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Step-By-Step Guidelines for Having Difficult Conversations

by Jan 15, 2022Personal Development


By Henry Chidgey

Having difficult conversations. Think of a conversation you’ve been putting off. Got it? Great. Then let’s dig in.

A lot has been written on the subject of difficult, important, challenging, crucial discussions and conversations. Those times when you understand you should talk to someone, however you do not. Perhaps you’ve tried and it went badly. Or maybe you fear that talking will just make the scenario worse. Still, there’s a sensation of being stuck, and you’d like to free up that energy for more useful activities.

What you have here is a short run-through of best practice methods: a checklist of action items entering into the conversation; some helpful concepts to practice during the conversation; and some ideas and recommendations to assist in staying focused. 

You’ll discover this key theme throughout: you have more power than you believe.

How To Prepare for having difficult conversations

Prior to going into the conversation, ask yourself some questions:

1. What is your vision of what you want as a result of the meeting? Then what are the strategies and tactics to achieve that? What would be a perfect result? 

Look for hidden purposes you might have. You might think you have uplifting goals, like educating a co-worker or increasing connection with them, just to observe that your language becomes judgmental or condescending. You think you want to support, but you wind up punishing someone. Some discussions go better than others. Work on yourself so that when you go into the conversation you go with the intent to benefit the other person, as well as achieve your goals.

2. What assumptions are you making about this person’s objectives? You may feel frightened, belittled, neglected, disrespected, or marginalized, however, beware about presuming that this was the speaker’s intention. 

3. What limiting beliefs might sabotage you in the meeting?

What “buttons ” of yours are being pushed? Are you more angry than the circumstance warrants? What individual history of yours is being triggered? You might still have the conversation; however, you’ll enter into it understanding the heightened emotional state involves you.

4. How is your mindset towards the discussion affecting your understanding of it? If you think this is going to go badly, it most likely will. If you truly think that whatever occurs, some good will come of it, that will likely be the case. What you expect is what you get.

5. Who is the opponent? Are they really an opponent? What might he or she be considering in this scenario? Are they knowledgeable about the problem? If so, how do you think they perceive it? What are their needs and fears? Begin to reframe the other person as a partner in finding resolution.

4 Steps to a Successful Outcome

Most of the work in any conflict-based conversation is the work you do on yourself. No matter how well or poorly the discussion begins, you’ll be required to stay in charge of yourself, and your emotional energy. Breathe, center, and continue to notice when you end up being off-center — and choose to return again. This is where your power lies. By picking the calm, focused state, you’ll assist the other person to be more focused, too. 

Step # 1: Inquiry

Cultivate a mindset of discovery and interest. 

Pretend you do not understand anything (you really don’t), and attempt to learn as much as possible about your opponent/partner and his point of view. Pretend you’re entertaining a visitor from another planet, and learn how things look on that planet, how specific events affect the other person, you’d be watching their body language and listening for unspoken energy too. What do they really want? What are they not saying? 

Let your partner talk until he is completed. Do not interrupt except to acknowledge. Whatever you hear, do not take it personally. It’s not actually about you. Attempt to learn as much as you can in this phase of the discussion. You’ll get your turn, however, do not hurry things. It is so important that they feel heard.

Step # 2: Acknowledgment 

Acknowledgment means showing that you’ve heard and understood. 

Attempt to comprehend the other individual so well you can make their argument for them. Then do it. Discuss back to him what you believe he’s actually opting for. Honor his position. He will not change unless he sees that you see where he stands. Then he might. No assurances.

Acknowledge whatever you can, including your own defensiveness if it comes up. It’s fine; it just is. You can choose later how to address it. For example, in an argument with a good friend, I stated: “I notice I’m ending up being defensive, and I think it’s because your voice simply got louder and sounded angry. I simply wish to talk about this subject. I’m not attempting to encourage you in either direction. ” The recommendation helped him (and me) to re-center.

Acknowledgment can be challenging if we associate it with agreement. Keep them separate. 

My saying, “this sounds really important to you, ” doesn’t indicate I’m going to accompany your choice.

Step # 3: Seek Understanding Through Collaboration 

When you notice the other person has revealed all his energy on the topic, it’s your turn. What can you see from your point of view that he’s missed? Help clarify your position without minimizing his. For instance: “From what you’ve said, I can see how you came to the conclusion that I’m not a team player. I am certainly committed to being one. When I introduce issues with a job, I’m focused about its long-lasting success. I don’t suggest being a critic, though possibly I may seem like one. Can we agree about how to resolve these concerns so you feel respected by me and we can accomplish great things together? 

Step # 4: Problem-Solving

Now you’re prepared to start developing options. Ask the other person what he thinks may work. 

Whatever they state, find something you like and consider it. If the conversation ends up being adversarial, return to inquiry. Asking for the other’s point of view generally develops security and encourages him to engage. If you’ve been successful in focusing, changing your attitude, and engaging with questions and helpful function, developing sustainable services will be easy.

Practice, Practice, Practice

The art of conversation resembles any art — with continued practice you obtain skill and ease. Here are some extra hints:

Tips and Suggestions:

An effective result will depend upon 2 things: how you are and what you say. How you are (centered, helpful, curious, problem-solving) will greatly affect what you state.

Acknowledge emotional energy — yours and your partner’s — and direct it toward a useful purpose.

Don’t take spoken attacks personally. 

Help the other person return to center.

Don’t presume the person can see things from your perspective. 

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

Psychologically practice the conversation. See different possibilities and imagine yourself managing them with ease. Picture the outcome you are expecting.

How Do I Begin?

A common concern I hear is How do I start the conversation? Here are a couple of conversation openers I’ve picked up throughout the years — and used lot of times!

I have something I ‘d like to go over with you that I think will assist us to collaborate better. 

I’d like to talk about ____________ with you, however, initially I’d like to get your viewpoint.

I require your help with what just happened. Do you have a couple of minutes to talk?

I need your help with something. 

Can we speak about it (quickly)? If the individual says, “Sure, let me return to you, ” follow up with him. 

I believe we have various perceptions about _____________________. I ‘d like to hear your thinking on this. 

I ‘d like to talk about ___________________. I believe we may have different ideas about how to _____________________.

I ‘d like to see if we might reach a better understanding about ___________. I truly want to hear your feelings about this and share my viewpoint as well.

Compose a possible opening for your discussion here: 


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About Henry:
Henry is a Leadership Coach and Mentor. He helps Owners and Executive Leaders develop their teams to grow their business so they can have more time, more results and more money. To learn more, Henry offers a FREE discovery call  check out the details on this website.