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5 Strategies for Navigating Tough Workplace Conversations

Difficult Work Conversations | Human Capital | Fahrenheit Advisors

You know that feeling.  The one in the pit of your stomach. The one that keeps you up at night.  The one you’re afraid to discuss with anyone.

It’s the “I don’t want to have this tough conversation at work” feeling.

In the season of performance management, this feeling is present for many managers and employees alike. Let’s face it – no one is really excited about hard conversations, but there is a way to make those conversations less about the pit in your stomach and more about feeling prepared. The goal of any workplace conversation should be to convey an accurate message with clarity and empathy. Particularly in the context of a difficult conversation, here are a few key practices you can employ to ensure your message is delivered appropriately, whatever the context.


5 Key Practices to Prepare for Tough Workplace Conversations

1) Research

Research is not an optional step. In the context of a difficult workplace discussion, whether you are the manager or the employee, you must do your homework.

If you are discussing deficient performance with one your direct reports, you need to have the full history of the performance issues, recall the details of past discussions about those issues, and be aware of prior performance issues for that same individual, perhaps under a different manager.

If you are an employee preparing for a difficult conversation with your supervisor, think through prior conversations you’ve had and dissect those that went well and those that went not so well. What made the difference? The best communication strategy when you are managing up is to understand the goals of the manager and ensure that your message either aligns to those goals or at least considers them. You have a better chance of securing buy-in, even with a tough message, if you consider the long-term vision and strategy of your manager as well as the overall organization.

2) No Surprises

Scenario 1: you know you missed a big deadline weeks ago. You were up front about it, but when you tried to discuss the impacts with your manager, she sheepishly said, “Oh, it’s fine.” Since then, she’s cancelled a few of your one-on-one meetings. Your end of year performance review is tomorrow, but you haven’t received a copy of your review from your manager. She also shifts the time 30 minutes back at the last minute. When you join the meeting, your skip-level manager walks in with your manager. <Gulp>

Scenario 2: you know you missed a big deadline weeks ago. You were up front about it, and, when you discussed with your manager, she was up front with you that there would likely be some downstream performance impacts for you. She committed to follow-up with you in your next one-on-one meeting. During that meeting, you came prepared with a solution to ensure that no future deadlines would be missed on the project. You and your manager discussed a higher touch communication strategy for the next several weeks to ensure she is up to date on your deliverables. She encouraged you to address the missed deadline head-on in your self-review. She informed you that she had discussed with her manager, as well, who wanted to participate in your year-end performance review meeting. With a copy of your performance appraisal in hand, you went into your year-end review meeting confident that you had a plan of action. You were a bit disappointed about your year-end rating, but you understood the reasoning behind it.

Dare I ask…which scenario would you prefer? The “surprise meeting” or “surprise news” should be the rarest of rare exceptions for workplace conversations, particularly performance management conversations. Set the stage for the ultimate conversation, and you’ll have a better outcome. Guaranteed.

3) Practice

The make-or-break factor to a bad versus good versus great conversation is practice. You can agonize over the notes and hone your written message until it’s absolutely perfect, but if you haven’t practiced the delivery, your conversation could fall flat. As with most things, you should find the presentation strategy that suits your style, but here are some options to consider.

Write the Script(s): While not much could be worse than reading from a script in a performance discussion, the physical act of scripting out the conversation can be immensely helpful. Write down what you’ll say, how the other person will respond, and then what you’ll say in return. Seeing the words on the page – whether electronically or handwritten – forces you to iterate on word choice and sentence structure. A simpler message is a clearer message. Tip – don’t memorize what you’ve scripted, or your conversation will feel stilted and fake to the other person.

Mirror, Mirror: How you say something can be just as important as what you say.  Maya Angelou famously wrote, “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” A tough performance message delivered with a smile is upsetting and condescending. A tough performance message delivered with a scowl is frightening. Role play in the mirror how you’ll react to tears, or anger, or silence. Practicing your facial expressions and your body language ensures that your physical presence is conveying the same empathy that you worked so hard to plan out with your language.

4) Time it Right

If you can avoid it, do not deliver a difficult message on a Friday afternoon. In most workplaces, this strategy leaves your employee with the weekend to *potentially* stew over the tough talk and, if questions arise, they have two days before they can ask those questions. Time the difficult conversation to occur mid-day, in the middle of the week.  If you are the manager, and your employee becomes overly upset during the conversation, consider allowing them to go home for the day with pay after you’ve finished the conversation. Similarly, give yourself time to get ready for and wind down after a difficult meeting. Block 30 minutes on your calendar before a tough conversation with your employee. Take a walk, close your eyes and breathe, review your notes, and please do not rush from a routine call to this meeting. The person to whom you are delivering the tough news deserves you un-flustered and ready for a calm and collected conversation. After the meeting, block time on your calendar to reflect on the conversation, make any necessary documentation notes, and calendar your next steps.

5) Follow-Up

The follow-up meeting – a simple, yet often overlooked component of the difficult discussion. A prompt follow-up demonstrates both empathy and seriousness. Failure to follow-up the day after the tough conversation could set the stage for the issue being relegated to the back-burner, so don’t let that happen! Tell your manager, or your employee, in the meeting that you will follow-up with them tomorrow and supply specific expectations for that follow-up meeting. Determine if it will be phone or in-person, and explain what you’ll be discussing or if it’s simply a “how are you” check-in. Whatever the method, do not neglect this critical step.

Do you need help preparing for a difficult conversation at work? To help you deliver a clear, empathetic, and accurate message. Fahrenheit Advisor’s Human Capital Consulting Practice offers training and coaching services for both individuals and teams. Contact us at

About the Author

Dana Dews Gates is a strategic human resource professional focused on connecting culture and employee engagement with practical policies and procedures. Dana has worked both externally as an attorney and internally in legal and HR for several companies providing advice and counsel on various human resources matters.