Season 1 | EPISODE 8

The Heart of Christian Leadership: Leading Through Weakness

57:15 · April 25, 2023

In this episode, Jim Lovelady sits down with Bob Osborne, the Executive Director of Serge, to discuss a counterintuitive idea—that, in Christ, our weakness doesn’t disqualify us from leadership. And while we may sometimes acknowledge our weakness intellectually, it’s tempting to hide our struggles behind our competence and achievements. Bob shares powerful stories of how embracing our need for Jesus, day after day, is the starting point for God to use us more powerfully in our ministries and relationships.

In this episode, Jim Lovelady sits down with Bob Osborne, the Executive Director of Serge, to discuss a counterintuitive idea—that, in Christ, our weakness doesn’t disqualify us from leadership. And while we may sometimes acknowledge our weakness intellectually, it’s tempting to hide our struggles behind our competence and achievements. Bob shares powerful stories of how embracing our need for Jesus, day after day, is the starting point for God to use us more powerfully in our ministries and relationships.

In this episode, they discuss...

  • Adversity in Childhood—Unlikely Preparation for Leadership [04:34]
  • The Power of God’s Love and Forgiveness to Redeem a Lost Childhood [11:54]
  • Walking Alongside Pastors and Leaders in Times of Burnout [20:24]
  • Christian Leadership and Humility [30:35]
  • Embracing Vulnerability and Brokenness as a Leader [33:20]
  • How Leading Through Weakness Has Transformed and Grown Serge [41:46]

Thank you for listening! If you found this conversation encouraging or helpful, please share this episode with your friends and loved ones. Or please leave us a review—it really helps!

Referenced in the episode...


This episode was hosted by Jim Lovelady. Production by Anna Madsen and Sunny Chi. Music by Tommy Leahy. 

Our guest for this episode was Bob Osborne, Serge’s Executive Director. He and his wife Nancy live near the Serge home office in Glenside, PA.

𝑮𝒓𝒂𝒄𝒆 𝒂𝒕 𝒕𝒉𝒆 𝑭𝒓𝒂𝒚 𝑷𝒐𝒅𝒄𝒂𝒔𝒕 is produced by SERGE, an international missions agency that sends and cares for missionaries and develops gospel-centered programs and resources for ongoing spiritual renewal. Learn more and get involved at serge.org.


Connect with us!

Get in touch:
Questions or comments? Feel free to reach out to Serge’s Renewal Team anytime at podcast@serge.org



Welcome to the Grace at the Fray—a podcast that explores the many dimensions of God’s grace that we find at the frayed edges of life. Come explore how God’s grace works to renew your life and send you on mission in His kingdom.


Jim Lovelady 00:25 Hello, beloved! Welcome to Episode 8 of Grace at the Fray. Okay, I’ve got to tell you: I love that you’re following this podcast. I love that you’re joining us as we explore how God’s grace meets us at the frayed edges of a life lived on mission wherever God calls you. But if you haven’t read The Lord of the Rings, or at least watched the movies, you’re going to miss a lot of my references, like this one: 

It’s the one where Samwise Gamgee, as he and Frodo are going to Mordor, says, “It’s the one place in Middle-earth we don’t want to see any closer, and the one place we’re trying to get to. It’s just where we can’t get.” And I feel that way about weakness and vulnerability. It’s the one place in ministry we don’t want to see any closer and the one place we are all called to get to. And so often, it’s the place where we just can’t get. 

So here’s my question for you. Are you weak enough to be used by God? It’s a counterintuitive question because we spend a lot of energy making ourselves fit for ministry and capable of leading. And we spend a lot of energy navigating other people’s expectations of our leadership, all the while trying to remember that Jesus’ power is made perfect in our weakness. 

So this episode is about leading through weakness. It’s not about leading in spite of weakness, as if weakness is prohibitive of good leadership. No, it’s actually through our weakness that the Lord chooses to lead through us. So join me in my conversation with Bob Osborne as we talk about what it looks like to lead from a place of weakness and vulnerability. He’s the Executive Director here at Serge, and he has a powerful story of a life spent learning to lead leaders.

And in this episode, he and I share stories of weakness and vulnerability from our own lives. And as I worked through prepping this episode, I was struck by the way Bob’s openness and vulnerability encouraged me and led me to be open and vulnerable. I was thinking, “Why am I sharing these stories? I don’t want these stories to go online forever.” But as we shared our stories, I discovered a sense of camaraderie forming between the two of us, and it was around this reality: we all have stories of brokenness, rejection, humility, abuse, suffering, and hardship. But those are the frayed edges of life, where our Heavenly Father surprises us with His overwhelming and beautiful grace. 

Jim Lovelady 02:53 So you’re a chunky peanut butter guy. 

Bob Osborne 02:56 Yeah. 

Jim Lovelady 02:57 My dad always hated peanut butter. And I always would have peanut butter and jelly with chips and salsa for an afternoon after-school snack growing up. But it was never chunky. It was always smooth.

Bob Osborne 03:12 I had kippers and crackers for a snack. 

Jim Lovelady 03:15 Wait, what’s kippers? 

Bob Osborne 03:16 Kippers is a sardine. I love anchovies.

Jim Lovelady 03:21 That was your snack? I mean, I guess peanut butter and jelly and chips and salsa is kind of random. And a glass of milk. That’s pretty weird. But it’s not as weird as sardines.

Bob Osborne 03:31 Yeah, I grew up on Cape Cod. And so we had a lot of fresh seafood.

Jim Lovelady 03:35 I grew up on the border of Mexico. So we had a lot of fresh salsa.

Bob Osborne 03:39 I’m sure you did.

