Accountability Without Micromanagement + Seller Reports Agents Have Been Waiting For

What if accountability didn’t feel like pressure
 And what if seller reports didn’t take hours to build

In this episode of Take It and Run, Kristi and Kelcie sit down with Derek Caldwell, Team Lead of The Caldwell Group at eXp Realty, to break down how he’s built real accountability systems using automation, trust, and AI.

Derek shares how his team replaced manual reporting, awkward check ins, and CRM overwhelm with weekly scorecards, transparent dashboards, and systems agents actually enjoy using. You’ll hear how empathy drives performance, why non negotiables create freedom, and how AI has become his second brain in operations.

Then Derek pulls back the curtain on North, the AI powered seller report generator he built to solve one of the biggest pain points in real estate. North automatically pulls listing data, social media activity, showing feedback, comps, and market analysis into a clean, branded report sellers actually read. No spreadsheets. No copying data. No guessing.

To make it even better, Derek gave Take It and Run listeners an exclusive offer.

🚨 Use code RUN20 to get 20% off North
You’ll also get a 14 day free trial to test it with your own listings.

If you lead a team, manage operations, or carry listings and want smarter systems without micromanaging people, this episode is required listening.

🔑 What You’ll Learn

• How to create accountability without confrontation
• Why weekly scorecards motivate agents naturally
• How AI replaces hours of manual reporting
• What sellers actually want to see in listing updates
• How North changes the listing conversation

👉 Try North at NorthReports.com
👉 Use code RUN20 for 20% off after your free 14 day trial

🙌 Connect with Derek Caldwell
Instagram: @dcaldwell
Email: derek@northreports.co or derek@caldwellrg.com

If this episode gave you an idea you can implement in your business, don’t just listen — take it and run.

🎤 Book me to speak at your event/team meeting: 
kristijencks.com

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🎙️ About the Podcast

Take It and Run is the podcast for ambitious professionals—especially real estate agents—who want practical strategies they can implement immediately. Each episode delivers mindset shifts, frameworks, and real-world insights to help you move from thinking about it… to doing it.

Transcript

Kelcie Dowd (00:00)
let me ask you this. What if accountability didn't mean micromanaging and AI didn't feel overwhelming? That's why we brought Derek Caldwell in today because that's exactly what he has built. So welcome back to Take It and Run. We're the show that helps real estate professionals stop overthinking and start moving with strategy, clarity and heart.

Kristi Jencks (00:20)
Yeah, I'm so excited and I know I say that every episode that we have a guest, but today's guest is going to absolutely blow your mind. If you've ever struggled with follow-up, accountability, or even like keeping your CRM from like turning into that monster like that you open it up and it's like, ⁓ Kristi so nice to see you. Are you gonna actually do something today in your CRM, right? Or it's like.

blaring like an alarm, like the submarine's gonna sink because you have 150,000 past two reminders. Right? Like if that's been you in your life, I was lucky enough to trick our guest into being into a mastermind with me. And I say trick because he is so smart and so smooth. But I wanted to get into a cadence where I could learn from him. And so I tricked him to be in a mastermind with me.

and just because I wanted to learn from him.

Kelcie Dowd (01:16)
Yep, today we're talking with Derek Caldwell. He's a team leader, operations strategist. So this episode is definitely not just for team leaders, but for anybody who's in an operations seat or marketing or even assistant work. And he's the tech genius behind the Caldwell Group in Northern Kentucky and Cincinnati.

Kristi Jencks (01:35)
Yeah, so Derek's been building automations, workflows, and giving time back to himself, his team, and his agents through hacking the systems and getting rid of the manual lifting. He's built smart accountability systems, which we're going to dive in today, AI tools that are going to blow your mind, mentorship. There's not a piece of running a real estate team that he hasn't touched. And he's really a real estate ops expert.

And he sits on the intersection of people, systems, AI, and he has a heart of gold and just one of the greatest people that I know. And, you know, he really is the brains behind the Coldwell group and he's going to open up his playbook for us today.

Kelcie Dowd (02:15)
Yep. And we're going to dig into specifically how Derek uses automation and smart systems to boost agent performance, protect databases and simplify growth. And I'll tell you that his approach is simple. Build tools that supports agents and not overwhelm them because we get overwhelmed. So Derek, welcome to the show.

Derek Caldwell (02:34)
Hey, thank you all for having me so much. I'm so excited to be here today. Those are some nice words.

Kelcie Dowd (02:39)
Hahaha

⁓

Kristi Jencks (02:40)
All true though, all true, all true.

So what didn't we cover? Like I know you're a father, you're a husband, tell us a little bit more about yourself. What do you want our audience to know about you so that they know that this is the real deal?

Derek Caldwell (02:54)
Yeah. So father, husband, I have a eight year old now and a three year old. so that's a lot of fun, both girls. So love being at home and definitely in a house full of girls. Been married to my wife for going on 13 years. So that's just so much fun. And I love nothing more than being a father and a husband.

but I love helping our agents as well. So the second passion I have beside my family and traveling and hiking and camping and all the things that we do outside is helping our team grow and be successful, living inside of AI and AI tools and just trying to help agents across the country better themselves with operations.

Kristi Jencks (03:36)
Awesome. Tell us a little bit about the team, like in 2025, tell us about your production, how many agents you have, and you know, even maybe share a little bit of your guys' goals for 2026.

Derek Caldwell (03:45)
Yeah. So this year we'll end the year. we count leadership on the team, we'll have 18 agents. Um, we started the year with, I think 12 or 13. So we grew up to about 20 have kind of had some attrition, which is okay. We'll close 225 ish, 230 deals this year for about $75 million worth of volume.

Which is fantastic for us because last year we did 208 transactions and only, I think it was like $67 million worth of volume. So for us to have an increase, we were thrilled. Um, so this year has been a year that has been very, very good for us. And we're very thankful for our agents and the team and everything. So this next year, we've kind of had this interesting approach because we brought on a recruiting as part of our business strategy, uh, in 2025. And we're really leaning into that

heavily in 2026. So the way that leadership looks at the team now is we have this recruiting aspect of the team and business, and we have transactions that we want to flow through recruiting. And then we also have the team as well. So we have all the graduated mentees that come as a part of the team. And the way that our coach talks about it is if we both do it somewhat well, then we all win and we'll meet the big goal. Because our big goal next year is 280 transactions.

