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young brunette woman at desk contemplating difficult conversation with boss about quitting

How to Have a Difficult Conversation with Your Boss About Leaving

Deciding to leave your job can be a tough decision. It can be even more challenging to have a difficult conversation with your boss about your departure. According to a 2019 survey by Randstad US, 60% of workers have left or considered leaving a job due to a difficult boss. Whether it’s due to a new opportunity, personal reasons, or a bad boss, it’s important to approach the conversation professionally and respectfully.

Here’s how to navigate the awkward and sometimes difficult conversation of letting your boss know you’re moving on.

Choose the right time and place

Timing is essential when initiating a difficult conversation with your boss. Try to find a private and quiet setting where you can discuss your decision without interruption. Avoid choosing a time when your boss is pressed for time. This will only make the conversation more challenging for both of you.

Be prepared

Before meeting with your boss, it’s essential to prepare yourself for the conversation. Reflect on your reasons for leaving. If it’s because you’re dissatisfied, reflect on any possible solutions before making your decision. Being well-prepared can help you articulate your thoughts clearly and respond to any questions or concerns your boss may have.

Be honest, yet professional

It’s important to be honest about your reasons for leaving while still maintaining a professional tone. Avoid blaming or criticizing your boss or the company, and instead, focus on the factors that led you to this decision. Keep the conversation respectful and constructive. Emphasize the positive aspects of your experience with the company.

Show appreciation

Express gratitude for the opportunities you’ve been given and the experiences you’ve had during your time at the company. Thank your boss for their support and guidance, and acknowledge the contributions of your colleagues. It may not have all been sunshine and roses, but showing appreciation can help leave a positive impression.

Provide adequate notice

In most cases, it’s standard practice to give at least two weeks’ notice when resigning from a job. However, this time frame can vary depending on your employment contract or company policy. Check your specific situation and provide an appropriate amount of notice to your boss. This allows them enough time to plan for your departure and find a suitable replacement.

Offer to help with the transition

To make the transition as smooth as possible, offer to help train your replacement, complete any unfinished tasks, or share important information with your team. You’ll likely have some requests for transferring work only you have access to or to train your teammates.

Follow up with a resignation letter

After discussing your decision to leave with your boss, it’s important to provide a formal resignation letter. This document should include the date, your intention to resign, and the last day of your employment. Providing a resignation letter helps to create a written record of your departure and ensures that all relevant parties are informed.

Remain professional and engaged

After announcing your resignation, continue to perform your job and maintain a professional demeanor until your last day. This helps you leave a positive lasting impression and maintain your reputation in the industry. According to a 2018 study by Accountemps, 83% of HR managers said the way employees quit a job affects their future career opportunities.

What to expect during the conversation

It’s important to be prepared for various reactions from your boss when discussing your resignation. They may be surprised, disappointed, or even frustrated by the news. Keep in mind that their reaction is likely a reflection of their concern for the team and the company, rather than a personal reflection on you.

Be prepared to answer questions about your decision to leave. They may ask about your plans for the future, and any potential concerns about the impact of your departure on the team. Remember to stay calm and composed, even if the conversation becomes emotional or tense.

Having a difficult conversation with your boss about leaving can be challenging. By following these tips and approaching the discussion with professionalism and respect, you can ensure a smooth and positive transition. Remember, it’s important to leave on good terms. You want to maintain your professional relationships and secure positive references for future opportunities.

Need help with your resignation letter? Check out our guide on how to write a resignation letter, or grab some of our free resignation letter templates.


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