Get Great at Hard Conversations

People tell me that one of my superpowers is my ability to productively have hard conversations. In other words I can get and keep people engaged in a conversation about a difficult topic, navigate the conversation to satisfactory (or at least clear) outcomes, and keep or improve relationships in the process. When I say it like it, maybe it does sound like a magical power, but, trust me, it isn’t. I didn’t start my life or my career with all of the skills I use to do this. I learned most of them along the way. And now I’m going to teach you how to do it, too. 

Today I’m kicking off a series of articles on how to have hard conversations. Each one will cover one topic that you can learn and apply. In some cases, you’re going to say “hey, I already knew that!” As we go along, you’ll discover skills you already have and add a few to help you become great at starting, driving, and finishing hard conversations. If this opinionated engineer could learn to do this, so can you!

The first step, as it is so often, is acknowledging the problem. Sometimes we aren’t consciously aware that we are facing a hard conversation because our brains are hiding that uncomfortable fact from us. Some clues that you might need to have a hard conversation are: you’re avoiding someone (or a group of someones), you’re avoiding a particular topic, or you’re hoping something you need will just happen, instead of having a definite plan. Or you know, just some sudden-onset free floating anxiety. 

To get you started being real about hard conversations you might be facing, or avoiding, here are some examples:

• You want to talk to your boss about a promotion or raise
• You want to talk to your boss about a difficult coworker
• You disagree with someone in power
• You need to talk to a poorly performing employee 
• You need someone to do something and what you’ve tried so far hasn’t worked 
• You have to deliver bad news about a project
• You have to tell someone that they can’t have something they want
• You need to facilitate an agreement between two or more people who are at odds

Probably a good heuristic is, if it’s a conversation you wish you could avoid it’s hard conversation ;). But conversations are just like any other problem-they can usually be solved. So, the good news is that once you’ve recognized it, you can start to plan an approach. Over the next several weeks I’ll be providing a lot of tools to help make it easier and increase your odds of success. Let’s go!

Your Dot Release: Identify hard conversations you’re facing. Or if you’re in a blessedly calm spot right now, listen for hard conversations happening around you. You don’t need to know why they’re hard, just trust your gut if it’s telling you it’s not happy. If you do know why they’re hard, drop me a note and let me know why. I’ve got a lot of ground to cover, so if there’s a burning topic I’ll see if I can start with what’s most immediately useful. As always you can hit reply to this newsletter to email me, or you can drop a comment on the article. 

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