May 11, 2022

Derwin Gray on Sermon Series Planning – Episode 244 | The Unstuck Church Podcast

derwin gray on sermon series planning

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Preaching Best Practices for 2022 (Part 2)

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“The greatest message we preach isn’t in the pulpit, but how we live our lives and our own personal holiness.”

In Part 1 of our current series on “Preaching Best Practices for 2022,” I had a conversation with Brian Tome (Founding and Senior Pastor of Crossroads Church) to get his insights on the future of preaching and teaching. This week, we’ll explore another relevant topic for preachers today: how to approach your series and sermon planning. (Listen to the rest of the series: Rick Warren on making preaching applicable and Andy Stanley on preaching for life change vs. belief).


Derwin Gray is a husband, father, and former NFL football player. He is also the the founding and lead pastor of Transformation Church, a multi-generational and multi-ethnic congregation in in Indian Land, South Carolina. I recently had the opportunity to sit down with Derwin, a gifted preacher and communicator, to discuss how he approaches:

  • Preparing messages and series in advance
  • Selecting sermon series topics
  • Developing a teaching team
  • Discovering the real needs your church is facing
  • Encouragement for preachers and teachers
"The greatest message we preach isn’t in the pulpit, but how we live our lives and our own personal holiness." @DerwinLGray [episode 244] #unstuckchurch Click To Tweet "Your identity is not preacher or teacher. Your identity is Beloved by God." @DerwinLGray [episode 244] #unstuckchurch Click To Tweet "If you're not willing to clean toilets, then you shouldn't be in the pulpit either." @DerwinLGray [episode 244] #unstuckchurch Click To Tweet
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Are you a pastor who is looking to...

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  • Clarify what you should be teaching about in this cultural season?
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Tony (00:00):

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Sean (01:10):

Welcome to The Unstuck Church Podcast where each week we are exploring what it means to be an unstuck church. My name is Sean. I’m on hosting duty today here with my teammate, Amy Anderson. Amy, it’s always fun to be on the podcast, but you and I, we both live in the Northern part of the US where it’s finally just gotten warm. So I think after this, I’m gonna go outside for a bit. What about you?

Amy (01:32):

How do you know I’m not already outside, Sean? Now, before I start digging in the dirt today, we get to continue a great series that we launched last week on preaching. As Tony mentioned last week, we decided to interview some experts for this series because on this topic, we don’t feel like the experts. We can sense when it’s done well as we visit churches that we work with, but we don’t know what it takes to pull that off, to deliver an engaging, impactful teaching that compels us to take next steps that help us look more like Jesus. And I’ll add in, Sean, in the conversations we have with pastors and the work they’re doing when we’re on site with them, we know that preachers are always looking for ways to get better at what they do.

Sean (02:13):

Yeah, exactly. And for this week’s podcast, we’re actually sharing a conversation that Tony had recently with Derwin Gray. Derwin is the founding and lead pastor of Transformation Church in the Charlotte area. And interestingly, Derwin took a pretty unique path to becoming a pastor. He spent six years in the NFL before starting Transformation Church. So I think you’ll hear in the interview that his athletic background in football has really influenced how he even approaches preaching. So with that, here’s Tony’s interview with Pastor Derwin Gray.

Tony (02:49):

Derwin thanks for joining this podcast series on teaching and preaching, and I’ve watched you teach, and you can tell that you’re well prepared for your messages. And my guess is that preparation for game day on Sunday morning maybe a reflection of your past football experience, but help us understand how do you approach message preparation? Give us a sense of what that journey looks like.

