. The person was counseled for over a year, and was given candid feedback that he needed to improve on X and Y, and that his job was at risk if he did not. And finally when the day came, he was shocked. As if it came out of the blue.

  3. nofelix*

    These are certainly tough conversations to have, particularly number 3. It’s so tough people can go their entire careers avoiding this conversation even when it’s due.

    I’ve not found quitting to be hard at all though, personally. I owe employer’s decent notice, not my life. So as long as I’m fulfilling my obligations I feel fine.

    1. some1*

      To your second point, I’m always surprised at people who feel like they need to offer a “good enough” reason to quit. Either you got a new job (and just say that) or you decided not to work there anymore. It’s not personal.

      1. SophiaB*

        I think it depends on the job and what they’ve done for you. I will be glad to leave my current place because it’s toxic, but I’ve learnt an awful lot here, and my co-workers are amazing people.

        It also depends how you leave things. One of my PMs went travelling and has left all the doors open to come back here if he wants. He has a similar attitude to you in that a job is a job and he wants to do something else now. That’s cool, but I’m not like that, and when I go it will likely be to work with a competitor, which more-or-less closes the door on me. I will feel sad about that, even as excited as I will be to move on.

      2. Not So NewReader*

        In toxic places it is personal. People struggle to explain why it is not personal because their survival over the next two weeks (or whatever the notice period is) depends on their boss understanding that it is not personal.

        1. nofelix*

          Eh… even that doesn’t have to be personal. Different preferred management styles is a business issue. If your boss’s style is to yell and demean people, that’s more personal but there’s no reason to go into that. Maybe it works for them. But it doesn’t work for you so you’re going elsewhere. That’s it.

      3. AnotherHRPro*

        Sometimes managers take resignations very personally. As if you are offending them. For me, that is what is so hard about resigning. But you have to do what is best for your own career and not get personal yourself.

        1. nofelix*

          Sometimes managers over-invest and over-rely on employees, forgetting that this still might not be enough to keep them.

    2. CrazyCatLady*

      I’ve never found the quitting conversation tough at all either. I mean, it’s awkward for a few minutes, but then I’m over it.

    3. NicoleK*

      For me, quitting is the easy part. I struggle more with how candid should I be during the exit interview especially if I’m leaving due to a terrible boss, coworker, or toxic workplace issue.

      1. CrazyCatLady*

        Yeah, same here. I think it’s good to be candid because maybe it will help with retention in the future, but many, many people do not want to hear the truth and I don’t want to burn bridges.

      2. Windchime*

        I left due to a horribly managed environment and I declined the exit interview. They didn’t care and weren’t concerned when I mentioned things while still employed; why would they care any more when I’m leaving?

        It’s been over 4 years and I still know a few people there. It’s worse than when I left, so I’m sure my comments would not have made a dent either way.

    4. Lily Rowan*

      I’ve hired a bunch of people into their first professional jobs, and they are so nervous to quit! And so relieved when I am fine about it. I think they really think I’m going to take it personally, but of course I’m not!

  4. Anonymous Educator*

    I’ve dreaded every time I’ve had to do the “I screwed up” with my supervisor, but every time I’ve done it, my supervisor has been really supportive and forgiving, because I owned up to it right away, and she or he has been immediately focused on working with me to fix the issue instead of punishing me. I don’t know that all managers are as reasonable as the ones I’ve had. I do think, though, that it’s always better to own up to a mistake right away than to try to cover it up and have it get discovered later.

    1. AnotherHRPro*

      We all screw up from time to time. I always think of the conversation very linearly.
      1) Here is the situation
      2) This is why it happened
      3) Here is how I’m fixing it
      4) This is what I’m going to do to make sure it doesn’t happen again

  5. Bend & Snap*

    Humane firing is a good thing…I think I’ve posted this here before, but I had to watch a firing at my last job and the person doing the firing absolutely annihilated the employee. To the point that he broke down in tears more than once. It was awful to watch and a huge lesson in how NOT to fire.

    1. Adonday Veeah*

      I do not understand this. You are ending a business relationship, and no matter how contentious it was, there is never any call to treat the person with anything less than respect. You are FIRING this person. You never have to see them again. Why make it personal?

      (That’s the impersonal “you,” B&S. Not you specifically. I know it was a good lesson for you, but I’m sorry you had to witness such assholery.)

      1. AdAgencyChick*

        I seriously don’t understand it either. I’ve fired several people with cause, and as much annoyance as it was to manage them until I could fire them, I cannot imagine taking *pleasure* in the process to the point where I would want to twist the knife.

      2. Charityb*

        In some organizations, getting fired is analogous to being punished as a political dissident. There’s the theatrical denunciations, the rumors, the maniacal ranting before you’re taken out back. I’m surprised they don’t make and distribute videos of firings to the employees who are left behind.

      3. Not So NewReader*

        In the end, I pity these ranting folks. Where would your mind have to be to think that this behavior is okay? Thinking of it this way made me realize that there was more than one problem running here.

