You Can't Delegate Confusion to AI

0:00About a year ago, my cousin, Sisters and I rented a house in downtown Stanton, Virginia, so that we could attend the Queen City Magic and Miss Jeff Festival. This is a full Harry Potter themed weekend where the entire downtown basically turns into Hogwarts. It was so much fun. And it's not what I want to talk about, but that's where the conversation happened. I was hanging out with my cousin Kendall, catching up as we do anytime we get together and asking her how her job was going. She works for a tech company and I knew there had been a lot of big changes. I was really curious because I know a lot about how she operates. I was curious how AI was impacting her role and her company as a whole. And she told me that her company had mandated the goal that everybody used AI about 70% of the time in their jobs.

1:01And as you can imagine, there was pushback. People weren't all bought in. Some people had different objections thinking that this is just coming ahead of layoffs. It's beneath me because I'm a tech genius. Some people are already using it and now just we're admitting it out loud. There's a lot of mixed feelings throughout the entire business around AI and the adoption of it. But Kendall explained what ended all of the pushback. And it wasn't some big town hall or memo or leadership making a better case for why they need to adopt AI. It was a sorting exercise that just took one afternoon, three columns on a piece of paper. And here's what I have not been able to stop thinking about since. When she described it to me, I recognize this exercise immediately because this is the exact same exercise that I have been walking women entrepreneurs through for decades.

2:02It has nothing really to do with AI. It has everything to do with delegation. And the only thing that has changed is who you are delegating to. So today I'm going to walk through this exercise with you so that you can get clarity around what you are delegating to AI exclusively, what you are delegating to AI plus a human and what you are delegating to the humans that work with you. Let's get into it. Are you ready to grow from solopreneur to CEO? You're in the right place. I'm your host Rachel Cook and I've spent the last decade helping women entrepreneurs start and scale service-based businesses. If you're serious about building a sustainable business, it's time to put the strategy, systems, and support in place to make it happen. Join me each week for candid conversations about stepping into your role as CEO, the hard lessons learned along the way, and practical, profitable strategies to grow a sustainable

3:04business without the hustle and burnout. Hey there, CEO Rachel Cookier, founder of the CEO Collective and host of the Promote Yourself to CEO podcast. I have really been enjoying putting together this series for you, human first AI for high trust businesses. I think this conversation is so important and it's one of those things where I see mistakes happening all the time and small business and it's easy to believe these mistakes are unique to AI. But truly, the more I dig into it, the more I'm realizing the mistakes people are making with AI are the same mistakes people have been making in small business for a really, really long time. I see people making mistakes where they aren't actually pressing pause to make thoughtful decisions as the leader of their business.

4:08If you are the CEO of your business, you are the keeper of the vision and the values. You are the one that your entire business culture comes from. And if you're making decisions, whether it's about AI or about hiring or any big move in your business and you're not running it through your vision and your values, then you're making decisions by default, just one convenient shortcut at a time. And that is leading a lot of people to take action without actually sifting through what the impact or the outcome is going to be. And that's why I think this conversation is so important because like I mentioned in the last episode, we're seeing a lot of people who jumped on the AI bandwagon who didn't press pause to really run this decision through their vision and values filter and they're breaking trust without intending to.

5:10If you're anything like me, the relationships that have built your business, your community, your colleagues, your clients, your team, this is the cornerstone of everything for me. And I have learned that if I'm not putting them at the forefront, if I'm not putting all of these relationships at the forefront and really protecting those relationships, protecting the trust that I have spent decades building, it really doesn't take much to break it. It really doesn't. In this episode and the following episode, I want to get really practical with you and help you decide on purpose, help you get really intentional about how you can use AI in a way that feels like it is in integrity for you as a small business owner, especially a values based small business owner. Now like I mentioned in the top of this episode, there's an exercise my cousin mentioned

6:12that I instantly recognized as a delegation exercise. But before I get into how to do that, I want to share with you how I've been talking about this for a long time. We have a tool inside of the CEO collective called the CEO scorecard. This is a tool that I have adapted from my background and consulting. And in fact, it has become a fully integrated part of how we support small business owners. If you ever have purchased our CEO planner, you have seen the CEO scorecard right there in front. It's built into how you're tracking what it is that you're doing throughout the course of your week. And I have a full episode, so I'm not going to go too deep into the CEO scorecard. But basically what it does is it takes time tracking and then adds another layer onto it. A lot of times if you work with a coach at some point, they'll ask you to track your time.

