She’s That Founder
126 | Female Founders Stop Planning Like You're Corporate. Use AI to Build a Business You Want Without the Soul-Crushing Burnout
You can scale the wrong thing successfully and still lose everything that matters. It's mid-December, and if you're avoiding your year end planning, it's not because you are lazy. I don't think it's because you're using the wrong operating system for your actual business. And today we're fixing that.
Hey, hey, hey. You're listening to She's That Founder, the show that helps ambitious women stop drowning in decisions and start owning their CEO seat with a little AI magic. I'm Dawn Andrews, and today we're talking about how to do strategic planning for your business, not the one you think you should want or the one other people think you have.
And we're using AI to help you see the truth that you may have been avoiding. By the end of this episode, you'll have three things. First, you'll understand why most year end planning fails, and it has nothing to do with your planning skills.
It's because you're planning for somebody else's business. Second, you'll have my three question, strategic truth framework. The only questions that matter when you're deciding what to do in 2026 and third, you'll know how to use AI to call yourself on your bullshit. Because the biggest thing blocking your strategic planning, it's not lack of data, it's lack of honesty.
This isn't about setting bigger goals. This is about building the business you actually want. Let's go. So I need to tell you about a conversation I had with a client. Brilliant founder, came out of corporate EVP level at a major company.
She shows up to our session with this gorgeous strategic plan. I'm talking quarterly OKRs, board ready, financials, market analysis, competitive positioning. The works. It's beautiful. It's totally impressive. So I ask her, is this the business you wanna run or the business you think you should wanna run?
Silence. And then I kid you not, her eyes welled up a little bit because here's what she realized in that moment. She'd spent three weeks building a strategic plan for the EVP job. She left not for the three person consultancy. She was actually running and building. She was planning like she still had a CFO.
A big marketing department, an ops team. She was planning for infrastructure that didn't exist yet in her company for a business model that she didn't actually want. And here's the thing, she's not alone. This is the pattern I see, especially with founders who come out of corporate and start something.
They try to port over the process from their old life into their startup life and the operating systems don't match. The stage of the business does not match. Now, I also see the opposite solopreneurs or very early stage businesses with just a couple of people in them who don't plan at all. They're making money.
Sure, which is fantastic, but they have no idea how they made it or what they actually spent to make it, or whether they even enjoyed the work that generated the revenue. with zero strategic thinking behind it.
Real talk. Depending upon the size of the business, most female founders don't actually do year end planning. Companies over a hundred million have a corporate process, but I've seen companies at 10 million that don't have a strategic planning process at all.
So we've got founders over planning with the wrong system and founders under planning with nothing. And look, I have been both of those people.
Let me tell you about the year I did strategic planning, right? I followed a very detailed process, a specific framework. I broke down each quarter, each month, every revenue line, all the marketing activities that went with each of them. I measured which particular steps I took, and with what frequency, how many calls I needed to make, workshops I needed to lead, follow up process, all of it.
I spent weeks on this plan. I was inspired by it. I was daunted by it. I focused on it, and then I just kind of threw away the plan. I didn't actually keep up with what I'd set up for myself. I just completely abandoned it. And you know why? Because I wasn't real about who I was as a leader and an operator.
I tried to shove myself into somebody else's process. Someone who loves spreadsheets and tracking and quarterly check-ins. That's not me. That is not how I operate. That is not my business. First I felt bad that I wasn't following my beautiful plan.
And then second, I just abandoned it all together. And here's the irony. It turned out to be one of my best years ever. So what was I actually doing wrong? I wasn't doing the strategic planning wrong. I was doing the strategic planning for someone else's business in somebody else's model, not for me in my own business.and that might be what's happening for you right now. You're planning for the business you think you should want. The business, your old boss would be impressed by, or your family or your friends. The business that looks great on LinkedIn, the business that matches someone else's framework, but not the business.
You actually wanna wake up and run every single day. Translation, strategic planning, that ignores who you actually are as an operator is just expensive. Procrastination. So these are the three questions that actually matter. We're gonna get into it. And this is also where AI becomes your secret weapon.
Not because it makes you more efficient, but because it makes you more honest. because the biggest block to good strategic planning isn't lack of data, it's lack of self-honesty. And you know this is true.
And you know how I know that. Because you know which clients drain you. You know which revenue streams feel exciting and which ones feel like death. You know what lights you up? And even if you don't know, you can feel it when something feels great and you can feel it when something doesn't feel great, but you keep planning around what you think you should do instead of what you actually want to do.