We want 75 of them to come from mentorship and then we want to hit at least 90 million dollars worth of volume. So, yeah, it'll be good. Yes.

Kristi Jencks (05:18)
Love it. Those are some good goals. Yes, I love it.

I love it. Okay, well, let's jump into our first topic. And I want to start with the pain because I know, again, if you're listening as a team leader, if you're listening as a small team, a big team, it doesn't matter if you have anybody that reports to you, right? So let's say you're just, you're getting ready to hire your first buyer's agent. So you don't even need to be necessarily big team leader. You can be an agent.

who's hiring an assistant or who's hiring a buyer's agent. I wanna talk about the pain. When we were masterminding together, just as peers, right? Like, you know, when we were together, we would come in and we were talking about, I remember we were talking about agent accountability. And at the time, what we were doing, we were both Boomtown users at the time. What we were doing is I was having my VA go in and use the limited smart filters. They didn't even call them smart filters. I forget what they called them, but.

You know, we were using the very limited tools we had inside Boomtown. My VA was going in and then she was emailing the agents like, hey, these are your new leads that haven't been touched. These are your people that been back on the website, haven't been called, right? And we would do that every single day. And I think you had told me you were doing something similar, although it was taking you like a full day to do these agent reports. And so my question to you is thinking about accountability.

What was the moment you realized that something had to change in your team's accountability and operations?

Derek Caldwell (06:46)
meaning like I was spending a full day doing it and it was just a complete waste of time. That was the moment. Yeah. mean, I have a very, I love data and I wouldn't call myself high C on the disc profile. I'd call myself more high D, but I love knowing numbers and having analytics. And I feel like the numbers help drive us to make decisions. And so

Kelcie Dowd (06:49)
I feel like if that wasn't it, I don't know what would've been.

Derek Caldwell (07:12)
coming from, in production. at the time I was coming out of production, doing more coaching and, also leading the team's operation efforts and kind of doing the whole entire backend. I realized that most CRM systems don't give, which is crazy to me that they don't give any good reporting. Like they have all of the data yet they don't give it to the team and the agents, which is so it's that's another rant that we could go on. But I felt like.

There's some way that the information that's inside of any CRM, whether it be, I we're on follow-up boss now, but Lofty or Boldtrail or whatever it might be, the data is there. If we can extract it, then maybe, just maybe, I can start giving some insights to the agents to help keep them accountable, maybe encourage them, because as an agent, we can get so caught up with the minutia of real estate and we don't get encouraged by the good things that we're doing.

So that was my big project maybe a couple of years ago was just how can I spend less time? Like I was spending all day giving agent reports on like what they were doing. So how could I do it where I build it once and it just happens weekly without me ever touching it again. So that was a huge effort that I went on maybe as probably a year ago, actually.

Kelcie Dowd (08:31)
Mm.

Kristi Jencks (08:32)
Yeah,

I was going to say it was right around the time that we were doing automation with Google Business, right? Like it was right around that time that you were doing it. And so what did that look like? Right. So it went from a full day, manual Derek pulling this. And then when you built it, what was the end result?

Derek Caldwell (08:37)
Yeah.

Yeah. So I feel like most, most people that want to build systems have to be good at least, it had to be dangerously comfortable with automation platforms. So whether you're a Zapier user, whether you're a make.com user, we're N8N users now, which is a little bit heavier for most people, but you have to be comfortable knowing how to have things that do things after other things. It's probably the easiest way to say it.

So what I found myself doing was repetitive tasks over and over and over again. I would go to the CRM and I would look at different smart lists and see how many leads were in those smart lists. And then I would change the agent to go to another agent to figure out that agent's number of leads in smart lists. So naturally, maybe this isn't naturally, but I just had a conversation with ChatGPT about it. I was like, hey,

Kristi Jencks (09:23)
you

Derek Caldwell (09:42)
I'm doing this repetitive task over and over and over and over again. Is there any way like that, that we could streamline this, make it more of a automation where it just happens automatically? And funny enough, it kind of asks more questions. I uploaded follow-up bosses documentation. It understood it way better than I do. And it came up with a solution for us. So it walked me through.

setting up an automation workflow where every single week it's just iterating through the smart lists through each agent and it's building a beautiful email that's being automatically sent every Monday morning. So my six hours worth of time that I was doing and creating each email for the agent and sending it, it happens literally within two minutes. is the like, if that's not buying your time back, then I don't know what it is. Cause I, that is like,

Kelcie Dowd (10:21)
Hmm.

Derek Caldwell (10:35)
thrilling to me that now I have something that works bulletproof every single week and the agents actually enjoy it. Like they like seeing because we get caught up. They like seeing what's in their smart lists. They like seeing how many appointments they went on. They like seeing how many calls they made. They like seeing how many text messages they sent because they feel productive. We all have the weeks where we feel like we're just doing nothing and making no progress. But then you get that report on Monday from the week prior and you're like, OK, I actually did something last week or you get it and you're like,

Kelcie Dowd (10:54)
Yeah.

Derek Caldwell (11:05)
crap, this is like the second week in a row that I haven't done anything. I need to get my act together. So it's helpful, but then it also brings good accountability too. Like I can sit down with the agents. We can have one-on-ones. It's very transparent. I know what they're doing. They know that I know what they're doing and it's just super helpful. It brings a whole bunch of transparency to what we do.

Kelcie Dowd (11:27)
Dang, yeah, that is like the testimony of buying your time back. So the segment that we're in right now, we're kind of talking about like team pains and growing pains. Can you think of any gaps that you noticed?

Derek Caldwell (11:33)
Yeah.

Kelcie Dowd (11:45)
that were showing up with agents that you could kind of trace back to systems, whether a system wasn't there or the system wasn't doing what it really should.

Derek Caldwell (11:54)
Yeah, I think as you grow, everything will kind of unravel itself on all the broken aspects of your SOPs and of your systems and all the tech that you use. And it just becomes apparent that this isn't working. And as we grew, like from a team lead aspect, it's easy to be intentional with agents when you have one buyer's agent. It's a whole different ball game when you have 18 agents to be intentional with.

