3 Painless Ways to Start a Difficult Conversation

As a communication coach, I find that the most common way people deal with difficult conversations is to avoid them as long as possible.

You already know that this is both painful and highly ineffective.

It takes a ton of energy to avoid something. The thoughts and feelings take up valuable real estate in our bodies and minds.

And nothing changes.

The best thing you can do for your well-being, and to improve every relationship you have, is to go forward and engage in those difficult conversations.

Getting these conversations started is often the hardest part.

Here are 3 tips to make it a little easier to get words to come out of your mouth.

1. Be gentle, calm, and straightforward

The way you start the conversation matters. The mantra you need is this: gentle, calm, straight-forward.

Here’s what that means:

Gentle: A neutral tone, devoid of hostility.

Calm: Feeling as grounded as possible.

Straight-forward: Use words that tell the person what this is about.

Starting from a neutral place when we are calm sets the right tone. You are more likely to have someone be open to you and your message.

Being clear about what you are saying prevents confusion and assumptions.

Here’s what this might sound like:

“I’ve been reflecting on the conversation we had the other day and some parts of it are unsettling to me. I’d like us to talk some more.”

“I’d like us to talk about what happened the other day. I still have a lot of feelings, and it’s uncomfortable but I think it’s important to clear the air.”

“This is uncomfortable for me, but I’d like to address something that happened recently.”

Remember, saying something is typically much better than saying nothing, so if you stumble and stammer, it’s okay. Let the words out however they need to come.

2. Use curiosity

Whenever you need to approach someone who might be on edge or defensive, a very effective technique is to take a position of curiosity.

To be curious is to be open. It’s the opposite of making a judgement. Therefore, people do not feel blamed or shamed.

And that’s a much better way to start a conversation.

It might sound like this:

“I know I had some feelings about our last conversation, but I’m really curious about how you felt…”

“I keep thinking about what happened in the meeting. I’m really wondering how you are making sense of it?”

“I have noticed tension between us lately. What do you think that’s about?”

While you need to get to the point of being able to express your thoughts and feelings, starting with curiosity can really open up the conversation and allow the other person to more fully hear and consider your words when it’s your time to speak.

3. Name your intention

During difficult conversation one area of tension and distraction is the subtext: “what is this person’s motivation right now?!”

Wondering what people are getting at and why they are engaging us in the conversation makes it hard to focus on what is being said.

It also leaves room for assumptions.

One way to start a difficult conversation is to name your intention from the get-go. You need to be honest and sincere—don’t make up something that sounds good.

Naming your intention sounds like:

“I care about us having a good working relationship. I’d like to address some areas of tension so we can both move forward.”

“I know that we are both good people who got heated. I’d like to start that conversation again and see if we can both feel better about it.”

“I want to make sure I’m clear on what you said. I think I was taking things too personally and I’d like to try to better understand.”

Clarity on where you are coming from and what you want to discuss is respectful and it puts people more at ease.

Why it matters to have a difficult conversation

As humans, we all crave connection and belonging. It’s an essential part of our being.

Avoidance creates disconnection, anxiety, a sense of isolation. It’s taxing for all involved. When you provide the chance for a conversation, you allow the opportunity to build, repair, or re-connect.

Even if these conversations are difficult, you are doing something that will ultimately be positive and relieving.


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