Have you been putting off a difficult and unpleasant conversation for a long time? Great, this is for you.

There are moments in life when you have to face your “demons” and it is not a pleasant space to be when you know you should talk to someone but won’t or don’t or can’t but you should or must-whatever your reason or excuse is, you can’t put it off any longer. Perhaps you’ve tried before and failed, or you’re afraid that participating would just make matters worse.

Still, there’s a sense of not knowing where to begin or how to approach it; you’re full of uncertainty and hesitation, and you’d like to free up that trapped, unsettling energy for more beneficial reasons, as the burden is unbearable and you want to be able to go on and ahead, but you’re not sure what to do or how to manage it.

What we have shared here is a brief checklist of action steps to think about before tackling a difficult conversation; some useful tips and tricks to practice before and during the conversation; and some helpful suggestions to help boost your energy to stay focused and flowing, including possible conversation openers.

You’ll notice a recurring theme throughout: You have more than you realize. Never ever doubt yourself. It is so TRUE!

handling difficult conversation

Work on yourself first: How To Prepare for the Conversation?

Before you start the conversation, ask yourself these very deep questions to probe your real intention, assumptions, expectations, perceptions, and how you contributed. Reply openly and honestly if you really want the best outcome:

1. What is the point of having this conversation? Why are we having this conversation? What do you want to achieve? What would be the optimal result?

Keep an eye out for disguised ulterior motives. You may believe that you have good intentions, such as resolving a serious explosive financial dispute with your spouse or strengthening your relationship with your teenager, or resolving a conflict with a sibling or family member only to discover that words and manners are unduly critical or condescending.

You intend to engage and support, yet you wind up pushing away the very same people you intend to help. Examining and improving yourself once off is not an end in itself, it is a continuous evaluation process so you can approach the dialogue with sincerity and empathy to support the cause and attain amicable consensual results.

2. What are your expectations and assumptions about this person’s intentions?

You may have been sensitive and emotional at the time, and your feelings of being intimidated, belittled, ignored, disrespected, or marginalized may have erupted into an uncontrollable rage and resulted in your failing to understand, causing some irritation and impatience on your part, but be wary of assuming that this was the speaker’s deliberate intention.

In some cases, the impact may not always imply a deliberate assumption that this was the other party’s initial intention. You may have to adjust the expectations of your upcoming conversation, taking into account what you went through and handled it differently than before as the circumstances may have changed or assumptions may have been misdirected.

3. Which of your buttons is being pressed? Are you overly sensitive and emotional about the situation?

Take a look at your history, as they say, and see what personal historical baggage you are carrying that has not been dealt with completely yet continues to be triggered. Effectively, it implies that the person still has a great influence over you and you have to let go and forgive not only yourself but also the other person who violated you in whatever way. This does not in any way imply that the distasteful misdemeanor was justifiable and made right by you. You can forgive but you can never forget.

Work on yourself

4. How is your attitude toward the conversation influencing your perception of it?

If you expect this to be a difficult task, you’re probably right. If you genuinely think whatever happens will result in some good, chances are that it will. As your mind is a co-creator of the real surroundings, anything you put out there will undoubtedly be mirrored (manifested). To be as effective as possible, try to adjust or change your mindset accordingly to achieve the best possible outcome.

5. Is this individual even aware of the situation? Who is the “opposing” party in this case? What is this person’s perspective on the situation? 

If so, how do you believe the individual sees it? What are their needs and fears? What do you believe they would recommend as a solution? If you want to win this cause, justly, equally, and fairly, begin to define the adversary as a collaborator. If the individual is not aware, what would you do to bring it to their attention? Again, examine the perceptions, assumptions, and expectations that you both share.

6. What are your requirements and legitimate concerns?

As a starting point, are there any shared concerns and needs that have not been addressed that must be examined? List them. Is it possible for both of you to explore them?

7. In what ways have you contributed to the problem?

How did the other individual fare? Is it possible to share the blame? We are aware that it takes two to tango. Here we are only interested in you and then the other party’s blame will be examined once the conversation takes place. In the meantime, the focus is on YOU. It is not easy, for sure, however for this to be resolved in a calm and reasonable manner, honesty has to prevail.

The more transparent and vulnerable (not a sign of weakness as we are meant to believe) you are, the better and easier the conversation will flow, yet we are all human and ego usually wants to have an upper hand, but there is no place for it here. It has to go!

reach out and touch for a successful conversation

4 Steps to handle the conversation to reach a Successful Outcome

The majority of the work in any conflict conversation is inner self-work. Regardless of how well the discussion begins, you must maintain control of yourself, your goal, and your emotional energy.

Breathe, center, and continue to notice when you drift off and choose to return again. This is where your power lies.

By choosing to remain calm, and centered, you’ll help your partner to be more centered as well. Centering is how you handle yourself as you take the steps forward.

Step 1: Inquiry

Cultivate an attitude of discovery and curiosity. Pretend you don’t know anything (you really don’t), and try to learn and understand as much as possible about your partner’s 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 the other person, and what their values and priorities are.