Derwin (03:13):

Yeah. You know, the first thing that I would say is more of a philosophy, right? You don’t rise to the level of the moment, you rise to the level of your habits. And for some of our younger ones on staff, they’ll say things like, Hey, you’re about to do a podcast in two minutes. Are you ready? Or, Hey, you’re gonna do an interview or, Hey, you’re gonna go and speak. Are you prepared? And it’s what Paul told Timothy, right? Be prepared in season and out of season. And so what that means for me is, I’m always in the process of filtering scripture, the Biblical narrative, the story like I love the Bible. Now I love Jesus more, but I love the Bible because it teaches us about who Jesus is. And Philippians 2:5 says we have the mind of Christ. And so I wanna always be steeped and saturated in the redemptive drama, but also want to be aware to culture. So now what I do with my teams is with the communication teams, the creative teams, the production team, all that, is I’m usually, now I’m about seven months ahead now. And so like, I have my sermon series all the way from now up until the end of this year. So what that does is that gives our teams time to prepare, time to pray, time to create scaffolding for the message. Now what I’m doing is a lot of those will come out of my own private reading in conjunction with what’s going on in the culture as well. Like it’s the old quote of, “the Bible in one hand, the newspaper in the other hand.” Of course, no one reads the newspaper anymore, like that. So it’s like your smartphone in your other hand, right? Yeah. Yeah. But the idea is, and this is one of the areas where I wanna speak prophetically, is that I want more pastors to teach more about what Jesus has done, declaring his redemptive work versus a consumptive model of here’s what Jesus can do for you. So Jesus is more of a means to an end instead of an end. And I think there’s been a loss of the wonder and the awe of God. And we as Americans, even with the pandemic, we’re still doing so well that I think people are getting to the point of like, okay, life coach Jesus is not that appealing. You know, like I want Jesus that puts me in awe because of his character, because of who he is and what he’s accomplished. That’s the guy that I wanna follow. I don’t want a life coach. I wanna savior and king.

Tony (06:10):

That’s so good. Derwin. Just ballpark it. How much time do you guess that you invest in every message? Any sense of that?

Derwin (06:19):

Oh man. You know, those questions don’t work well with me because my Enneagram Eight Challenger wants to go, well my whole life.

Tony (06:26):

Yeah, yeah, I get it.

Derwin (06:28):

But you know, so various weeks, it varies. I mean, it’s definitely not 30 hours a week. I don’t even know how anybody could do that. I would say anywhere from five to 10, but I’m always like, I’m chewing on my message. I’m not preaching Sunday. I’m gonna preach to follow one, and I’ve already been chewing on it. So I want to embody it, but yes, I have time where I’m exclusively in it. So I would say in a week, probably anywhere from five to 10.

Tony (07:04):

Okay. So here’s a follow up then with that in mind. As a senior pastor, as a lead pastor, you have other job responsibilities too, aside from the priority of teaching God’s words. And so when you are invested, I mean, that’s maybe up to a quarter of your week in message.

Derwin (07:23):

Maybe. Yeah.

Tony (07:24):

Preparation study, crafting and so on. How do you free up your time so that you’re able to focus on your message in light of all the other responsibilities you have as a senior pastor?

Derwin (07:38):

You know, I think the first thing that I learned from my NFL days is the best coaches have a meticulous routine. And so I have a very meticulous routine that I go through. And so I stay like, so Monday I’m getting my sermon outline in to the team. I’m marinating on it. Tuesday before staff meetings,. I’m marinating in it. And then we launch it to the creative and communications team. Wednesday I’m marinating in it Thursday, I’m fully pouring into it. Friday is sabbatical or Sabbath. Saturday morning, I’m at Starbucks and I’m just going over and over it. And by that time, it’s just seeped up inside of me. So preaching and teaching for me, as I understand it, is that people’s eternities are shaped. So when I think of my life, and I see what God has done, the trajectory of my family has been utterly changed. People in my family have come to faith. My daughters graduated college. There was no one in my family before me who’s graduated college. Our son is about to graduate college. And so there’s like, this is a big deal, you know? And so, because of the way I grew up, there’s always a sense of like urgency. Like guys, I’m not up here just giving a little talk to give a talk. This is waging war against dark powers. This is walking in a victory of Jesus.

Tony (09:20):

Derwin. I know you aren’t the only teacher preacher at Transformation Church. In fact, it looks like you’re trying to build a multi-ethnic, multi-generational teaching team. Go figure, right? Because that’s what your church is all about. Why do you share the teaching load? Because I think a lot of pastors, and this is probably expectation from the congregation, that pastors are carrying. They feel like I need to be the person that’s up every Sunday, but you’re actually, I mean, you’re the primary teacher, no doubt. But you’re involving others in the teaching and preaching as well. I’m assuming that’s intentional.