7:13And they're asking you to track your time so that you can bring awareness to where and how you're spending your time. It's a great exercise. Highly recommend doing time tracking at least once a quarter just to see what is happening and where your time is going. But I like to add this additional layer of this CEO scorecard where once you try to do track your time, you're also assigning a value to each hour of your time. And the value you're assigning is based on the types of tasks you have been focused on. On the CEO scorecard, we have this broken up into four categories. And it's $10 an hour, $100 an hour, $1,000 an hour, and $10,000 an hour. Click note for anyone who is already asking. This is an exercise about clarity for you as a small business owner. This has nothing to do with accounting or money actually flowing in and out of your business. This is basically a way for you to quickly assess whether or not you are focused your

8:19time, your attention, and your energy on CEO level work on work that is growth oriented or if you're focused on more maintenance level work that doesn't move your business forward. It's what your business needs to operate to maintain its current status, but not growth oriented. So as you're using this CEO scorecard, you're tracking your time and then you're going through and deciding for every hour of your time, what about is that hour worth you? If you're doing $10 an hour tasks, these are going to be the types of tasks that are very repetitive, that are very yes or no oriented. There's no additional level of skill really needed once you understand how to do the task. So I would say these are going to be a lot of really basic administrative tasks, ups, tasks, maybe some basic customer service tasks. Because it are pretty easy to train someone on that you can have very clear SOPs.

9:25Here's how you run this report. Here's how you input this data. Here's how we categorize the bookkeeping. Here's how we update the website. These are very repetitive tasks. So these are generally going to be considered the $10 an hour tasks. Then we move a little bit higher up to $100 an hour. Starting in this bucket is a little bit more skilled, meaning you do have to bring some of your own experience and expertise to the table in order to do this skill well. So this is where design comes in. This is where copywriting comes in. This is where content creation and creative for ads, all of that requires a level of skill. I would also say this is where people management comes in. So project management and things along those lines. So you do have to be skilled here. You have to know what done looks like.

10:27You have to know what the end result is supposed to be. And you're going to have to bring to the table your skills, your background, your knowledge, your point of view into that piece. So this takes a little bit more time to train. It takes a lot more communication to get on the same page. But still a lot of this is not directly revenue generating, right? It supports the business. It maintains the business, but not as closely tied to generating more revenue and growing the business. And we get into the next two categories, which is $1,000 an hour and $10,000 an hour. This is what I identify as CEO level work. Once you get into these categories, this is the higher level, more directly connected to revenue generation work that truly only you are going to be able to do or much more

11:30skilled team members are going to be able to do. This includes things like strategic planning, business development, product development. This includes sales, especially if you are doing sales one to one. This is going to be the work that is a lot closer to how you generate revenue in the business. And the final category is the $10,000 an hour. This is going to be the type of work where you are doing the revenue generating work at scale, meaning you're not just having a sales conversation with one person. You're hosting a sales event, maybe a webinar or a conference where you're selling from the stage in front of a lot of people at once. This is where you're getting into really high visibility that fills your pipeline with potential clients. So this is the highest level revenue generating work that you do in your business.

12:36So when I teach this, and I'm going to link up the entire episode about the CEO scorecard if you want to learn more, you don't have to buy a planner in order to adopt this. You can learn about it and try it out yourself. No purchase necessary. But the reason I bring this up is when I teach this, it's not just an awareness exercise. It also is an exercise to help my clients see where they need to fire themselves, where they need to hire someone so that they can move further in to more of their time being spent on the higher value work in their business, the growth oriented work in their business. The scorecard already tells you where to focus first, the $10 an hour task, the $100 an hour task next. You start at the simplest tasks to get off your plate, the things that are the easiest to train, the things that are the most repetitive, and then you move up from there and you train

13:37up from there. Where I see people getting AI wrong is so many people are trying to apply AI out the gate at a higher level. They're trying to get AI to do the growth oriented work for them. This work like write my sales strategy, come up with my content, come up with my next offer, come up with the copywriting for this new sales campaign, and then they're disappointed and they conclude that AI isn't going to work for them. This is interesting to me as I'm watching this pattern play out because most small business owners don't go out and hire their first team member to take over strategy. The first team member they hire is for the administrative tasks. The first team member they hire is the bookkeeper.