  6. Jennifer*

    The one time I got let go (it had nothing to do with my performance) it was a restructuring of tasks that made my job redundant and I was let go in the nicest way possible. It was early in the morning before most people were there and I was asked to come into the HR manager’s office. She told me I would get a good reference and she had my paycheck right there. I was in tears with the upset but it was not public at all.

    1. Adonday Veeah*

      I got let go early from a temp job one time. It was right in the middle of the recession. The manager attempted to mitigate her discomfort by spending an HOUR with me, telling me how hard it was for her and her family since her husband lost his job (“Yep, I understand how hard this is for you.”) It was all I could do not to point out to her that at least she had some income into her family, which I no longer did. I nodded and smiled through the ordeal, then went back to my desk to finish out the day and hand off my tasks.

      Lesson: Make it short and sweet, folks, and hear this — you are taking someone’s job away. Don’t talk about your own problems.

    2. Elizabeth West*

      Same here, last time–I got called in to the office right after I returned from lunch. No notice except watching my coworker (who also got laid off that day ) packing up his things. We were all like “Did they just–” and then my phone rang. Our two positions had been eliminated.

      I had to pack up and leave right then. They weren’t mean about it, though, and even though I had previously gone through a successful PIP, my boss made a point of saying it was NOT performance-based. I got severance–a week for each year I had been there–and they did it on a Thursday, which meant I had a weekday to get stuff done. I didn’t cry or anything. But it was pretty shocking. I called my bf-at-the-time on the way home and he was gobsmacked.

      I got online and filed for UI the second I got home. Now I have a much better job. :)

    3. T3k*

      Mine was similar but they didn’t call me in until near the end of the day. I didn’t cry there, as I think my mind was in shock at suddenly realizing I didn’t have a job anymore after that day, but later I cried in private.

  7. cajun2core*

    The one time I quit a job at a hostile workplace, I didn’t have any trouble doing it. I was so glad to leave.

    1. the gold digger*

      Me too! My boss had just called me in to his office to give me my midyear evaluation – I had been there only seven months – and I was able to say, “We don’t need to go through the evaluation – Friday, July X, will be my last day. I have found a new job.”

      It. Was. Glorious.

  8. Lamington*

    For me the hardest one was dealing with harrasment. This man will spread rumours and trash talk about me in meetings when I was not on the room and always refer to me with contempt and make me feel like an idiot :( Fortunately my track record in all project (but his) was strong and the pther groups liked me and my work.

    I don’t even remember what was the straw that broke the camel’s back, but I went to my boss and HR and told them about his actions. Apparently, he had a record of mistreating women and minorities…. He was put on probation and forbidden to talk to me or about me. I never heard from him again…

    On that final meeting, his manager showed up as well and he was so embarrased for his subprdinate.

  9. AnonPi*

    ugh, while I’m hoping I’ll have to give notice soon because I’ve accepted a new position (crosses fingers), I’m expecting all kinds of drama over it which I’m not looking forward to. My supervisor at my contracting company will be happy for me, but its the place I work at that will be a mess. One of many reasons I want to leave – I am sick of drama lamas!

  10. F.*

    My manager (the General Manager) simply will not personally fire someone. We had to fire one of his direct reports, and he made me (HR Manager) do it. This employee had been given plenty of warnings and specific plans for correction, but never followed through. When I finally had to tell her that her employment with us was being terminated (I don’t like to tell employees they’re being “fired”), she was stunned. She simply sat there for about ten minutes, then when we went to her office to get her personal belongings, she v-e-r-y s-l-o-w-l-y started cleaning out her desk, one paper at a time. I finally had to tell her that we would clean out her desk and mail any personal items to her. She had many times stated that the company could not function without her, like that gave her license to behave any way she wanted and to do her job duties whenever or not at all. That was my first time delivering the termination message, and definitely my worst.

    1. TCO*

      This is so relevant to Alison’s other post today! What’s your rationale for using “terminated” instead of “fired?” I completely understand that it makes that tough conversation easier, but I wonder if it leaves people unclear about the circumstances that led to their termination. It seems like it would be a disservice to not be very clear that they have performance problems. (Though I understand that in this specific instance, the employee should have already been aware of that.)

      1. F.*

        The unfortunate popularity of a certain TV show has made the phrase “You’re fired” into a punchline. I would not have an employment termination conversation with anyone without making it clear why they were leaving. It shouldn’t be a lengthy, nasty diatribe; a one or two-sentence statement about their failure to improve their performance delivered in a calm and matter-of-fact manner should suffice.

  11. YWD*

    Planning to have conversation #1 either tomorrow or Wednesday. It’s not a straight up “I’m quitting” but close enough. I wrote a short script because I have a tendency to over explain sometimes and I really don’t want to in this case. I think I will include in my script “Stop talking!” after a specific point.

  12. Not So NewReader*

    Maybe it’s me. But growing up, being laid off meant you would be called back in a bit. Could be six months, if you were not lucky it might be a year. I am having a hard time connecting “lay off” with “permanently let go”. I never noticed this until the economic down turn.

