Avoiding or Failing at a Conversation – Which is Worse?

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No one wakes up in the morning and says, “I want to get it wrong today.” We want to be successful. However, fear usually gets in our way. We don’t want to look stupid.

For example, when I have an out-of-the-box idea I want to pitch to my boss or a sensitive issue to bring to my colleague, I inherently evaluate if it is worth having the conversation. Can I bear the rejection? Can they bear the idea?

What if I lose my job? What if I lose that project? What if he thinks less of me? What if…what if…

Let’s shift our context. What if missing the conversation is more risky than having it?

When you never have the conversation, each party makes up stories about the situation. Whether it is my boss never knowing I deeply care about a project or my colleague never knowing that I want our relationship to be better – neither party can know if I don’t have the courage to have a conversation.

That’s costly.

It’s more economical to have a beautiful, failed conversation. When you have a failed conversation, the kind that just doesn’t go as “planned”, or you don’t get what you hoped, at least you mustered the courage and cared enough to take on the conversation – to bring it to that person. This creates a place to move forward, a jumping board. The next conversation may start with the words,“Last time, I didn't approach it the way that I had hoped to…”

This less fearful approach to conversations is not only a good investment for the individual but also for the organization.

In a recent article in the Wall Street Journal, Better Ideas Through Failure, Tor Myhren, Chief Creative Officer of Grey New York, was showcased for creating the “Heroic Failure” award. An employee receives this quarterly reward by taking a “big, edgy risk”. He created this award because he was worried that with the fast growth of the agency, employees were becoming more conservative and slow. Dig a little deeper and that is code for: He doesn’t want fear to win. Myhren wants to encourage conversations that might fail, rather than never having the conversations.

What conversation would you have, if you weren’t scared to fail?

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