So there are only three questions that matter, and funny enough, this is exactly what I'd ask my best friend if she came to me in late December saying, help me plan next year.
Question one, what made you money last year? Not what you wish made you money, not what should have made you money according to your business plan.
What actually moved the revenue needle? Question two, did you enjoy doing it? You're a service-based business owner. You're providing services. Did you enjoy providing those services? because here's what nobody tells you. You can scale something you hate and hit your revenue goals and be absolutely miserable.
Ask me how I know. Question three, did it make the difference you hoped it would? For your team, for your clients, for your larger community, for the mission. You said you cared about when you started this thing. If something made you money, but you hated it and it didn't matter, stop doing it. I don't care how profitable it was.
You're building the wrong business and this is your heartbeats. You only get so many of them, and we don't even know how many you'll get. So why spend it on stuff that you don't like? if something made you money and you loved it and it mattered, do more of it. Build your entire next year's strategy around amplifying that.
And if you loved it and it mattered, but it didn't make you money yet, well that's your scenario modeling question. How do we make this sustainable? And if not, how can we pivot it so that it is. Okay, I'm gonna give you your first prompt. This is the AI strategic truth prompt. You can open chat, GPT, Claude Gemini, co-pilot, whatever you use, and try this. Here's the prompt.
“I'm doing my yearend review. Help me honestly evaluate my business activities from the last year across three dimensions, revenue, what actually made money enjoyment, what energized me versus drained me and impact what actually mattered to my client's team And Mission ask me clarifying questions to help me see where these three things align and where they don't.”
Now, here's what's brilliant about this. AI is going to ask you questions. It's going to make you get specific, it's gonna surface activities you conveniently forgot about because you can't see your own patterns. You're too close, you're too invested in the story that you've been telling yourself.
And just so you know, I've been there, I've done it, I know it. This is. You're a human being, it's all right. But ai, AI doesn't care about your story. It just looks at the data and asks, based on what you've told me, what's actually true here. So real example from my own business, when I did this exercise, AI identified that my highest revenue work wasn't actually my most sustainable work because it was one-off consulting projects that required me personally for every single hour.
Meanwhile, my retainer programs, which generated slightly less revenue, was building repeatable systems, return clients, sustainable infrastructure, and compound returns over time. And that single insight changed my entire strategy, not because I set a bigger revenue goal, but because I got honest about what business I actually wanted to build.
One pro tip for you. Along with that prompt, you can add in, ask me for any documents that you need from me, and here's information about my company, my industry, and my ideal client. And if you add all of those things to that prompt, you're gonna get into a really juicy conversation with ai.
Quick recap. The problem isn't your planning skills. It's that you're using the wrong operating system or planning for someone else's business instead of your business. In your industry. At this stage, the three questions that matter what made you money, did you enjoy it, did it matter? And AI helps you answer these honestly.
Okay. Quick pause. If this is hitting home and you're realizing that you're. 2026. Success depends on your team actually executing on your strategy, not you doing everything you need. The feedback fix. It's my free guide on giving feedback that actually lands and drives accountability because strategic planning only works if your team can run it without you.
Grab it at hellodawn.live/feedback. All right, let's keep going. you ready for the self-honesty check? This is where we use AI to see what you don't want to see. I'm pretty sure in a previous episode I shared with you one of the sassy conversations that I had with AI where it basically knocked me back into place.
If you've done the three question truth check, we're gonna go deeper because here's what I've learned after 23 years of doing this kind of work, the patterns you can't see are the ones that are killing your business. So for instance, you say you wanna scale, but you keep taking on custom one-off projects.
Or you say you want time freedom, but your highest revenue activities all require your personal involvement. You say you wanna build a team, but you can't let go of client communication and the reason you can't see those patterns. Because admitting them would mean admitting that you're the bottleneck and that you're scared that you don't actually want what you say you want perhaps.
But ai, AI has no ego. It just looks at your data and says, here's what's actually happening. So this is the operating system check prompt. Here's the second prompt I want you to use.
“I came from, [describe your corporate background or previous role.] Help me identify where I might be trying to run, and then describe your business size and structure using processes that don't match my current reality. What am I overcomplicating? What corporate habits am I clinging to that don't serve me?”
Yes, girl. This one is uncomfortable because AI is gonna call you out.
Real example, I had a client, a strategist, who came from a Fortune 100 company who was running a five person consultancy. Like she still had a 200 person marketing department. She had quarterly board decks for herself. There's no board. It's just her. She had OKR trackers for her two contractors. She had a content calendar that required three full-time people to execute, and she only had herself to do it with a very small team.