Derwin (09:57):

Absolutely. I would recommend for every primary teacher/preacher to make sure that they’re cultivating and developing others to teach and preach, right? So we have, Pastor Paul will teach and preach. My wife and I will co-teach and preach, and I have two others that I’m developing as well. And so, yeah, that is very important because you need rest. But also it’s a way of multiplying and investing in the next generation. So with Pastor Paul, Pastor Paul, he’s white. He’s 65-66. So he’s gonna come at it from a different perspective. And I think that’s important. My wife comes at it from a different perspective. My role as lead elder/teaching pastor is to form and shape the theology and the doctrine of the church and to preach anywhere from 70 to 75% of the time. Like I don’t want to limit the gifting God has given me, but also teaching others to participate in that. And as you know, not everybody gets to teach just because they want to, you know? Right. And so like there’s a real danger, and I’ve seen it firsthand, when someone who has misdirected ambition gets the pulpit, it will destroy their souls, and sadly, Tony, as you and I have seen just over the last several years, these incredible ministries just falling with senior pastor blowups. And I thank God that one of the things he’s blessed me with is, you know, I’ve been signing autographs since I was 17. I played in the NFL. And so like being known as a preacher/pastor is really, it’s not that big of a deal compared to the NFL. Neither is it financially. And so God has graced me. And then, at the base level, it’s Jesus’ message. It’s the the Holy Spirit’s power. It’s the Father’s people. What is there to be arrogant or boast about ?everything is pure gift. And so making sure that people are prepared. And another thing that I look for too in communicators is are you always learning? You know, preaching, like you gotta watch and learn and you gotta want it. It’s not a step by step class, right? So if you haven’t been to hermeneutics class in school, then a part of it is, yeah, we can sit down and talk, but you have to watch and learn. That’s really, a lot of how I learned to preach. I learned passion from a guy named Adrian Despres. He was a youth evangelist. I learned dynamic preaching and sound theology from Tony Evans. I learned to sit in a chair from Andy Stanley and that only worked for about three messages. And I went, yeah, that’s not me. Spits flying. I’m crying. I’m like, no, let Andy rock that. You know, but the thing about Andy, and one of the things that I’ve prayed for, and he’s just like his dad is, I’m a compulsive stutterer. So words, to get a word out, is really hard. It requires maximum focus. And I believe God has used that, but for a guy like Andy, I mean the words just, I mean, they just sing out of his mouth, right? And so that’s one of the things watching him. I’ve prayed for that. So, so yeah, developing other teachers is really important, and it’s not programmatic. It’s relational. And for those listening who want to preach? When you get a chance and it say, Hey, the pastor says preach for 15 minutes, you stop at 12. You know? And if you’re not willing to clean toilets, then you shouldn’t be in the pulpit either.

Tony (14:19):

All right. So Derwin, in addition to all those things that you mentioned that keep you grounded as a pastor and as a preacher, on top of that, I would argue having a bold wife for me has kind of kept me in check, to not let me feel like too full of myself. She kind of helps keep me grounded. And I’m guessing Vicki does that for you too. Yes. And what’s been fun is I’ve watched you and Vicki do quite a bit of teaching together. And I’m curious, what’s that dynamic like when the two of you are teaching together?

Derwin (14:53):

