How to have the difficult conversations

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Yesterday I had the pleasure of joining my good friend Taylor Desseyn (torc) live on LinkedIn to discuss a heavy topic: how to have the difficult conversations.

I don’t think anyone really likes conflict, but some people are better at navigating conflict than others—mostly because they’re willing to have the conversations that others don’t want to have. This is such a critical component of being a strong leader.

When I say difficult conversation, this can mean anything that makes you or makes the other individual on the receiving end uncomfortable or anxious in some way, including (but definitely not limited to):

• Dealing with a performance issue with one of your team members

• Dealing with your own performance issues

• Asking for a raise

• Asking for a promotion

• Leaving an organization

Picture yourself handling one of those conversations. Did your hands just start to sweat? You’re in good company!

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Here’s how I handle these conversations:

1. Arm yourself with data. Any time you’re about to make a request for more of something or give someone critical feedback, you need to be ready to show your work. On the raise or performance side this may be accomplishments, and on the performance side this may be proof of less-than-desired behavior or even your own growth if you’re dealing with a performance issue yourself.

2. Prepare the other individual on the receiving end for this conversation. Don’t just spring it on them during your next 1:1. “Hey, I’m going to put time on our calendar to talk about X topic” or “I’d like to use the first half of our 1:1 time to discuss Y issue”. You’ve done the prep work; giving the other individual time to prepare will make for a better dialogue.

3. Write down some talking points. If you’re nervous (and quite often we are with these types of conversations), you may forget what you intended to say. Don’t write a script—just jot down some highlights you want to make sure you hit. I do this for every important conversation I have.

4. Embrace the nerves. It’s okay to be nervous! It means you care. My hope is the individual on the receiving end also cares, and if it’s your manager, for example, they’re wanting you to succeed as well. Conversations like these are always over before you know it.

5. Take notes. On that same document you wrote down your talking points, make sure you’re taking some notes while you’re having a discussion. For heavier conversations, it’s good to get the highlights of the conversation down in the moment so you can expand on it later. You’ll forget a lot after the conversation is over.

6. Write a recap note. Make sure there are next steps to your conversation and you’ve written them down somewhere, and ideally you also shared these notes with the individual on the receiving end if applicable.

7. Follow through. The hardest part is over—you had the conversation. Don’t let it stop here. Hold yourself (or the other individual depending on the situation) accountable until you have a firm resolution.

While these conversations are rarely fun, they are inevitable in your career (and in your personal life for that matter). A good friend of mine reminded me recently: growth doesn’t happen when you stay within your comfort zone. (Thanks, Tim!) Give yourself kudos for handling this challenging conversation with grace!

Want to work with me? Here are 3 ways I can help you:

1. Upgrade to paid membership: You’ll get VIP access to Friday deep dives on newsletter topics shared on Tuesdays, as well as the archive of all free Tuesday posts. This includes scripts and templates you can put to use immediately.

2. Sign up for a future session of my course: I’ll help you learn how to identify and coach team members, manage conflict up and down the chain of command, and give and receive effective feedback.

3. Sign up for 1-on-1 coaching: If you prefer to learn alone, I offer one-on-one coaching to aspiring and new tech leaders.