Jim Lovelady 03:41 So, I wanted to talk about leadership. And you said, “I’ve tried to develop my adult career leading leaders, learning how to lead leaders.” So I found that very interesting, especially when it comes to what it looks like to lead out of weakness. And since part of Serge’s DNA is ministry out of weakness, that means leadership out of weakness. So, Bob, tell me your story. I want to hear some of these big points in your life where the Lord has been teaching you how to lead, how to lead out of weakness, and then how to teach others how to lead leaders.

Bob Osborne 04:24 Right. Wow. Well, thanks, Jim. I think it’s a fascinating topic. There’s a fascinating connection between weakness and leadership. 

Jim Lovelady 04:33 Counterintuitive, right? 

Bob Osborne 04:34 Very, absolutely. And I will say, for the record, I’d much rather talk about weakness than actually experience weakness. So let me start right there. So my childhood was extremely, extremely difficult. It was painful. When I was born, my parents divorced. I went immediately into the foster care system, several foster care homes where I was abused physically, emotionally, and sexually, over a long period of time. And so those experiences left their scars on me. But I made this pact with myself when I turned 16 that I was going to leave home. My father fell down drunk on my 16th birthday. I grew up in the foster care system, but then when I was 12, I went to live with my father and stepmother. And that was a living hell because they were both fall-down drunks. They would work during the day and start drinking at 4 or 5 in the afternoon. By 6 or 7 pm, they were plastered, and they were falling. And so I would usually wait until they conked out, then I would go out of the house and be with my friends, and I did that for about four years. On my 16th birthday, I invited my father and stepmother to my friend’s house. And it was this beautiful clambake on Cape Cod. I loved the clambakes—lobster and clams. You throw those in a pit on the beach with coals and cover them with seaweed. 

Jim Lovelady 06:13 Oh, that’s awesome.

Bob Osborne 06:14 It is so good. So, so good. Well, my father drank and kept on drinking and then just fell down drunk. And I was so embarrassed. I said to him, “Look, I’m leaving home today. And I’m never going to talk to you again until you’re sober.” So I literally left home that day on my 16th birthday and went to live in a rooming house with Irish immigrants right off the boat. So I washed dishes at night. I put myself through a vocational high school. I studied carpentry. So the extent of my academic training was doing the Word Power in the back of the Reader’s Digest book. And so we’d have a week of shop and then a week of ridiculous academic made-up stuff. We were called “vokies.” We were the stupidest of the stupid. We were social outcasts. We were rowdy. We were mean. We were socially unacceptable. And so that was my high school. But then, in my senior year, my English teacher said, “You need to go to college.” And I just laughed, like a belly laugh.

Jim Lovelady 07:26 Don’t you know I’m one of those loser outcasts?

Bob Osborne 07:29 Absolutely. I said, “I have literally,” without bragging,” I have literally flunked every grade since first grade until now.” Not only did he want me to go to Cape Cod Community College, but he also wanted me to study philosophy and psychology. At that point, I nearly fell over laughing. Like, “Really? You want me to go from no academics to all this reading, philosophy, and psychology?”

Jim Lovelady 07:52 God loves you, and your English teacher has a wonderful plan for your life.

Bob Osborne 07:56 So he got me to apply, and then I got accepted. And so I spent the first year taking remedial math, remedial English, regular math, and regular English, and just slogged my way through it. I was on the honor roll. I went from having no academic background to being on the honor roll. And it was all because of that teacher, Bob Helmes, who took an interest in me. And yeah, so he took a risk.

Jim Lovelady 08:31 That’s amazing. There’s something symbolic about it being on your 16th birthday. Something clicked. There’s this switch in your mind and heart where you’re like, “Wait a second, I’m not going to live life this way.” I went through something similar when I turned 13 or 14. Between eighth grade and ninth grade, there was a switch that I made in my mind that I was not going to be the loser that I was. I think mine was different, but it’s interesting how our childhood shapes us. And relative to the story that you just told, my childhood was very benign. But I was a nerd who got made fun of, a little guy who got picked on, and my last name is “Lovelady.” And so all the kids in kindergarten would say, “Jim loves the ladies.” And then, in high school, everybody was like, “Oh, cool last name.” It took a while, but there were insecurities. When I went from eighth to ninth grade, I made a switch: “I don’t want to live the life the way that I’ve been living.” And this is where I think it’s different from your story, but to this day, I’m not sure if I made a good or bad decision. I’m kind of looking back on my life, going, “Okay, now I got to figure out who I am and how I’m going to be.” That’s just a significant decision. So I look at your story, and I’m comparing my story to your story in the sense that that is a significant decision you made, and it has shaped your life. So how do you look back on that moment? And what do you look back on and go, “This is how that changed my life. This is how this made me into who I am today”?

Bob Osborne 10:34 The moment was profound on lots of levels. So when I was 16, I said to myself, “I’m not going to let my broken childhood and all of that abuse define who I am.” And so I started plowing my way through life and became an achiever. So, achievement became my god and my idol, and competence. And so if I felt like internally I was weak or unworthy or not measuring up, I would just work harder. I would be the best at whatever I could and hide that insecurity. I would say even today, at nearly 66, I still have this pit in my gut like, “Really, Lord? Am I really leading Serge? I mean, You’re really leading Serge. I’m like a distant, not even like a chief. I’m not even a sub-chief. I’m like a sub-sub chief.” And so that’s how I feel. I feel like most people in Serge are much more qualified to lead this organization than I am.

Jim Lovelady 11:43 Right. So you’re saying imposter syndrome doesn’t end? 

Bob Osborne 11:48 I feel like an imposter today!

Jim Lovelady 11:50 I know. Hey, this room is always filled with an impostor.

