Tough Conversations with Your Boss: Surviving the Uncomfortable

You agonize over it. You try to prepare for it. You put it off. And then you worry some more. Having conversations with your boss about sensitive subjects like admitting a mistake or requesting a raise is sometimes uncomfortable. And, gearing up for a difficult conversation can be a little bit like preparing for battle. It’s hard to know what you’ll face.

See Dwight Schrute’s action packed effort to get ready to ask for a raise on The Office.

But, tough conversations are an inevitable part of the workplace. At one time or another, you will probably be faced with an awkward conversation with a supervisor or co-worker. By choosing to address your concerns – instead of ignoring them – with your manager, you could open the door for big progress in your career, like improvements in your relationship with your boss, broken processes, your attitude, and even your paycheck. Plus, how you handle a difficult conversation with your boss now can be a great learning experience for future conversations you could have as a leader or supervisor in the future.

To help you effectively handle a tough conversation with your boss, Express is excited to share a free podcast training series on difficult workplace conversations. So, before your next uncomfortable conversation with your supervisor, gear up with these tips and advice to make discussions a little bit easier.

Clarifying Priorities
When your workload is overwhelming and your task list seems endless, things can quickly get out of hand. Having a clear understanding of your work priorities and deadlines is important. When you need direction on your responsibilities, have a conversation with your boss to keep things from falling through the cracks. Knowing exactly what’s expected of you will allow you to do your job as efficiently as possible. When you meet with your manager, be specific and honest about your concerns. Together, come up with a solution that works for you both. Check out this podcast for tips and advice on having a tough conversation about priorities with your boss.

Admitting a Mistake
Admitting that you’ve made a mistake can be one of the most difficult conversations to have. It’s always hard to swallow your pride and tell someone you messed up. But, instigating a conversation about a mistake you made is far better than being confronted about it later. If you’ve made an error that could affect your company or co-workers, don’t try to hide it. Be proactive and take responsibility. Be honest with your supervisor no matter how difficult it may feel and admit your mistake. The longer you put it off the bigger the issue could become. Together you can come up with a solution to help prevent a future mistake from occurring. Listen to this podcast for the right way to admit a mistake at work.

Requesting a Raise
Asking for a pay raise can be uncomfortable no matter the economic environment. But, if you feel your diligent work merits a pay raise, don’t be afraid to talk to your supervisor about it. Most employers want to retain top talent and understand that having competitive wages is necessary to keep their employees. Before you talk with your boss, be sure you’re prepared to explain the reasons why you feel you deserve a raise and be able to give evidence to support it. If you want a pay raise, listen to this podcast before you meet with your boss.

Difficult conversations don’t have to feel like a battle. You can make your tough conversations with your boss easier by following the advice of the Tough Conversations podcast series. For more information on having difficult discussions with your supervisor or leader, visit jobs.expresspros.com.

Please note, the video clips herein and their sponsors do not necessarily represent the views of Express and are used for educational purposes only.

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