And so what we started learning was accountability is really needed. mean, that's, think that's one of the biggest things why people join or agents join teams is they want to be the, maybe they might say accountability that they like the interaction between what they're doing and what they want to be doing. And so what we found as we grew was my, the time that I had to be intentional one-on-one got cut because there's so much more, you know,

there's so much more that people need from you when you're a bigger team than when you're a smaller team. So what we started doing was I think ⁓ we did a whole systems breakdown where we just stripped every single platform that we were using and we rebuilt it from the ground up knowing that we wanted to scale. Cause before we started growing, the systems were just built for a super ninja team. Cause it was only three agents at the time.

Kristi Jencks (13:14)
Mm-hmm.

Derek Caldwell (13:16)
But as we grew every, nothing worked because we were so like it it worked really well for just a small team. But when you throw a bunch of transactions at it, when you throw a bunch of leads at it, it just fell apart. So I spent the whole of 2023, probably like ground up rebuilding our whole entire infrastructure to knowing that our biggest push was scale. And what that brought was a whole lot more intentionality on

having really good reports on what agents were doing using systems like follow up boss that could scale with us and just building a whole entire backend solution that it works for us and it works really well for us. And it went super unconventional because like we use air table air table is not a real estate platform. It is like the most all encompassing platform, but we made it work for real estate. So it was just not being scared to make changes that weren't

Kristi Jencks (14:03)
Mm-hmm.

Derek Caldwell (14:12)
real estate products and then having really good conversations with AI on how we actually implemented those into our system. And now I feel like our team is super well-oiled. we just, our ops is just super fluid right

Kristi Jencks (14:25)
I love that you said that because that wasn't even something that I was going to put into the questions, but I'm finding more and more without mentioning any lawsuits that are going on or companies that have been purchased without going political at all. But because you were not afraid to go industry agnostic, like something like Airtable, and because you were exploring

Derek Caldwell (14:36)
Hahaha.

Kristi Jencks (14:49)
you know, that led you to go from Zapier to Make to NAN. And also, there's so many people out there trying to nickel and dime real estate agents to death. Like, it's only $25 a month for this and $25 a month for that. And before you know it, you're tracking your production in one system. And there are inexpensive systems that I absolutely love that we both used.

Derek Caldwell (15:08)
Mm-hmm.

Kristi Jencks (15:11)
And then there's the expensive ones that are supposed to have, you know, the stuff that always feel broken, right? They're all over the place. You've been able to just kind of bring everything in house and not rely on third party products that could get purchased, that could get shut down, that could not update. mean, yeah, we won't go into that, but let's come back. in terms of this idea of accountability, because this was one of the first times that you and I had really delved into this and

Derek Caldwell (15:18)
Yeah.

Yes.

Hahaha

Kristi Jencks (15:41)
And you bought back your time. A lot of team leaders fear accountability or are they're like, I hear this as a coach all the time. They're like, how do I hold my agents accountable? How do I motivate my agents? That doesn't feel like micromanagement and many team leaders are in production. like Diana in production, who also at the time, you know, when, again, when it was a seal team, it was very easy for her to.

Derek Caldwell (16:02)
Mm-hmm.

Kristi Jencks (16:09)
have that imprint and have that accountability because you only had three agents. And then as you guys grew, so how did you, you how did these changes go, you know, increase accountability without micromanagement?

Derek Caldwell (16:23)
Yeah, that's a great question. so Diana is my mom. She's our co-team leader and, yeah, at the time, like three, four years ago, when we were sealed team, she's 99 transactions, a hundred and transactions a year. Yeah. So, but what's funny is now both her and I combined or 30 transactions this year. So that whole transition came from, well, we know that we can't like,

Kristi Jencks (16:35)
It's a beast, I love it.

Kelcie Dowd (16:43)
Mm-hmm.

Derek Caldwell (16:50)
As the team grows, the team gets more valuable as the lead reduces production. And there's nothing more encouraging in a recruiting conversation where we can say, well, most of our production comes from our agents. It's not the team. It's not the team lead. But we know that we have a past client database of 2,000 plus clients.

So we've been able to leverage that into accountability. So we're really heavy users of the follow up boss scoreboard. If they do anything really, really, really, really well, it's the scoreboard. And I feel like the agents can buy into that. So we leverage that. And what we do is we have a goat award that we have a little goat statue that we bought and it travels around the office with who's the next goat. And the agents vibe for that. mean, our follow up boss

Kristi Jencks (17:24)
Mm-hmm.

I love this.

Derek Caldwell (17:42)
point structure is most of our agents are hitting above 15,000 points to 25,000 points a month. It's a pretty competitive race. And whoever gets that top spot at the end of the month, they get the goat award, but the goat award also comes with a referral. So the next time that myself or Diana might have a past client or we have an agent referral, maybe from the TF network or somewhere in our brokerage or from other relationships that we have.

That goes directly to the goat winner. So it's, it's allowing us to kind of give back to the team and give them higher quality leads that we know we're going to transact. Like there's a pretty, there's an, I'm not going to say bulletproof likelihood, but like a 99.9 % chance. I pass a personal lead to another agent that unless you don't screw it up, it's going to close. They will buy or sell something.

And so that has helped us level up accountability. Like I think you can do accountability so much differently than just sitting one-on-one with an agent and looking at, did you make calls last week? And did you send emails? Like accountability can look much different. And I think as you build trust with your team, as you build trust and you have empathy with your agents, accountability almost comes in natural.

Because as you're sitting and as you're talking, they're sharing the struggles that they have and they're sharing the pain that they have. And through that, you can have really, really good questions that point them back to, the only thing that matters is appointments, conversations. Like that's the only thing that matters. And so I think the empathy and trust that you build with your team will naturally give itself to accountability if you're open to it. But I think most people think of accountability as this like,

super rigid. Did you do this and did you do that? And it doesn't have to be that way. It doesn't have to be that way at all.

Kristi Jencks (19:33)
Yeah, mean, yeah.