Bob Osborne 11:54 I woke up as an imposter. But looking back on that pact that I made with myself when I was 16, on the one hand, it was good for my survival emotionally. It was also really, really bad in walling off those emotions. It wasn’t until I went through a Sonship Week 25 or 30 years ago in Charlottesville, Virginia. Rose Marie had her hands on me and was praying for me, and the dams just burst. And I think at that moment, I really experienced the Father’s love and forgiveness for all of those years that were destroyed. My childhood years that were destroyed were redeemed in that moment, where I just cried and cried and cried. And I would say today, I have tremendous empathy for leaders and pastors—for pastors in particular. And so it’s a huge privilege for me to come alongside pastors to coach, counsel, and mentor just because of how God wired me. 

Jim Lovelady 13:12 These stories that I hear about people going through Sonship and the dam finally breaks—that’s my story, too. I was a crier as a kid. I was so embarrassed and ashamed that I would cry about anything. And one of the things that I decided when I turned 14 was I would never cry again. And my mom remembers seeing that “Oh, he doesn’t cry anymore. Interesting.” And so there was something, and she’s like, “You blocked this off.” I’m not going to show this kind of weakness because crying is a symbol of weakness. And, as I’ve been growing, recovering from that, since I’m 44, that was 30 years ago–30 years of trying to go, “Wait a second, what was it that I was walling off?” When Lori and I went through Sonship after I had been a burned-out missionary, we came back from the field, and we went through Sonship, and I cried in every session. And it was Sonship in person. We were one of the few that got to do Sonship in person. We would come into the home office, and it was just the way that the Lord, by His Spirit, would move in and say, “Hey, it’s okay.” And He would dismantle this dam walling up so many fears, emotions, and hurts. He dismantled it brick by brick and just the waterworks. I mean, now it’s funny because I will be watching a show, and everyone will be like, if it’s an emotional moment, everybody will look at me and say, “Look, Dad’s crying.“ So when you took Sonship and Rose Marie had her hand on you, and you’re just weeping, you’re experiencing the love and forgiveness of God, you’re kind of opening yourself up to weakness. So where did the Lord take you from there?

Bob Osborne 15:27 So I was on staff at a large PCA church. I was directing missions. I was directing the staff. I was like a chief of staff. I think my title was Director of Missions and Ministries. And so my wife and I had gone through Sonship as a part of elder training. But I think I got just enough to be inoculated against more of it. So I was actually the person responsible on staff for bringing Sonship Week to Trinity. And we had about 300 people there. As you know, Sonship Week consists of worship, small groups, and one-on-one time. I remember the forgiveness talk that Ruth Ann Batstone gave. Going into that talk, I thought, “I don’t have to forgive anybody. Nobody has to forgive me, and I’m not sure this is going to be valuable.” Well, within five minutes, I was weeping. And I don’t know how that happened or why that happened. But I just started thinking about all these people I had wronged, all these people who had wronged me, and that I had never brought that to the Lord.

Jim Lovelady 16:33 Dealt with that. 

Bob Osborne 16:34 So it was just sort of bubbling there. So then we went for our one-on-one discipleship, which was hilarious because there’s this guy from North Carolina. And I love North Carolinians. But they have this sort of prefix before saying anything like “Brother” or “Sister.” Okay, I know he’s going to start with “Brother.” So he didn’t. He started with “Sister.” So he’s like this six-foot-something guy in the Sunday school classroom. And I’m 6’4” in children’s Sunday school classroom seats that are like miniaturized. And so I’m hunched over, and my wife, Nancy, is hunched over, and this guy’s over here, and he starts with, “Sister, why are we here?” I’m thinking that has got to be the stupidest entry to a counseling session I’ve ever heard. And she said, “Well, my marriage is a mess. And I hate this church.” And I’m thinking, “What? We have an awesome marriage. This is an unbelievable church. Why are you telling this guy? A complete stranger?”

Jim Lovelady 17:37 You’re throwing me under the bus and throwing the church under the bus.

Bob Osborne 17:39 He looked at me and said, “Brother, you’re going down.” And I did. A lot of my idols were exposed at that point: idols of competence, comfort, and control. I mean, I had all these idols that I needed to really offer up to the Lord as a result of being exposed that week.

Jim Lovelady 18:00 That was Sonship Week. 

Bob Osborne 18:02 That was Sonship Week.

Jim Lovelady 18:03 Okay. Ruth Ann Batstone’s Sonship Week talk. It’s so funny. I do Sonship coaching. And so it’s fun to hear these different stories about how the Sonship curriculum has affected people and changed their lives. And you’re talking about the forgiveness lesson. And I tell people, everyone that I take through the Sonship curriculum, when we come to the forgiveness talk, I say, “Hey, I just wanna let you know, this is my least favorite.” Because I realized every time I take somebody through the forgiveness lesson, it’s a reminder that I thought I was really good at forgiving: I thought I was a very forgiving person; I’ve thought of myself as chill. And I realized this just recently, just over the last couple of years of being a Sonship mentor, that the reason why I think I’m a forgiving person is that I’m too arrogant to let people actually hurt me. So to come to a place where I need to forgive, 

Bob Osborne 19:07 That’s being self-protective. 

Jim Lovelady 19:08 Exactly. It means that I have to admit that I have been hurt. And I don’t want to do that. I don’t want to be weak like that. I don’t want to show that vulnerability. I want to be impervious to any kind of hurt. So if someone harms me or feels convicted about harming me, they come and say, “Hey, I just want to apologize.” I go, “Oh, hey, totally forgiven. No big deal.” 

Bob Osborne 19:30 You minimize. 

