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.
For me, a helpful awkward conversation starts before the meeting: clarify what you want for both people and the relationship, separate facts from your interpretation, listen to the other person’s view and agree who will do what next.
Key Takeaways
- Prepare before you speak.
- Consider your own contribution to the tension.
- Share observations separately from your interpretation.
- Explore the other person’s facts and perspective.
- Agree on actions, responsibility and timing.
This Book Changed My Life
Then a few years ago I read a life-changing book, Crucial Conversations.
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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.
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 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. It is in my all-time top ten most influential books.
It changed my life because it gave me the practical tools to prepare for and lead 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.
Technology
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 and my frustrations. Thankfully, we arrived at a simple conclusion that has guided us in the last two years in significantly reducing 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.
Prepare Thoroughly
Prepare for the conversation by writing down your answers to these simple but profound questions.
- What do I want for myself? The other person? The relationship?
- How would I behave if I 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, respect the fact that 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?
My reflection questions for church leaders offer a wider framework for taking stock before you act.
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 don’t need to have the conversation now. Answering these questions has clarified the whole matter for me.
Use these three steps to help you guide the conversation.
Step One: Share Your Facts, Tell Your Story
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.
Step Two: Explore Their Facts, Understand Their Story
Understand their view, their facts, and their story.
Endeavour to understand their reasonable, rational, and decent thought process.
Ask:
How do you see the situation?
What did you see and hear?
How did you feel?
What actions did you take?
Step Three: Move To Action
Decide who does what and by when.
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.
Frequently Asked Questions
How do I prepare for an awkward conversation?
I write down what I want for myself, the other person and the relationship. Then I consider my concerns, my thinking and what I might be doing to make the situation difficult.
What is the difference between facts and my story?
Facts are what I have noticed. My story is the interpretation I am placing on those facts. I start with “I’ve noticed…” and present my interpretation tentatively, using words such as “I’m beginning to wonder…”.
What should I ask the other person?
I ask how they see the situation, what they saw and heard, how they felt and what actions they took. I want to understand their perspective rather than assume I already know it.
What if preparation changes my mind about having the conversation?
I have seen leaders realise, while preparing, that they needed to adjust their own thinking. Answering the questions can sometimes clarify the issue before a meeting is needed.
How do I finish the conversation?
I move towards clear action: who will do what, and by when? Di and I agreed on a weekly tech appointment. That practical arrangement helped reduce an ongoing point of tension.
For conversations with employees, I also explore the relationship between being pastor and employer in my guide to leading church staff. To grow the people around you, consider my approach to developing emerging leaders.