14:37The first team member they hire is someone who's going to answer the emails and organize your schedule. But for some reason, I'm seeing a lot of people jump into AI is going to now become the marketing department for my business or the sales department for my business. And there's no foundation in place. The important thing to remember about building a team and delegating tasks is that as you get into the more complex, the more nuanced tasks that you are handing over, there's a lot more training that needs to happen. There's a lot more context people need in order to do a good job. And this is the missing piece, I think, when it comes to the adoption of AI, you still have to put the foundation in place. And that brings us to the exercise that my cousin shared with me that I instantly recognized

15:43as a delegation exercise. Now I want you to imagine and maybe even draw out for yourself a Venn diagram. We all know what a Venn diagram is, right? Two overlapping circles. On one side on the left hand side is human. Human only. On the right hand side of the Venn diagram is AI only. And the overlap there is human plus AI. Another version of this, by the way, could be a Venn diagram with CEO on the left replacing human, team on the right replacing AI and the overlap being CEO plus team. And what this Venn diagram represents is how you go through the process of determining what gets handed off.

16:45So in the context of humans and AI, the left side of the Venn diagram, we need to think about what are the things that are exclusively human domain. In your business, humans are going to be the ones to be responsible for this, to drive the outcome for this. So in my Venn diagram for my business, one big piece of that is anything that requires my point of view, my judgment, my experience, my expertise, my relationships, my stories, my thoughts about something, my opinions. That is uniquely human. AI is not going to be able to replicate any of those things. The next piece that I think is really important here is the strategy. Okay, again, this could be human, this could be CEO specific.

17:47As you build your team, you can have your team do this exercise. But in my business, I maintain responsibility for the vision of the business and the values of the business, which then informs the strategy. So even as I have a team member do this exercise, they might be responsible for a portion of this strategy, right? So I hand off ads to Gabby and she's responsible for the ads strategy for how we're getting in front of more people and growing our audience. But I'm responsible for the bigger strategy that feeds into. So humans are responsible for big picture strategy. Humans are responsible for developing the intellectual property. So the actual intellectual property that runs our business, the intellectual property that we teach our clients, all of the frameworks, all of the systems, all of the strategies, all of that is uniquely human.

18:51And the next piece is relationship driven, right? This is going to be community. This is going to be clients, this is going to be colleagues, communication with all of the above. Any time we're actually interacting with, communicating with people, other humans, there's going to be a human on both sides of that equation, right? So this is one of the most important things is to identify what is uniquely human when it comes to any of the tasks that you are looking at. Then we get to the right side of this Venn diagram, right? So now that right side is AI without a human, AI without a human. Now the first things that I can very easily hand off to AI without a human are going to be the $10 an hour tasks. You're going to be the repetitive, the super defined, the very easy to teach and train

19:54a low judgment, meaning you don't have to have a point of view or an opinion. This is pulling metrics into a dashboard, keeping the financial numbers updated. This is transcribing the podcast episodes. This is the trigger based automations. This is any data work or any research work. So these are things that can run unattended in my business. Once AI knows how to do it and do it well to the level that I want it done, okay? And here's the important piece. Nothing just starts in this bucket. You have to teach and train AI how to do those things to the level that you want them done. And that's really important. It's sitting in this side of the Venn diagram of AI only in my business is there right now because it's straightforward and it doesn't need to have a whole lot of input from

20:55me. Things that are taking longer are the things that need time to be trained, need time to be refined. And this is the missing piece of the puzzle for a lot of people when it comes to using AI. Again, you can replace human on the left and AI on the right with CEO on the left and team on the right and the overlap of this Venn diagram in the middle is where the real work lives and almost no one is spending time or attention here. This is the training. This is the collaboration. This is the upskilling. This is where you are actually getting that team member to fully understand what the output needs to look like to your standards, to your specification. And then once they really, really have it, then you fully delegate that out to your team