Jim Lovelady 19:31 Do you know why it’s no big deal? Because I think I’m amazing. And so every time I’ve come to the forgiveness talk, Jesus goes, “Hey, there are things in your life, if you really want to admit it, that you can’t forgive. And you’re having a really hard time forgiving so and so for such and such.” And this reminder brings me to this place of desperation where I go, “Oh, Lord.” Or just even that the sin of being too strong to need forgiveness. Well, Jesus put himself in vulnerable positions where He was hurt. And Jesus is someone who has been hurt and forgives. But I go, “I’m too impervious to be hurt.”

Bob Osborne 20:24 Well, I think that’s one of the biggest challenges as a leader, frankly, is to keep your heart open and tender to let the Holy Spirit continue to put you in those situations where you’re vulnerable. Most pastors I know and most Christian leaders that I know are isolated. They’re lonely. I think, especially during COVID, when you had all the George Floyd stuff, you had COVID stuff, you had political stuff that really pushed a lot of pastors, frankly, over the edge because they just couldn’t share their heart with anybody. And so it led to all sorts of really bad coping mechanisms, and a lot of pastors I know just left the pastorate and got involved in addictions, and it’s just awful.

Jim Lovelady 21:21 Yeah, one of the things that brought me to this is watching pastors throughout the last two or three years come to places of burnout. And for all the reasons you described and more. They’re just going, “You know what? I’m going to go work in finance, or I’m going to go be an insurance salesman.” or, 

Bob Osborne 21:42 “I’m going to work at Home Depot.”

Jim Lovelady 21:44 Yeah. “I’m going to do anything but this. Please, just anything but this.” And I don’t necessarily know how to fix that other than empathize with it and walk alongside, which I think is beautiful. So what have you seen? How have you walked alongside pastors over the last couple of years?

Bob Osborne 22:05 Well, it’s taken a lot of different forms. It started with me and several other pastors about 20 years ago. We recognized then, which is true today, that a lot of pastors were falling for whatever reasons: they were isolated; they were lonely. I like to say that pastors often drink a deadly cocktail made up of two parts: narcissism and isolation. So that’s a deadly combination. So what we started doing, we call ourselves the Stout Monks. So there are some reasons why we call ourselves stout monks. We like to enjoy one another; we like to enjoy good drinks, occasionally good cigars, and just good time together, but also delving deeply into one another’s hearts. So we tend to look at three areas. First, where do you struggle relationally? And so relationally, is it with God, your spouse, and your kids? Is it with colleagues? So it’s where you are struggling relationally? So that’s one. And then second: what are your glass ceilings? You want to be here, but you keep hitting your head, whether it’s not enough education, access, or whatever. But you can see where you want to be, but you just can’t get there. And the third thing is, what is your ten-year vision? What are you doing today that moves you ten years from now into that? And so then what we would do after each person shared, we would pray for that person and talk about those struggles, and then commit those to prayer for a year. And so we wanted to be actively involved in one another’s lives. And this continues for me today. I have two pastor friends that I do this with regularly. So I think the operative word is intentionality. I think that these kinds of things are the first to get cut from your schedule when you try to block out a week. And that’s the first thing to go, whether it’s work, kids, or whatever. So I’d say just being intentional and committed to one another, being real, honest, and not hiding.

Jim Lovelady 24:19 You’re talking about ministry to leaders. Where was it that you first turned outside of yourself, looked up, and saw all these leaders that were relationally vocationally crashing and burning? How did that happen?

Bob Osborne 24:37 Well, I think that really started back when I first became a Christian, how that happened, and then my first substantive job after that. So both of those were foundational in terms of how I relate to leaders today. So after we got married, my wife and I lived in Mozambique, and we also lived in Kenya. And we were not believers. But this Mennonite couple in Mozambique would have us over for food and Bible study. And there were only about 15 Americans in the whole country of Mozambique. So we said, “Yeah, we like the food. We like to have fun.” “The Bible study is a part of it.” “Sure. We’ll just do that.” And they never once said, “If you were to die tomorrow, why would God let you in?” They were never that blunt. They just fed us with the More-with-Less Cookbook, and we ate and had fun. And so then we moved to Kenya. So at that point, I thought, “Okay, missionaries aren’t so bad.” I didn’t grow up liking Christians very much. I thought they were rude, judgmental, critical, and just self-righteous, mean human beings. So I didn’t really gravitate towards Christians, but this Mennonite couple warmed my heart to think, “Okay, I guess not all missionaries are awful.” And so we moved to Kenya, and I started playing squash with this Nazarene guy. And we had a Thanksgiving meal with Australians, British, New Zealanders, and Americans. And so it was very international. But many of them worshiped at this old stone chapel on the shores of Lake Victoria in Kenya. It’s really quite beautiful. So they would worship in the evenings. And so we got grafted into that community, but as non-believers. So we’re kind of going through the motions, just so we could have the fun, the volleyball, the food, the movies…

Jim Lovelady 26:41 You belonged to that community before you believed with the community that believes.

Bob Osborne 26:45 Yeah, we were total belongers. And I would say if you ask the average person in that church, “Are Bob and Nancy Christians?” they would have said, “Absolutely. They’re Christians.” Well, we were absolutely not Christians. And they asked me to preach one Sunday. And so, I think just out of sheer ignorance and maybe arrogance, I said, “Yes.” And so I remember getting out a Bible and just having to get a Bible, and I opened it up to John, “In the beginning.” And so I started writing a sermon. I figured that I’d watched these people do it, so I can do this. 

Jim Lovelady 27:20 I can do this. How hard can this be?

Bob Osborne 27:22 Right, yeah. So I started making my outline. As I was making my outline, I became convicted of my sins; I just sort of stopped and wept in my preparation. And then Sunday evening came along, and I said, “Look, this is going to be a one-point sermon; I’m going to declare my need for Jesus tonight.” And I looked at all these missionary faces, they’re like, “Whoa, that dude’s not a believer. And we asked him to preach.” 

