How to Tell a Boss that You’re Quitting
Updated: Feb 16, 2022
While most of us have fantasized at some point in our life about quitting after telling our boss that he can stick his TPS Report where the sun doesn’t shine, the reality is that for most people quitting is really hard. It isn’t so much that we fear leaving a job in which we feel stagnant or uninspired – it’s that we dread telling our bosses that we’ve decided to resign. It’s akin to breaking up with someone, filling us with guilt that we’re leaving someone in the lurch or that our boss will feel that we haven’t appreciate their mentorship and investment in our professional development.
Even if you haven’t enjoyed a healthy relationship with a manager, the act of telling them that you have decided to move on requires preparation and consideration. Just as getting off to the right start in a new job is critical, ending your relationship with your current boss in a professional manner will give you the peace of mind and clarity you need to move forward in your career with intention, grace and self-respect.
1. Be clear about your decision and how you articulate your decision to resign.
If you are having second thoughts about leaving your job, telling your boss will be more difficult because it will hard for you to articulate your reasons. Gain the clarity you need about your decision so you can speak with confidence and conviction. In the book Burnout: The Secret to Unlocking the Stress Cycle, Emily Nagoski and Amelia Nagoski recommend that people contemplating quitting their job create a matrix with two columns with the headings Staying the Same and Quitting. Under each heading they recommend listing the immediate benefits, the longer-term benefits, the immediate costs and the longer-term costs for each choice. (See the Decision Grid below.) If you’re feeling squeamish about your decision, I recommend filling out this grid. It’s a variation of a PROs and CONs list but takes the process a bit deeper since our reasons for leaving are not necessarily equally weighted. When you have a chance to pull back and think about the long-term outcomes of your choices, hopefully it will clear up any doubt and make the best decision.
Decision Grid (Source: Burnout: The Secret to Unlocking the Stress Cycle, ©2019)
STAYING THE SAME QUITTING
Benefits – Immediate Benefits – Immediate
Benefits – Longer-Term Benefits – Longer-Term
Costs – Immediate Costs – Immediate
Costs – Longer-Term Costs – Longer-Term
2. Write down all the reasons that you are quitting.
This will help you do a bit of a brain dump about the logic behind your decision and make it easier to have a constructive conversation with your boss. If you have more than three reasons for quitting, narrow your list down to the top three reasons. For each of these three, write out a counter point that your boss might make to this reason. For instance, if you crave more autonomy in your work and have been vocal about this, your boss might respond to the news that you’re quitting by saying, “Well, I know you’ve wanted more autonomy in your work, and I have some ideas for how we can make that happen.” You might want to write out a counterpoint like, “By now I was really hoping to hear specifics about my desire to work more independently, and I have been waiting patiently, but I think it’s clear to me now that that I need to move on to a position that is more fully autonomous.” Even if you don’t imagine yourself speaking this directly on a given point, writing it down will help you clear your mind and help you find your words at the moment you need them.
3. Stay positive and constructive in your communication style.
Remember when your parents told you to avoid burning bridges with any authority figures in your life? Your ability to stay optimistic and forward thinking will make or break your ability to achieve that goal here. The last thing you want to do is get into a negative back-and-forth discussion about any resentments, broken promises or dashed expectations. Use your energy and deeper thinking on these points to focus on how to cultivate what you want in your next position. With this resignation conversation, you will gain more by staying focused on insights and knowledge you did gain from your boss and freeing yourself of any long-term grudges. Even if you do have bitter feelings towards your employer, this is the better long-term approach. If you believe you would benefit from the emotional outlet of giving your boss a good telling off, write it out in a letter by hand that you never send and watch a movie with a great quitting or telling-off-the-boss scene (i.e., Jerry Maguire, Working Girl, Office Space, Fight Club, etc.). Take it a step further by creating a quitting-themed music compilation with songs like Johnny Paycheck’s Take This Job and Shove Itand Kanye West’s Gone. (Speaking of Gone, check out this video a woman made when she quit her job as a video producer.)
4. When speaking with your boss, remember to use a downward inflection in your voice.
You don’t leave any reason for doubt about your meaning, and when we use an upward inflection in our voice, we run the risk of making our words sound like a question rather than a statement. (There are times the upward inflection is more helpful, like when you’re making a sales pitch or encouraging others to brainstorm ideas in a meeting, but in a conversation in which you’re offering your resignation or negotiating a salary or other terms, a downward inflection is more effective.) Practice this technique out loud if it doesn’t come naturally to you and pay attention to how it makes you sound more definitive in your statements.
5. Show and express appreciation for everything you’ve learned.
This can feel unnatural if you are boiling with animosity towards your boss, but I know from firsthand experience that it will leave you with a better perspective and greater confidence. I once had to toast a boss who had been verbally and emotionally abusive towards me for several months before he moved to New York for a promotion. The office threw him a going-away party, and we were all directed to toast him with champagne. (Believe me, it was every bit as cringe-worthy as it sounds, but I wasn’t really able to get out of it without making a scene.) Truthfully, I had learned a lot from him, and I spoke about that without addressing his questionable management style. While it felt awkward, I was left with the feeling that I had taken the high road and was able to savor the accomplishments I had logged under his leadership. If your mind is scrambling for positive things to say, write out some ideas first. Focus on your personal growth even if your boss cannot rightly take credit for it. You will learn something in the process and leave with a more positive, mindful outlook overall.
6. Think about what you would like your boss’ response to be.
Be honest with yourself about whether to anticipate this ideal response, but understanding what you hope your boss will say elucidates your own expectations of future managers. For instance, if you would like your boss to say something like, “I have enjoyed seeing you emerge as an expert in digital marketing, far surpassing my expectations for your achievements in this role,” the acknowledgement of this desired response will help build skills in articulating your specific needs for professional development support. If you have leadership ambitions, these deeper considerations will also enable you to reflect on how your future self can cultivate and motivate employees who report to you, helping you to refine your managerial communication style.
7. Ask for a reference and a LinkedIn recommendation.
Save this request for the end of your conversation, and be sure to follow up on it. This will allow you to gracefully end your working relationship with your boss and make it clear that you intend to stay in touch and value their professional reputation. It will also enhance your LinkedIn profile, and give you an entrée to ask for references when you apply for future job openings.
Kristin Schuchman, MSW is a career counselor and author based in Portland, Oregon who works with creative and mission-driven professionals. She writes resumes and coaches individuals seeking support for career indecision, next steps, work re-entry, advancement, and work-life-balance. She offers a free 30-minute Zoom or phone session and presently works with clients remotely. You can find her books The DIY Website Workbook and Jump Start: How to redirect a career that has stalled, lost direction or reached a crossroads on Amazon.