Special 3: The Imperfect CEO - Dan Underhill | Faithly Podcast

In this episode of The Imperfect CEO, Rev. Adam Durso is joined once again by Jim Brown for a practical and deeply relevant conversation on leadership, humility, and building a healthy church culture with guest Pastor Dan Underhill of Cornerstone Church ATX.
Together, they explore the pressure many leaders feel to appear strong, polished, and certain at all times, and how that mindset can quietly limit collaboration and growth. At the center of the conversation is Jim’s “Ascent Model,” outlining four key elements of healthy leadership: collaborative culture, leadership accountability, strategic momentum, and talent magnetism. Dan shares how working through these principles revealed that his tendency to move quickly with answers had unintentionally trained his team to hold back—becoming a turning point that reshaped how he leads his ministry today.
A key theme throughout the discussion is vulnerability. Rather than building trust through perfection, effective leaders create space for others by asking better questions, admitting what they don’t know and inviting contribution. As Dan has seen firsthand, this shift not only strengthens teams but also resonates deeply with younger generations, who are drawn to authenticity over performance.
Website: https://ccatx.com/
(00:00) Learning Not to Have Every Answer
(00:27) Introducing The Imperfect CEO and Pastor Dan Underhill
(01:38) Why Leaders Feel Pressure to Appear Perfect
(03:54) The Ascent Model and the Four Peaks of Healthy Leadership
(06:52) Leadership Accountability and the Cost of Always Answering
(09:22) Strategic Momentum and Talent Magnetism
(10:50) How the Book Exposed the Imperfect CEO
(14:01) Resources, Assessments, and Building Healthier Teams
(21:29) Vulnerability, Clarity, and Leading with Humility
(31:12) Free Church Leadership Resource and Closing Challenge
Connect with Jim Brown, and DM the word “BUILD" at linkedin.com/in/authorjimbrown for a free resource, and preorder your copy of The Imperfect CEO now at http://imperfectceobook.com/
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00:00 - Learning Not to Have Every Answer
27:00 - Introducing The Imperfect CEO and Pastor Dan Underhill
01:38:00 - Why Leaders Feel Pressure to Appear Perfect
03:54:00 - The Ascent Model and the Four Peaks of Healthy Leadership
06:52:00 - Leadership Accountability and the Cost of Always Answering
09:22:00 - Strategic Momentum and Talent Magnetism
10:50:00 - How the Book Exposed the Imperfect CEO
14:01:00 - Resources, Assessments, and Building Healthier Teams
21:29:00 - Vulnerability, Clarity, and Leading with Humility
31:12:00 - Free Church Leadership Resource and Closing Challenge
What I was doing is I was teaching my culture to be quiet at the table to wait for me to answer the question And I was greening so much frustration going why aren't these guys listening? Why aren't they leaning in? I'm trying to empower them so much like you do it you run you go and they wouldn't go because I always ended up having the answer Welcome to the Imperfect CEO, a special series by the Faithly Podcasts with your host, Reverend Adam Dersow, and author Jim Brown Welcome to an episode of Faithly Podcasts. I'm your host, Pastor Adam Dersow and I'm sitting here with the author of the Imperfect CEO Jim Brown Say what's up to the audience Jim. Hey, what's up everyone and my good friend pastor Dan underhill senior and lead pastor at the cornerstone church ATX and Austin Texas my friends say hello. Hey, welcome glad to be here. We are so excited for this episode because we explore the Imperfect CEO, the book Jim with you as the author. We're also exploring a case study where pastor Dan and his team went through this. His lead team has already been through this and a pre-release copy and then you guided us through the conversation and now we're going to be able to see some of the results now eight months later that Dan is living in as a result of having applied the principles that are in the Imperfect CEO. So talk to us a little bit why do so many leaders feel the pressure to appear strong and certain all the time there's this tendency, especially in the church that the way we get into the position of CEO is because we're so good we know so much. It's even worse in the church because we've got this example of Jesus was perfect right and we have this thought that well people are thinking of Jesus as the example so I guess I have to be a lot more like Jesus meaning I should be perfect I should know everything. Beautifully Jesus never expects us to be flawless we just need to change our paradigm the truth is as the book title says we're all imperfect and Jesus is fine with it and we can just learn to walk in that and we're going to get to the fact that um Dan didn't realize that the title of the book was the Imperfect CEO do that second but why why why Jim why is it so dangerous especially in ministry for that guy to say man I'm. i've got to be i've got to be the perfect CEO i've got to be i've got to have all the answers i got to know what you know but the healthiest organizations are really led by leaders who are willing to learn lesson grow talk to us a little bit about why it's dangerous in the church ministry culture particularly. If we're going to make a difference for the kingdom it's got to be bigger than any one of us that means in our role as the CEO we have to create the context that everyone feels like what they bring counts. What they are thinking the ideas they have make a difference yes and if we are not making space for them to bring the best thinking ask your hardest questions