201 | Why Teaching AI Your Voice First Might Be the Wrong Strategy | Leadership, Delegation & Systems with AI Frameworks

What if the reason AI still misses the mark isn’t your prompts, but that you’ve taught it how you sound without ever teaching it how you decide?

Getting AI to mimic your words is one thing. Getting it to understand the judgment behind your leadership is another.

In this episode, Dawn breaks down the difference between an AI voice profile and a thinking profile and shares four questions that help you capture the decision rules AI needs to work more effectively alongside you. If you’re a founder using AI for business, delegation, or decision-making, this is where personalization gets a whole lot more useful.

Want a space to test, ask, and grow with AI alongside other founders doing the same thing? Join the free AI for Founders Community. Bring your answer to Dawn’s question: What’s the thing you never cut, even when it costs you? The community is designed as a low-stakes place for founders to experiment with AI, share what’s working, and build confidence using it in their businesses.

Key Takeaways

• Why teaching AI your tone and vocabulary isn’t enough when you need it to handle decisions and situations it hasn’t seen before.
• How capturing your decision rules and judgment helps AI work more like a strategic partner and less like a really enthusiastic impersonator.
• The four questions that reveal how you make decisions when you’re working, overwhelmed, finished, or completely stuck.
• Why understanding your own failure modes can make AI more useful when decision fatigue hits not just when everything is going according to plan.
• How turning the judgment trapped in your head into something explicit can support smarter delegation, stronger leadership, and less founder-dependent decision-making.

Resources & Links

• AI for Founders Community

Related Episodes

• 193 | Why Female Founders Using AI Still Can't Get It to Say No For Them 
• 177 | Why Your AI Strategy Keeps Stalling & The One Decision Making Shift That Finally Moves It Forward 
• 122 | The 4-Stage AI Process Female Founders Use to Stop Losing 10 Hours Each Week Answering Questions Their Team Should Own 

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Transcript

She’s That Founder
201 | Why Teaching AI Your Voice First Might Be the Wrong Strategy

Your AI tool doesn't sound like you because you never taught it how you decide. You taught it how you talk Let's fix that.

Hey, hey, hey. You're listening to She's That Founder, the podcast for ambitious female leaders who are ready to stop being the bottleneck in their business by using AI frameworks for faster delegation and decision-making.

I'm Dawn Andrews, and today you'll discover why teaching AI your voice and teaching AI how you think are two completely different projects, and why almost everyone stops at the first one.

We'll talk about what actually showed up when I aimed 110 questions at how I decide instead of how I write, and the four questions you can ask yourself this week that will do more for how AI works alongside you than any prompt you'll ever copy and paste. Let's do this. Okay, so a few weeks ago, I did something that sounds simple on paper.

I was on a treadmill, because that's where my brain actually works, and I answered 110 questions about myself over the course of a week in the middle of maybe the hardest season I've had in a long time.

And the point of it was supposed to be straightforward: build a voice profile so AI stops sounding like a template when it writes for me. I thought I knew exactly what that meant. Feed it my favorite words, banish the em dash, tell it I say legit and no doubt, and never, ever say circle back. It's easy, right?

It's like a costume fitting. That is not what happened. What happened is I ended up writing things down I never once have had to say out loud. My actual failure mode, the thing I would never cut from a piece, even when it's the wrong length, how I know something is actually done versus just finished. And somewhere around question 60, it hit me.

I wasn't building a voice style guide, I was building a record of how I think, and those are not the same document. And that is the whole episode today, voice versus thinking, costume versus spine. Let's get into it.

So let's break it down. I've watched so many of us, myself included, chase the same thing when we try to get AI to sound like us.

We chase tone, we feed it old LinkedIn posts, we tell it our $5 words, our slang, the phrases we'd never touch with a 10-foot pole, and that's not nothing. It matters, but it's still really surface level. And when I walked into my own volume of questions, that's exactly what I thought I was there for. I actually remember thinking, "This is gonna be fun.

I get to talk about how much I love the word audaciousness, and how much I hate the word delve." The greatest hits tour of Dawnisms. But here's the problem with stopping there. A voice guide teaches AI what you sound like in the situations you already gave it examples for. The second something new comes up, a client story I've never seen, a decision with no clean precedent, the tone holds, but the judgment underneath it doesn't, because you never actually trained your tool in your judgment.

