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The Art of Hard Conversations: This Is Not Easy

Remember a time when you needed to confront a colleague. Was it an easy conversation? Most of us struggle with giving negative feedback in a constructive way while keeping our work relationships intact. Maybe we don’t have the gift of an even-keeled tone. Maybe we aren’t skilled in setting clear boundaries. Whatever our challenges, these hard conversations are necessary for a healthy team. So Bold TV hosts David Grasso and Julia Sun have an easy and informative discussion with Victoria Montgomery-Brown, the CEO and co-founder of Big Think and author of Digital Goddess: The Unfiltered Lessons of a Female Entrepreneur.

When it’s time to talk it out

For leaders, one of their most difficult conversations is telling someone that they need to improve. How do you know when it’s time to address them? First, the conversation shouldn’t happen without a series of events. It’s not prudent to have this type of conversation at the first glimpse of a problem. But once you’ve seen a chain of similar situations, you need to have a hard conversation. Make sure your head is in the right place. Are you still angry or judgmental? Taking these feelings into the meeting will be counterproductive. Take some time to find empathy, and realize that both parties want a positive result. Finally, realize that while you may enter a conversation with empathy, the outcome may still not be positive. It may become obvious that the work situation isn’t working out.

Watch your approach

Is it possible to have a difficult work conversation without using the word “you”?  The work environment can feel like a pressure cooker, and when we’ve had enough, our temper can put us on the offense. Often, we tend to blame others with a string of accusations. How do we stay away from this sometimes harmful approach? Montgomery-Brown says to replace “you” with “we.” How can we do better? How can we succeed? Your colleague is more likely to respond to a brainstorm rather than an attack session. Also, difficult conversations should not be sudden or unexpected. If you need to talk to someone, trade your explosive mindset for preparedness. Remember that better communication leads to a better relationship.

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