Have you watched ‘The Hobbit’?  Do you remember this scene? Bilbo Baggins is running out of the Shire with arms flailing. Someone from the Shire calls out, “Mr. Bilbo where are you off to?”  Bilbo shouts back, “I’m going on an adventure!”  There are lots of great scenes in that movie but this one is my favourite.

How do you experience adventure? For me, it’s taking a journey that begins in a place of familiarity (my Shire).  The adventure begins outside the Shire. Adventure is experienced in places where I have little control over the outcome. When I go on an adventure I am placing my trust in a story bigger than myself. As a result, I change, and so do those who are on the adventure with me.


It is kind of like that for me every Wednesday at 9 am when I arrive at a local coffee shop. Each week I have a ‘standing’ conversation gig with a fellow co-worker. Seldom is there a week that goes by without the two of us getting together for coffee. Our conversations seem like only 20 minutes when in fact they are more like 90.

Last Wednesday, I prepared for another adventure (through conversation) with my friend. We’ve been doing this for over a year now. Because of the type of jobs we have, I’m always the first one there. My friend often arrives about 15 minutes later. So, here I am getting two coffees with single cream from the barista at Tim Hortons. Do they call them baristas at Tim Hortons? I get a table and I pray a simple prayer. ‘Father, how do you want me to start the conversation today?

Maybe now is a good time to interject something. The only part of the conversation I plan is the beginning part. ‘How do I start?’ It is the answer to the above prayer. I’m trusting Jesus to show me which conversational path to start out on. That’s it. Once I get the conversation started I leave my Shire and off I go on another adventure as I make no attempt to control the outcome.

Back to the story… My friend comes in and I notice there is something about his demeanor that is different. We go through our weekly ritual of saying hello to each other. But we like to do it in such a way that usually halts the conversations going on at the tables near us. We’re not very Canadian in that respect. He sits down, and I begin the conversation. Today I blurt out… “My friend, tell me a story.”

He looks at me and then begins to tell me, what happened the day before. He had exploratory surgery.

For the next 20 minutes I listen to everything he shares and I ask a few questions here and there.  I agree with the experts that the key to being a good conversationalist is listening and asking good questions. Every time I ask a question I try to do two things….show the person that I care about who they are and to let them know I’m interested in their story. With that always in mind, my three ‘go to’ questions are ‘How, When, & Why’ questions.

My friend began to share intimate details of the surgery. Along with that, he included all his emotions from before and after the surgery.  In a sense he was re-living the experience. You don’t have these kinds of procedures without wondering if your life is about to take a major turn.

In this case, I am happy to say that my friend was celebrating life, because he received an ‘all is well’ report. What they discovered was benign.

Are you kidding, I wouldn’t miss this time for anything!!

Yet, this conversation was different from our normal pattern. Instead of 90 minutes or more it ended after about 45 minutes. He was physically uncomfortable. Remember, it was only 24 hours after the invasive procedure. He should have been home resting and not sitting in a coffee shop with me.  I suggested that maybe we should call it a day so he could go home and get some rest. As we were walking out of the coffee shop I said, ‘you know, we didn’t have to get together this morning. We could have skipped coffee this week. His response: “Are you kidding, I wouldn’t miss this time for anything”.


That phrase alone is ‘gold’. It tells me that our conversations are meaningful to him. I think it might be helpful for you to know that my friend is not yet a follower of Jesus. But every week we have some of the richest conversations. They are meaningful to him and they are an adventure for me. More important, I know God is work in both of our hearts.

The most important skill to develop as an encourager is the skill of conversation. Not the kind of conversations that draw attention to yourself (remember you are the encourager). Instead, aim for conversations that are meaningful to the person you are with.

For me it comes down to two things. More than anything, I want every person I have a conversation with to walk away believing l value them as a person. Second, during every conversation I am learning to ask specific kinds of questions that help the conversation go to the core of what is most important to them.

My hero in this style of conversation was Jesus. Have you ever noticed how he engaged people in conversation? He was a master at meeting people on their terms and he zeroed in on where they were at, not on where he wished they were.

I believe that Jesus is always providing me opportunities to encourage the people I’m with. My task is to let him show me how to start the conversation and then follow his promptings throughout the conversation. I do that by learning to listen with all my being, and to ask better questions.


Here are four things I now focus on as I learn to improve my ability to host meaningful conversations with others.

  1. Whenever I begin thinking about something to add to what they are sharing, I am training myself to immediately toss it out. Trash it. Hit the delete button. No matter how brilliant or insightful I think it might be I drop it. I’m learning to immediately refocus on what they are saying.
  1. I listen for anything that piques my curiosity, especially these three things. Aspirations. Goals. Priorities. By the way a great question to ask if you want to learn someone’s priorities at the moment is to ask: “What challenges are you facing these days?
  1. My 3 favourite questions to keep the conversation going are questions that begin with ‘How? When? or Why?’ Whenever I ask a question I try to frame the question in such a way that they know I validate them as a person.
  1. If I listen well I can usually detect what is important to the person I am speaking with within minutes of starting a conversation. People usually don’t take long too talk about what is important to them if they know you care. Building trust is my highest priority when I start a conversation with someone.

If you want to become more effective as an encourager begin here. Start to grow in your skill of having Jesus like conversations with people. Like Jesus, ask great questions. Focus on where they are now. Show them that you value them as a person. Leave them with the understanding that you care about their thoughts and opinions on matters that are important to them. Help people understand how valuable they are, no matter where they are on their journey.

Before you leave I want to invite you to consider the value of having a coach in your life right now.
 Here are some thoughts I have that might help you explore that idea further. 

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