offer their strongest gifts then it turns out we're making it about us we might say we aren't but we are becoming the bottleneck rather than the multiplier the enabler you know we're we're out here in southern. California we just hosted 55 plus leaders Jim you did the opening talk and you built just an incredibly established just an incredible model called the asset model could you walk us through that just a little bit so that the audience understands kind of the framework for the imperfect CEO based on that model sure. What we've observed is there are four peaks that contribute to a healthy organization the first one being the central one being a collaborative culture where we're all working together because we can build bigger go further make more happen if we lock arms and we're doing it together sure. That is the starting point the next piece the next peak that we have to summit is collaborative sorry is leadership accountability and this is actually a curious situation it's the one of the four that leaders have the most control over. It also happens to be the one of the four that leaders fail at most offer Jim I know you all enough you're the chairman of my board and I've heard you say that before take into that a little bit I mean it's leadership accountability matters leaders have the most control but do it the least. Not that they're conscious of failing but yeah we we are all human and somewhat selfish at least I will admit that I am right and so we are we work hard to be messaging properly to our everyone on our team. But if we are not demonstrating exemplifying what we are asking of everyone else that's what everybody sees right and they know that wait if you're not doing it we don't need to do it if we don't have the courage to notice when that's happening and call each other up not in a you know beat your just in a hey we said we were going to do this in a healthy way can we help what can I do to help you. It demoralizes everyone else it it's like it just cancels the effort. We just have to be more determined and committed and receptive to the feedback that we get from our peers at the leadership level to follow through there are two more peaks in this ascent model Jim I want to I want to come back to but president when he talks about leadership accountability and you know you've been around Jim you were in the sessions with these other. 50 plus leaders you help me lead leading leaders collective right here you're you're in the what is that saying to you as the imperfect CEO as a pastor of a growing church three campuses I mean you're crushing it out the gate six years you've been in ministry for over 25 what is leadership accountability mean to you as Jim talks about it I think for me it was being aware of all the gifts God gave me and how those gifts have a. Light side and a shadow side to you know even though I walk in the room having to have the answer if nobody else does that usually closes the mouth of the people sitting around the table wow and it teaches what I was doing I was teaching my culture to be quiet at the table to wait for me to answer the question and I was greening so much frustration going why aren't these guys listening why aren't they leaning in I'm trying to empower them so much like you do it you run you go and they wouldn't go because I always ended up having the answer and I would be the one who is stifling the question that's where you taught me hey Dan use this sentence the answers in the room and that became a trigger for my team to know oh he's waiting for us to engage and he is going to be patient and wait so I think that's the accountability that I needed so powerful and and it's net well I shouldn't say never but almost never intended by the leader to be shutting down the people on their team no they're they're just we need to keep moving let's this wouldn't this help us move faster so not hearing anything from everyone what about this and everybody yeah but the more we get the head nodding and the mouth closed sure the more we're actually slipping away from collaborative culture back into command and control okay which is not how we want to lead right that is and again we're talking about the church Jesus modeled how to lead the church he was never a command and control leader how did we get there scripture actually says let's let's not be like the leaders of the world right but who dominate and and Lord it over you yeah yes and yet somehow that keeps showing up in the church wow so collaborative culture leadership accountability Jim next two peaks so then we get to strategic momentum this is where we really are clear about where we're going and we don't just talk about it we do it if we get the plans accomplished this year and then next year and the next year we get momentum strategic momentum and everything starts to change people start to realize they're on a winning team yes they want to be on a winning team now they like you know they're just off their chest up a little bit more because yeah cornerstone is crushing it and I'm a part of this more people should be here they're going to love it and that takes us to the fourth peak which is talent magnetism okay where it's working people love their job so much people feel like it matters so much that they become contagious essentially they are like the ambassadors to the world saying you're gonna love this church yeah you should come yeah hey we need someone to really help in our sound area and that don't you do that I think you really love doing it at cornerstone why don't you why don't you just sign up I think that we get a great interview so rather than oh my goodness