Celebrating the 12th Anniversary of LeadingWithQuestions.com

All this week, we are celebrating the 12th Anniversary of LeadingWithQuestions.com with the release of my newest free eBook: “340 Questions Jesus Asked”   You can request the download of your free eBook @ LeadingWithQuestions.com/books

Today sharing from Chapter 14: 


By Lesley Cheesman


How do you go about making friends? One of the most fundamental needs you and I have in common is our need for deep relational connection. For friendship. Societies and communities are built on human connection. As vital as food and water is to our bodies, so is our need for people who are close to us. Despite travel and technology making it easier than ever to be in touch with others wherever they are, loneliness is now one of the great scourges of the 21st century. So much so that in the UK, where I live, the government have appointed a Minister for Loneliness to tackle the issue.

And it’s particularly an issue for the younger generations. In 2023, a study on loneliness in in the UK discovered that people aged 16 to 29 were twice as likely to experience loneliness as people who are over 70. It seems the younger people of our society are having a crisis of friendship. But those who are 30 to 49 are not far behind.

Loneliness is not a small issue. It has the capacity to wreak devastation on many fronts. It impacts our health, our ability to learn, our productivity at work, our economy . . . I could go on.

Friendship is not a luxury. We need friends. God made us that way.


Jesus demonstrated the importance of friendship throughout his life and showed what true friendship is. In fact, the greatest gift he gave to people, then and now, is a way for each of us to find the ultimate friendship—friendship with our Creator.

Jesus, the great question asker, made strong connections with people by asking questions and giving them the space to ask him questions also. Some people are cautious in question asking, fearing it’s rude or risky to ask too many questions, particularly personal ones. Charles Dickens famously wrote in Great Expectations: “Ask no questions, and you’ll be told no lies.” Dare I say, that is a rather cynical approach to life and one that Jesus was not signed up to! Of course, asking questions doesn’t mean that someone automatically bares their soul in response, but it’s the doorway to discovering each other’s stories. As we take the risks of inquiring and revealing more of ourselves, not only does it enable a person to access who we are, but we also often discover something of ourselves in the process. This is the joy of friend-making.


Let me take you back to first century Palestine.

It’s the middle of the day and Jesus is passing through the region of Samaria. Tired from his journey, he stops at a well. Instead of helping himself to a drink at the well, he waits until a woman arrives at the well and he asks her, “Will you give me a drink?” Now, Jesus is perfectly capable of getting a drink for himself—he’s the Lord of all creation! So what’s his motivation for asking for water from this woman, who as a Samaritan would be shocked and embarrassed to be spoken to by a Jewish man? Jesus is looking to make a connection with this woman. He is taking the initiative to start a conversation that would lead to an unlikely but life-transforming friendship. Their conversation begins with a simple ask, “Will you give me a drink?” but that ask creates the pathway to a much deeper conversation. The conversation, a dance of questioning and responding, listening, and understanding, paves the way to friendship.

Great friendships often begin with a simple question.


I love reading books. So when someone I knew asked, “Would you like to start a book group with me?” I jumped at the chance! The idea was to invite some of the other moms from the school where our children attended. Books and people, what’s not to like! In truth, as much as I enjoy a good read, I wasn’t as interested in chatting about books as much as I was interested in investing time in friendship.

The people were invited, and a date was set for our first gathering. To be honest, the book that we’d chosen to read turned out to not be “my cup of tea,” but that didn’t matter. We were going to get together, over a cup of tea and some cake, to chat.

Through the process of asking each other questions about what we thought of the storyline and the characters, we started to discover something more about who we were as people, particularly as we related some of the things that happened in the book to things in our own lives. As we asked each other questions about the book, it took us to much more personal questions (and even more so over the years that we got together), but a particular question from that evening has stayed with me ever since, mainly because of the response it elicited. A question was asked of the whole group: “Why do you go to church?” In many ways this wasn’t a strange question as all our children attended a Church of England school. However, the answers we all gave were quite different. We all took turns to talk about our motivations and experiences and I happened to be the last one to answer. My answer seemed to be a little different to the others as I didn’t so much as talk about going to church as I did about how I’d come to know Jesus as my friend. One of the ladies who I knew a little better than the others responded, “I can’t get enough of you talking about Jesus. It’s like you really know him!”

I do know Jesus. And he has helped me to understand many things, including the importance of friendship and how being curious and asking great questions paves the way to deep friendship. We all have a story. When we give space by asking open curious questions, listening well to the answers, responding with grace, and asking further questions to go even deeper, we make friends.


Being curious is powerful when it comes to making friends because it enables us to ask real questions. According to Harvard University research, your likability grows when you ask someone questions, especially follow-up questions that demonstrate that you’re listening, that you’re interested, and that you care. Showing a genuine interest, “wondering” our way into the conversation, often reciprocates itself. Here are some things that I’ve learned in my own wonderings and pursuit of friendship.


School-aged children learn that, to make new friends, you need to walk across the playground and ask someone if they want to play. As adults we sometimes overcomplicate it. But the principle for us is still the same: walk across the room or across the street, introduce yourself, and ask an opening question. Our neighbour’s favorite question is “Can I help you?” An opening question doesn’t need to be deep (in fact it’s best at this stage if it’s not); it just needs show interest and start the conversation.


I confess I don’t love small talk. I’m the kind of person that wants to jump in deep straight away, but I have learned that seemingly small talk about where you are from, what you enjoy, and how your weekend was, is a gentle way to connect and establishes some common ground and shared interests that eases the conversation into deeper topics. It’s like starting in the shallows on the beach, testing the temperature and current of the water, before being ready to wade into the deep and go for a good swim. Be genuinely interested.


Building a mutual friendship happens when each person is given the space to ask questions as well as to answer them. It’s about discovering each other. If we ask all the questions and don’t give space either for their questions or to share information about ourselves, it can come across as more of an interrogation than a conversation!


An invitational question is one of the best ways to build new friendships! Friendship takes time. Asking someone if they would like to invest time with you beyond this conversation communicates value to that person and shows a commitment to developing the connection.


 What a question! As someone takes the courage to share something a little more personal in their lives asking to hear more about it shows interest and a desire to know more of who they really are. It shows you like them. Friend-building conversations are not just sharing information, they are a process of discovery upon discovery through curiosity and insightful questions. It’s this kind of connection that starts to touch the soul.


Our stories are important. When we give space by asking open questions and hold a nonjudgmental space with what people share, we get to share a beautiful exchange of life and experience that inspires hope and the possibility of something more. To be seen and understood and embraced as who we are creates a generosity of friendship that enriches our lives and spurs us on towards all we can be. A mutual sharing with empathy and kindness in ways that Jesus himself fully demonstrated for us. Time and again I have experienced this with new friends and old.

The pursuit of friendship is a life-giving adventure full of discovery aided by great questions. Who are you going to take the initiative with this week?

Lesley Cheesman is the National Director of Agapé UK, part of Campus Crusade for Christ International. With 35 years of missions experience, she also serves on the regional leadership team for CCCI in Europe and is a trustee of Saltmine Theatre Company. Lesley is passionate about helping people to discover Jesus. She is married to Paul, and they have two grown children both of whom have now “flown the nest.” For more information, go to agape.org.uk

Click HERE to request your free “340 Questions Jesus Asked” eBook today!

Bob Tiede


Bob has been on the staff of Cru for 52 years. He currently serves on the U.S. Leadership Development Team and is passionate about seeing leaders grow and multiply their effectiveness. Bob and his wife, Sherry, live in Plano, TX and are blessed with 4 incredible children and 8 remarkable grandchildren.


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