5 Tips for Having an Uncomfortable Conversation

The experts agree that having uncomfortable conversations is the best way to succeed in your business.

Timothy Ferriss, author of The Four Week Work Week talks about the importance of having uncomfortable conversations in this current economy and how it relates to small business success.

Personally, I think a lot of us come to life when someone mentions the unmentionable. Think of Seinfeld. They brought up so many taboo topics, they had viewers coming back for more. When I look back at my own business, I realize how it stagnated when I held back saying something that needed to be said. There’s something very gutsy and admirable about people who say what others might be thinking. Why don’t more of us do it? If you’re like most people, you've heard the old cliche, “If you don’t have anything nice to say, don’t say anything at all.” Well, those days are over. If you don’t want to be the 'nice guy' who finishes last, it’s time to learn how to have an uncomfortable conversation. You can do it without burning bridges and actually be more connected. It is possible to have uncomfortable conversation while adding a twist of compassion.

Here are 5 tips for making uncomfortable conversations a little easier for everyone.

1. Plan for it when you can think critically rather than emotionally. Set up a time that works for both of you. Tell them you have something important you’d like to talk with them about, what it is and about how long it will take. Having an appointment insures that you’ll be proactive rather than reactive. Just because you heard it’s a good idea to have an uncomfortable conversation doesn’t mean you’ll want have it when you’re stressed out. It can be tempting to send an e-mail, but it’s not the best way to have an uncomfortable conversation. After all, e-mail is a one way point of view (your view), conversation is two way. Letting the other person have a voice and then understanding it from their point of view helps them feel good about it too.

2. Focus on what will change because of having the conversation, not how uncomfortable it might be. Reward yourself for having the courage to initiate the conversation. You might even say to yourself, “As soon as I’ve had this conversation, I’m going to celebrate by… (The more difficult the conversation, the greater the reward!)

3. Put your attention on a common goal. If it’s a stressful situation and you’re really at odds with one another, you can always focus on how both of you would like less stress in your life. Keep in mind how this will help move you both forward. If you're reluctant to having the conversation, you might ask yourself, “What’s the payoff for me not having this conversation?” (e.g. pity from my friends, I get to stay small, etc. etc.)

4. Ask more questions with compassion. Not to be swayed, but to understand what’s going on for them. It’s easy to start assuming when we haven’t opened up the dialogue. The stories can get pretty elaborate in the circus of own minds. Maybe they’ve been looking for a way to bring it up with you. If you feel it’s uncomfortable, chances are they feel tension too. We don’t really know what’s going on for them until we hear it directly from them.

5. Plan enough time so neither of you feels rushed. Keep in mind the impression this conversation will have on your brand. While you’ve carved out enough time for this conversation, you'll also want to be deliberate on your next step. Leave when everything has been said and move on to your next goal. Don’t spend too much time replaying it in your mind.

Think of the last uncomfortable conversation you've had. What were some things that made it go well for you? What would you do differently next time? Thanks for sharing and adding to this conversation.