Should I Hold That Difficult Conversation? 7 Clues to Help You Step Up

What prevents you from stepping up to a difficult conversation? At what point does a conversation become a problem rather than an opportunity to clarify, collaborate, and connect?

When I’m working with organizational leaders stuck in conflict, it’s usually because someone has not held a difficult conversation early enough or well. The suppressed energy causes relationship problems, workflow interruptions, and team divisiveness. The longer the delay, the harder it is to address the issue or even know what it is. The delay adds fuel to the fire, and issues grow larger and more diverse until the original problem is lost in the crowd.

This may sound strange coming from me, but sometimes avoiding a conversation is the right move, especially if you think you might not contribute anything useful or positive.

However, most of the time, fear drives our actions, and our positive intentions are overridden. We withhold instead of clearing the air; we conceal and collude instead of seizing the moment to rebuild trust; and we end up more deeply divided, finding it harder and harder to get back on track.

7 Clues to Help You Step Up

How do you know, then, if this is a conversation you should hold? Oddly, the fears that keep you silent might also serve as clues. When you find yourself in one of these traps, it’s probably time to step up to the conversation.

If you’re waking up nights worrying and unable to sleep, this is a clue — it’s time to hold the conversation.

If I hold the conversation, things will only get worse. I’ll say something wrong, and it will end in a shouting match — or worse. When you hear yourself saying these words, note: This is a conversation that wants to happen.

It’s not that big a deal. If I ignore it, it will go away. No one else is bothered by it, why should I be the one to address it? It could be true — perhaps there really is no issue here. However, if these thoughts continue, you’re probably masking an issue that deserves attention. If you’re concerned, others almost surely are also. You be the one to address it, because you can do it skillfully.

It won’t make any difference. Nothing will change. No one ever listens to anything I say anyway. It’s been like this forever, so why speak up? Is this you? I have a suggestion…. Hold the conversation and see what you learn.

I’m so sick of him getting more perks than the rest of us! You know it’s a clue if you’re talking to the wrong person about the problem. The wrong person is someone who can’t help you solve it.

How long can you ignore a problem that’s having a serious impact on your team? If your people are polarizing around an issue, squabbling, shutting down, or otherwise not operating efficiently, there is a conversation that’s not being held.

· Well, at least someone is listening!

· Nice perfume (cough, cough)!

· Good luck getting an answer from her. That’s where questions go to die.

If you find yourself acting out of anger or frustration, you might consider talking it out instead.

We know a leader by their confidence in situations that others avoid. Don’t be held hostage by fear. Engage the energy of conflict and deal with it. You will do well if you practice the following as you prepare to hold your conversation:

· Determine your purpose and positive intention. What do you really want to accomplish?

· Practice the conversation — by yourself or with a coach or colleague. Prepare.

· Be curious, listen, and acknowledge. Ask questions and listen long enough to hear their story.

· Advocate. Tell your story. What do you see that they don’t?

· Problem-find and problem-solve. What is the real issue that you’re trying to solve and what needs to happen to resolve it?

When we don’t step up to a conversation, the difficult energy gets stuck and interferes with the free flow of workplace productivity. Those who address issues skillfully from a learning stance show leadership and model the way for the rest of us.

Written by

Judy Ringer is the author of Turn Enemies Into Allies: The Art of Peace in the Workplace and Unlikely Teachers: Finding the Hidden Gifts in Daily Conflict.

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