Yeah. Okay. So when we first started teaching together, we would argue the whole week. And so the opening of the message was, well, let us tell you, as we prepared to preach this good news, all the arguing we did this week. Both of us are so competitive, but now in our older years, we’ve learned that our differences actually unite us. So Vicki actually doesn’t like to preach and teach from the pulpit, but I know she’s gifted. And what she’s gifted with, it isn’t the oratory capacity. It’s the wisdom and the best way I can describe it, it’s like the surgical specificness of the words that she’ll say, and the way we play off of each other at this point. And so a part of my role as her husband and as her pastor is to kind of pull her back, cause she loves organization, discipleship, spiritual formation, and I’m like, okay, we’ll teach together. So I’ll prepare the outlines, and then she’ll write in, here’s a story I wanna share. Here’s the exegesis I wanna share. And so we’ve just learned to do that. And the thing that I hear over and over and over again is this, the congregation says, we love it when you two teach. It brings this element of like, wow, mom and dad is home. It’s like, there’s this stability. And they see the way we love each other, the way we interact. And those are things that you can’t practice or are planned. That is 32 years of being together, being in Christ. And she loves the word as much or more than I do. And she’s incredibly wise.

Tony (16:52):

She is incredibly wise. We both married up, Derwin. We’ve talked a little bit actually in the past about how you decide what to teach in a particular series. In other words, and I’d love for you to share again, what drives the selection of topics or Biblical passages that you’re unpacking in a particular series?

Derwin (17:14):

Yeah, so basically, when I go on a study break in the summertime, I will just read the Bible and from that our sermon series have developed, but also when I’m involved in pastoral care, when I’m talking to our care team, when I’m talking to other pastors and ministry leaders, I’m hearing what’s happening, right? So I’m hearing, what’s taking place. So for example, in the last few weeks, we’ve had two teenagers try to take their life. And so I’m going, okay, I need to start talking more about the value of life and mental health month is gonna come up and all those things. But ideally what I do is I want to use a topic to draw people to Jesus through the text. So I am an exegetical preacher, not an exposition, like word for word. Now we have done series like that and we will, but I do believe in explaining what was the author saying at that time to those people about what Jesus has accomplished, and then how do we approximate that and apply that in our cultural context? But I think it’s super important that we have an ear to the needs of the people around us. And if I could throw out a challenge here, lovingly, I’m thankful for the big name speakers. They’re awesome. But God spoke that to them, for their people and their context. Just because it works good for Craig Groeschel or Andy Stanley in their context, what is the Lord speaking to you and in your heart? Now learn from other communicators. Like we should always be in learning mode, but I know for our church. So like we’re going through a series right now called “Color Blessed.” And the idea is God’s people, Jew and Gentile, Jesus doesn’t just forgive sins, he creates this family with different colored skins in covenant with Abraham. So we want to be color blessed, not color blind. And so we’re walking. What does a color blessed family look like? Last week we looked at, how do you have color blessed conversations around race and the gospel? So we looked at Ephesians 4:1-6.

Tony (19:51):

That’s good. Yeah. And speaking of your current series, it’s actually based on your new book, How to Heal our Racial Divide. I just finished it last night, Derwin. It’s fabulous.

Derwin (20:01):

Thank you.

Tony (20:02):

And so first of all, thank you for writing the book, but will you share a little bit more of the story behind it? Why you wrote it? Because as I was reading it, I was thinking this is actually a reflection of why you started Transformation Church in the first place.

Derwin (20:18):

Yeah. Tony, I wrote the book primarily because I am tired of the name of Jesus being dragged through the mud. I expect unbelievers to act like unbelievers, but when the church is actually the problem and not the solution, I couldn’t stand by. And so what I wanted to do was add my voice to this conversation, that it’s not an American conversation. This is a Jesus conversation that beyond a shadow of a doubt, Jesus Christ, a Jewish Messiah, came to give his father a multiethnic family of Jews and Gentiles. And this family is to love each other. “You will know my disciples because you love one another.” But what we’ve done is we’ve allowed a racialized culture to shape us. We’ve allowed Christian nationalism to divide us. We’ve allowed politics to con us, and we need the gospel. So when I say the gospel, this is what I mean. I don’t mean believe in Christ and a trip to heaven when you die. I mean this, that there is a good God who wanted a family. The world was corrupted. He called Abraham, told him I’m gonna give you a family. And through Abraham, the nation of Israel comes, but through Israel comes a Jewish Messiah to live a sinless life we couldn’t live, to die our death on the cross, to raise again and to be seated on high as Lord and King, and through the sending of the spirit, the family God promised Abraham is born into being. So what I like to say is not only do you get, I’m declared righteous. I’m forgiven. I’m God’s friend. I’m the temple, but you also get brothers and sisters. It’s not just vertical, it’s horizontal. And when we are committed to loving each other, we no longer see each other as Democrats or Republicans. And if I could just say, please understand this folks, the term Democrat and Republican is fairly new on the world’s stage. The early church was birthed in the Roman empire. There was no religious, I mean, there was no freedom of speech, right? It was the ruling empire, but yet these early Christian Jews and Gentiles around Jesus, through the power of the spirit, understood that unity was something Jesus created and a gift that they were to guard.

