How to Master Difficult Conversations

The following is a chapter from my free eBook “Overcoming the Two Roadblocks to Change”
Grab your free copy here!

Mastering Difficult Conversations

A person’s success in life can usually be determined by the number of uncomfortable conversations he or she is willing to have.
— Tim Ferris

It’s impossible to change our lives without an uncomfortable conversation coming up at least once. For many people, it can be as simple as saying no, asking for what we want or communicating our preferences.

Or it can be a conversation with a boss letting them know we’re leaving, with an employee letting them know they’re fired, with a date letting them know they’re not the one or with our children about what we will no longer tolerate.

Difficult conversations are a part of life and mastering them is the key to healthy, supportive relationships.

So what stops us from speaking our truth? From being honest about the person we are changing into?

People have expectations of us. Perhaps we made agreements that are no longer true for us.

Whatever the case, we always have permission to change our minds and to express our newfound clarity with the people in our lives.

After having gone through countless interactions where I could literally feel my pulse going up and my biological responses going haywire, I’ve learned how to make them a lot easier.

One thing I noticed, from looking at my past, was that when I approached a conversation that was uncomfortable (where I thought the other person would be upset), my whole demeanor would change, as if my somber tone would somehow prepare them to receive the “bad news.”

But after getting a little perspective, I realized if I stay in a situation that’s out of alignment, no one wins.

So now I see conversations, where the truth is being revealed, as a gift to the other person.

When I sit down with them or call them, I stay in the emotion / vibration I want them to feel, which is a positive one. I also expect them to receive the news well, so my tone and delivery completely changes.

I show them all the benefits that are in it for them and how, without this change taking place, it's not going to be good for either of us.

No one can really argue with that.

If these conversations are approached in the right way, everyone walks away feeling lighter because everyone’s finally on the same page.

They are no longer believing in a reality that is untrue and they will thank you for that. Maybe not immediately but in time, they will.


1. Think of a conversation (or two) that you’ve been avoiding.

2. Next, write down what you’re afraid of. Is it hurting the other person's feelings? Are you afraid of their reaction? Of exerting your power or of the outcome? Are you afraid they’ll walk away?

3. Next, write down the consequences of staying. Sometimes we’re afraid the other person will walk away from us (whether it’s a friend, romantic or business partner), but what happens if we stay and nothing changes? Is that a relationship we want to be in?

4. Maybe you lack clarity around a delicate topic. What happens if you don’t get the clarity you need?

5. What we might find from looking at the consequences, is that, unless there’s a shift, maybe we’re the ones who actually want to leave.

6. This is about releasing attachment to the outcome and instead choosing the truth as our anchor at all times. It’s about learning to speak our truth in the most loving way, while honoring our boundaries and not giving our power away to others.

7. Next, write down all the ways they will benefit from knowing the truth. Consider their best interest. How can you communicate this? Perhaps you want to leave your job because you daydream all day about your new business venture and you’re not getting anything done. Maybe you can help them find a replacement? Think about how you can serve or support the person even if you’re planning on walking away.

8. Then, ask yourself how you’d like them feel? Empowered? Optimistic? Understanding? Even if it feels like a stretch, try to imagine it. Then when you start the conversation, start off with that tone and try to leave with that tone, while staying as authentic as possible.

9. Lastly, schedule a time to meet or make the call (Try not to make it sound serious, just let them know you’d like to talk).

*The article is an excerpt from my free eBook (Chapter: Mastering Difficult Conversations) Overcoming the Two Roadblocks to Change – Grab your free copy here! 

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