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Handling Difficult Workplace Conversations

Guest writer Judge Ruth Kraft, an employment law expert at Kirschenbaum & Kirschenbaum, offers five tips to help managers discuss difficult subject matters with employees.

I think that one of the most challenging elements of being a manager is how to finesse the tough conversations that inevitably occur in the workplace. My clients regularly call me to hash through how they should approach problems of poor performance, failure of workers to achieve established goals, and inability to get along with others. It’s easy for me to say, but the truth is that you are the ones in the trenches and these conversations can be painful and even go toxic. Here are some tips to prepare you for your next difficult conversation with an employee.

1. Deal With the Issue. Stay on topic. Focus on the facts, not opinions or emotions. Don’t let the employee control the interaction. Don’t personalize it. Stick to the facts—outline them as a foundation for the next step.

2. Make a Plan. The simplest way to do this is to consult your employee handbook. Read it and see if it delineates consequences applicable to the situation. This will structure your discussion with the worker. If the manual provides for progressive discipline, then assess whether you should issue a verbal warning, written warning, suspension or even discharge. Think about how you want to implement the disciplinary action and prepare for it. Write out the warning and then review. Does it go to the essence of the matter? Have you spelled out consequences for continued violation of your policy or poor performance? If you are seeking an improvement, does it articulate a performance improvement program including objectives and period for re-review?

3. Address the Issue. Plan a meeting. Make sure that you have a witness present in case the employee becomes hostile or argumentative. Know how you want the conversation to go. Practice in the mirror if necessary so that you are comfortable with your own presentation and demeanor. Set a location with which you are comfortable—and it should be private and at a time which will reduce embarrassment and avoid gossiping. Timing is also important. Delay will affect the message and any proposed constructive action. Issues should be resolved promptly.

4. Be Clear in Your Message. Keep it simple and direct. Try not to get into a debate. Appear to be listening carefully. At the close of the meeting, repeat and clarify so there is no confusion.

5. Document. Take the approach that, if it isn’t written down, then it didn’t happen! Include the date and year, time, those present, the substance of the conversation and sign the documentation. This is two-pronged: the corrective action or warning should be completed and signed but also write a memo for your own files.

And, if you aren’t sure how to navigate through these waters alone, call me to review your approach—before it happens!

Judge Ruth Kraft, an employment law expert at Kirschenbaum & Kirschenbaum. She can be reached at (516) 747-6700 ext. 326 or at

Article Topics
Blogs · Business Management · Laying Down the Law · Managing Your Business · Managing Your Employees · All Topics
Business Management, Laying Down the Law, Managing Your Business, Managing Your Employees