AI looked at her setup and basically said, you're using enterprise software for a bicycle. Yeah, I mean, ouch. That hurts your ego because when you're coming from a big, fancy corporate situation where perhaps it was your identity being called a bicycle instead of a corporate enterprise, smarts a little bit, but once she saw it, she couldn't unsee it.
She started to simplify everything and when she simplified, she cut her planning time by 75% and grew revenue by 40% because she finally had time to actually do the strategic work instead of managing her own bureaucracy.
Now, look. you might be thinking, but Dawn, shouldn't I be planning for the business I want, not the business I have?
Maybe I should be hiring ahead of growth. For example, and here's where I'm going to get really specific with you. If you're a VC backed company building for massive scale. If you've got investor capital to burn through while you capture market share, if you're in a product or sales model where more people directly equals more predictable revenue, hell yes, hire ahead.
Build that org chart, grow into it, go get it. But if you're my ideal client. A service-based business founder doing anywhere from $500,000 a year to 5 million, 10 million, and maybe you're self-funded or modestly invested, where your revenue is tied to relationships and expertise that doesn't scale linearly, that strategy will bankrupt you.
Here's what happens. You hire the team for the business you want, but your revenue model can't yet support them. Your delivery model requires you for quality control, and now you're drowning in payroll. You can't afford managing people who can't actually take work off your plate, and you're more trapped than before.
So when I say plan for your business, I don't mean think small. Think freaking big. Go for it. But do get strategic about what business model will actually make you profitable, sustainable, and happy. ' cause otherwise it is broke and burnt out. So maybe that's a 10 million consulting firm with 30 people.
Great. But make sure your delivery model and revenue model can support that without requiring you personally and every client engagement. And maybe that's a $3 million boutique with eight people and premium pricing also great. But stop trying to build systems for a $50 million enterprise. The question isn't, how big should I grow?
The question is, what business model creates compound returns without destroying your life? That is strategic.
Okay, here's your third prompt, and this one is the most important. This is the what do you actually want prompt. Here's your prompt.
“Based on what I've shared about what made money, what I enjoyed, and what mattered, help me articulate what business I actually wanna build next year, not what I think I should want. What do the patterns suggest”
I'm naturally drawn to, and this is where I need you to listen. This is the question that most founders won't ask themselves because they don't even know to ask it. And especially because the answer based on the data may not be the quote unquote right answer. Maybe you don't actually want a big team.
Maybe you don't want recurring revenue. Maybe you don't wanna scale the way everyone says you should, and here's where I need to tell you another story. About five years into my business, I really, really wanted to grow. So I decided to hire some coaches to work with me. I was gonna train them to do what I do, scale my expertise, serve more clients.
I felt like that was gonna be a game changer moment, and I found out pretty quickly that transferring my expertise, my approach, my thinking, my sales skills, quantifying and codifying how I'd like to work. I didn't wanna do it.
Nobody was gonna do it like I was gonna do it, and I shouldn't have expected them to because each person is an individual with different experiences that have guided them. I know that I talk all the time on the podcast about SOPs, and I have my versions of those for my business. But I wasn't interested in creating SOPs for an ultimately corporate situation.
It just wasn't for me. So here's the truth, having additional coaches lasted about a year, and when I had to let everyone go, I felt like a big old failure, but it was the right thing to do. Because what I learned is that the way I deliver services, the uniqueness and personal attention that I give to my clients, really couldn't be replicated by multiple people.
And it was where my greatest joy was and also my greatest revenue. So what made you money? Did you like it and did it make a difference? Hell yes to all three. I had to realize, ultimately, in my heart of hearts, I didn't wanna grow a big enterprise. I just wanted to be in a relationship with my clients and deliver excellent service and make changes for the folks that chose to engage with me.
to be clear though, that doesn't change my love for scaling businesses, I have helped more businesses than I can count with doing exactly that. I love teaching it and guiding it. it's just not what I want for my business.
I am a bespoke luxury. Good. And once I had that realization, it changed everything. Not because I failed at scaling, but because I got honest about what I really wanted. I was fighting myself, and that's why I wasn't growing and that's why things were not getting done. So what about you?
What do you actually want? Not what looks good on LinkedIn, not what your old boss would be impressed by. What business do you actually want to wake up and run every single day? What feels good to you? Because if your strategic plan doesn't align with that truth, you're just building an expensive superhighway to burnout or even a prison for yourself.
To sum it up, AI helps you see those patterns that you're avoiding the corporate hangover, the gap between what you say you want and what you're actually building the truth about what business would actually make you happy. And for service-based businesses, hire ahead isn't always the answer, but strategic alignment 100% is.