we're putting out ads hoping that we get somebody that knows something talking to 17 different people or 77 people oh we've got five people in a row eager hungry ready already connected to the people in the culture it's just magical I mean if we're gonna speak about magnetic personalities and magnetism it's obviously past and Dan underhill right here so you had this opportunity we were talking about your lead team and what it would look like to have Jim come in as a consultant yeah and Jim was so gracious to get your team a copy of a pre-release of the book and you guys read it and then he came in to speak and talk to me about what that experience was like man well it was so wild because you know as the CEO or the lead pastor I want to bring in the consultant to fix the people that are working for me because they're not getting the mission and the vision done as quick as I wanted them to or so there was my mentality walking into it so oh it's worth the investment this will accelerate us this will be the thing that pushes us forward not realizing that as we read the book the imperfect CEO it wasn't called the imperfect lead team no no no no no perfect leadership of the NGO the project church ministry no it was imperfect CEO he should have named the book the imperfect CEO slash pastor Dan underhill and so legitimately I'm reading it and even after I read it I was walking into those means going this is gonna be great as soon as we can harness this this will be awesome and then the meeting because you let it so so smoothly and so beautifully and it just moved the whole conversation around oh I'm the imperfect CEO and then as soon as that light went off it lifted so much of the burden in the room where it's like oh well that's easy because I one thing I can do is I can control me I can't control other people right and as a CEO you're always trying to control other well you shouldn't be but you are you're always trying to control other people and manage them and I realize like oh this is now right inside of my wheelhouse this is on my dashboard and I can move the needle on this personally yeah and and as soon as that we did and we leaned into it and said oh what I was given naturally was to make sure I have the answer was again causing the problem in the room and having the answer stifled the creativity and we saw the results some of my staff members have ballooned yes so much beautiful in times where I was like man I was like we're not sure if they've got the capacity to do this one but let's let's lay it on them and there they go and they're just opening up and they're leading like they've never led before I don't want to get ahead of us because you know we had the chance to do this and then we've watched this now for six to eight months and see the ROI the return on the investment for sure but but Jim leading into that moment and I don't I don't want to take a pit stop here for a second because if a leader buys at least ten books they get the staff assessment that his team used yeah right talk to me about one what that staff assessment which by the way in and of itself is a $1900 plus value yeah and you're giving away for ten books which is not even I mean it's not even going to tie of that right and then on top of it how does that works and then how do how do we how does the audience that's listening right now make sure that they get a hold of that so we're I'm going to take a pit stop because his staff actually went through the process you're ordering right now yeah we are so excited about the picture in in our minds and and I know it's in yours to Dan and Adam that leaders will create the context that allows their people to be the best that they can be yes to do the work that really matters in the world to feel the gratification of it counting and rather than kind of grinding every day there's a a skip to their step there's they just feel better sure I guess what when you feel better about your whole work day you go home oh yeah and you're better at home yes and when you come back you've got more energy and especially in the marketplace you bring your better ideas the whole organization prosperous and if leaders are thinking well they're using some of that overflow to pay people more which means they go back and there's it's like it there's this just upward spiral of benefit yeah we want that to happen more quickly so we're creating these packages that make it easy for leaders to say yeah I'm going to get everyone on my lead team to buy yes better yet I'm going to get everyone in leadership so buy a hundred of them right and you get even more and not just a free assessment one of our team that is expert at debriefing will lead your team sure through that assessment and make it make sense for you yeah we just want to make organizations healthy and leaders are responsible to do that and and your feeling is hey if organizations are better if they're healthier it changes the game it changes the world it changes the world it changes the world what would happen if a million Americans and think about this that means there's only well I don't know like 150 organizations when you multiply out how many people work anyways the the math means we can change the entire country if we would just get a critical mass of people doing this past then when you think about the impact of the staff assessment how it impacted your lead team and then having Jim and his team debrief your team now six months later looking back on it talk to us it is an absolute accelerator yes because what happens is you are not using your voice when you're the imperfect CEO in the room which then creates the culture