Jim Lovelady 27:46 I love this.

Bob Osborne 27:47 So three days later, I was baptized with a Hindu, a Brit, and a Kenyan. So I literally got converted in my very first sermon. 

Jim Lovelady 27:56 That’s amazing. 

Bob Osborne 27:58 That’s a God thing. 

Jim Lovelady 27:59 I love that. I love that.

Bob Osborne 28:00 So that moment just sort of opened my eyes. I had been following, motivationally, a humanitarian motivation for work. I wanted to help poor people. I still want to help poor people. But my motivation had nothing to do with spirituality or their spiritual well-being. And so that’s what really shifted when I became a believer. I started looking at the world through spiritual eyes. So we came back to the States. And there’s this little fledgling ministry in Virginia called Love in the Name of Christ (Love INC). It is an outreach ministry to the poor. The basic model is assessing the needs of the poor and mobilizing churches to meet those needs in Jesus’s name; giving a cup of cold water, if you will, in Jesus’ name to the poor. So I love that model of mobilizing the church. So I did that as a director for about eight years. We went from about zero to 900 volunteers during that time. And I just fell in love with pastors, with leaders; I would just go and spend hours with pastors. So I remember spending one hour—this is an amazing pastor story. So this guy was also a Mennonite, a charismatic Mennonite, and his church building was an old Episcopalian building. So imagine this: we’re on kneelers. So I would go, not so much talk about Love INC because I was just talking about “how are you doing?” And, so we were kneeling, and I started weeping. And he looked at me and said, “Brother, you have unforgiveness in your heart. And God wants to remove that so that you can be more effective in your ministry to pastors.” And he said, “It’s a burden that you’ve been carrying against your father for abandoning you at foster care. And until you can forgive your father, God can’t really fully use you.” So it was really heavy, really powerful. And then, two weeks later, I was at this conference of national Love INC directors, and I was very zealous. If there was a prayer meeting, I was there. And so, at 5 o’clock in the morning, there was a prayer meeting. And there was this woman from California. When she started praying, she fell down and started weeping. And I thought, “This is a little weird. I’m a little outside of my comfort zone right now.” And she said, “I’m weeping for you,” and pointed at me. 

Jim Lovelady 30:35 It got really awkward.

Bob Osborne 30:37 And then I thought, “Okay, now this is over the top.” And so she started naming things, specifically in my childhood, my childhood abuse. God’s desire to use me, but I needed to forgive my father. I had no connection. She had no connection to Love INC. And she said money arrived in her mailbox to go to Chicago to this conference to pray for this young leader.

Jim Lovelady 31:00 Interesting. 

Bob Osborne 31:01 And that’s you. 

Jim Lovelady 31:02 Yeah. 

Bob Osborne 31:03 I thought, “Okay.” 

Jim Lovelady 31:05 Spirit’s moving.

Bob Osborne 31:06 So that was really huge in my spiritual development, realizing that I live in a spiritual world. There are forces of darkness, there are forces of light, and they’re colliding all of the time. 

Jim Lovelady 31:18 There is more going on than meets the eye. Absolutely.

Bob Osborne 31:21 So, however you want to parse that theologically, I’ll leave that up to you. But it really endeared me to pastors. So I would say I have a beautiful relationship with hundreds of pastors today. And we just connect very, very quickly over some really key aspects of just leading. I think God has taken down so many leaders who have been proud and not humble and not broken. So I would say, if any key characteristic of Christian leadership is missing in many leaders today, it’s that humility and brokenness and ability to sit as a son, but also as a sinner needing grace day after day.

Jim Lovelady 32:09 Yeah, this is fascinating because, in our culture, it feels like a bit of a catch-22. Here’s the cycle that we get into in terms of leadership: I have to put on my best face; I have to look amazing to get noticed and lead people. That’s the lie. That’s the normal trajectory that we all have, and we get rewarded for that. We don’t get rewarded for humility. So what you’re describing in terms of leading through humility and embracing vulnerability and brokenness is very counterintuitive to the natural way that we would look at someone who is qualified to be a leader. And there are so many times when we will put somebody in leadership because they’re “qualified for leadership.” And you’re saying, “No, humility, brokenness, vulnerability, and weakness are actually what make somebody qualified.” And so it’s counterintuitive for us, and it’s also counterintuitive for the people that we lead. So how do you navigate that?

Bob Osborne 33:20 I think you have to go further than that. I think it’s one thing to acknowledge your brokenness and your weakness, and your frailty, your besetting sins and your sin patterns and all of that; that’s important. It’s important for you to acknowledge those things. But it’s also important to live a life of dependence, faith, and prayer. And so I think people around you need to see that you are led by Jesus, not just by your own ideas, strength, or human abilities. There are too many leaders functioning out of their natural abilities. And if you can discern that, that’s powerful for you as a leader. You probably need input from other people. And that’s where you need to humble yourself as you need to seek critique and criticism from your peers, frankly. 

Jim Lovelady 34:15 Yeah, that’s really true.

Bob Osborne 34:16 I remember one of the first times I was leading a staff meeting of mostly pastors, and I said something like, “You know, I have an idea. I think that on Monday mornings, what we need to do is start critiquing one another’s sermons from the day before.” Well, you would have thought that I farted. There was complete silence. No one wanted to talk about that. I thought,” Why not? You’re obviously very secure men. You’re secure, and your identity is in Jesus; you’re His sons, and you know this. This would make you better. It would be good for everybody else.” Crickets. Okay, this is a sensitive topic.