I love that you said that accountability doesn't have to be confrontation. You didn't say it that way, but that's what you said essentially, because most people do. think accountability means they got to be mean and I'm not a mean person. I'm a nice person. And that's not truly like I would never allow my friends to do something that would harm them. And that is a level of accountability. Like, hey, don't touch that stove. It's hot.

Derek Caldwell (19:43)
No.

Kelcie Dowd (19:51)
Mm-hmm.

Derek Caldwell (19:51)
Yeah.

Yeah.

Kristi Jencks (20:03)
Right? Or if you don't, know, yeah, I love it. Okay.

Derek Caldwell (20:04)
Yes.

Yeah, we can. One of the biggest questions I ask when I do sit down is, well, how can I help you this week? And what do you want me to help you with this week so that you rock it out next week? It's just a little bit. It's a different rephrasing of the question of what can I hold you accountable to you? Like that seems very abrasive, but if I know their goals and I know what they're chasing after, can ask. It's like the simple swap from Phil Jones. I can make it sound just a little bit prettier.

but it's the same question. just sounds different, which I think any good team lead can do that. Like we're so good at that on the fly. So yeah, that's what I think.

Kelcie Dowd (20:45)
And I don't think that, I think that being mean, just still thinking about that, it isn't like sustainable. You know, sometimes I even think like, man, I just need a swift kick in the ass or something like that. But even that, like, that's not something that like...

Derek Caldwell (20:56)
Ha ha ha ha!

Kelcie Dowd (21:00)
Unless you're a bit more on the sadistic side, it's not something that agents keep coming back to. It's something that's helping them. It might help them once. But then what really keeps them going is that empathy and that understanding and that accountability and like, hey, I'm here with you instead of I'm behind you kicking you.

Derek Caldwell (21:19)
Yeah.

Yeah. It's a whole, it's a whole different, like, ⁓ it took me a while to learn coming from agent into admin and into leadership that I can't want it more than my team agents. And I found myself in that mode more than not of I wanted success, maybe more than they wanted success, or I wanted this because I want to like, so

We're all adults and I feel like if it's a conversation of condemnation or anything that just it's not healthy because like they should be able to make decisions on their own and they should be able to if they want it bad enough, they'll get into action to go. So who's me to sit in front of them and be like a dictator on their production when maybe there is having a bad week and I just need to be empathetic and like.

help them because, well, I've learned this because I'm a team of 18 girls. I'm the only guy on my team. So you learn a lot through that. but yeah, I think there's just a whole lot different that goes into accountability. It doesn't have to be so rigid. And like, we're all adults. I'm not maybe some days it feels like we're meaning our clients feel like we're babysitting kids, but I'm not, I'm we're all grown. Most of my team is older than me.

Kelcie Dowd (22:18)
That's awesome.

Derek Caldwell (22:37)
Not most, but some of them are. So it's, how do you balance that and be a leader of care and not a leader of fire. And I think that's a, that's a hard lesson for a lot of agents that are in leadership have to learn.

Kelcie Dowd (22:49)
Yeah, I didn't know you were running a sorority. That's awesome.

Derek Caldwell (22:53)
No, it's a full blown sorority. ⁓ We actually so

we have we had one guy join the team last week and we did like a gender reveal with a box and the balloons that come out. That was blue. It was great.

Kelcie Dowd (23:02)
haha

Kristi Jencks (23:04)
That's hilarious. I love it.

Kelcie Dowd (23:05)
That's great.

Okay, so, you know, we've covered a lot of like, how you interact with the team and like you just said, you can't want it more than them. how did you get them to like, we, we, Kristi and I, we've seen a lot of different team, like operations and ways of running things. It's difficult to get agents to use the CRM. It's difficult to get them to use the systems. How do you do that?

Derek Caldwell (23:28)
some things you have to be a little bit non-negotiable on, but you can do it with care and structure and then show the benefit later. So not a lot of agents, not a lot of team agents or team leaders and teams know that. with follow up boss, it is a requirement. It's a non-negotiable on our team that you use their FUB phone number to make calls and texts. And you put all your appointments in FUB.

Because we live in a world where unfortunately we have to track everything that we do because we never know when someone might get upset at us and file a lawsuit against us. So if it's just housed and happens chance elsewhere, then that ultimately hurts the agent and also the team too. So one of the biggest hacks that we did when we made that kind of declaration was it's very easy to just start a three-way text message thread.

between your personal number, your follow-up boss number and the client. Cause all the history and messages are still going to be housed in the follow-up boss, but you still feel like you have the freedom of texting through iMessage or through Android message as well. Like that still feels normal. And then over time, the agents just naturally migrate to FUB. But I think if you're a team lead, that's very, um, interactive with your agents.

What you'll find yourself asking is when they ask questions about your clients, you'll just say, why I didn't see that you had that conversation follow boss because I'm looking at it right now. I can't really help you if I don't know what they were talking about because everything is historical. So it makes it a lot more challenging to help solve agents problems. If they can't help me by at least having their conversations in the CRM. Cause then it's a whole lot easier to go in and help them.

So over time, was it painful at first? Absolutely. painful at first. Like we had pushback, but now the whole entire team is on FUB. Like that is a non-negotiable and it's just part of our, it's part of our onboarding now. Like you have your personal number, which is for your friends and family. And then you have your follow up boss number, which is for your business. And it helps them segment everything out. And I feel like that is a, it's, it's kind of nice.

for the client not to have your personal info, like personal personal info. It's kind of nice for them to have it segmented, which is, which I think is beneficial.

Kelcie Dowd (25:53)
Yeah.

Yeah, anybody can be crazy.

Kristi Jencks (25:56)
Yeah, so.

Okay, so I want to see, I want you to tell me what does this actually look like week to week? As an agent on the team, what do I get, whether it's physical or via email or like I walk in and there's like a scoreboard, what does all of this, because it sounds fantastic, like I want to join, send me my ICA. I want to join, so, but what does it look like and what's included in this rhythm and this accountability reports?

Derek Caldwell (26:19)
Yeah. Yeah.

