Ep 131: The Creative Leader's Guide to Transformative 1:1's
Most Leaders Miss This
SUMMARY
Most creative leaders sacrifice their people on the altar of excellence without even realizing it. But what if the key to better creative work wasn't pushing harder on your team, but actually investing 30 minutes a week in genuine conversation?
In this powerful episode, Dustin Pead shares insights from his talk at the SALT 2025 conference, revealing how intentional one-on-ones transformed his leadership approach after 15 years of prioritizing product over people. Whether you're a creative director, worship pastor, agency owner, or team leader, this episode provides a practical roadmap for conducting one-on-ones that actually work.
KEY TAKEAWAYS
⚡️ The 3:1 Question Ratio Changes Everything. Modern psychology shows that effective leaders ask three questions for every one statement they make. This simple ratio transforms one-on-ones from broadcasts into genuine conversations that build trust and unlock creative potential.
⚡️ Consistency Builds Trust in Pennies, Loses It in Dimes. The number one complaint from creatives about their organization is lack of consistency from leadership. Canceling or rescheduling one-on-ones speaks louder than words—it tells your team they don't deserve 30 minutes of your time.
⚡️ Personal Connection Precedes Performance. Your first one-on-one with each person should be 80% personal check-in. Great creative work comes from teams who feel genuinely seen, heard, and invested in—not from those who only discuss projects and performance.
NOTABLE QUOTES
💬 "For the first 10 to 15 years of my 20-year ministry career, I cared more about the product that showed up on Sunday than the people that I led to help create it."
💬 "Your introverted creatives have brilliant ideas that they never share in a group setting, but they may do it in a one-on-one."
💬 "Maybe excellence is more about the people than the product. Maybe the best creative work comes from teams who feel genuinely seen, heard and invested in."
EPISODE RESOURCES
The Creative Guide to One-on-Ones - Free download with templates and worksheets
"How to Lead When You're Not in Charge" by Clay Scroggins - Essential reading for middle leaders
Fathom AI Note-Taker - Tracks talk percentage and takes meeting notes
dustinpead.com - More frameworks and resources for creative leaders
TRANSCRIPT
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Most creative leaders sacrifice their people on the altar of excellence without even realizing it. But what if the key to better creative work wasn't pushing harder on your team, but actually investing 30 minutes a week in genuine conversation? Let's get into it.
Welcome back to Creativity Made Easy, where we help creative professionals move from chaos to clarity through their processes and systems. I'm your host Dustin Pead and I'm here to share practical systems and processes that will transform how you lead your creative team. Whether you're a creative director, worship pastor, or you're leading volunteers, this show is designed to give you actionable strategies that you can implement today.
Now what I'm about to share with you is a regurgitated version of my talk at the SALT 2025 conference. We set everything up to record and we listened to the playback and the microphone didn't work. This time you're gonna hear me kind of like give the talk again on a podcast form. Understand that when I was talking at the Salt Conference that it was a conference for local church ministry creatives, which if you don't know what that means, most local churches have some sort of creative person on their staff. Usually it's a musician, sometimes a designer, whatever the case may be, they have a live, basically a live event that they have to produce. Often in cases multiple times a week, they have to pull these things off. And so the Salt Conference is an opportunity for church creatives to come and just kind of decompress a little bit, learn some things, be challenged a little bit and be encouraged along the way.
So what I'm going to share with you today, I gave the talk to church creatives. But I really do think that this is applicable no matter where we're at and it's something that I walk all of my clients through no matter what sector they're in and how to have these effective one-on-ones.
So before we get into it as well, I need to be honest with you about something. For the first 10 to 15 years of my 20-year ministry career, I cared more about the product that showed up on Sunday than the people that I led to help create it. Now I would have told you that I loved my team and I would have said that I valued them, but my actions told a completely different story. I was so focused on excellence and making sure that everything was perfect, that I was literally sacrificing people on the altar of Sunday morning. Maybe that's you, maybe you're sacrificing your team on the altar of your creative endeavor or your business.
Now here's the thing, I didn't realize that I was doing it. It wasn't until I started having intentional, consistent one-on-ones with my team that had discovered what was really going on in their lives and their struggles and their creative blocks and their burnout. So that shift from product focus to people focus changed everything, not just for my team, but for the quality of our creative work. It turns out when you invest in people, they actually create better work. It's a revolutionary concept, right?