you're allowing a third party to come in and unroot what you can't even see in blind spots and the the advancement that I think our team got from it was because there was a third party perspective so I've read so many books we've all read so many books you retain so little of what you read you're now doubling tripling and quadrupling down on the return on investment of what's in the book to get it to the ground through your people when you get the assessment from the team it was an absolute game changer because there are points in our meetings where I didn't know what to say right I had staff members locking up in just like communication just came to a grinding halt sure and Jim knew exactly what to do where I was like I give up I don't know what to do here's my problem I mean he and his team are literally experts yes and then when they lean in brilliant it becomes a exponential multiplier of what the book it is but this is what's interesting about the book Jim and I brought this up when we were here with all these leaders because the book is written as a fable nobody feels like the finger is being pointed at them including the imperfect CEO who's bringing it the entire time the beauty behind it being a fable Jim is that I can identify what a character in the story without feeling like oh my pastor's yelling at me or oh the CEO is yelling at me or my my my direct report is is is picking on me what about the beauty just about the way it's written as a fable Jim well this conversation is fun for me because we're especially focusing on how do we apply these principles from this book to the church right well let's be reminded that most of the really important messages that Jesus delivered he delivered in parables in stories right there's got to be a reason for that yeah I believe it's because it engages the listener in in his case the reader in this case where they see themselves in the story and that's what we've experienced from the first book that I wrote the imperfect board member 20 years have passed all kinds of great stories about how that's been used now we've got this story and I wonder Dan can you talk with the the group because this is written as a a story focused more on the business world but the principles are completely applicable to churches help help our listeners recognize that even though it's about a tech company it actually is applicable to church oh abs a hundred percent because at the end of the day every church has to be organized if it's going to be organized it's going to have a system of business to it yes I currently have 11 employees it's not a huge organization but the amount of time energy and budget and thinking and strategic planning and organization that goes into that I think pastors would be foolish to not buy it and distribute to their entire team you know I know that I'm going to get it once it's out to all the rest of my team only my lead team got to experience it but the rest of my staff members need to because even though the church isn't a business there's a business side to running the organization otherwise you can't stay afloat I mean it's 11 staff members that are impacting 400 right people who are attending your church on a very regular basis right and then beyond that through all of the other outreach it's impacting the city of Austin right particularly in the areas where the three campuses are located what are some of the disciplines that strengthen a healthy church culture we've kind of pinpointed some things that were concerned what what are some of the disciplines that a leader that's listening right now you'd say these strengthen a healthy church culture and then pastor I'd love for you to weigh in based on what Jim says and say I've actually applied some or specifically this and now we've seen these results well this is where it's it's somewhat counterintuitive because the old script that many of us in the leadership world have played is that we should be the smart one we should be the strong one right we should you know stiff upper lip and it's like change the whole plan be the first one to be vulnerable hmm be the first one to admit when you make a mistake be the first one to ask for help when you don't have the answer yeah which again most people fear that that makes them look weak that that disqualifies them from being in the leadership chair and it's just not true because the the impact on people is that when the leader is vulnerable they start to think hmm maybe it's okay if I'm real too right I don't have to pretend all the time because they know they're not perfect sure truth is they know you're not perfect so it's a curious list of personal disciplines about how we show up in conversations in meetings whether it's with five people are 500 people we are not Mr. Noah at all we are more humble more real and we are in a new leadership era where real carries way more weight than you know it all right that's like a disqualifier and yes it used to be I've got the answers here's a curious thing and I don't know if we've talked about this then the more rather than standing before the church and saying hey we've just done a lot of work on a strategic plan here's the plan and you maybe have but don't start by saying here's the plan start by saying this has been quite a journey I want to just share some of the very difficult questions that we've had to grapple with as we've been pressing into what God has for us as a church we're asking ourselves how is our community changed right what did we think five years ago or 40 years ago that doesn't actually apply in our community anymore and what does that mean about our plan in the