21:56member, right? Well, the same thing is true for a lot of AI, a lot of what you're hearing right now about building AI employees or AI agents. It's got to run through this bucket first of collaboration to sharpen the skill set. So you want to keep that in mind. A lot of the tasks in here are actually things that are being trained, things that are being upskilled. And once AI hasn't dialed in, then it can run most of it with very little interference from you or your team. So a great example of this is going to be the way that we do our podcast. So our podcast is a system like we've had this done for years and years and years. I've had a podcast producer for years and then my husband took that over several years ago. So we had a very, very detailed SOP for what happens each stage of the podcast. If I had this Venn diagram and I'm outlining all the tasks for the podcast, the things that

23:00remain in my side of the Venn diagram are going to be things like coming up with the ideas for the podcast, outlining the podcast, actually sitting down and recording the podcast. Those are things that only I can do. No one else is going to touch those. That's what I'm responsible for. Then I start passing it off, right? And the pass off means I've got to train someone until they know how to do it exactly the way that I want it and then they can take full ownership over every part of delivering the podcast. So in that training, it looked like teaching exactly how I wanted the show notes being done, exactly how we edit the podcast. Where does the intro go? How does the music go? Any of those types of preferences? How do we put together the show notes and the social media post and the newsletter? All of that had to be trained. And then once it's trained, they know exactly how to do it and it's 100% their responsibility.

24:02One of the biggest mistakes I see small business owners make is they hope that just by delegating something or outsourcing something that all of their problems will be solved and they'll get that thing off of their plate. And what they neglect is taking the time to truly build strong onboarding and training for their teams. And understanding that that process of onboarding and training takes real hours. People who do this well understand this. They know that you have to have an onboarding process where you're giving your new team members all of the context they need about your business. They need to understand the vision and the values and how you make decisions. They need to understand the current strategy and how their work fits into that. They need to understand who is your client and what are your offers and how do you do the

25:04things that you do? All of that is context they need in order to do their job well. And then they need actual real on the job training. You can throw an SOP at somebody, but there needs to be some rounds of feedback to make sure that they truly understand what the end result needs to look like according to your specific standards and requirements. So when we skip all of that, when we just throw someone in a role across our fingers and say good luck, we aren't setting them up for success. And then we run into more problems, right? We run into, well, should I just let this person go? Or maybe you don't really know how to train and give feedback. And so you find yourself constantly saying, well, it's just faster for me to do it myself. It's just easier if I take it back. You end up redoing work.

26:05All of these become massive problems within a business. So it's essential that you understand you can't delegate confusion. You can't delegate chaos. That was always true with hiring a team. And it's still going to be true here with AI. You have to slow down before you can speed up. You have to take the time to really train AI to understand what you want the outcome to look like and define it before it will do it to the standard that you actually want. So I want you to choose an area of your business that you are already maybe dabbling with AI in and run it through run that workflow through this exercise through this Venn diagram. I just gave the podcast exercise. Maybe for you, it's your newsletter or your social media. I know from so many conversations with this community that marketing is one of the biggest

27:08bottlenecks that we have. And I truly feel like it's one of the biggest opportunities for AI to support small business owners. But I want you to be crystal clear about what parts of that marketing workflow are uniquely yours, the human only parts. What do you want the AI to ultimately be able to do? And then identify what do you need to do in that AI plus human, the intersection between both circles and that Venn diagram. What is it that you need to train your AI on in order to get the result that you truly want? This is going to be a game changer for every single business. Now when I sit down and do this exercise, I do it quite often. Whenever I'm going through, especially because I'm still building out a lot of my AI infrastructure, I'm still going through and training a lot of our workflows in our AI. I'm constantly going back and doing this exercise for each new workflow.

28:11I find it's helpful to pull out a new Venn diagram for each new workflow. So I'm doing it for the podcast. And then I have one for social media and then I have one for other projects going on. And I found there's a lot of similarities that I often can just transfer across the board. And it helps me really see where humans role is solidified in my business. This actually reminds me of another exercise I did years ago, which was redefining my role as the CEO of this business. And I give this exercise to my clients all the time because one of the challenges that I also see as you start to delegate, whether again, it's to someone on your team or to AI is as you move things off your plate, it's really easy to have these new team members or these AI assistants, if you will, and not really reevaluate your own role.