So today I want to share with you what I learned about making one on ones actually work, not just another meeting to check off, but a genuine tool for transformation. And we're going to go through the who, the what, the why, the when, the where, all of that today.
But let's start right out the gate with the who. Who should you meet with? Well, a one on one by definition is two people, right? But I think there's multiple different avenues that you can take here. Yes, you may have direct reports like volunteers or different staff or contractors that report to you. That one's obvious. But what about cross-department leaders? Maybe there's another department within your organization that you need to meet with. When's the last time you sat down with the director of another department just to understand their world? And doing that regularly helps a ton.
What about meeting with promising young talent? There are different people in your community that are ready to step up to the plate and the things that you are doing. So why not meet with them? Or how about if you aren't the boss or you aren't the top dog leader at the top of the chart, why not request to meet with them? Why not request to meet with your own leader and model the behavior that you want to see carried out throughout the rest of the organization?
So obviously, like I said, the critical rule is that one on ones must be between two people. If you add a third person, it fundamentally changes that dynamic. So don't necessarily invite your admin or anybody like that to just sit in on it because then it kind of feels like a two against one even before a word is ever spoken.
All right. So that's the who. Now let's move on to the what. What are we actually trying to achieve in these one on ones here? I would say a few things. Number one, alignment. This is to ensure that creative work meets our strategic objectives. Number two, unblocking. This is an opportunity to identify and remove obstacles before they derail creative projects. Development. This is kind of the discipleship in the church world or the development or the growth and opportunities in the secular world that we need within the work context. How are you growing? How are you developing in your skill here?
Relationship building is another one to strengthen the trust bond that enables creative risk taking to inspire change during these one on ones, right? Your introverted creatives have brilliant ideas that they never share in a group setting, but they may do it in a one on one. And then lastly, early problem detection. You can begin to catch burnout, personal struggles and performance issues before they explode in your face.
Andy Stanley, who is a well-renowned leader in the local church world teaches that effective ministry, I would say effective business in general, requires you to replace yourself. But here's the hard truth, many of us don't want to replace ourselves. We like being the person who everybody depends on. And a one-on-one forces us to invest in developing others, which is exactly what our business is and what the church world should look like.
All right, let's get into the when and the where. All right, so when to schedule one-on-ones. There's three kind of categories here or three different kind of timeframes that I recommend when we talk about when to schedule one-on-ones. First off, if we're direct reports, like they directly report to you, I'm going to suggest weekly, 30 minutes, set a timer, honor that time. Both of you need to honor that time, create that expectation. We'll talk about that kind of here in a little bit.
So direct reports, I think you need to be meeting weekly for 30 minutes. If it's a cross department situation, like we talked about, someone else in the organization, I think you need to be meeting monthly for 30 minutes. And then if it's a freelancer or a contractor, you need to be meeting at the beginning, the middle, and the end of every single project.
But the key is consistency. The number one complaint I hear from creatives about their organization is a lack of consistency from leadership. If your boss keeps getting a new fresh vision or a new fresh idea that changes every single quarter, you know what that does. It destroys trust sometimes and it pivots and there's lack of consistency there. So if you set up a one-on-one schedule and constantly cancel or postpone, just save everybody the trouble and don't start it anyway. Canceling or rescheduling speaks louder than words. It tells your team that they don't deserve 30 minutes of your time, that there's something else that's more important than them.
All right, so that's the when. Let's talk about where. Where do we do these one on ones? Look, creative people, you know this, are influenced by their surroundings, not the windowless office with gray paint. That's not ideal for inspiring conversation. So consider places like a coffee shop or a walking meeting, which is great for 30 minutes because people get tired and they want to wrap it up naturally. Galleries or museums are a great place to be visually inspired anywhere that sparks creativity.
But I would say try at your best. If you're to have four one on ones a month, I say three of them probably need to be in the same place, but all of them need to be in the same time. So pick one consistent place as much as possible, one consistent time and do not waiver.
All right. So now we're in the one on one, what do we need to do when we get in on that one-on-one? The very first thing I tell every leader is that they have to master the art of questions. Your one-on-ones have historically been terrible because you're not asking the right questions. Listen, great leaders ask more questions than they make statements, period, right? So if your one-on-one sounds like this, how are you? Fine. Things good? Yep. You love your job? Sure. Then you're doing it wrong.