So since our whole entire business is on Airtable, we have completely overhauled our infrastructure to send everything to Airtable. So Airtable is not real estate software. It's kind of like monday.com, click up. It's a database essentially where you can put pretty interfaces or pages in front of it. So we run all of our transactions at Airtable.

rerun all of our lead structure out of Airtable, rerun all of our Google reviews out of Airtable, rerun all of our transaction ⁓ intakes out of it. Like every single thing in our business is inside of Airtable. But what that allows me to do is build beautiful like dashboards and interfaces for agents. So we have an internal website that if you have one of our...

CaldwellRG email addresses, can access intranet.caldwellrg.com. It's just for our team. And in there we have our apps where we list every single resource, application that the team has for the benefit of the team. And in there is our Airtable dashboards. So in real time, it's always up to date, always live. If you submit a pending, it's going to be an Airtable within 30 seconds. If you make a phone call, it's going to be an Airtable

in 30 seconds, if you, whatever you do, if you set an appointment, it's going to go to air table. So instead of going to follow up boss to try to find a report of how you're doing, it's all an air table. So the agents just hit their air table dashboards and they have these beautiful. This, it looks, they can know if they're winning or losing and how close they are to their goals within 30 seconds because

all the data is there from them. So just from that aspect, that's one tool that we have that the whole entire business feeds into where the agent can see if they're winning or losing. Then we have all of our email reports. So it's, have a lot.

Kelcie Dowd (28:26)
Man, just, yeah.

Kristi Jencks (28:26)
You know what?

Let's hear

about that. I was gonna say real quick though, you know, cause this, I know this is happening to you where if you didn't have that automation, say, but I have another, that's not right, right? When they look at the scoreboard, they're like, that's not right. I have another one. I have another one. And then the scoreboard loses its value because it's not up to date in their eyes. And you've solved that problem. But I interrupted you. Let's, I can't wait for our audience to hear about your email reports.

Kelcie Dowd (28:30)
Yeah, let's hear.

Derek Caldwell (28:48)
Mm-hmm.

Yeah. yeah.

So because we track everything in Airtable, we also can track moment by moment, week by week, who is the leading agents on the team. Like we can, since we know their goals, we know their production, we know what they're doing. We kind of figured out this formula of, um, it's a very personalized. So Kristi might have a larger goal than Derek who might have a different goal than Kelcie

We're all chasing after something different. Every single agent has a different outcome that they want to have in December. So we took that logic and said, well, if I scored everybody the same, then it's really unfair because someone might have a different goal than me. So if we're weighted the same, then I'll never look like I'm achieving something. So we've figured out a way to score the agents against the team, but also against their set themselves. So weekly.

We run a scorecard where we take the agent's production and what they've accomplished year to date and week over week. And we compare that to their goal of what they want to accomplish by the end of the year. And then they're weighted on a scale from zero to 100 on how well they've done in their business. And then that score is put into a table where we can rank the agents from one to 18.

on who's the number one agent on the team all the way down to our mentees. And that report goes out weekly. So every agent, every single week on Monday gets their scorecard on how they're ranking against the other agents on the team. That brings a little bit of accountability too, because if you were number two and then jumped to number five, that hurts a little bit.

Kelcie Dowd (30:28)
Hmm.

Kristi Jencks (30:47)
Yeah.

Derek Caldwell (30:48)
And if you're constantly at number one, there's nothing more that someone in that third place spot that wants to go chase after that first place spot. So it brought a little bit of healthy competition to the agents because now it's super transparent. I really believe that all teams should be super transparent on like how the team is producing. I think it brings this like healthy thought of the team is not out to get me. The team is there to help me.

And so we just became super transparent. think it was a conversation that I had with Jason Pantana knowing that Katie Day did this for her team. Like she just sent a scorecard out every single week on ranking the agents. And so we adapted that. It's now automated. Like it happens every Monday without my input and I don't have to think about it or do anything, but we save those outcomes week over week.

so that eventually we can run year over year analysis. Like that's the ultimate end goal of this, because we started this like six or seven weeks ago. But as we get more information, so over time we'll be able to run analysis. Like how did they fare last quarter? How did they fare last week? How did they fare last year? And the report, the scorecard will become more powerful. But it has a bunch of AI built.

Kristi Jencks (31:53)
Kate, you know you just did that, right?

Derek Caldwell (32:09)
in the backend, which I love. So based on how they've scored according to their goal and against the other agents on the team, AI will actually analyze that and give some either encouragement, give some praise, give some next steps. And the report will actually tell them like what the next steps are to keep achieving their goals.

Kristi Jencks (32:32)
Love that.

Kelcie Dowd (32:32)
I just know that there is an operations manager listening to this with their jaw on the floor and they're wondering if they're hallucinating right now because everything that you just shared like solves so many like qualms that operation managers face every day, but not just like, you know, people who love systems and, and, and want to improve, people operations managers who are working with team leaders who want to, you know, get their team going.

Derek Caldwell (32:39)
Mm.

Kelcie Dowd (33:02)
And so it meets so many people in the seats that they're at, these tools and these systems that you've built. at end of the day, right, yeah.

Derek Caldwell (33:02)
Yeah.

And that's just the agent report. Like that doesn't even, that's

not, we have a mentorship report because again, earlier I said, like we segmented the businesses this past year. We have the mentorship business and the team business. So now our recruiter, they get a weekly report on how their mentees are doing. Like we pull the mentees out of the agent production and we just score them against themselves in the mentorship program. Cause the mentees want to get out of mentorship. Like they don't want to be in mentorship for very long. And then quarterly or end of the month.

We get a leadership report where we take everything, all the data and aggregate it all together. And Diana and I get a team leader report on how the team's health is doing this month. And it allows us to make decisions without having our feelings or bias built back into it. Cause we can have a frustrating week and feel like the team is falling apart. But then that report comes at the end of the month and it's like, you're operating above health. You're doing this, you're doing that. And that's really encouraging.

Kristi Jencks (33:57)
Mm-hmm.

Kelcie Dowd (33:58)
Mm-hmm. Mm-hmm.

Derek Caldwell (34:09)
Or it says we're not operating above health and that leans us to go, okay, we need to have some more training. We need to do this and that. And it's, it's been super beneficial. So yeah, we have agent reports, mentor reports and leadership reports.