Jim Lovelady 34:52 That’s a great example of an insecurity that probably most pastors have. I hate it when someone would be like, “Hey, that was a good sermon, but….” Your guard goes up. So that is a common insecurity. So how do you wiggle your way into the pastor’s life to where you can actually have constructive conversation and speak into their life?

Bob Osborne 35:19 I think you need to tell stories. I think you need to use the powerful medium of stories. Throughout the Bible, there are stories, like how David was confronted, for example. And I think for most pastors if you can say, “Look, you have to think of all of your fears. Like if we talk about X, just start naming your fears privately or publicly and then put those on the altar. And just leave them there and invite critique because those things are not you. Those things are not your identity as a son or a daughter. They’re going to either add or detract from something that doesn’t need to be added to or detracted from.” You start there. As I’m interviewing potential staff people, I want to know three things right off the bat: Do they know just how messed up they are? Do they realize just what a sinner they are? And so that’s one. And number two: Do they have a gospel framework to apply to that? And can they say, “Oh, yeah, I know that I really struggle with X, Y, or Z sins. But you know, God is bigger than that. I mean, He first loved me, so I can love other people,” and just sit in your adoption as a son. But the third thing is, can you get along with other people? If you can’t get along with other people, if you can’t play nicely in the sandbox, I don’t want you to be a part of my staff. And I don’t want you anywhere near Serge. Because that just creates all sorts of distractions. And humility, obviously. I’m much more impressed; I think God’s much more impressed with people’s teachability; and their humility than just their competence. I want people who acknowledge their sin, can apply the gospel to it, are humble, and can play nicely with others.

Jim Lovelady 37:13 Yeah. And it’s really tricky. People’s tendency to want to look at their leader, and kind of apply messianic Messiah kind of expectations on that person. Especially when you look at the average job description of a pastor—who is capable of actually fulfilling these job descriptions? And it’s just basically Jesus. So this is what’s crazy—Jesus goes, “Hey, I’m calling you to go say yes to that job description, which you are not able to do; only I can do it. But I will meet you there. In the middle of you failing all over the place, I will meet you there.” So there’s that reality. Then there’s a covenant or an agreement or a familial bond in the best scenario where the congregation goes, “Hey, we know that you’re not Jesus. We know that you’re not the person who is going to save us. But we do know that the Lord has called you to be our leader.” And so there’s this sober understanding of who everybody is in this relationship. The moment we start to confuse things—and it’s so easy! Here’s a story. I was pastoring a church that wasn’t doing things the way I thought they should, and so I was shaking my finger at God like, “This church you gave me, Lord….” My children were young, and I was disciplining one of my kids. I was disciplining Ephram, “Dude, you can’t do that. Blah, blah, blah.” Talitha, my youngest, was standing next to me with her shoulder up against my leg, with her arms crossed saying, “Yeah, Daddy, and you know what else he’s doing? He did this, and this, and this.” And I turned to her, and I said, “You’re not the daddy. You don’t have to worry about him. I’ll take care of you. And I’ll take care of him. You go off and play.” And the Spirit goes, “Timeout. Hey, did you hear what you just said? Hey, timeout. You’re not the daddy. I’ll take care of you. And I’ll take care of the church that belongs to me. It doesn’t belong to you.” And there was this moment when I realized that I was trying to be the Savior. I was acting like the Savior. And Jesus loves me too much to let me put on shoes that are way too big for me. But the beauty of that repentance was there was this exchange where Jesus goes, “Hey, do you want to let me be the Lord of my church?” “Yes, not just intellectually, but actually, I’m feeling it—the burden of this. I cannot carry it.” And He goes, “Alright, in exchange, I’m going to free you from these burdens.” And there was this repentance turned into this real legitimate, “Oh, why didn’t I do that earlier?” The joy of repentance is, “Why didn’t I do that earlier?” You know? 

Bob Osborne 40:15 Absolutely. 

Jim Lovelady 40:16 Out of the Spirit moving through my children, and in the way that I was disciplining my children is the way that the Lord even way better than me, disciplined me. Timeout. All right, you’re not the Lord of your church. And time in. And so that’s when I realized it’s okay to let go.

Bob Osborne 40:39 I think that God often uses things that are out of your control to shape who you are, especially relationships with your spouse, with your kids and with your colleagues. So that’s one huge area. Another one is health. I have been dealing with so many health issues this past year; it has been so frustrating, but also a hugely rich spiritual battle that’s been raging inside of me. That’s another whole podcast of how you deal with aging health issues, who’s in charge of your life kind of stuff. But then money. So I think that those are the three areas: relationships, health, and money that typically bring people to their knees, to surrender, and to give the steering wheel back to the Lord. I think again, sort of being desperate and acknowledging your need is the starting point for God to really use you more powerfully.

Jim Lovelady 41:46 So, how long have you been at Serge?

Bob Osborne 41:50 I’ve been with Serge now for 21, almost 22 years. 

Jim Lovelady 41:53 Oh, my goodness. So now, what does that look like in terms of the legacy of Bob Osborne at Serge and leadership out of weakness? What does that look like here lately as we’re thinking about the future of Serge?

Bob Osborne 42:12 Yeah, it really goes back to 2005 when the Board asked me to become the director. Back then, there was a lot of strife and turmoil on the Board and with the staff. We were asking questions like, “Are we a renewal organization? Are we a mission organization? Are we a publications organization?”

Jim Lovelady 42:34 All those things?

Bob Osborne 42:35 Yeah, consultants would say, “You’re really three organizations,” applying Good to Great’s hedgehog principle, “What are you best at? Don’t do other things.” And then at that point, we had been leading the culture in terms of talking about grace, forgiveness, repentance, gospel-centered, kingdom focus, and all those things were really our core message. And then they got adopted by some well-known people like Tim Keller, and then many others after him. And so, my response to being asked if I wanted to be the executive director was, “Do you want me to turn the lights out? Have we accomplished what we need to accomplish?” 