You taught it the wrapping paper on the outside. And sounding like you is a costume. Deciding like you is the spine. It's the real deal. And that difference is exactly what cracked open for me around question 60, and I can't believe it took that long to get there, but it just was what it was.

Hey, if any of this is making you want an actual space to test this out instead of just theorizing about it on your commute, we've got you. Want a space to test and ask and grow with AI alongside other founders doing the same thing?

Join our free AI for Founders community. The link's in the show notes. Let's get back to it So here I am, trodding along on the treadmill thinking that this is a style guide that I'm building, question after question. And question after question, it kept... The way that I set up the tool kept pulling somewhere else.

Not what words do you love, but what do you never cut even when it makes the piece worse for length? Not how do you write a hook, but what's your failure mode when you're tired and you just want it done? Not what's your tone, but how do you know when a piece is actually finished?

My answer to that last question surprised me when I said it out loud. It's not about polish, it's before and after. This is what matters to me. This is how I know a piece is actually finished. It's before and after. Did the person listening or the person reading move from stuck to unstuck, from no system to having one, from not knowing what to say to knowing?

And once I said that, I realized those are not style choices. Those are decision rules. The same rule shows up whether I'm writing for you right now or coaching someone through the worst Tuesday of their month.

Teach a tool a rule, and it can apply it somewhere your training examples never covered. Teach it a sentence, and it can only ever repeat the sentence. A voice profile is a costume fitting. A thinking profile is a deposition, and let me tell you, girl, it felt like that as I was speaking everything into the computer on the treadmill.

One dresses up the output. The other tells the truth under oath about how you actually decide. So you don't necessarily need 100 questions and a hard season and a treadmill to get a version of this for yourself. However, I do have it as a tool, and you can buy it.

But in the meantime, let me give you a shortcut. Picture your own business for a second, not your writing voice, but your actual judgment, the stuff that lives in your head that nobody ever asked you to put into words because you're usually too busy running the thing to stop and write down how you're running the thing.

So here are four questions. Answer them plainly, no polish, three sentences each, and your answer is plenty. First question: what do I never cut, even when it makes the work longer or messier than it needs to be? That could be something that you say, something that you do in a process. Whatever it is, what do you never cut if it, even if it makes the work longer or messier than it needs to be?

Second question, question two: what's my failure mode when I'm tired or overwhelmed? Not the flattering version, the real one. Oof, that was a rough one for me to answer. Question three: what actually tells me something is finished versus just done? And that's the example I gave you earlier. And finally, question four: what do I do when I'm stuck?

Not what I wish I did, what I actually do. Mine involves Trader Joe's Sea Salt Caramels. I'm just saying. So that's it. Four answers written honestly is worth more to how AI works alongside you than 1,000 words of prompt engineering because now you've handed it your judgment instead of your greatest hits.

Feed it your judgment, not your greatest hits. That's part of the reason I'm an early and very messy adopter over here. Not because these tools are magic, but because most people are still teaching it their costumes, and the ones who teach it their spine, their heart and soul really, are gonna be impossible to catch up to And before I wrap up today, I just wanna share a little caveat, because I come from the entertainment industry, I have entertainment industry clients.

I adore you, and I fully respect your decision to not share any of your writing or anything with AI. I use it because it makes such a difference for me and my business, but I also understand how unique and special and one of a kind so many voices are that I have the opportunity to work with. Protect your voice.

Keep it to yourself. It's all good. For those of you that wanna use AI, get after it. So here's what we covered today. Sounding like you is a costume. Deciding like you is a spine. And mimicry, which is sounding like you, breaks the second something new shows up that you're using AI to solve for.

Those questions that were supposed to build me a voice guide actually built me a record of my own judgment, and that's the thing that's actually transferable. And now you have four questions that can start you on that same path without needing a treadmill, unless that's your jam, or a hard season to get there.

Here's what I'm inviting you to do today. Pick one of these four questions, just one. Answer it in a few honest sentences. No editing. Be sloppy. Spell it wrong. It's all good. And put it somewhere you'll actually find it again. That's the whole assignment. And if you want a place to keep going with this, come find us in the free AI for Founders community, the link's in the show notes.

Bring your answers. I'd love to see what you'd never cut. So again, what's the thing you'd never cut, even when it costs you? Sit with that one this week. That's it for today's episode of She's That Founder. I'll see you on Thursday, and until then, go teach your AI tool your spine, not your costume.

See you soon, Lovey.