Kristi Jencks (34:22)
When I saw the sample team lead report, I loved, yes, it had the like metrics of like performance towards your goal, but then there was a section in there that talked about like almost like a red flag, like Susie R has gone 30 days without a new transaction or Jonathan is not performing in his normal cadence. So was almost like, hey,

Derek Caldwell (34:43)
Yeah.

Kristi Jencks (34:48)
go love on these agents. by the way, here's your diamonds. I think you've been had to diamond. was like, here's your diamonds. Go love on this agent for the positive that they're doing. Like they, they rose in the rank. did this. So I love that team leader report because it, it, it went just on pure metrics, but then it also gave you opportunities to highlight agents, to nurture agents and to, if you need to have that, like, Hey, what's going on serious conversation. It kind of pulled it out.

Derek Caldwell (35:13)
Yeah.

Kristi Jencks (35:16)
⁓ but again, not just going on gut feeling, but going on here's what's actually happening. And to your point, it was, it was going back to their goals. Cause I think one of the sections that you have in there is like, Hey, we got to have a conversation with Derek because he's not in alignment with his goals. And, you know, it's funny because my, ⁓ we just went on a, we just went on a vacation as our whole family. we went on a cruise, which cruising, cruising is fun, but it's also not like very

Derek Caldwell (35:39)
Nice.

Kristi Jencks (35:43)
good for your health. Although Meryl and I made a goal to not take the elevator at all and we made that, but there's so much food, there's food all the time, any kind of food that you want, any kind of treat that you want, know what mean? Coming back Meryl, right? It was like the day after, it was like 12 hours after, I was like, I could really use a frozen yogurt right now. I was addicted, but my husband said something to my daughter last night. She's like, hey dad.

Derek Caldwell (35:44)
Hahaha!

The ice cream machine.

Kelcie Dowd (36:02)
You

Derek Caldwell (36:03)
Ha ha ha!

Kristi Jencks (36:09)
do you want a cookie?" And he says, no, that's not in alignment with my health goals. And I was like, I love that. coming back, like this is our first week back, he and I were like, we have to get back on track because this is our identity of who we are going through our health transformation. And the way that he phrased that, it wasn't like, no, I can't have that. you know what I mean? It was no, thank you. That's not in alignment with my health goals. And I feel like your reports do that in a way that's like,

⁓ am I in alignment with what I said that I wanted and why I am in real estate and why I am going to do the things that might be uncomfortable like an open house or door knocking or calling? That report brings it back into alignment, but it also gives you that oversight without 20 hours of manual labor to try to find that.

Derek Caldwell (36:43)
Yeah.

Mm hmm. Absolutely. Yeah. It goes back to what Tom always says. Like what happens if you don't hit your goals? Like we can all, we can think about all the positive, we can vision board and do all the different things, but what happens if we don't do it? Like there is repercussion at some point in time. And if it's not large now, the not hitting your aspirations compounds over time.

Kelcie Dowd (37:07)
Mm.

Kristi Jencks (37:07)
⁓ yeah.

Derek Caldwell (37:27)
And maybe it's you set too high of goals and that is a, like an emotional factor for you. Then just make your goals attainable. Like if, if not hitting your goals makes you plummet, then set attainable goals. So that way you feel inspired to go after it more. And yeah, I mean, that's a whole different rant to that. But yes, our reports help us tremendously in staying in tune with what the team is doing in the agents.

Kelcie Dowd (37:55)
That's awesome. You've teed us up perfectly for our next segment here, which is about your mentorship model. You've got one that actually works. So can you walk us through just real rapid fire, what does an onboarding a new agent look like for you? What's their first 30 days, tools, support, meetings, all that?

Derek Caldwell (38:04)
Hahaha

Yeah.

We kind of stole the model actually from Doug Edrington's team. They have a great mentorship program too, and we just stole it and they gave it to us and they gave us the framework and we had to figure out how to, how to make it work in our team. We were told at a retreat from Tom, couple, maybe it was last year that if it's easy to do and easy to reverse, then you have to do it.

Kristi Jencks (38:19)
Good luck, Doug.

Mm-hmm.

Derek Caldwell (38:41)
And if it's harder to do and harder to reverse, then you should think about it. And the easy to do, easy to reverse thing for us a year ago was moving our highest performing agent from an agent to a recruiter because that agent was super like, she is so, she's the team's biggest cheerleader and a recruiter has to be the biggest cheerleader for the team. And it's the same type of business.

Kristi Jencks (39:03)
Mmm.

Derek Caldwell (39:09)
I'm just prospecting agents now instead of home buyers and sellers. And so when we are able to bring a agent on, of course it's all automated. Like they fill out their onboarding form, that onboarding form triggers Canva to be created. It triggers their email to get created. It triggers their payments to get create. Like everything triggers in the backend. that way, whenever they walk in on day one, we're not playing the operational catch up of

we have to create your email account. We have to add you to Slack. We have to do this. We had to do that. Like you can spend a whole day just checking off, adding people to things and operations, but through automation, I can add people to things as they do things, as they complete their onboarding form. So when they come in day one, we actually have like a three course, platform that we put them on, on contract learning and being able to recite a contract and write a contract and

negotiate and like that is all phase one. And then they moved to prospecting and what does it mean to prospect and how do you prospect and like, what do you say when you're prospecting and how do you build lead pillars? And then the third is like, how do we put it all together and just start performing? And cause we believe that we want to build, we want to build someone's confidence so that if they do go show a house for the first time with a first client, they say, I love it. They don't feel like they're scrambling because they've never seen a contract before.

So for us, the first thing we train on is the buyer agency contract, all the agency disclosure, all of that things we train first and they don't go show until they can write and recite the full contract back to us and get approved on that. Cause we want to set them up so that they go out there and they want to, someone wants to buy a house. They're like, let's do this thing.

Kelcie Dowd (40:50)
Mm.

Kristi Jencks (40:57)
Yeah, I like that. Okay, so obviously the mentorship is like absolutely incredible. could go on, we could do, we might have to have him come back and do a whole thing on that. But before we run out of time, I wanna switch gears. You know, we're still in automation, we're still in AI. But I wanna talk about a project that you did that blew my mind because this was another pain point. So again,

Derek Caldwell (41:08)
Hahaha.