future what about our own demographics what do we wish what do we believe God is saying our congregation should look like in the next five years and what do we need to do to get there you might share like 10 questions yeah and I promise you for sure Gen Z people sitting in the room they're saying oh this is so real such a relief yeah my leader knows the questions yeah they're not asking if you know the answers they want to know if you know the questions yeah and if you can share questions that they've been asking then there's this comfort that oh you know they're not going to get blindsided like at least even I know they should be asking these questions but then you share some questions that they haven't even thought of oh now they just relax it's like I think I'm safe it's totally contrary to what the old model of leadership was and if we don't understand that the whole world has changed we're leading the wrong group right and they're just gonna walk and find someone else and and that's really what they're doing and we're seeing that in our church the next generation they are going to leave okay because they're not interested in the lights and the show and the production the perfection they are walking out they're saying if you can't disciple me if you can't walk along this journey and train me up I'm out because content is on overload yes they can get content anywhere right it's in their pocket from millions of different platforms and great yeah and it's probably better than the average pastor's content definitely and so they're saying we're out so how I would say or how I would you know answer your question pastor Adam was you know you can't lead people where you're unwilling to go yourself oh that's good yeah and so when your team needs to face hard questions and deal with really tough difficult realities of who they are personally you've got to start first you've got to be willing to go in and say look man I'm not getting this right and I'm here at the table first what I've seen happen with my team is again they just absolutely open up and even beyond our team I see it in our church um I think I've been preaching this this way before it was cool to preach very vulnerable very raw very exposed nerve you know and it was actually worked against me in many cases but now we're seeing a generation saying look we are so tired of descriptive and produced and they're perfected and polished and airbrushed we need to know the reality yes okay because we've been given that prescription before and we see where it ends and failure so Dan when we talk about calling out real yeah and saying hey this is what it is what does that look like specifically in your context oh man well you have to be able to speak the truth in love to your people and my people in our church they love it like they are salivating for the real application when you when I tell a story that a lot of other pastors sometimes look me and go oh you you shared how you're struggling like I don't know if that's okay to say you're the pastor right and I'm in a church in Texas which is southern church which has a little more pretense yeah yes yes and now we're watching them just be drawn to it saying this is the place that I want to die for young leaders you know young CEOs I got a couple guys in my church they're 30 years old they own companies they're like this place I knew that I could be safe and I could be fed and I could be spiritually formed because when you are not afraid to go to those hard spaces we knew we could trust you to walk through all the spaces of our life so when you talk about calling out the real and then you talk about 24 hour clarity yeah what does that mean okay so the killer of momentum is confusion when people ask a question that was on the lower third with the bouncing ball can you say that one more time the killer of momentum is confusion that's brilliant yeah and this is tricky for us as leaders because it's clear in our head yeah we've told people at least once multiple times twice three times yeah and then so somebody says well what about this and we think I already told you that for crying out loud a 24 hour rule should be we will get an answer to everyone in 24 hours that's good now that answer might be here's the clear answer or it could be here's the next step we're gonna take okay or it could be here's what we're gonna do so we will get the clear answer but we just need to move from we're not sure people saying we're not sure what we're supposed to do to make it easy for them so we're moving from ambiguity towards something but it doesn't have to get all the way there yet don't just keep moving in the right direction so it's okay to say I'm not entirely sure that we're gonna get to the destination right now but we're gonna take the next step what does that look like for a leader that's working through that with their team again this is about vulnerability it's it's like you know what our commitment as leaders is to discern with the Holy Spirit what our path is supposed to be and we've been on our knees and praying all we can tell you for sure at this moment is the next step is this and it's reasonable that you're wondering what comes after that we don't actually know right here's what we've experienced from God as we drive forward our headlights push a little further we can't see way down the road yet but we know that the next step is there when we get there we're expecting God's gonna reveal what the step after that we're supposed to be again if we can just demonstrate we don't have to have all the answers we're trusting God God is faithful we're good let's go there together you know Jim