Uncomfortable Conversations Toolkit

Why Managers Avoid Difficult Conversations

This post explores the reasons why managers avoid having difficult conversations with employees, despite the negative consequences, and instead advocates for training to help overcome those barriers.

Prep Sheet for Difficult Conversations in the Workplace

Managers must be ready to handle a variety of challenging situations, including conversations that may be uncomfortable or difficult. This job aid helps prepare for the meeting and maintain a positive, productive tone. 

Helping First-Time Managers Master Difficult Conversations

New managers often struggle with difficult employee conversations; the article promotes behavioral training as key for equipping first-time leaders to handle these challenging situations successfully.

Tips Sheets: Letting Someone Go

Letting someone go is one of the most difficult aspects of a manager’s job. Whether it’s a layoff due to organizational restructuring or termination for cause, these tips can help ensure your conversation is both legally sound and delivered with heart.

Benefits of Having Difficult Conversations

For various reasons managers shun difficult conversations with employees. But failure to carry out those responsibilities can cause big problems. This post explains the benefits of training managers to be comfortable with uncomfortable conversations.

Tips Sheet: Addressing Deeply Personal Issues

Talking with an employee about a sensitive or personal issue is uncomfortable...even awkward. But it’s also a clear indication that you care and want to help your employee be successful. Here's how to address the problem with professionalism and gentleness.

5 Difficult Conversations Managers Avoid

Because difficult conversations can involve sensitive subjects they are among the most nerve-wracking job expectations of people managers. Here are five of the most commonly encountered and potentially uncomfortable interactions.

Tips Sheet: Addressing Poor Performance

No one likes being called out for something they did wrong (or could have done better)—and this makes many managers uncomfortable with employee performance discussions. These tips will help keep conversations positive and constructive.

Are You Listening? Training Activity

Here's an activity anyone can use to become a more effective listener. By identifying behaviors seen in the best listener you know (as well as the worst listener you know), you hone in on the things you can do to build better listening habits.

Tips Sheet: Addressing Political Discussions

These days, political discussions are popping up everywhere...including the workplace. Here are tips for setting the ground rules and handling a situation where the rules aren't being followed.