Tony (22:55):

Yeah. See right there, you were teaching and a little bit of preaching right there, which I love. So that’s good. I’m not gonna ask you to answer the how question today, Derwin, because I’d prefer for others to actually read the book. And by the way, great Biblical foundation for why this is such a key topic for us. But here’s my question for you. As I’m reading about how to heal the racial divide, this is the question I have for you. Can we actually heal? Is it possible? Are you seeing any signs of hope for us?

Derwin (23:30):

Yeah. So let me answer this in a few ways. Number one, yes, we can heal the racial divide because that’s called resurrection and the new heavens and new earth. There’s gonna be nation, tribe and tongue, in the new heavens and new earth. Our colors and our cultures go with us. We are fully redeemed. So healing in that sense is guaranteed. Secondly, a vision of the future transforms what you do today. So therefore, I’m gonna use a big word, eschatologically, the end of times, we know we’re gonna be this multiethnic, beautiful family in oneness. So that’s the future. So in the present, we wanna start practicing now, through the power of the Holy Spirit. So just like sanctification, sanctification is progressively growing in holiness. If you wanna know what holiness is, look up Jesus Christ. Romans 8:28 says we’re being conformed to the image of Christ. So healing is a sanctifying process. So it will never be fully healed until Jesus returns. But because of our guaranteed future, we have present power now to move towards it. And let me say this. Racial injustice and racism and prejudices, those are sins that Jesus came to conquer just like sexual immorality, just like greed, just like all those things. Let’s stop moving it into a political box and put it into a spiritual box where it belongs.

Tony (25:07):

That’s right. That’s right. That’s so good. Derwin, again, thank you for joining us for this series, but any final encouragement you’d like to give pastors as it relates to their teaching and preaching?

Derwin (25:18):

Yeah. What I would like to say to those who teach and preach, I’m for you, I’m with you. I know the last few years have been hard, and we probably won’t know how hard it’s been until about three or four more years where we could look back, but it’s been really hard. And what I wanna say to you is first and foremost is you’re not a preacher. You’re not someone who’s just created to teach. God recreated you in Christ to be his beloved, to be his beloved. Live in the belovedness of God, not in church attendance, not in budgets, not in buildings, not in Instagram followers. Live in the belovedness of God, that everything that’s true about Jesus is true about you, regardless of the impact of your ministry. Secondly, the healthier you are as a disciple, may your greatest message you ever preach is your own personal holiness. The way you love your spouse, the way you love your children, the way you apologize, the way you walk in humility, may the greatest sermon that you and I preach is Philippians 2:3, “Do nothing out of selfish ambition or vein conceit, but consider others better than yourself.”

Sean (26:39):

Well, Amy, there was a ton of great insight from Derwin in that brief conversation. What are some of the highlights that he shared for you?

Amy (26:46):

Well, I hope that pastors listening tuned into what Derwin shared about his process for preparation. I loved his quote. See if I can say it right? You don’t rise to the level of the moment, you rise to the level of your habits. And preparation for him clearly is a habit, not something he tries to fit into an already busy calendar. And here’s a couple of other things that he said. He works on series direction seven months out. I love that. As someone who led the weekend, I didn’t need to know the scripture verse, but to have some direction, it helped all of us on the creative side start thinking with our lead pastor.

Sean (27:21):

Yeah, absolutely.