Haha

Kristi Jencks (41:22)
What I love about your process there, because you're like, okay, what's the bottleneck? What's the pain point? Whether it's a pain point for the team, a pain point for the agent on the team, or even a pain point for the client. We didn't even touch pain points for the transaction team, which I know you've completely overhauled. But I wanna talk about North. I wanna talk about North. I want you to introduce it. I want you to talk about what it is.

Derek Caldwell (41:38)
Hahaha.

Okay.

Kristi Jencks (41:45)
and the problem that it solves because you've created something that I know that every person on this call or this podcast or this YouTube video that's listening has struggled with and that is seller reports.

Derek Caldwell (41:56)
Yeah. So North started as a project between myself and the team where, so I've been on a kick this year where if there's been a problem that the team has suffered and instead of trying to just subscribe to a solution, because that in itself can be done, could I build a internal solution that is specific to the Caldwell group? So for example, like we'll get to North, but

⁓ All the agents want to do more open houses and they want to have like pretty intake forms and being able to register people through a QR code. And there's things out there for that. But we rebuilt a whole entire open house platform from the ground up that has a beautiful like tablet style and desktop style graphics that allow the user to scan and like registered automatically goes to fob. AI analyzes everything like

So I've just been on this kick of rebuilding and building solutions for our team. And our social media person on the team was spending hours every single week diving into showing time, going to our Facebook and Instagram and ads and figuring out interactions and engagement, getting into flow desk and building out a seller report card so that

we can show the client, show the seller that we're working on their behalf. And I just thought to myself, there has to be a way around that. And so I started building this platform. At the time I was just calling it reports by the Caldwell group because it was, it was never meant to be something more than just for our team. And then about like maybe a hundred hours into the project, I thought,

Kelcie Dowd (43:21)
Mm-hmm.

Kristi Jencks (43:21)
Mm-hmm.

Derek Caldwell (43:41)
this could be something that other agents might be benefiting from too. So I completely scrapped it, deleted the whole entire project, started again from the ground up with the whole viewpoint of agents across the country being able to generate seller report cards that look absolutely beautiful. They look beautiful on desktop and mobile. They are branded to that agent. They have beautiful metrics from Zillow and Realtor.com and all their social media accounts.

And then AI is completely baked in the background, creating this dialogue of what's happening in the market. What does it look like in this zip code right now? How's their house performing against other homes in the market? Like, are they positioned price-wise good? And to top it all off, the agent gets to go in and provide some feedback about the house. And then the AI gets to generate this like agent recommendation that the client gets to see.

So it's just this touch point that I think most agents struggle with as crazy as it sounds is how's our home doing right now on the market? it's days on market are getting longer. The client deserves an agent who is working on their behalf and like showing them the sweat equity of getting their home sold. And the reason why most homes expire and most

Kristi Jencks (45:01)
Mm-hmm.

Derek Caldwell (45:04)
⁓ clients decide to work with another agent is because they're told that they never heard from their agent. And so North solves this unique, very, very micro problem of getting information back to the seller. Because yes, they like we can send showing time feedback. That's easy to do. It can be done automatically. But how do we leverage that feedback with how their home is positioned in the market and give them actual information that helps them make a decision?

Kelcie Dowd (45:32)
you

Derek Caldwell (45:32)
And

it's all run with AI and it is, I think it's, I'm very biased. I think it's very beautiful. And it's phase one for me. Like I, I envision North one day being as synonymous with real estate as like Carfax is with the automobile industry. Like how can we leverage North to give really good insights to buyers, to sellers, to agents. Right now we're just tackling the micro problem of seller report cards and giving sellers really good data about their home.

but I feel like there's so much more that we could give the industry. yeah, North has been my side project.

Kelcie Dowd (46:07)
So it shows the data, it shows like social media analytics, what else does it show and what does the agent have to do or not do with those to get the reports out.

Derek Caldwell (46:17)
Yeah.

The one thing I love about it is it's the only platform that solves this issue that has a direct API integration. So there's a Zapier app for North. There's a make.com app for North. So what does that mean for the agent? Well, what it means for the agent is they can set up a Zapier workflow or a make.com workflow that looks at their email so that every single time they get a showing confirmation,

or showing cancellation or feedback received, that information just gets fed right into North automatically. So manually entering things doesn't happen anymore. And so if you imagine looking at the report, there's a beautiful image of the home at the top. It shows the price. It shows the listing agent with their headshot. then at the bottom underneath that, you get a really, really beautiful summary of what the house is doing right now. So how much

They're getting seen on social, what's their showing activity look like? Have we had any open houses and how it's fairing in the market? So that first paragraph is kind of the all encompassing what is going on. And then below that you see the social media analytics. You can see post by post, the video by video, what the agent has done on their behalf to market their home on social or through YouTube or Instagram or Facebook. And then it gives like engagement. So you can see how many likes that it has.

And that all aggregates into their total engagement as well. And then below that, if there's a 3d tour or floor plan from Zillow, it automatically pulls that into the report. So that way they can see that and interact with that, which is, think is just an added cake benefit. Then we see showing information, how many showings the home has had, all the feedback, and any open houses and what that has looked like. And then below that we show cops. So.

What are other homes around their homes sold for and what does that look like in a really tight radius? And then AI analyzes that and gives kind of a synopsis of how your active home is fairing against other sold homes. And then the very bottom is the neighborhood analysis. So how is your home fairing against other homes in your zip code? And what does that look like? And then the very last section is the agent recommendations.

Kelcie Dowd (48:30)
Mm-hmm.

Derek Caldwell (48:35)
And then all of this can be edited on the backend where the agent can like put specific comps in. They can put, they can rerun the market analysis and they can refresh their North every day if they wanted to, pull in new data. And then the very last thing is they can share it with their clients. So when they share their North AI generates this beautiful email for them and they can copy that email, which has the link to the, to the client's North report and email it right to them.

Kristi Jencks (48:37)
Yeah.

