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4 Ways to Have Difficult Conversations at Work

Human Resources

Difficult conversations at work are something people often strive to avoid. However, for managers, it's impossible to avoid challenging conversations. Whether you're giving critical feedback or simply having to say no to an employee request, it's important to have the confidence and strategies needed to keep hard conversations productive. Here's a closer look at four different approaches that may help new managers and veterans alike have tough conversations and keep positive relationships in place in the process.

Establish a Clear Agenda

What do you want to accomplish in the conversation? Before initiating a difficult discussion, think about your goals. Often, this can be broken down into four parts:

  • What's the big message or takeaway that your employee should get from the meeting?
  • What specific examples or data points can you use to illustrate the issue, and to illustrate how you want it solved?
  • What clear, measurable action steps should this person take after the meeting to solve the problem?
  • What questions or information gaps do you have, which can be the basis of asking questions and getting more insight from your colleague?

Ask Questions and Prioritize Listening

When preparing for difficult conversations at work, it's natural to focus on what you want to say. How can you ensure that your points are clearly made while ensuring the other person feels respected? However, in addition to getting clear about your own agenda, it's critical to prioritize listening. Actively structure conversations in a way that asks for information. If an employee is falling behind on their work, you might ask what obstacles may be causing the delays. If team members are dealing with interpersonal conflict, try to uncover what's causing it. Ask questions, give people time to consider their answers, and when in doubt, dig deeper on "why." Listening can help you gather important information, and help you empower your team with solutions that solve the problem.

In addition to getting clear about your own agenda, it's critical to prioritize listening. Actively structure conversations in a way that asks for information.

Link the Discussion to What's Important to the Employee

Each strategy should be customized with the person you're talking to in mind. Why does what you're discussing matter to the employee? For example, consider the case where an employee isn't taking advantage of training opportunities and this reflects negatively on his performance. If the employee's goal is a promotion, explore how these choices affect the worker's long-term chances for growth. Productivity improvements, for example, can lead to a better work-life balance or the chance to work on more interesting projects. Focus on how your goal aligns with your employee's objectives and you may have a much more successful conversation that generates long-term results. Another factor to consider is communication styles. Does the employee appreciate concise, direct communication or do you need to frame it differently to maximize how receptive they are? Targeting your style to what will resonate with your employee can help increase the positive impact of the conversation.

Manage the Emotions

Managing the emotions involved in tough conversations is critical. Approach conversations professionally, and leave your personal emotions at the door. Be prepared for a range of possible emotions from your employee, from sadness to anger to defensiveness, depending on the situation. Avoid reacting from a negative emotional state yourself, such as yelling, using sarcasm, or stonewalling. Instead, acknowledge the emotions but then bring the focus back to the objective at hand. For example, consider a statement such as "I know it can be frustrating to have to clarify why you missed a deadline, and it sounds like there were reasonable circumstances here. Let's work together long-term to ensure this doesn't happen again."

Managers have to be prepared to have difficult conversations in the workplace. Smart conflict resolution skills require managing your emotions, having clear objectives, committing to asking questions and listening, and tying the conversation back to the employee's priorities. Investing in your ability to manage a range of conversations will serve you as a manager throughout your career.


This website contains articles posted for informational and educational value. Paychex is not responsible for information contained within any of these materials. Any opinions expressed within materials are not necessarily the opinion of, or supported by, Paychex. The information in these materials should not be considered legal or accounting advice, and it should not substitute for legal, accounting, and other professional advice where the facts and circumstances warrant.