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We Have to Talk:
A Step-By-Step Checklist
for Difficult Conversations

by Judy Ringer


Think of a conversation you’ve been putting off. Got it? Great. Then let’s go.

There are dozens of books on the topic of difficult, crucial, challenging, important (you get the idea) kinds of conversations. Those times when you know you should talk to someone, but you don’t. Maybe you’ve tried before and it went badly. Or maybe you fear that talking will only make the situation worse. Still, there’s a feeling of being stuck, and you’d like to free up that stuck energy for more useful purposes.

There are many well-written and informative books on how to have these important, crucial, and difficult conversations. At the end of the article, I list them. Get at least one and read it. They’re all great.

What you have here is a brief synopsis of best practice strategies: a checklist of action items to think about before going into the conversation; some useful concepts to practice during the conversation; and some tips and suggestions to help you’re energy stay focused and flowing, including possible conversational openings.

You’ll notice one key theme throughout: you have more power than you think.

Working on yourself: How to prepare for the conversation

Before going into the conversation, ask yourself some questions:

1. What is your purpose for having the conversation? What do you hope to accomplish? What would be an ideal outcome?

Watch for hidden purposes. You may think you have honorable goals, like educating an employee or increasing connection with your teen, only to notice that your language is excessively critical or condescending. You think you want to support, but you end up punishing. Some purposes are more useful than others. Work on yourself so that you enter the conversation with a supportive purpose.

2. What assumptions are you making about this person’s intentions? You may feel intimidated, belittled, ignored, disrespected, or marginalized, but be cautious about assuming that that was their intention. Impact does not necessarily equal intent.

3. What “buttons” of yours are being pushed? Are you more emotional than the situation warrants? Take a look at your “backstory,” as they say in the movies. What personal history is being triggered? You may still have the conversation, but you’ll go into it knowing that some of the heightened emotional state has to do with you.

4. How is your attitude toward the conversation influencing your perception of it? If you think this is going to be horribly difficult, it probably will be. If you truly believe that whatever happens, some good will come of it, that will likely be the case. Try to adjust your attitude for maximum effectiveness.

5. Who is the opponent? What might they be thinking about this situation? Are they aware of the problem? If so, how do you think they perceive it? What are their needs and fears? What solution do you think they would suggest? Begin to reframe the opponent as partner.

6. What are your needs and fears? Are there any common concerns? Could there be?

7. How have you contributed to the problem? How have they?

4 Steps to a Successful Outcome

The majority of the work in any conflict conversation is work you do on yourself. No matter how well the conversation begins, you’ll need to stay in charge of yourself, your purpose and your emotional energy.

Breathe, center, and continue to notice when you become off-center – and choose to return again.This is where your power lies. By choosing the calm, centered state, you’ll help your opponent/partner to be more centered, too.

Centering is not a step; centering is how you are as you take the steps. (For more on Centering, see the Resource section at the end of the article.)

Step #1: Inquiry

Cultivate an attitude of discovery and curiosity. Pretend you don’t know anything (you really don’t), and try to learn as much as possible about your opponent/partner and their point of view. Pretend you’re entertaining a visitor from another planet, and find out how things look on that planet, how certain events affect them, and what the values and priorities are there.

If they really were from another planet, you’d be watching their body language and listening for the unspoken energy as well. Do that here. What do they really want? What are they not saying?

Let them talk until they’re finished. Don’t interrupt except to acknowledge. Whatever you hear, don’t take it personally. It’s not really about you. Try to learn as much as you can in this phase of the conversation. You’ll get your turn, but don’t rush it.

Step #2: Acknowledgment

Acknowledgment means to show that you’ve heard and understood. Try to understand them so well you can make their argument for them.

Then do it. Explain back to them what you think they’re really going for. Guess at their hopes and honor their position. They won’t change unless they see that you see where they stand. Then they might. No guarantees.

Acknowledge whatever you can, including your own defensiveness if it comes up. It’s fine; it just is. You can decide later how to address it.

For example, in an argument with a friend I said: “I notice I’m becoming defensive, and I think it’s because your voice just got louder and sounded angry. I just want to talk about this topic. I’m not trying to persuade you in either direction.” The acknowledgment helped him (and me) to recenter.

Acknowledgment can be difficult if we associate it with agreement. Keep them separate. My saying, “this sounds really important to you,” doesn’t mean I’m going to go along with your decision.

Step #3: Advocacy

When you sense that they’ve expressed all their energy on the topic, it’s your turn. What can you see from your perspective that they’ve missed? Help clarify your position without minimizing theirs.

For example: “From what you’ve told me, I can see how you came to the conclusion that I’m not a team player. And I think I am. When I introduce problems with a project, I’m thinking about its long-term success. I don’t mean to be a critic, though perhaps I sound like one. Maybe we can talk about how to address these issues so that my intention is clear.”

Step #4: Problem-Solving

Now you’re ready to begin building solutions. Brainstorming is useful, and continued inquiry. Ask your opponent/partner what they think would work. Whatever they say, find something that you like and build on it.

If the conversation becomes adversarial, go back to inquiry. Asking for the other’s point of view usually creates safety, and they’ll be more willing to engage.

If you’ve been successful in centering, adjusting your attitude, and in engaging with inquiry and useful purpose, building sustainable solutions will be easy.

Practice, practice, practice!

The art of conversation is like any art – with continued practice you acquire skill and ease.

You, too, can create better working and family relationships, ease communication problems and improve the quality of your work and home environment. You’re on the way, and here are some additional hints:

Tips and suggestions

  1. A successful outcome will depend on two things: how you are and what you say. How you are (centered, supportive, curious, problem-solving) will greatly influence what you say.

  2. Acknowledge emotional energy – yours and theirs – and direct it towards a useful purpose.

  3. Know and return to your purpose at difficult moments.

  4. Don’t take verbal attacks personally. Help your opponent/partner come back to center.

  5. Don’t assume they can see things from your point of view.

  6. Practice the conversation with a friend before holding the real one.

  7. Mentally practice the conversation. See various possibilities and visualize yourself handling them with ease. Envision the outcome you’re hoping for.

How do I begin?: Opening the conversation

In my workshops, a common question is How do I begin the conversation? Here are a few conversation openers I’ve picked up over the years – and used many times!




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