How to have difficult conversations, under any circumstance?

This post will really help if you’re unable to speak up.; if you run away from difficult conversations and lose your peace. I’ve been there and I feel you. This post is a sum total of my experience, findings and coaching. After reading this post, you can have difficult conversations, under any circumstance.

Most people, yes most people avoid having difficult conversations because they don’t know how to go about them, where to start and how to come to a resolution. These conversations are difficult to have and that is why I’ve written this article to provide you with simple & practical steps on how to have a difficult conversation. When you know how to have a difficult conversation, you will be in charge of the situation, feel so much more confident to go and do it! Don’t miss out on reading this post!

Hope you get value, take action and implement my tips.

Most people don’t speak up, don’t say when things don’t work out and end up with a big wound. The build up inside us makes us view the other person with a tinted glass and most often that doesn’t work for us in the longer run. We do not speak up because of fear, insecurity, judgements and lack of intention. These are just some of the reasons; there can be more.

Do the conversation early and nip it in the bud. I see a lot of people struggling at the workplace; people separating; relationships going sour; employees leaving the job and what bewilders is that people don’t even know what went wrong.

Here are 10 steps of How to have difficult conversations, under any circumstance.

1. Check in with yourself before having the difficult conversation

Please don’t do it if you aren’t calm. You need to be in a balanced state before having a difficult conversation. Do not, I repeat Do not have a difficult conversation when you’re angry. Calm yourself before the conversation. Walk, meditate, sip a cup of tea, deep breathe before diving in. We need to respond, not react while having the conversation. We need to be going forward, not backwards.

2. Don’t just dive in. Prepare for these conversations.

Ask yourself- “What am I trying to achieve out of this conversation?”

Sometimes we just go and blame- is that what you want to do? Certainly not! Think about your intention and goal to be achieved through the conversation. You intention might be an apology or telling someone that you can’t work with them anymore. You may want to tell your partner about the things not working out and how to solve them or you may want to end a relationship. Go with a clear intention of what you want to get out of the conversation.

I’ll give two examples. If you want to work out a relationship, you go with the intention of working things out viz-a-viz blaming your partner. At work, you may want to tell you employee that you want her to stay working with you but there are certain areas where she has to improve upon.

Prepare yourself with the intention and goal you want to achieve.

3. Check in with the other person

Don’t just go and jump into the conversation with things like- “This is what I need. This is what is not working.” Make the other person ready for the conversation. People are mostly on the edge due to work issues or personal issues. Make the extra effort of checking with them if they are ok to have a conversation. If not, take an alternate time.

Make the other person comfortable and interested in you. Check how they are doing. They may open up about their struggle or issue and it would give you an insight into their mind and life. This will help you to take the conversation to a positive tangent.

4. Never make assumptions and ask questions instead

Most often we make assumptions about the other person. My boss didn’t give me a good appraisal which means he wants me to leave. My partner is fighting everyday which clearly means he doesn’t love me any more. We look for evidence to further support our assumptions.

Instead of making these assumptions, simply ask your partner about his behaviour. He may be having a hard time at work. Your boss is maybe committed to your staying in the organisation and it was really your performance that led to a disappointing appraisal.

Do the regular chit chats with people around you. The coffee chit chats are important to find the struggles in the life of others around you. People share what they are dealing with and it’ll help you understand their side as well.

Read this post to Improve How YOU Think, Feel and Act by REDUCING Generalisation, deletion and distortion.

5. Give the context before starting the conversation

Give the other person the context of the conversation. Tell them what the conversation is about before giving a difficult message to the other person.

For example, tell your employee that they haven’t stepped up but you still want them to continue working with you. Tell your friend that you want to mend the friendship but you’re struggling with these issues. Giving a context prepares the other person to better respond and accept our point of view.

6. Be straight but empathetic

Do the above 5 steps before getting to this step. Don’t beat around the bush and end up giving an unclear message. The other person may just get confused and end up asking you- ‘What are you talking about?’ It may even create more drama.

Be empathetic and straight. It works better. Less is more.

Have straight conversations. Ask the other person- ‘Can I be honest with you?’ They will say a Yes and things will become easier from there. People in fact do the opposite. They say things like- ‘I don’t want to be rude but…..’ and end up being rude and offensive. Come from a space of empathy and deliver your message clearly and straight to the point. If it’s a constructive criticism, your employee will appreciate it.

7. Give time to respond

Give people time to respond after you have delivered your message. Give them space to respond. Some people are quick to respond while some take time. Some conversations need time and acceptance.

Let them speak and respond. Their response may upset you or make you feel uncomfortable but that’s part of life. You have also made them uncomfortable. Get comfortable about being uncomfortable.

When I get into such conversations, I ask people- ‘Is there anything else you want to say?’ Ask them till they have nothing more to say. This will ensure there is no resentment later on.

8. Respond appropriately to them

Show empathy and understand they must be upset. Be clear about what you can do and can’t do whether in romantic or work relationships. Don’t make promises you can’t keep because that will worsen the situation in the future and escalate it to another level.

Tell them clearly what you can and can’t do and WHY. You must explain the why to help them understand your point. A lot of people miss the WHY and make the other person feel less worthy. Have an in-depth conversation and this is where negotiation starts.

9. Negotiate to get a solution

This is the delicate and important part of the conversation. You can use the following sentences for help.

I can do this. Or I can’t do this because…

How will this work? What works for you?

Then you make agreements and solve the issue. Happy ending and a good night sleep!

But what if you can’t reach a solution. Happens so many times right? Let it go then. No clarity will lead to more conflict. Make an agreement or take a break. Give time to yourself and the other person to analyse the situation, find out more facts/information and what is possible. Tell them that you would see them later or the next day or the next week- whatever works but make the appointment then only so that both of you know the time in hand. Finish the conversation. Move ahead with clarity and fixing the next appointment is also clarity.

Meet them on the next appointment and finish the conversation. Go with the mindset of achieving an outcome (whether you agree or reject their proposal). Be prepared for the consequences. You will be able to complete the conversation and find peace.

10. Actually go and have the conversation

Most often than not we avoid the difficult conversation. Being scared will not help; you gotta be brave. You have to muster up the courage and cross the bridge because life is beautiful at the other end. Difficult conversations are like storms but once you cross the storm, you’re not the same person again.

Don’t sit too long on these conversations or carry them around or find excuses not to do them. Your body reacts to your anxiousness and nervousness. Call or text the person that you need to speak to them. Take the action so that you can’t back out.

You got to do it and get better at it with time. We’ll face a lot of circumstances in our lives where difficult conversations will be the only way out. And trust me, there is peace on the other side.

Super Tip: Create relationships where resolutions are possible.

If you don’t do difficult conversations in time, you’ll have more problems in the future. Do them today to have a beautiful tomorrow.

Join my 4 weeks programme to help you out with having difficult conversations in order to live a life of dignity and peace. Talk to me if you need clarity, strength, courage & mindset to reach ur goal- personal, professional or both. Mail me at and I’ll schedule a call with you to let you know the details of my coaching programme. I’ve helped a lot of professionals get unstuck and live freely.
It’s one life and make it worth it.
Write to me at and we’ll find solutions to your problems, whatever they are!

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