Real quick before we wrap up, if you haven't grabbed the feedback fix yet, Do it now because the whole reason you're doing strategic planning is so you can delegate the execution, and that only works if your team knows how to take feedback and run with it. So go to Hello Don live slash feedback.
Okay, last piece friend.
You've done the three question truth check. You've used AI to see your blind spots and you've gotten honest about what you actually want. Now what? Now you make decisions, not goals, not intentions, not vision. Board wishes. I mean, look, if any of those things fire you up, go for it.
but decisions, decisions are what separates strategic founders from reactive founders. Strategic founders make decisions that create constraints. And let me explain what I mean. A goal is I wanna hit 2 million in revenue. A decision is I'm only taking on clients that fit my group program model.
I'm saying no to everything else. See the difference? The decision creates a constraint. It forces you to say no to the things that don't serve your strategy, even if they could make you money in the short term.
So let's talk about the strategic decision framework. After all this AI powered analysis, you need to make three types of decisions. decision. One, what am I stopping because it doesn't match who I actually am as an operator. Not deprioritizing, stopping full stop, not doing anymore what's making you money, but draining your soul?
What are you only doing because you think you should? What process are you clinging to from your old corporate life that doesn't fit your actual business? for me. This year, I'm stopping custom consulting projects that don't feed into my frameworks, even if they're lucrative because they're strategically misaligned with the business that I want.
Okay, decision two, what am I amplifying? Because it made money and I loved it, and it mattered. So what work that you're doubling down on? Not just what made you money, but what created compound returns in all three areas. For me, my podcast,AI Powered Frameworks, my AI community, these are getting more time, more energy, more investment.
And decision. Three, what am I building that serves the business that I actually want? What new infrastructure system or offering do you need to create to support your strategy? For me, I'm building frameworks at scale, and I'm building partnerships that amplify my reach. These aren't goals. These are decisions that create strategic constraints on my calendar, my hiring, my business model, and my daily life.
Here's your final AI reality check. Last thing, after you've made your strategic decisions, I want you to do one final AI check. Here's the prompt.
“Here are my three strategic decisions for 2026, and then list your decisions based on everything you know about my business, my patterns, my goals, what am I likely to struggle with in executing these decisions? What obstacles should I plan for? What support systems will I need?”
Because here's the thing. Your brain wants to believe these decisions will be easy, but AI can help you reality. Check yourself. Where are you likely to self-sabotage? Where are you underestimating complexity? Where do you need to build support systems now instead of reacting later? This is the difference between strategic planning and wishful thinking. All right, sister, let's bring this home. Here's what we covered today. First, most founders fail at year end planning because they're using the wrong operating system.
Corporate processes for startup realities or no process when they actually need one second, the only three questions that matter what made money. Did you enjoy it? Did it matter if all three aligned, do it more, pour some gasoline on that fire? And if they don't. Stop lying to yourself about it.
It's okay. Let it go. Third, AI helps you see the patterns that you can't see the corporate hangover, the gap between what you say you want and what you're actually building and the truth about what would actually make you happy. And fourth, strategic planning is about decisions that create constraints, what you're stopping, amplifying, and building.
Here's what I'd love for you to do before the end of the year, before December 31st, Block 90 minutes on your calendar. label it strategic truth session, and do not move it. Use that first ai. Prompt the three question, truth check.
Just start there and see what comes up. make one strategic decision based on what you learn. Just one. What are you stopping next year? Because it doesn't align with the business you actually want. Because here's the truth, most founders won't do this. I mean, I have told you they won't plan at all.
Or they'll skip straight to goal setting. They'll make a vision board for someone else's business and wonder why they're miserable in March. But you girl, you're different. You're the founder who gets honest, who makes decisions. As well as setting intentions. Who uses AI to see around corners and call yourself on your own bullshit.
Remember what I said at the beginning? You can scale the wrong thing successfully and still lose everything that matters. I don't want you planning for someone else's business. I don't want you using Microsoft's strategic planning process when you're three people in a dream. And I don't want you scaling something you hate just because it's profitable.
I want you planning for your business, the one you actually want run by you, the actual operator that you are creating, the life and impact that you actually care about. And that is why next year is going to be your most intentional year yet.
So one more time, if you want your team. To execute your strategy without you having to do everything yourself, grab the feedback fix, because strategic planning without team execution is just an expensive hobby. You can grab it at hellodawn.live/feedback.
I'm Dawn Andrews. This is, she's that founder. You are freaking amazing.
I'll see you next time. Lovey.