Amy (27:21):

And that he spends five to 10 hours preparing his messages, you know, the week that he’s speaking. In addition to all the other time he puts in, he has concentrated time for that. And I like that he said he’s always preparing because he’s living it, not just focusing on it certain hours of the day. And I think I heard this right. That he spends up to a quarter of his week on message study. So, you know, he mentioned, he feels like he’s always preparing, you know, his life to share scripture, which I hope many of our listeners who teach can identify with that. I know my husband always is challenged to be putting himself in places where he can be learning and capturing story for upcoming messages.

Sean (28:02):

Yeah, that’s so good. Yeah. I also thought it was pretty insightful that he doesn’t have to work hard to free up time to focus on his message prep because he already has what he called a meticulous routine, another thing that he seems to have picked up from his football experience, but he said he is outlining on Monday and then really just ruminating in his message preparation throughout the week before taking his Sabbath day off on Friday. And I’m really glad that he included that part of his routine in particular, because we know from the data that we looked at from some of our assessments and surveys we’ve done, that you know, commonly pastors struggle to actually take a Sabbath day in their week, but it’s actually, it’s an important part of his weekly habits, of Derwin’s weekly habits. So I just hope that can be an encouragement to any of our listeners who don’t have a Sabbath day built into their routine. Make sure you’re setting aside a day for you so that you can be healthy as you’re sharing with others on the weekend too. So, Amy, any other highlights from the conversation for you?

Amy (29:07):

Yeah. Another thing that stood out for me was that he’s working to intentionally develop a teaching team. You know this, Sean, but this is something we recommend to all of our churches that we work with. And Derwin reinforced that it’s important to cultivate and develop other teachers. You know, there’s some benefits. It gives your primary preacher a chance for rest, right? We can be creative for a while, but if it’s week on week on week, that it’s a challenge. It also allows the church, of course, to hear from other voices and other perspectives, and that it helps you maintain humility. There were a few other key insights he shared that I think are important too, by the way. He said he’s looking for people who are always learning, when identifying other teachers. I love that because developing other teachers is relational, not programmatic. So you have to be willing to invest in the relationship. And then the last thing was, if you’re not willing to clean toilets, you shouldn’t be in the pulpit either. Preaching is about serving. And that’s a really important reminder, I think, for everyone who stands on a stage, not just the preachers.

Sean (30:08):

Exactly. I love that line. Well, Amy, I think this has been another really solid conversation with encouragement and really some practical ideas for pastors. So any other thoughts before we wrap up today’s conversation?

Amy (30:20):

Sean, I think I’ll just leave us with a reminder of those final thoughts that Derwin shared, because it’s so important, that your identity is not preacher or teacher. Derwin reminded us that our identity is beloved by God, and the greatest message we preach isn’t in the pulpit, but how we live our lives and how we address our own personal holiness, the way we love our spouses, right? And the others around us, the way we apologize, the humility we have. So I think, Sean, if we leave this conversation today with nothing other than that, we’d all be better for it.

Sean (30:53):

Yeah. Great reminder, Amy. Thank you. And thanks to everyone out there for joining us on this week’s podcast. Before we wrap up today’s episode, I want to take a moment and thank this week’s sponsor, Overflow. Overflow is an online software that empowers donors to seamlessly give crypto and stock donations to churches and non-profits within minutes. The average donation to churches and nonprofits is $128. But the average donation through Overflow is $9,500. That’s $9,500. Your donors want to give stock and crypto because it’s the most tax efficient way to give. Why? There’s no capital gains tax, so churches get the full donation and donors get the full tax deduction. As a result, churches have seen up to 32 times the return on their own investment with Overflow. With Overflow, you can unlock unprecedented generosity together. So visit That’s Next week, we’re back with another brand new episode. So until then, have a great week.

Tony Morgan

Tony is the Founder and Lead Strategist of The Unstuck Group. Started in 2009, The Unstuck Group has served 500 churches throughout the United States and several countries around the world. Previously, Tony served on the senior leadership teams of three rapidly growing churches including NewSpring Church in South Carolina. He has five published books including, The Unstuck Church, and, with Amy Anderson, he hosts The Unstuck Church Podcast which has thousands of listeners each month.

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