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How to Prepare for Difficult Conversations in the Workplace

There’s nothing comfortable about having to inform a valued employee that her project performance missed the mark. Equally as tough is telling another employee that his negative attitude is creating a culture of discontent. “Handling difficult conversations well is not just a skill, it is an act of courage,” Jean-Francois Manzoni, professor of human resources and organizational development at INSEAD, tells Harvard Business Review.

Going into difficult conversations with employees armed with a strategic plan—not to be confused with a script—can help you stay confidently calm. The more poised and prepared you are as a business leader, the better the chances are that the meeting will achieve the results you want. It also ensures your employee feels valued and therefore more willing to align with your goals for the team.

Use the following tips to help you prepare for any type of challenging workplace conversation so you can better manage emotions and orchestrate a productive talk that lets everyone win.

Reframe your perspective

One of the most important things you can do to empower yourself is to modulate your self-talk. Shift your mental label for the meeting from “difficult conversations” to “helpful feedback session” or “coming into agreement talk.” This helps tamp down your own anxiety and discomfort and reframes the conversation in a more positive, proactive way.

Professor Manzoni suggests you choose a less binary way to view the encounter. “For instance, you’re not giving negative performance feedback; you’re having a constructive conversation about development. You’re not telling your boss: “no”; you’re offering up an alternate solution.”

Choose the appropriate setting

Obviously, you don’t want to hold the difficult discussion in an open-office setting, but a conference room with a lot of glass is an equally bad choice if you suspect the talk may get emotional. Choose a private room with soundproofing if possible, and consider having an H.R. representative or another manager present as a neutral witness.

Inform the employee of the meeting

Let the other party know you need to speak with them, and provide the day, time, and location. Tell them the reason for the meeting, such as “discussing your attendance record,” “improving office morale,” or “reviewing the work you did on XYZ project.”

You want to give them enough notice to prepare for the conversation so they don’t feel ambushed, but you don’t want days to pass between the notification and the meeting in which their anxiety and stress levels build.

Draft an outline of the facts with key talking points

Make a bulleted list that concisely states the problem behavior or the issue under discussion. You want to be direct, specific, and get to the point quickly. For example:

  • Late more than 30 minutes three times in the past 30 days.
  • No phone call to direct manager advising of the tardiness.
  • Resulted in another employee having to cover and perform two roles, which was stressful.
  • Customers were frustrated due to the unusually long wait times.

The Balance Careers suggests you write an opening sentence that “identifies the behavior, links it to the business’ impact, and indicates the need for change.” While you don’t want to waste time with chitchat or false flattery upfront, it’s OK to preface your opening sentence with something like: “What I’m about to say is difficult for me, but I feel it’s important for your growth and development and the team’s ability to function efficiently.”

You also want to be clear about your objectives for the meeting by defining what a successful outcome would look like. This might involve asking the employee to commit to consistent punctuality with an agreement to notify a manager in case of an emergency.

Acknowledge your part

Few workplace glitches are totally one-sided, so it’s helpful to spend some time in self-reflection using radical honesty. When thinking about the current situation that’s up for discussion, ask yourself:

  • How could you have been a more effective leader?
  • Were your instructions/expectations unclear?
  • Did you provide all the necessary training to help your employee succeed?

This practice can help you go into the meeting in a much more balanced, solution-seeking frame of mind. Offering your insights about your contribution to the problem helps your employee feel less blamed and more eager to share the responsibility for finding a resolution with you.

Anticipate the emotional fallout

Becoming familiar with your own emotional triggers is a key component of the emotional intelligence you need to be a strong business leader. Do you prefer to avoid conflict? Do you get uncomfortable and impatient when others express emotions like sadness? Knowing your emotional weak spots and anticipating which of your buttons might get pushed during the meeting can help you preempt any knee-jerk reactions that might surface.

Prepare yourself to offer empathy in the face of an emotional reaction from your employee. You might need to pause the conversation if heightened emotions are preventing him from processing the information you’re discussing. Pay attention to body language too. Folded arms and an unwillingness to look into your eyes can signal an employee’s anger and resistance.

Being an effective planner is one of the most important qualities great leaders possess. For those who aren’t quite sure how to have difficult conversations in the workplace, creating a plan in advance that covers key contingencies can smooth the way. But remember to keep your strategy flexible so you can respond appropriately to whatever comes your way.

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