Right? So you need to be asking great questions. And there's a rule here when we're asking great questions. Modern psychology shows us that effective leaders ask three questions for every one statement they make. It's the three to one ratio. So I would actually get someone on your team to track this for you. Or ask the other person say hey, I'm gonna work on asking more questions. Can you make a little hash mark on your paper every time I ask you a question? Just so at end of this meeting I know that I'm asking a good amount of questions. Or you do it yourself and you go I'm asking you a question and you hash it down whatever it takes but just track that stuff because seeing where that actually tracks out for you. It's humbling, but it's also transformative.
Something else to consider when asking questions is to consider personality differences, right? If you have like an Enneagram 5 on your team and you spring a question on them without warning, you're probably not gonna get an answer. They're probably gonna say, after a long period of silence, they're gonna say, let me think about that. And you'll both forget to ever revisit it. But if you send those questions two or three days ahead of time to someone like that on their team, then they can be prepared to answer and you can actually have conversation.
So let's get back to that question phrasing, right? So bad example of question phrasing is to say, give me an example, right? This feels defensive and pushy, but instead tell me about a time when, right? Feels more collaborative and open. It's the same information, but a totally different emotional response.
Resist the urge to solve every problem. If your creative comes to you and says, my leg is broken, you're going to go, well, go to the hospital. And they're going to go, but it hurts so bad. And you're going to go, yeah, I can see the bone. It's sticking out. Go to the hospital. Right. It sounds really familiar. And it's a dramatization of some of our conversations with creatives. But creatives often want to know that you're with them in their struggle before they're ready for solutions. So ask instead, hey, what solutions have you considered already at this point? And the transformation inside of them will go from problem-oriented to solution-oriented, and that's how you build a great team.
One of the top three people that I've learned about asking great questions from is Oprah Winfrey, right? You go back and watch any of her interviews, become a student of how to ask really great questions. Dan Patrick is another sports broadcaster. He has a regular show that I watch just about every day. Also great interviews, great questions. And then David Letterman is the other one. David Letterman, I think he has a show on Netflix. My next guest needs no introduction, incredible questions in that show. Become a student of how to ask really great questions. Leaders, regardless of industry, they excel when they master the skill of asking those great questions.
All right, let's get into the four part structure and some common mistakes to close this out. What's the four part structure of every single one on one? A simple structure will prevent wandering and conversations and help you understand common pitfalls that can keep you on track.
So number one, you have to start with personal check-in. Personal check-in, don't jump straight into business, right? What's giving you energy right now on a scale of one to 10? What's your creative capacity feel like inside of you right now? What's inspiring you outside of work? How's your family? How's your spouse? What hobbies did you do this weekend? And tell me more about that and how did you get into it, right? Spend a good significant amount of time. Don't rush this personal check-in process because if you rush it, everything else will suffer.
So number one, personal check-in. Number two, progress review, right? What progress are you most proud of? Where do you feel stuck? What roadblocks can I help remove for you?
Progress number three growth planning. What skills are you excited to develop next? We should always be growing and encouraging our creatives to grow as well. So what skills are you excited to develop next? That implies that they actually have something that they're thinking about, right? It's leading that question. How does your current work align with where you want to grow? And what resources would help you level up? Again, solution-oriented, not problem-oriented questions.
And then lastly, number four, end with some creative inspiration. Share something cool that you found. In larger group meetings that I used to lead with the whole creative team, we actually did show and tell and you had to come show something cool that you found. Show and tell is actually something really good. And I want one as well where you can say, I found this. This is why I think it's cool. Now you bring something. So show it to me why you think it's cool. We can watch a video together. You can ask what they're seeing in the creative landscape. Or on social media, we're constantly dropping stuff and sharing stuff into people's DMs. And so, hey, you should see this, you should see this. This time you're just doing it in person. That's the only difference. But ending with creative inspiration, ending on a high note, an inspiring note, is a great way to wrap up the one-on-one.
Now I want to talk about the agenda. You should send an agenda about two to three days ahead of time with the key three to five discussion points. It doesn't need to be the personal topics that we're going to talk about, but the key three to five discussion points that you're going to focus on. Send those ahead of time, include both standing items and meeting specific topics. Hey, every time we meet, we're going to ask about this and this and this. But then also in this meeting, we're going to talk about this and this and this. So it's critical to include those things. And also when you send that agenda, ask them because you're sending it in advance. Ask the one that you're meeting with, is there anything that they would like to add? Right. Because otherwise it's not a conversation, it's a broadcast and it could be shared in an email.
