Eight Tips On Having A Difficult Conversation With Your Boss

Eight Tips On Having A Difficult Conversation With Your Boss

By Joe Carbone

The past few years have taught us a lot. The pandemic forced us all to look at the way we operate in our day-to-day lives. Mental health has become a top priority, work-from-home policies are the new normal, a record number of workers quitting started the “great resignation,” “quiet quitting” is now a career strategy, and what they all have in common is that they have had a major impact on expectations of both employees and employers.

Another major change is that tough conversations that used to happen in person are now often taking place during video meetings. As an employee, confronting your supervisor about a concern or challenge you’re facing can either be character-shaping or soul-destroying. But whether you’re in a virtual or office setting, it is ultimately up to you on how you handle your career. Below are my tips on how you can prepare to have a difficult conversation with a direct supervisor so that when you are faced with confrontation, you stand firm and feel heard.

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1. Ensure the timing is appropriate. Don’t linger after a meeting and ask to have a few minutes afterward. The other person might feel like you are ambushing them and most likely will go on the defensive. Schedule something in person, if you are able, and plan it a day or two ahead of time.

2. Write down your talking points. Write down what you think their rebuttal might be as well. Become familiar with each scenario so that you are comfortable regardless of which outcome you face. This will help you with the next step.

3. Check your emotions. After 20 years of interviewing people and getting to know all sides of the emotional spectrum, it is clear that cooler heads prevail. Although you might not get what you want, remaining calm will keep your reputation intact and possibly save a relationship or job.

4. Outline your agenda upfront. Be forthcoming as to why you called the meeting. Trust in your instincts and stick to the scripts you became familiar with. Stand firm.

5. Listen. After you’ve said what was needed, listen to your supervisor’s response, and do not react emotionally. Remember, cooler heads prevail, and you want to be in a position to influence an outcome that you are satisfied with.

6. Find common ground and work toward a solution. Share that you understand their positioning and want what is best for you both, but do not wavier on what you need, especially if you’ve crossed all other bridges before having this difficult conversation.

7. Confirm the next steps and schedule a second meeting. Allow time for each of you to think about what has been said and what the potential of change might look like for you both.

8. Thank them for listening and for their time. Follow up with a thank-you email, even if the meeting didn’t go as planned; think about how you want to be perceived after these types of conversations.

Times have changed and will continue to do so. It is up to you to make things happen for yourself inside of your career and in your personal life. Confrontation does not need to be a dirty word if done properly. I have learned that growth comes at the edge of comfort.

*Joe Carbone is the Founder & CEO of Eastward Partners; an Executive Search & Human Capital Consultancy firm

*This article first appeared on the forbes.com website


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