Stop Avoiding Hard Conversations

Are you avoiding a difficult conversation with someone right now?

If your skin crawls and your stomach does summersaults when you think about talking to that one person on your staff or leadership team because you dread having that tough conversation, you’re not alone. This is normal.

One of the hallmarks of a great leader is the ability to have the hardest of conversations with grace, candor, and conviction. It’s not natural for most of us. But the good news is that it’s a skill you can learn and develop. You can get better at it every day. If you embrace it and practice having hard conversations regularly, you can master the skills of stepping into discomfort and working through it to achieve positive outcomes. Continual practice can help you build the skills necessary to have hard conversations while also developing the courage to rise to the challenge when necessary.

When you need to have a hard conversation with someone, here’s the framework I recommend for success:

1. Schedule the time – Don’t just “drop in” and surprise the other person. Set a meeting and be clear that you want to talk about something important.
2. Don’t meander – You’ll be tempted to skirt around the issue, make small talk, and do just about anything possible to remove the discomfort. This is a mistake. Instead of doing this, be direct.
3. Be specific – Don’t speak in generalities. Be direct and specific. Tell the other person what your perspective and position are on the issue and why.
4. Illustrate with examples – In addition to being specific, it’s important to highlight examples that reinforce your point. This provides context for the conversation.
5. Clarify the problem – As you make your point, be clear not just about what the issue is, but why it’s a problem. Explain how the situation impacts your business, customers, staff, and yourself.
6. Personalize the message – Frame the conversation in how the situation impacts you and makes you feel. You can use statements like, When you did X, here’s how it impacted me, and here’s how that made me feel. 
7. Avoid exaggerations – Shy away from words like all, none, always, never, etc., because it’s highly unlikely that someone is always one way or another or that they never do things correctly, etc. By avoiding these exaggerations, you help to focus the conversation on the specific situation at hand.
8. Don’t hold back – Once you start this conversation, you need to finish it. You might be tempted to hold something back, to avoid saying something that you feel is important. Don’t. Get everything out on the table so that you and the other party can deal directly with everything. Holding back keeps you from fully repairing the relationship and moving forward effectively together.
9. Focus on solutions – The purpose of a direct, difficult conversation like this isn’t just to complain and beat the other person up. If that’s how you’re approaching it, you are in the wrong. The purpose of having difficult conversations is to clear the air, to rebuild broken trust, and to figure out how the two parties can move forward effectively. Focus on resolutions and the future, and what that should look like for your partnership.
10. Say your piece then open the door for discussion – You shouldn’t do all the talking in a conversation like this. You should say your piece, make your point, and then invite the other party to share their perspective on the situation as well. In most cases the two parties will go back and forth, hashing out the situation, sharing perspectives, and (ideally) coming to a positive resolution. Once you open the door for feedback, you also need to welcome it. Don’t be defensive. Open the door and then shut up. Let your silence create space for dialogue.
11. Be curious – Once you’ve made your points and opened the door for dialogue, be open and inquisitive. Ask clarifying questions to help you understand the other person’s perspective and to build consensus towards a resolution for the issue at hand. Being curious also means you need to be open to hearing, understanding, and to some degree, accepting the other person’s perspective.
12. Set ground rules for the future – As you work through these difficult conversations, be intentional about setting relational ground rules for future discussions and challenges. Talk openly about what you feel a successful, healthy engagement looks like and ask the other party to share their perspective on this as well. Then work together to gain agreement about how you’ll partner together in the future to maintain a healthy partnership.
13. Say “thank you” – These conversations are always tense. Emotions run hot. People are afraid of confrontation. There’s a lot of emotional, positional, relational and career risks in having difficult conversations. Remember to be kind. Whether you get everything you want or not in a conversation like this, remember that the relationship is essential for success. It’s not a zero-sum game. Be grateful and thank the other person for engaging with you in the discussion.