If your partner really was from another planet, you would be watching his body language and listening for unspoken words or energy too. Do that here. What do they really want or deeply craving for? What are they not saying?

Let your partner talk until they are finished. Don’t interrupt except to acknowledge. Whatever you hear, don’t take it personally. It’s not really about you, and you’d rather take notes. Try to learn, and understand as much as you can in this phase of the conversation.

You’ll get your turn but don’t rush things. When things get heated up, which often happens, if a sensitive issue comes up, call it out and take a timeout. Set another time to meet where an opening is immediately possible, but do not delay.

Step 2: Acknowledgement

Acknowledgement means showing that you’ve heard and understood the other party’s grievances or concerns and doing it sincerely. Make a concerted effort to try and understand the other person so well that you can make an argument on their behalf. Then do it.

Explain back to them what you understood what they are really going through and believe what they are aiming towards. Understand their hopes and fears and honor their position—walk in their shoes. They will not change their stance unless they see that you are on their side, standing head and shoulders with them. Then they might adjust their position. No promises, though.

Recognize where they are coming from and whatever you can glean from it, including your own defensiveness if it comes up. It’s fine; it simply is. You can decide later how to handle it afterward.

For example, in a disagreement with a friend of mine, I realize I am feeling defensive and I believe it is because “your voice suddenly became louder and sounded furious.” I just want to talk about this topic. I’m not trying to persuade you in either direction. The acknowledgement helped us to re-center ourselves.

When we link acknowledgement with an agreement, it might be challenging. Keep them apart by simply stating, “This appears t be very important to you, it does not mean that I will agree with your decision”

Step 3: Advocacy

When you have a sense that your partner has expressed all their energy on the topic, and also verify by asking for permission to proceed, do not make any assumptions, then it’s your turn.

What can you see from your perspective that was missed or not clearly stated or implied? This will help clarify your position without minimizing your position. 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 problem-solving with a project or a question, I’m thinking about its long-term sustainability and success for our progress. I don’t mean to be a critic, perhaps I may have sounded like one. I apologize.

Maybe we can talk about how to address these issues in the future so that my intention is clear. Always apologizing and appealing to people’s better nature, they disarm very quickly without putting up any defense.

Before proceeding to problem-solving, just ensure all the bases are covered by asking any further questions or any clarification.

Step 4: Problem-Solving

Now you’re ready to begin building solutions. Brainstorming and continued inquiry are useful here. Ask your partner what they think could work. Whatever they say, find something you both share, like, and build on it. If the conversation becomes adversarial, go back to inquiry (Step 1).

Asking for the other’s point of view usually creates safety and encourages them to engage. If you’ve been successful in centering, adjusting your attitude, engaging with inquiry, and always focusing on the purpose, building sustainable solutions will be easy, and you will finally reach the end goal with success.

It then builds a template (blueprint) that you can use and follow going forward so you do not repeat the same mistakes again.

couple reaching out to each other to solve a problem

Practice, Practice, Practice!

Conversations are an art form, like any other, that improves with practice. Here are some  more useful tips:

Tips and Suggestions:

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

  • Acknowledge the emotional energy that exists between you and your partner and direct it toward a useful helpful and amicable outcome.

  • Know and return to your initial intent at difficult moments. Humour can also help here as well to break the monotony or the tension if used properly.

  • Don’t take verbal attacks personally. Help your partner come back to the center.

  • Don’t assume your partner can see things from your point of view at all times and vice versa

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

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

I’m convinced of this: Good done anywhere is good done everywhere. For a change, start by speaking to people rather than walking by them like they’re stones that don’t matter. As long as you’re breathing, it’s never too late to do some good.

Maya Angelou

How Do I Begin?

A common question is “How do I begin the conversation”? Here are a few prompting conversation openers that can be of help!

  • I have something I would like to discuss with you that I think will help us work together more effectively.

  • I would like to talk about ____________ with you, but first I would like to get your point of view.

  • I need your help with what just happened. Do you have a few minutes to talk?

  • I need your help with something. Can we talk about it (soon)? If the person says, Sure, let me get back to you, follow up with them.

  • I think we have different perceptions about _____________________. I would like to hear your viewpoint or standpoint on this.

  • I would like to talk about ___________________. I think we may have different ideas about how to _____________________.

  • I would d like to see if we might reach a better understanding about ___________. I really want to hear your feelings about this and share my perspective as well.

  • Write a possible opening for your conversation here:



It is not easy to tackle a difficult conversation with the closest people in our lives, especially the ones we love the most. I trust that this checklist of tips and hints will go a long way to help alleviate any blocks or hindrances that may come up during difficult conversations. This list is not at all exhaustive. You are more than welcome to add your own flavor to the mix.

Thank you for taking the time to read this article. Are there any other tips that you would like to add to the checklist, or was there any tip that stood out for you? Perhaps you can share an experience of how you handled a difficult conversation with a loved one. Please leave a comment below and we will definitely engage. Thank you once again for gracing us with your presence.