6 Tips for Having Difficult Conversations

“I’d rather have dental work done,” thought Arthur, as he prepared for a meeting with an employee who seemed increasingly disengaged and had recently missed two important project deadlines.

Having difficult conversations with others about job performance, work quality, and workplace behavior is perhaps the least-liked aspect of management and leadership. Our aversion and dread of the potential for confrontation, conflict, and raw emotion often cause us to make a tough situation even worse.

Here are six ways to have that much needed, but difficult, conversation:

1. Sit down with yourself and make sure you can articulate clearly the core “why” of your concern or frustration. Can you objectively and specifically identify the reason, or reasons, you need to have this conversation? “We need to talk about how terrible your work with the team has been lately” is not helpful — for either of you. “I’d like to discuss the fact that you have missed two recent project deadlines” is straightforward and understandable. There’s a basis for the beginning of a productive conversation. For more, read Arden Coaching’s “How to Prepare for a Difficult Conversation.”

2. Make it a separate meeting. “Don’t take a regular meeting or chance encounter and append the issue you need to discuss at the end,” said Maren Perry, president of Arden Coaching. “You haven’t prepared, and the other person will be caught completely off guard, feeling angry, defensive, and set-up.”

3. Schedule the conversation now. What’s worse than having a difficult conversation? Not having it! Procrastination makes mountains out of mole hills, creating exaggerated visions of disaster and conflict. Procrastinating also ramps up unhelpful emotion — waiting until something gets so bad (real or perceived) — that the pressure erupts into a frustrated tirade. And, there are some surprising benefits when you deal with difficult situations promptly. Read Arden Coaching’s article, “The Upside of Having Difficult Conversations.”

4. Prepare for your difficult conversation. Bullet point your thoughts and main points. Filter out the emotion and focus on the essence of the issue. What are the core, essential elements that need to be discussed, understood, and addressed?

5. Talk about what’s on your mind — then listen. It’s important for the person you are meeting with to hear and understand your specific concerns. However, if you really want to engage in a conversation to improve a situation and move forward, you need to listen to understand. We often enter these conversations armed with assumptions about the other’s motivation, attitude, and capabilities. Deeper listening is required to understand the true root causes of a problem. Check out. “Beyond Active Listening: The Power of Level Three Listening” and “Help for Those Difficult Conversations.” 

6. Be thinking about next steps. “You’re doing this to make things better, right? A tough conversation should not be an opportunity to blow the other person up,” notes Perry. “You want to improve the situation and help the other person be more productive and successful. So be thinking in advance, after you talk this through, what might be the things you can do together to make things work?” 

To learn more about having difficult conversations, leadership skills, and executive coaching, contact Arden Coaching at [email protected] or 646.684.3777.