Jim Lovelady 43:19 Do you want me to end this well?

Bob Osborne 43:22 Is the goal to make reformed theology a lot kinder, a lot more inviting, a lot more accessible? I think we had made some good inroads there. Financially, there was this big New Era Ponzi scheme, and we had lost a lot of money. So financially, it was going to be a big upward battle. The Board had just asked for my predecessor’s resignation, and so many major donors went with that individual. And so it was a formidable thing for me to say, “Yes, I’m willing to be the executive director,” because I had to focus on the vision, strategy, and mission. I had to rebuild the board and the staff and attract significant financial resources to turn this ship around. But first, we needed to be in a posture of lament, humility, and brokenness because we had really blown it relationally. So for 2 or 3 years, I set out to make the office and our leadership kinder and gentler. We spent more time praying together and living out of our values. There was a huge disconnect between what we taught; our preaching and our writing did not match our behavior. So my first big job was to align our messaging with our actual actions as a culture of broken people trying to live out of this grace paradigm, but failing miserably to do that. By God’s grace, we got to a point where we were tremendously much, much healthier. Then we became really healthy around unifying this theme about missions leading to renewal, and renewal leading to missions. You can’t separate those. They’re part of the same dynamic. And so once you have good vision and good staff, resources will follow that. And so over the past 10 or 15 years, we have grown tremendously. I think when I first came, we were about, I don’t know, $5 to $7 million organization, with maybe 80 missionaries. Today, we’re nearly $30 million and nearly 350 folks overseas. And I say that not to be proud but to say God has been working in all of that. God’s Spirit has been working in all of that. And when you say legacy, for me, the greatest legacy would be that people won’t remember who Bob Osborne is. When I said to the Board, “I am not going to follow a charismatic leader model. I am going to be a behind-the-scenes leader. I’m going to lead from underneath; I am going to encourage; I’m going to build up; I’m going to strengthen folks to lead. But I’m not going to be an out-front charismatic leader. That’s not me.”

Jim Lovelady 46:21 I love that. It’s so counterintuitive. But it’s kind of a testament to your desire to be someone who leads from behind the scenes and to hear other people say, “What would we do? What would Serge have done without Bob?” Particularly when I was in London, and hanging out with Rose Marie, and the respect that she has for you, and the love that she has for you.

Bob Osborne 46:46 It’s mutual. 

Jim Lovelady 46:47 So to think about legacy, where the organization continues to move forward because you’ve tried your hardest to lead and point people to Jesus in such a way where you go, “I think I’m going to need to make this decision because I think it’s going to move us to Jesus,” in spite of how angry people may be with you, or how frustrated they may be with your leadership.

Bob Osborne 47:13 Well, there’s so much dying involved in leadership. And I would say, while the past 22 years have been enormously rewarding and gratifying on so many levels, just being a part of God’s movement here in America and around the world, I’ve had so many little dyings in terms of the people that I’ve had to let go or discipline and just all sorts of the pain, anger, and frustration of leading a growing organization. We’re very, very tight relationally within Serge. And so it often feels like you’re firing your mother, father, or something. But you know, many of the people that I’ve had to make those hard decisions about are actually still with us in some capacity or another. I’m not one of those heartless leaders who can make a tough call that will hurt someone’s life and not feel it. I mean, I feel it intensely. And so there’s a lot of dying in leadership. But there are also lots of principles that I have followed in my leadership that hopefully will continue: being transparent, being inviting, being generous, and playing bocce. You cannot play enough bocce. There’s so much you can learn about a person when you play bocce with that person. If I’m going to try to interview somebody I want to play, I want to play bocce with that person.

Jim Lovelady 48:46 Let’s play bocce together. If you find yourself playing bocce with Bob, you know you’re being watched.

Bob Osborne 48:50 That’s right. I’m evaluating here. 

Jim Lovelady 48:53 That’s amazing. 

Bob Osborne 48:54 But also, I have been trying to invest in the next generation for years. There’s an older, wiser mentor of mine; when I was turning 40, he said, “Bob, when I turned 40, I made a decision to invest 10% of my time in the next generation and then increase it after that.” And so I’ve been slowly trying to do that since I was 40. And so I spend a tremendous amount of my time investing in the next generation. And so I think in terms of a legacy, we have invited, empowered, and positioned young leaders throughout the organization, which I think leads to its healthiness. So, raising up young leaders and frankly giving women the opportunity to lead as well. I think that in many reformed circles, we’ve done a very bad job of providing opportunities for women in leadership. You just have to ask yourself this really basic question: “Have you ever seen a woman exercise leadership gifts?” Obvious answer to that is “Yes.” Okay. Do you think that those leadership gifts came from Satan or from Jesus? Well, I’ll go with Jesus. Okay, so Jesus gave women leadership gifts. Do you think Jesus would like to see those gifts exercised somewhere? Yeah, I think there’s an answer to that as well.

Jim Lovelady 50:18 Yeah, yeah. It kind of writes itself here.

Bob Osborne 50:21 I think we have some of the most amazing women at Serge that have tremendous gifts and capacity to lead and have been frustrated living under a predominantly male-dominated vocation. And so I believe we have a tremendous benefit from a mix of both men and women in leadership.

Jim Lovelady 50:44 Yeah, we have a lot to learn, and there’s a lot to move forward on that. I feel like I’ve just barely scratched the surface in this conversation. So I definitely want to have you on again. 

Bob Osborne 50:53 Let’s do it. 

