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How Smart Leaders Start Difficult Conversations

How Smart Leaders Start Difficult Conversations

By Dr. Chris White

2 years ago

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Education, Business 

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If you would prefer to read this content instead of watching the video, the transcript is available below.

We’re launching this blog in April, so in honor of April Fools’ Day, let’s talk about some “Fool-ish” ways to start a tough conversation.

All fooling aside. If you’ve been a leader for at least 10 minutes, there is a good chance you have had at least one tough conversation with a coworker. I’ve been there myself. And there’s also an equally good chance that the conversation didn’t go very well. I want you to learn from some common mistakes. So, in the spirit of the season, here are two foolish ways to start a tough conversation.

This first foolish way is so bad, but I hear people not only say it but even teach and recommend it. Here it is: “Are you open to some feedback?” Wow, really? That’s supposed to disarm me? In fact, let’s see what Siri does when you ask that question. Are you open to some feedback? Siri: “We were talking about you not me.” Okay…what is that? We were talking about you, not me! Even a smartphone doesn’t want anything to do with that question. How about number two: “I need to talk to you about something serious.” Wow! Thank you for the powerful introduction. Why don’t you take this over the top and even add some creepy music to really set the stage? I’ll say it again with the music: “I need to talk to you about something serious.” What, did you just get a bad health diagnosis? Did my favorite restaurant close down? Or do you have an algebra question? That’s a serious subject – no laughing matter for most of us!

Now those two tips may keep you from looking foolish, but let’s take it one step further. Here are the five smart ways to start that difficult conversation. Number 1: “What are your thoughts on the meeting/conversation/project/ hiccup?” Maybe they self-identify some of the things you were about to say. If so, even better. Save your unsolicited feedback for when it’s really needed. Number two can be used if they don’t bite on the first intro: “I had a couple of simple thoughts about the conversation/meeting/project/hiccup.” Notice how this one doesn’t even use the word ‘feedback’! Feedback sounds so heavy and corrective and one-sided. Number three is: “How would you want me to handle it if you were to…” I could ask a colleague who interrupted a few times in a meeting, “How would you want me to handle it if I noticed you interrupting someone in a meeting?” WARNING: This option could feel like a setup, so be careful. You’re trying to let them know they did something or could do something in the future, but you’re giving them the chance to let you know what approach would work best. Number four is an easier one: “One thing that would help me is…” Maybe you have a person at work who doesn’t say positive things. Instead of telling them, “You are so negative,” or “You need to say more positives,” you could say, “One thing that would help me is when I’m brainstorming, I’d love to hear more about how something could work instead of starting with why it won’t work.” With this option, you are saying it in a way that makes it less about a flaw of theirs and more about how they can help you in terms of communication preference. Number five is this: “In our recent meeting/discussion, what could I have done better?” Wait…aren’t we supposed to be talking about clever ways to have a difficult conversation with someone else? I’m supposed to be giving them feedback, not asking for feedback. Well, sometimes it’s best to put yourself in the hot seat first! It makes it clear that it’s a mutual growth opportunity. And they’ll usually reciprocate the question. If they don’t, you could always sneak in: “Speaking of that, one thing I wanted to throw out there is…”

Can I add two quick disclaimers for the skeptics out there? Aren’t there times when I should just hit someone with the truth? Honestly, Yes! If someone is embezzling, should you tell them, “One thing that would help me would be if you could return some of the money, if you don’t mind – maybe half?” Of course not! But we’re not talking about embezzling here, we’re talking about typical behaviors and how people could improve. Even in a more corrective conversation, you could still start with one of the above ‘smart ways’ and then use more force later if needed!

Here’s your homework: Think of a difficult conversation you initiated recently and reflect on how you started it. Were you smart enough? Which of the above strategies could you employ in the future to get a better outcome? One other quick homework assignment: If you want to learn something, it helps with retention to teach or share it, so print this out and share it during an upcoming meeting. Let the group process it. Maybe they’ll point out some legitimate exceptions or possible complications. If so, great! The goal is to get people thinking and discussing, not to corner them.



Dr. Chris White

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