29:18And that can become a major issue. If you don't redefine your role as CEO and get clear about where you add the most value to your business, you can find yourself keep getting sucked in to other things. So I realized every time I was hiring a new team member, I was writing a new job description. So I realized every time I was hiring a new team member, I was writing a super detailed job description for them. I was getting them on board it, I was getting them trained up, but I was missing something and I kept getting in the way and I kept getting in the way because I hadn't redefined my role as CEO. For example, when I hired my first ever virtual assistant, I hired an amazing virtual assistant. She was fantastic. But because I never redefined my role, I was kind of a helicopter CEO. I kept checking in on the inbox, I kept responding to people before she could even respond

30:20for me. And finally, I got a message from her saying, Rach, get out of the inbox. This is what you hired me to do. I've got it. And she was right. I loved that she called me out on that. Nothing was wrong with her. And she definitely was showing me what a great job I did hiring her because she was willing to say, Hey, this is why I'm here. Let me support you. What I was doing wrong was that I hadn't redefined my role. So the lines continued to be blurry and I continued to get in the way. And that's what I find a lot of people are doing. Not only as a hire, they're team, but as they are delegating things to AI. They sort their tasks, right? They start training AI to take things off their plate. But they don't have clarity on what are the most important things that only they can do. That is what they need to maintain control over as the CEO.

31:20For me, my role as CEO really comes down to three things. First content, content because it requires my point of view, content because it requires my opinion and my take content because it requires my intellectual property. That's one of the things that I'm not going to hand off to anybody. Not a team member, not AI. All of the ideas are still coming from me. Community because I don't want to outsource relationships. Every time I spend real time with my people, my community, my colleagues, my clients, business gets better. More opportunities show up. Things pop up that we never could have imagined, right? So the more time I spend with people, the better everything gets. So I will never step away from that. And finally, for me, is going to be communication.

32:25And in and out of the business, I think I've really gotten clear on that because while I have worked with copywriters in the past, I have seen over and over again the power of people not only being able to read my newsletter or read my content, but when people can see and hear you, it adds a whole other layer to it. And they can hear the way that you sound when you talk, the inflection your voice makes, the pacing when you're telling stories. There's something so much deeper that connects you on this much more personal level. So those are the things that, as I do these exercises again and again for different things I'm trying to build with AI, it just continues to be reinforced to me. The most important parts of my role as CEO and that gives me permission to hand more

33:27things out to my team or to AI. So we're going to wrap here in a second and I just want to zoom out because what's happening in the broader economy is happening for small business too, just on a different scale. AI still is going to replace entry level work. We're already seeing that. We're already seeing that. I have been seeing this for years, okay? The repetitive, the lower level, highly repeatable tasks that don't require any high skill set, they don't require a lot of judgment. They are very clear cut. Those are always the first things that are going to go. I remember years ago when I started the podcast, I actually used to have to pay a dollar a minute for transcripts because we didn't have AI that could create transcripts

34:27for us. That meant every time I had a new episode going out, if there was a transcript going alongside of it, I mean that could have cost me anywhere from 30 to 60 dollars an hour just for the raw transcript to be hand transcribed. AI has already replaced that and now it's built into a tool, it's built into descript and I pay less for a descript every month than I used to pay for one podcast episode to be transcribed and descript does the whole editing process for me. It's wild. This is not a prediction. This is already happening. This is the same pattern as when automation started showing up in factories. Think about how automation showed up in factories where now there are robots that can build cars or robots that can build products. This is the way that honestly progress continues to happen.

35:29Automation was already there. AI is just automation at scale and that's what's going to happen. Here's where I think a lot of small business owners are getting it wrong though. I think that this is an opportunity to really reevaluate what your future business is going to look like and the future shape of your organization. I think a lot of people are letting go of the lower level work and they just let people go and these could be really skilled people, really smart people who have a lot more to offer. I think this is the next level opportunity for a lot of us as we are thinking through this and I'm thinking through this too is thinking about how the roles are going to change in my business moving forward. How am I going to move people up in their role?

