grow a healthy church


How To Have An Awkward Conversation

How To Have An Awkward Conversation

I knew it was going to be an awkward conversation.

This leader had been a loyal and fruitful staff member for some years. But something had gone wrong.

I didn’t know what had happened but I knew attitudes had changed, demeanour had altered and now we were both unhappy with how things were panning out.

So I had the awkward conversation.

It was uncomfortable to tell them that their time on our staff was coming to an end and they needed to talk with their spouse and start processing this major change.

It was awkward but then again we shouldn’t be surprised that awkward conversations are just that, awkward.

I’m not sure anyone ever trained me how to have these types of conversations. I just developed my own techniques over the years and stumbled my way through them.

Some went well. Others headed south pretty quickly.

This Book Changed My Life

Then a few years ago I read a life-changing book, Crucial Conversations.

I was coaching a group of Salvation Army officers at the time and this book was one of the key texts in our coaching sessions. Our focus was on how to grow a healthy church.

I was amazed at the impact it had not only on me but on these officers. Like me, they were used to dealing with conflict in church life as they led their corps.

In fact, every pastor faces conflict. Sometimes it’s a church member who disagrees with a leadership direction or is angry that a program they loved has now ceased.

At other times the conflict can be with a key leader and this is particularly stressful. Why?  The stakes are higher when you are in conflict with a key leader because this can send a disruptive ripple through your entire church.

Also, you may have walked with this leader for many years and you love them and the friendship is a precious thing that you don’t want to lose.

Of course, the conflict can be closer to home and impact our marriage and relationships with our children or wider family.

I love this book. In fact, it is in my all-time top ten most influential books.

It literally changed my life because it gave me the practical tools to prepare for and lead an awkward conversation.

how to have an awkward conversation

An Awkward Conversation Changed Our Marriage

I used these tools in a key conversation with my wife Di a couple of years ago.

Di and I have had a genuinely happy marriage. We rarely argue and never really get angry with each other. Grumpy. Yes. Ticked off. Yes. Out of sorts. Yes. But never shouting and sulking for days. It’s just not our style.

However, we’ve had one ongoing point of tension.


I’m a geek. Di isn’t. She has an innate ability to do terrible things to phones, computers and iPads.

Then I have to step in and fix those problems.

Over the years I’ve been less than gracious when she’s needed me to step up and be her tech help desk.

Reluctant doesn’t even begin to describe my attitude.

It caused ongoing and unnecessary tension in our marriage so I decided to use the tools I had discovered in Crucial Conversations.

We had our awkward conversation and it went well.

I came to understand Di’s frustrations and her mine. Thankfully we arrived at a simple conclusion that has guided us in the last two years to significantly reduced tension in our marriage.

We now have a weekly tech appointment in which I solve her problems.

It works!

Let me guide you through the process of having an awkward conversation.

how to have an awkward conversation

Photo courtesy of Sharon Mollerus(CC Attribution)


Prepare Thoroughly

Prepare for the conversation by writing down your answers to these simple but profound questions.

What do I really want for myself? The other person? The relationship?

How would I behave if I really did want that?

What is at the heart of my concern?

How am I thinking about this issue?

What am I doing to make this difficult?

Is there Mutual Respect?  If not, what will it take to create it?If you don’t respect the person then respect the fact Jesus died for them

Am I telling myself a Victim or Villain story? A victim story is basically a self-pity, poor me story. A villain story frames the person as a horrible person. These stories will be playing out in your mind.

What am I pretending not to notice about my role in the situation?

Preparation is the key to an awkward conversation. As I’ve trained leaders in how to have an awkward conversation I’ve also noticed that preparing for the conversation can be enough to settle the issue in a leader’s mind.

They realise that the issue is primarily in their mind and they need to make adjustments to their thinking.

More than once a leader has said, I actually don’t need to have the conversation now. Answering these questions has clarified the whole matter for me.


Improve your leadership with my

Reflection Toolkit

Use it immediately

Guide The Awkward Conversation

Use these three steps to help you guide the conversation:


Share your facts. Start with, “I’ve noticed that…”

Tell your story as a story, not as a fact. Use statements such as “I’m beginning to wonder…”

Talk tentatively and encourage testing.


Understand their view, their facts and their story.

Endeavour to understand their reasonable, rational and decent thought process.


How do you see the situation?

What did you see and hear?

How did you feel?

What actions did you take?


Make a decision as to who does what by when.

how to have an awkward conversation

Photo courtesy of schalkandreas(CC Attribution)

Who Needs An Awkward Conversation?

How many crucial conversations do you need to have at the moment?

Who would benefit from an awkward conversation?

Is there a leader that needs a crucial conversation?

What about in your family?

Why not take the time now to prepare for an awkward conversation?

Even better why not train some of your leaders how to have an awkward conversation. But you might need to have one first to try out this methodology.

John is a wellspring of information, experience and advice in all things church. His responses were often out of the box of what's been said before.
Ps Christie Blaikie
Oasis Church

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