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The Truth About Difficult Conversations

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Most of us avoid difficult conversations the way we avoid unpleasant situations and difficult people. Yet often the three are connected: the conversation is difficult because the situation or the person involved is difficult. Handling a difficult conversation begins with preparation and knowing exactly what you are dealing with, then moves on to finding a resolution. Part of that resolution should be a commitment to prevention: strategies that reduce the need for difficult conversations in the future.

Visualize the Best

We all have situations where we refuse to consider change; are absolutely sure we are right; prioritize blaming over the search for solutions; or agree for the sake of agreeing and then do what we want anyway. At those moments, we ourselves fall into the category of difficult people. It helps to remember those times before starting a conversation with a “difficult person”—it helps to visualize the other person as someone with humanness.

Three types of visualization help ease a difficult conversation: visualizing the strengths of the other person, the attitude you want to project, and the resolution.

By visualizing the strengths of the other person, you may realize that the traits you consider difficult or extreme—assertiveness, optimism, self-esteem—are actually strengths in that individual. For example, people from different cultures have ideas about personal space that don’t align. You may feel that an individual is encroaching on your space or acting distant when they are merely conforming to the highest standards of their culture. Similarly, introverts and extroverts tolerate different levels of noise and personal interaction; even though they may annoy each other, a well-functioning team needs both. Consider what drives you crazy about the other person to be a compliment strength to yours.

Your attitude towards a difficult conversation will set many, different tones. If you start with the assumption that both parties are invested in the difficult conversation, have a willingness to listen, and are eager for a solution, you are more likely to turn a difficult conversation into a potential win-win situation. Your visualization should concentrate on your own words and gestures and the steps you can take ahead of time to prepare.

To visualize the best possible resolutions, you want to know your own goals for the conversation. Do you want a change in behavior? An apology? An action plan to prevent future conflicts? You may not get exactly what you want, so visualize what the second and third wins would look like.

If you are still hesitant to undertake the conversation, a neutral third-party may be valuable as a facilitator.

TIP: Rehearsing a difficult conversation with another person may help you frame your language, gestures and expressions to avoid further confrontation and enable a true conversation.

Ask Questions and Listen to the Answers

By going into a difficult conversation with the assumption that you do not know everything, you give the other party a chance to provide new information or explanations and increasing your curiousity. Perhaps they are going through a rough time personally; perhaps they are working with an injury or illness that affects their mood; perhaps they would appreciate some time off or referral to professional help; or perhaps others have been less supportive than you supposed.

Listening is a major factor in turning around both difficult people and difficult conversations. For example, in an engineering office, many people complained about a team member’s assumption that her work was more important. She bullied her way to more resources, refused to offer help but often requested it, and constantly complained of overwork. When talking over the situation, her team leader realized that the majority of complaints occurred at the same time each month, when a specific project report was due. The team leader and the team member consulted together to set priorities and improve time management for that particular time. With the new priorities in place, the complaints stopped, and the team member regained the trust of the team.

Aim for Resolution, With Expectations

Resolution for a difficult conversation has a different focus than winning. It includes talking face-to-face and in private, rather than gossiping about the problem or involving witnesses; recognizing that your own or a third party’s actions may have contributed to the issue; and finding common ground.

In a difficult conversation with someone you manage, you may aim for agreement on specific next steps—and those steps should be specific, including a time frame for completion and re-evaluation. In a difficult conversation with a peer, resolution may consist of acknowledging your mutual goals and agreeing to a détente. In a conversation with a superior, resolution might include your own request for specific next steps and an action plan, perhaps including training in leadership, crisis management, delegation, or team building.

Most difficult conversations reach a resolution. Yet, sometimes that resolution fails to reach the level of mutual benefit, of win-win. Some conflicts are too deeply rooted in personality or in the organization’s culture. For issues that involve harassment, discrimination, or other violations of company rules and ethics, you may need to call in Human Resources, which is better equipped to deal with legal problems or major team dysfunctions.

TIP: You may not be able to make everyone happy; but allow yourself to be satisfied with resolving the conflict.

Preventing Difficult Conversations

One of the best ways to handle difficult conversations is prevention. If you find yourself having difficult conversations over and over with the same person or team, you may want to call in outside help. These strategies will also help to prevent the need for difficult conversations:

  • Encourage regular feedback to and from your team. You will then know about issues right away. Even more important, you will be able to take every opportunity to give positive feedback to keep the team motivated and show them what positive interactions look like.
  • Be sure you have correctly identified the cause of conflict, as the cause is key to resolution. Conflicts that may appear personal may instead reflect limited resources, unrealistic timelines, or other issues related to processes and goals.
  • Mentor your team in resolving their conflicts themselves, without your interference. Make sure the team has agreed on standards of respectful language and behavior so that the rules are clear to everyone. Create a formal complaint process if none exists.
  • Treat everyone fairly and be clear on roles and goals. During one 18-month research project, researchers found that in most instances team conflict seemed to begin with personalities, but actually began with confusion over expectations, goals, roles, and procedures.
  • Hire people who understand how to work in a team and how to resolve conflicts respectfully. Having the right people on the team in the first place is a key step to avoiding difficulties.

As you institute these strategies, realize that you are also likely to become better at handling difficult conversations over time, leading to more win-win resolutions when a difficult conversation becomes necessary.

Key Takeaways

Difficult conversations are easier to handle if you visualize the conversation beforehand, have a specific goal in mind, listen carefully, strive for a resolution, and—most important—work to prevent the need for difficult conversations in the future.

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