But we're trying to have conversations here, which leads me to my final portion of today's episode in this talk, which is the five fatal mistakes of one-on-ones.
Number one, number one mistake of one-on-ones is to turn one-on-ones into status updates, right? That's what email and Slack is for.
Number two, dominating the conversation. Aim for 50 percent or less of talk time. I love it when I have meetings online because I use my Fathom note taker and Fathom will actually tell me how long I've been monologuing and I can see that percentage. It'll pop up in the corner and then it'll adjust throughout so that I can step back and be a good conversationalist, not just an informationalist, just putting all that stuff out there.
Number three mistake, inconsistent scheduling. They shouldn't have to ask when the next one is or where it is. They should have all that information already because you're being consistent with it.
Number four, focusing exclusively on problems, right? This is not the principal's office. This is not a time to just focus on what we could be doing better. It's also time to celebrate wins and to figure out how did we win so that we can replicate it again.
Lastly, number five mistake, failing to follow through, right? Trust is earned in pennies, but it's spent in dimes. If you fail to follow through with what you said you were going to do or what you said you were going to talk about next time, then it will lower the trust factor between you and the person that you're meeting with.
So what now? This week, number one, this week audit your current practice, right? I want you to list out everybody who reports to you, whether they're contractor, volunteer, staff, whatever it is. And I want you to honestly assess when's the last time that you've had a real conversation with each of these people and identify the three to five people that you need to start weekly one-on-ones with immediately. That's your audit.
Secondly, block the time. Choose one consistent time and one place for each person, send calendar invites for the next 12 weeks. Name those invites correctly, right? We're gonna use both names on it. And then don't ask permission, just do it and explain the value when you meet. You're gonna show up and you're gonna give them the value of what this 30 minutes can bring.
Number three, download the creative guide to one-on-ones. This is on my website, absolutely free for you, dustinpead.com/1-on-1. Go ahead and grab your copy, it includes everything that we've discussed here today plus some question templates, some meeting structures and some practical worksheets as well. You can customize it for your specific team dynamics. You don't have to follow it word for word. Just use it as a guide or as a roadmap for the next 12 weeks, the next 90 days.
Number four, practice the three to one ratio. In your next team meeting, have someone track how many questions versus statements do you make. Just start paying attention to that. Be honest with yourself about the results. Commit to improvement, not perfection.
And lastly, start with personal, not with business. Your first one-on-one with each person, each person should be about an 80 percent personal check-in because you're really trying to create some trust there, right? So ask about their creative journey. What brought them to the team? What energizes them? Resist the urge to dive right into projects and performance and build relationships and set that foundation first.
There are several resources that I mentioned today and in the talk that I gave at a salt conference. If you're in ministry, actually, if you're not, if you're in ministry or not, this is a great book by Clay Scroggins. If you find yourself kind of leading from the middle, it's called How to Lead When You're Not in Charge. Definitely check that out. My free resource, the Creative Guide to One-on-ones, you can get at dustinpead.com/1-on-1. And then I mentioned the Fathom AI Note-Taker that I use to record, note take, all that stuff from my meetings, but also tracks the talk percentage in my meetings as well.
So in conclusion, here's what I want you to remember. If you hear nothing else from this entire episode, hear this. In order to have effective one on ones, you have to genuinely put people over performance. You cannot fake it. I spent over a decade caring more about what showed up on a Sunday morning than the people who created it. I'm asking you today, don't make the same mistake that I did. Maybe excellence is more about the people than the product. Maybe the best creative work comes from teams who feel genuinely seen, heard and invested in. Right. 30 minutes a week. That's what we're talking about. Just 30 minutes to transform not just your team's performance, but their lives. 30 minutes to model what leadership actually looks like.
The trust that you build in pennies of investment, it will compound over time. But the trust you lose by canceling, postponing or half listening, it will evaporate in time. So here's my challenge. Pick one person on your team, schedule that first one on one, show up prepared, ask great questions, really listen and watch what happens.
Remember, helping creative scale with efficiency starts with helping them know that they matter and that happens one conversation at a time.
Next week, we're gonna be back and I'm gonna share my other talk from SALT 2025. Actually gonna share the live recording from it because the microphone did work in that one. Where it's all about gaining and sustaining margin in your creativity. And I'll wait to share that talk with you next time on Creativity Made Easy. Have a great week.