Derek Caldwell (49:02)
I mean, phase two for me, I'd love to have email baked in where it just emails the client automatically. That would be pretty awesome. But for now, I like this. I think there should be a little bit of agent touch in there that can like, you know, make it sound more like them. but I'm very proud of like the analytics that have gone in behind the scenes because it's been a lot of work prompting and getting like the information, right? So that way the report just sounds really beautiful to the end user. And it's.

Kristi Jencks (49:14)
Yeah.

Derek Caldwell (49:31)
So much information, but it's really accurate information and it's information that I feel like any seller would be very appreciative having. And we're through beta now. And so just getting feedback from other agents has been really encouraging because it solves a problem, a unique problem that our agents suffer with, with their clients.

Kristi Jencks (49:51)
Yeah, I've been testing it for him and have been, yeah, some of the things that you said, like just the ability of being like, I don't want to include that home. I can take it out or, I know about this one. And then the AI ride up, when I first started testing, was like, Ooh, I don't quite like that. And then I was able to like reprompt it, you know, through the thing. And I was like, wow. And then when I got the report, I was like, this is so amazing knowing how much time

our virtual assistant spends going and getting that data. like we've, you know, here in the Phoenix metro area, days on market is now top to a hundred, right? So if you're carrying 25 listings for some of them go fast and some of them take longer, that's a lot of reporting. And then just the ability, I think it also increases accountability to the team to make sure that they are doing the things that they said they were going to do because pulling in the metrics.

Kelcie Dowd (50:22)
Yeah.

Derek Caldwell (50:32)
Yeah.

Kelcie Dowd (50:45)
.

Kristi Jencks (50:46)
from social media, but then also showing off what you're doing on social media in a way that they can see all of the assets. for everybody listening, if they want, you said you scrapped it, you opened it up. I know you shared it with our team and several other teams. Where can they go if they want to try North? Like where should they go?

Derek Caldwell (50:48)
Yep.

Yep. So you can go to Northreports.com and I did a special coupon code for the Take It and Run podcast. So if you sign up for North, you'll get a 14 day free trial, but then you'll also get 20 % off your subscription if you use the code RUN20. And yeah, I would love feedback. You can find me on Instagram at @dcaldwell and you can also email me. I can use

Derek@Northreports.com or also Derek@CaldwellRG.com. But I've built this platform to help solve a problem. anytime I had Doug Eddington's team beta-ing it with me too, and his ops person sent me like a laundry list of things I should consider. And within like three days, it was all implemented. So it's a platform built by an agent who knows that there's a struggle between

Kelcie Dowd (51:48)
Thank

Okay.

Derek Caldwell (51:56)
the conversation between a listing agent and a seller. And I want it to become something super powerful that the agent feels very, very, very comfortable using. You can spin up a North report for your client in less than two minutes, and then you can hide every single section on there and make it truly what you want. And you can brand it your colors and put your logo on there like it feels just like you. So yeah.

Kelcie Dowd (52:09)
Mm.

Kristi Jencks (52:09)
Yeah.

Derek Caldwell (52:19)
I would love for more people to be jumping on it and providing feedback and making it grow to something that is super special.

Kelcie Dowd (52:27)
That's awesome. Thanks so much for that code. We're definitely going to push that. can see that. Okay, so let's wrap this up like we always do, Derek. What's one small move that our listeners can take this week to apply what they've learned today?

Derek Caldwell (52:29)
Yeah.

The thing I've been on right now is not being scared to use AI as my like second brain because I have ideas on things I want to implement. And AI is very good at figuring out ways of implementation. Like everything that I've built over the past two years has been through a conversation between myself and chat, GBT or Claude. And I've only like

I now will only use products that have an open API system where you can build with them. And that's why we lean into Airtable heavily because most people don't know this, but the CEO of Airtable is one of like the top 10 power users of ChatGPT. Like if they released a report a couple of months ago showing the top 30 token users for the open AI API.

And the CEO of air table was one of them. And so to me, it's like, if I can get behind companies that are also leveraging AI, then I will win. So everything that I built operationally has been through a conversation with chat, GPT and Claude. And I just ask it, how do I build that? Like what information do you need? What, how do I do this inside of Zapier? How do I do this inside of make? Like this is what happened. This is what broke. I'm just, it's becoming my second brain on.

everything that I do and through it, it's creating some just unbelievable processes for us. And we're buying, we're buying back probably 200 hours a week now, just from automating everything that we do. So the one insight is like spend your time with AI, explaining your goals and your pains and your struggles and what you're trying to build. And if you built this, it would solve this problem. And don't be afraid to

build that with the help of AI and break it and fail and give it that insight so that way it can help you build it to something better.

Kelcie Dowd (54:35)
I love it. Yeah. So basically if everybody listening pick, pick one thing in your business that, know, maybe you found yourself like Derek was saying, you just do over and over and over and over again and simplify it. You know, bring AI into it. Look into follow up onboarding accountability, make everything cleaner and smarter.

Kristi Jencks (54:58)
Yeah, and he, you know, he, if you go back to the top, mean, this was a great, this is a long episode. It was great. Um, he, started with one problem, like, don't try to solve all 25, get overwhelmed. Then you have all these open loops, right? So Derek, thank you so much. It was so insightful. Yeah. You made it, you made it feel very doable, very approachable. So, um, that's what our listeners need.

Derek Caldwell (55:08)
Yeah. ⁓

Thanks for having me.

Kristi Jencks (55:20)
And I want to remind everybody to, if you haven't subscribed to the Take It and Run newsletter, if you are not subscribed to our YouTube channel, please, please, please do that. And make sure to check out Derek's seller reports. One more time, Derek, where can they find you?

Derek Caldwell (55:33)
Northreports.com is North. Then you can find me on Instagram @dcaldwell

Kristi Jencks (55:40)
Perfect, we'll put it in the show notes.

Kelcie Dowd (55:40)
And then it's RUN 20,

RUN 20 is the coupon code. Okay.

Derek Caldwell (55:43)
RUN 20. Yep.

Kristi Jencks (55:45)
Excellent. Okay, so whether you're automating one piece of follow-up or setting a simple weekly check-in system, we've given you the tools. It's now on you guys to take it and run. Thanks so much. We'll see you next time.