    1. F.*

      In certain industries, construction, for example, being laid off is a normal part of the annual cycle. Some of our employees look forward to it so they can hunt, go south, work indoor side jobs, etc. We hire the good ones back in the spring and let the others fade away. They all get unemployment.

      I was laid off twice from the very large financial services company I used to work for. Both times my position was eliminated. My managers could have transferred me into open requisitions but chose not to. I received unemployment both times and severance the second time. I called it “fired with benefits”.

    2. Windchime*

      That’s what “laid off” always meant to me, too. Years ago, I worked in apple packing plants and we would get laid off several times during a season. We would all file for unemployment, collect for a few weeks, and then get called back to work again for a month or two. It was very seasonal and it was a normal part of working in that kind of industry.

  13. Sarahnova*

    I’m glad (and a little sad) that Alison included the ‘you’re being harassed’ conversation. When I started my professional life, I expected the “you’re fired” and “I quit” conversations”, but not how many of us would need to have the “my coworker is sexually harassing me” one. :(

  14. Searching*

    I had to have the harassment conversation with a coworker. Was working in an area of the country where religion plays a large role. I really don’t talk about being an atheist much (“politics & religion are best left out of workplace conversations”), but it was not a secret in my workplace either. One day I overheard coworker making a comment to my staff along the lines of “well, your manager is an atheist, so what do you expect” (and it was not meant in a positive way!). I immediately stormed over to said coworker and proclaimed that if I EVER heard something like that coming out of coworker’s mouth again, I would immediately file a complaint with HR about coworker creating a hostile work environment. Not one of my calmest moments, but it stopped that behavior in its tracks.

  15. subuhi nigar*

    Dear Alison,

    Last month i lost my job abruptly . after searching for around 1 month i got an offer from an org . since i was in need of job and could not survive without money for a long time , i accepted that on same salary structure that i was getting in previous org. Now after joining , i have a feeling that i must have asked a bit more . at least 5-6 % more . Because once i accept the offer , the next hike will occur only next year and that means this year hike is skipped .

    My hesitation is , i myself asked for current salary structure that the management readily accepted. Now , is it wise to ask for revised salary structure ?If yes, what shall i mention as reason for re-discussion of salary ?

    Please advice .


  16. ChrisH*

    I remember the first person I fired I was so upset at their lack of performance because it caused a series of significant problems for me. I was young and management immature. I got angry enough about the problems and stayed angry. Not a good approach.

    I used to struggle with quitting until I learned an easy solution from my (then) girlfriend’s grandfather, which was ‘never quit a job until you have a new one’. This has made the transition easier…sometimes.

    One time I had decided to leave my then abusive boss and go nowhere job , but in order to find time to interview I was forced to combine it with scheduled vacation, which they did not want me to take. I took it (I was entitled to it), and the first day that I came back I approached my boss and he proceeded to berate me and yell at me, and told me that I was going to go write up a plan about how I was going to repay the time I took off (all the while yelling at me). I told him no, and added that under the circumstance I was giving my notice. After he got done yelling at me some more he told me that I was going to go write up a transition plan to handoff my work, and I could quit after I repaid vacation and completed the handoff. Then he told me to get the F out of his office and not come back until I had my proposals in order. I looked at him and said no, I wasn’t going to do that. I then told him that I had originally intended to work another week but under the circumstances I was giving notice effective immediately. I left with him shouting obscenities at me as I exited the building. I was maybe 38, had a solid 10 years of industry experience and this was a professional services firm.

    One time I had a boss who invited me into work one day and smugly told me that he was firing me. I had worked for this very large company for 3 years and was a top performer. I asked whether they were offering anything? (No). He told me that as an At Will state they didn’t need to provide notice. I asked if HR was available or even aware, and he told me that they would be in touch. I called them when I got home, very upset. They told me they had no idea, that I wasn’t fired and to sit tight while they worked everything out. Due to restructuring (they were going trough a huge merger and all positions were frozen), they couldn’t find me another position. They ended up offering me a sizable severance package, but I would have preferred to have kept my employment relationship if it had been possible. I liked the company a lot.

    As a hiring manager I constantly have problems with HR in my current company because they think that they own all employee administrative and performance interactions. Megalomania term comes to mind.

    Bottom line is that you have to do what’s right for you and your family and your own situation, because it’s pretty rare these days that your employer will. Most companies in my industry act like they don’t care because they don’t. HR is generally not all that helpful.

    And above all, bad management exists everywhere. I’ve been guilty of it myself as a new manager. The scenarios I spoke of where I was in the receiving end we’re all with managers who were not good at their jobs. The irony is that their bosses continued to hire and promote them into these roles, so trust me when I say that the number of really good managers I’ve encountered is low. Most of them have workplace cultural biases and are only interested in managing up.

    When I interview now I specifically target interview the hiring manager who will be my boss. I cross-interview extensively, and I turn down jobs and stop interviews when they fail to convince me that they know what they’re doing. I’ve gotten pretty good at this, and the few times I’ve gone against my gut instinct I’ve regretted it.

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