36:32How am I going to help them up skill? How am I going to train them up? For example, my husband has been helping me behind the scenes with my podcast for years now. So now that we have collapsed the amount of time it takes to do that job, he's not necessarily going to work less in the business. Now I look at it as he's freed up to take on other projects, other tasks that I still need to move off my plate. I can give him more to work on. This also gives an opportunity to move people up to roles that allow them to have more creativity, more autonomy, more responsibility and that also should look like more pay. This is what I see that recirculation looking like on the team level. And I really think this is not just a nice gesture. This is a smart business decision because when you take care of your people, they take

37:34care of you. That was my thesis for the very beginning of this whole series. When you take care of people, they take care of you. And I find people want to learn, people want to be valuable. They want to continue to contribute. And if you give them ways, they can do the work better and faster and free them up to do something else. That is an opportunity for both of you, especially if you already have people who are culturally an amazing fit, who values wise are an amazing fit. They already know your business inside and out. They already have relationships within your business, within your team, within your community and your clientele. Now you can have people grow with you as you're able to ride this wave of AI. I think this is such an incredible thing that we can all lean into even more. The way I hire from here is going to change. I know that because this is such a new technology and the way I'm applying it is probably a little

38:39unique and different than a lot of other small businesses, I know that I'm still going to hire primarily for the things that I can't teach. I'm going to hire for creativity. I'm going to hire for strategic thinking. I'm going to hire for collaboration skills. I'm going to hire for values alignment. I'm going to hire for people who are on board with our vision. I'm going to hire for people who are thinking out of the box. I'm going to train them for how AI can be the system behind the scenes. It makes it easier for us to do what it is that we do in this business. My next hires are all going to be the people who bring their own genius. If your business is about to get more productive, I want you to start thinking about how does that change the shape of your business in the coming years?

39:39This is CEO level strategic thinking. I want to be ahead of that. I don't want to fall into things happening by default because I didn't press pause long enough to say, oh, here's how it's going to change the shape of my company. Changing the shape of your company, changing the future of what it looks like starts with this simple exercise that I gave you today. Here's your homework. I mean it. This is homework. You all pick one area of your business this week, one function. I recommend marketing because in my experience talking with so many people, this becomes the bottleneck where a lot of people are stuck where a lot of people drop the ball and find themselves in the feast or famine cycle. I want you to even drill this down a little bit more, not all of your marketing because there's probably a lot of moving parts there. Think about the core part of your marketing.

40:41The one thing that is your core marketing system, the one that drives the most results for your business. For me, it's everything tied into my podcast. For a lot of us, it's going to be our signature long form content, but it could be something else. Doesn't hurt my feelings if you pick something else, y'all. Just pick something that is taking a significant amount of your time that you know you need to stay consistent with it and that you know AI could support you with. The first part of the process is to actually document yourself going through the whole process. If you don't already have an SOP for this task or this workflow, then document yourself going through the whole process. I like to do this by literally recording a loom of me walking through. Here's how I do every single part of this in order to send out a podcast every single

41:42week. Then I can put it into my Venn diagram. Then I can go through and say, okay, what parts of this process do I need to be involved in? What's part of this process could AI take over completely? And then what is it that I need to train? What is it that I need to work through with AI in order to get it to the point where I could potentially automate that? First people sort at the function level or the job level and they get stuck. This is why I'm saying take one small thing. It probably would take you maybe an hour to go through this process. But you'll quickly start to see what are the areas that you are going to retain that only you can do where your point of view, your opinions, your discernment is also important. Then what is your goal for what AI can take over and you're going to start highlighting?

42:44What are the areas that I need to start training my AI so that it can get to the end result that I know I want? And then when you finish it, I want you to come back and let me know how's it going. I want you to think about, okay, how do I actually start training this up? How do I make sure I'm giving AI everything it needs to truly succeed? If you do this exercise, you're going to be ready for what I'm going to share in the next episode. All right. I will see you in the next practical, profitable step of human first AI for high-trust businesses because I'm going to share with you what you need to have in place in order to effectively train your AI. It is a big missing piece for so many people. I'll see you in the next episode.