Jim Lovelady 50:54 I feel like you have an enormous amount of wisdom. I think you would say, “Well, you just got to come and do life.” It seems like that’s been your ministry style: “Hey, let’s go shoulder to shoulder with whatever’s going on.”

Bob Osborne 51:07 Let’s take a trip.

Jim Lovelady 51:08 Exactly. And bocce ball may be a symbol of bigger things like, “Hey, let’s travel to Kenya, or let’s go to Ireland,” or whatever it is. “Let’s deal with this conflict,” or “Let’s figure out this or that.” 

Bob Osborne 51:23 Together.

Jim Lovelady 51:24 Yeah, together.

Bob Osborne 51:25 Yeah, absolutely. I feel like that’s been tremendously rewarding in inviting potential board members to serve. I love our board. I love board recruiting. I love just inviting our board members to help us solve or resolve real issues together. And so our board has a high, high, high stake in the health and success of Serge because they’re so invested.

Jim Lovelady 51:58 Yeah, in the stories that we’re making everywhere.

Bob Osborne 52:01 Their story becomes a part of ours as our story becomes a part of theirs. And it’s just—it’s actually quite magical. It’s hard to explain. I’ve often thought about that if I’m on a stage talking to an audience that has never heard of Serge at all—doesn’t know Serge—what would I say to that audience? My temptation is to say, “We’re really great people. You just need to hang out with us a little bit and do life together and see how we lean on Jesus, how we do brokenness, how we do celebration, how we pray and play. That’s who we are.” But you can’t do that. So we talk about our vision, our mission, and our strategies. Those are really good, but what’s best about Serge is life-on-life.

Jim Lovelady 53:01 Yeah. It really goes back to the people that made you who you are. The Mennonite couple that said, “Come over. Have a meal. Come belong.” And then the Christian group that said, “Hey, come along. Hey, you know what? Preach a sermon!” Again, we’re not saying, “Hey, come be this amazing thing. Come be this. And then you can belong.” It’s trying to run an organization. Of course, there are boundaries for all of those things. But to have an ethos that says, “Hey, let’s do life together and see what the Lord can make of that.” And it’s so messy, which is part of what makes it so beautiful. 

Bob Osborne 53:42 We’re all beggars showing one beggar where to find bread at the foot of the cross. That’s who we are. 

Jim Lovelady 53:51 Well, amen. 

Bob Osborne 53:52 Amen. So that’s a wrap?

Jim Lovelady 53:53 Yeah, that’s a wrap. Thank you so much.

Jim Lovelady 54:01 2 Corinthians 12:9-10 says this: “‘My grace is sufficient for you, for my power is made perfect in weakness.’ So I will boast all the more gladly of my weaknesses, so that the power of Christ may dwell in me. Therefore, I am content with weaknesses, insults, hardships, persecutions, and calamities for the sake of Christ; for whenever I’m weak, then I am strong.” So this is the question that keeps coming to my mind: Are you weak enough to be used by God?

This conversation with Bob Osborne was very convicting for me because as we were talking about one of my least favorite things to do, be vulnerable, I started to realize something. Here’s what you need in order to lead out of a dependence on Jesus: You need to be honest, and you need to have a community of people who can handle that honesty, and then show you forgiveness and grace. 

So I want to start with you: If you’re listening to this, I want you to think about all the things that make you feel like an imposter that “disqualifies you” from ministry, the things that make you feel too broken to be used by God. And hear this: your sins, past, present, and future, are forgiven in Christ Jesus, who holds the keys to death and hell and salvation. And He says, “There is no condemnation.” It’s from this place that the Lord calls you to a life of faithfulness and joy. 

Bob talked about how weakness feels like death. And you may understand intellectually that God’s power is made perfect in weakness, but everything in you wants to hide from that kind of death in the shelter of your own competence. Your mind understands, but your heart isn’t on the same page. You may feel the need to prove yourself or defend your reputation, or hide in shame.

If you’re aware of this struggle in your own heart, I hope you’ll join us in October for Sonship Week. It’s a week-long retreat designed to help you take the core theological truths of the gospel and apply them, so they begin to show up in your daily life, in your relationship with your Heavenly Father, and then overflow with joy to those around you. So join us October 22nd-27th at Park Road Presbyterian Church in Hollywood, Florida, and find a place to be honest, and find a community of people that are safe to be honest with, as we explore more of God’s love for us. 

But for now, beloved, as you go into the frayed edges of life, emboldened by the glorious grace of God, go with this blessing: May the Lord bless you and keep you; may his face smile down on you; may the Lord be gracious to you, and turn his bright eyes to you and give you his Peace. In the name of the Father, the Son, and the Holy Spirit, one God, life everlasting. Amen.

Bob Osborne

A graduate of the University of Massachusetts, Bob’s career began in Africa with relief and development organizations including UNICEF and CARE. It was during his time in Kenya and Mozambique that Bob came to Christ through the influence of missionaries serving there. That not only changed the trajectory of his life but also his work. Upon returning to the U.S., Bob served as Executive Director of the Charlottesville, Va., affiliate of Love INC and then as Director of Missions and Ministries at Trinity Presbyterian Church. Bringing together many aspects of his background, Bob joined Serge in 2002 as U.S. Director and was appointed Executive Director in 2005. Bob and his wife Nancy have two grown children and in his spare time, he loves to garden and play bocce ball.


Jim Lovelady

Jim Lovelady is a Texas-born pastor, musician, and liturgist, doing ministry in Philadelphia with his wife, Lori, and 3 kids, Lucia, Ephram, and Talitha. He is passionate about the ministry of liberating religious people from the anxieties of religion and liberating secular people from the anxieties of secularism through the story of the gospel.

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