How to Start a Difficult Conversation

Is there a conversation you’ve been putting off because it’s too difficult or you don’t know how to get started?


  • you’re angry with someone for something they did or did not do
  • you feel guilty or embarrassed about something you did
  • you need to confront inappropriate behaviour
  • you need to share something you see needs adjustment in the other person

Difficult, awkward conversations crop up everywhere.

Why are difficult conversations so hard?

Difficult conversations can be hard for a number of reasons:

  • You hate conflict
  • You’re afraid of saying the wrong thing
  • You’re afraid nothing will change
  • You fear a blow up or losing the relationship
  • You lack healthy boundaries
  • You’re embarrassed to talk about it

As a result you often avoid difficult conversations, delay having them, or keep silent.

Why are difficult conversations important?

Difficult conversations can strengthen your most important relationships because they create understanding and connection.

If you can’t initiate an interaction, you can’t fully express your needs, wants and concerns, and you won’t resolve any of the issues you are having.

Avoiding a difficult conversation leaves you with feelings that fester and turn to resentment which impacts your relationship.

How to start a difficult conversation

How do you overcome your fear of conflict and dive into a difficult conversation without making things worse?

Ask permission to talk about something that may be difficult

You could say, “I’m not sure how to say this, but I wanted to talk to you about ________. Would it be ok if we talked about it soon?”

Saying something like this immediately paves the way for the tough conversation.

If they refuse, ask them when they will be ready because it’s important.

Don’t let not knowing how to start be the reason you remain silent.

Plan what you will say in advance

The Bible gives good counsel on how to plan for tough conversations:

“The heart of the righteous studieth to answer: but the mouth of the wicked poureth out evil things.” Proverbs 15:28 (KJV)

Think and pray about what you want to say, then write down your thoughts.

Doing this does two things for you:

  1. It helps you stay on track when having the conversation so you don’t get side-tracked by other issues.
  2. It helps you stay on track if you tend to lose your thoughts due to fear of conflict.

If possible, sleep on it. It’s very likely that you will have new thoughts about the situation the next morning.

However, sometimes feelings simmer down with time and the need for talking about the issue diminishes.

If this conversation is important, don’t let fear or the desire to avoid conflict prevent you from having it. This is the time to operate on principle.

Deal with yourself

As you plan what you will say, figure out your purpose for the conversation. Be honest with yourself – our purposes are not always honourable:

  • What are your intentions?
  • What do you hope to accomplish?
  • Are you trying to punish?

Your intention should not be to have a toxic dump on the other person, but to either heal or grow your relationship.

Check what “buttons” of yours are being pushed. If you are you feeling more strongly than the situation warrants, there’s likely a trigger. What is your backstory? What personal history is colouring your thinking?

Consider how you may have contributed to the problem. Have you provoked? Have you neglected to establish and express boundaries? Have you misunderstood the other person?

Agree on ground rules

If you think there’s potential for a blow up, set ground rules before you start:

  • No swearing
  • No shouting
  • No name-calling
  • No interrupting
  • Give each of you sufficient time to express yourselves
  • Take time out if things get heated but agree to come back and continue the conversation

Related: 14 Things not to do when you’re in a fight

Be willing to listen

James 1:19 says, “…let every man be swift to hear, slow to speak…” (KJV)

Part of good communication is listening well. Don’t listen to reply, listen to understand.

Put yourself in the other person’s shoes. See the problem from their perspective.

Give each of you fair opportunity to express yourselves.

Related: 2 Ways to improve communication skills

Be willing to be wrong

Sometimes hearing the other side of the story gives a totally different perspective. Be willing to acknowledge that you were wrong if that is so.

However, don’t take the blame or apologise when you are not at fault.

Get clarity on the next step

At the end of the conversation be sure you both know what the expectations are.

Will you continue the conversation another time?

Is there something either of you needs to do?

Related: How to talk about issues in marriage instead of ignoring them

Leave the conversation open

Agree that, at any time, both of you can come back and re-engage about the issue you’ve been discussing.

Sometimes a little distance creates different perspective and allows new thoughts to surface. Give each other freedom to share those new thoughts without being blamed for digging up old issues, “I thought we discussed this. Why are you bringing it up again?”

Difficult conversations are … difficult, but if you can’t say what’s on your mind, then you’re not fully taking care of yourself.

Your ideas and feelings are as important as the other person’s, and unless you have the difficult conversation, the other person may never know what’s going on.

Ephesians 4:15 tells us to “speak the truth in love” so that we “may grow up into Him (Christ) in all things”.

The result of successful difficult conversations is growth and maturity. Let that be your aim as you tackle your tough conversations.

How do you initiate difficult conversations? Do you avoid them?

About The Author

Jennifer Lovemore

Jennifer has three grown kids and is married to her best friend, Richard. She started this website as a platform to help families, and specifically women, to take control of their lives and grow themselves spiritually, mentally & emotionally, and to discover their God-given purpose and live it out with confidence. She is a trained Life Coach and has diplomas in relationship counselling and CBT (Cognitive Behavioural Therapy). She is a certified SYMBIS (Save Your Marriage Before It Starts) facilitator. She lives in sunny South Africa.

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