I've seen firsthand up close your heart for the church why this particular like you're you're helping obviously companies all over the globe and that's incredible and that's probably but your passion level even ratchets it up a little bit when you talk about the church and pastors and building a healthy church culture you've got a resource and and I'm privileged because I get to read them read your articles and read the things that you're doing before it comes out and you've even invited me to weigh in on it I have no idea what value I'm adding at any point to anything you're writing but talk about this leading a healthy church deal that you're writing and how people can get a hold of that basically for free see it comes back to the book is a story that's more in the business world and even though we've already talked about it's totally applicable to the church 100 percent I love the church so much that I want to make it like so obvious this is how it applies to the church sure so I've written I'm continuing to get some feedback I'm going to get a copy to you so that you can give me some feedback too please Dan wait not just me I've already got it to you I'm not special you are special you've got first one pastor I told a lot of times that I'm special all the wrong reasons yeah I want to continue to refine this but I promise you it's already helpful in fact we're prepared to send it to you right away even though the book's not actually available until May 19th sure if you are listening and you're interested please find me on LinkedIn at author Jim Brown and DM me the word build and I will get that resource to you directly it's it's something like a 35 page PDF booklet type thing promise you it's a that's a tool that will help you source yeah absolutely let's let's let's be very clear it is 35 page PDF but it is an absolute tool in your arsenal it is going to help you immediately and if you DM Jim Brown at author Jim Brown on LinkedIn and you just put the word build into that DM you will send that to them for free because yeah because you love the church and you love to help people yeah and so let me ask you this final question to to both of you if a pastor is listening today maybe it's a chairman of a board of for a church maybe it's a denominational leader yeah if they decided to make one leadership change this month if they decided right now a leadership change this month to improve and make their church or ministry healthier what should it be start with you Dan and then we'll go to you Jim I think you've got to be willing to walk in the room and be humble you've got to start and lead with humility because at that point then God can lift you up sure until you get low there's no place to build from and too many pastors in my experience and in my own personal life we come in thinking that we are going to be the next great thing and the reality is the Lord says look humble yourself on the side of the Lord he will lift you up the great Bishop Bronner said it today very few many very few men fall when they're on their knees yeah and so I say starting low in the humility point to say I need to get the book I need to walk through this with my staff I need to start with humility and honesty and openness and vulnerability I think that is a great platform there's got nothing but up to go it's it's hard to stumble when you're on your knees and let's be honest we're not the next great thing because we're preaching about the only one who's really great that's the truth temperature well I love this so I'm all for it I would add the to underscore that when we're the CEO and we're the lead pastor when we're the chair of the board we're in a leadership role and leadership is about people we do not manage people we lead people right that's good and if we would put our attention to leading rather than doing everyone will be will will be more clear about what they're supposed to do yeah we'll feel more valued we'll actually amplify and accelerate the the work of the of the church yes we're leading people focus on people leading a healthy church if you DM at author Jim Brown on LinkedIn and type the word build he'll send you that free resource I'm telling you it's going to have an impact it's going to be a tool in your arsenal otherwise they can go to the website yeah if you go to imperfect CEO book dot com imperfect CEO book dot com then you're going to find these packages that aren't just bundles of books but all kinds of other resources that we're just adding yeah pre-order 10 for your leadership team 100 for a bigger group you might be leading a denomination you should get a thousand and there's so much more that we're offering with that yeah because the book comes out May 19th you need to get the book right away absolutely let me tell you you're going to be blessed by getting a hold of the book getting hold of the resources having Jim's team work with your team to unpack it the staff the team assessment all of this is going to be an incredible blessing so either DM Jim at author Jim Brown on LinkedIn type in the word build or go to imperfect CEO book dot com and get to all those resources there I promise you Jim not only has a passion for the church he has the expertise to help your church your NGO your ministry your nonprofit become a healthier version of itself which by itself will be a multiplier and a blessing to you my name is pastor Adam Derr so this has been a faithly podcast sitting with pastor Dan under Hill author Jim Brown God bless you continue to follow us on all of the faithfully platforms as we continue to move forward and see your church and ministry blessed












