111 | Hey Girl, Stop Playing Santa and Use AI to Set December Boundaries So That You Start Q1 Energized Not Resentful

Is your calendar full of holiday chaos and client deadlines, but you’re the one burning the midnight oil? A yes in December = resentment in January.

In this Thursday rant, Dawn Andrews drops a boundary-setting truth bomb every female founder needs before year-end burnout hits. If your Slack is full of time-off requests and your inbox is brimming with client deliverables, this episode shows you how to stop playing Santa and start leading like a CEO. Learn how to use AI to draft warm, clear boundary scripts that don’t make you sound like the Grinch — and walk into Q1 energized, not resentful.

Download The Feedback Fix — Get the free script-filled guide that shows you how to say what you mean without sounding harsh. Perfect for holiday boundary-setting, team feedback, and boss moves that actually land.

Key Takeaways

• Yes in December = Resentment in January — Boundaries aren't mean; they're strategic and essential for sustainable leadership.
• The 3 Boundary Buckets — Know your non-negotiables, your flex zones, and your intentional gifts.
• Real Scenarios, Real Scripts — Dawn shares 3 holiday-season dilemmas and gives you the exact AI prompts to handle them with clarity and compassion.
• Train Your AI to Talk Like You — Use AI as your boundary translator, not your boss. It works with your voice, not against it.
• Leadership Is Not a Popularity Contest — Your team will respect you more when you're clear and consistent, not just "cool."

 Resources & Links

• The Feedback Fix (Free Download) — Scripts to help you set boundaries and give feedback that sticks.
• AI for Founders Community — A safe space to test prompts and talk boundaries without burnout.

Related Episodes

• Ep 108 — 3 AI Systems That Help Female Founders Manage Time, Clients, and Business During the Holidays
  → A perfect companion episode if you’re juggling end-of-year chaos and wondering where AI can take real work off your plate.
• Ep 102 — 3 Standard Operating Procedures Every Founder Should Build in 30 Minutes (Using AI to Write Your SOPs)
  → If you're ready to stop reinventing the wheel every December, this one shows you how to use AI to streamline team ops.

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Transcript

She's That Founder
111 | Hey Girl, Stop Playing Santa and Use AI to Set December Boundaries So That You Start Q1 Energized Not Resentful

Your slack is exploding with “Can I leave early Friday” while your inbox has a client expecting December 20th deliverables and you're sitting there at midnight Googling, am I a bad boss? But here's the truth.

Boundaries aren't mean they're strategic. And if one more person tells you to just set boundaries without showing you how to do it. Without being the Grinch, I'm gonna lose it. 

Real talk. You're not the bad guy here. Let's fix this. 

Hey, hey, hey. Welcome to She's That Founder Thursday edition. These are the quick rants kick in the pants, velvet boot moments that represent me standing in the future, pulling you toward the even stronger, better, more powerful version of yourself with AI as your co-pilot, I'm Dawn Andrews, and today we're talking about why you need to stop playing Santa to your team and how to actually set boundaries that stick without torching your culture.

So last year I had a client, we'll call her Maya. Maya, runs a digital marketing agency, a seven person team crushing it all year. December rolls around and it starts. Hey, Maya, can I work remote the week before Christmas? Maya, I need to leave at 3:00 PM every day next week for all of my kids' concerts.

Maya, can we push that client deliverable to January? And Maya because she's a good human, because she cares about her people because she doesn't wanna be that boss says yes, yes to everything. 

Meanwhile, her clients haven't gotten the memo that it's December. They still want their stuff. They still have year end deadlines. They're still expecting her to be available. So you know what Maya's doing? She's working until 2:00 AM. She's covering for her team. She's delivering everything herself, and she's telling herself, it's just December. It's fine. I'm being flexible this is what good leaders do.

By January 3rd. Maya is sitting in her car in the target parking lot crying before she goes into the office because she has nothing left in the tank, and her team is asking when they're getting their Q1 bonuses and whether they can take a long weekend in February.

Sound familiar? I mean, I truly, truly hope not, but it is all too common and here's what nobody tells you. A yes in December equals resentment in January. Every single time. And listen, this is uniquely hard. 

For female founders, especially female founders with families. We've been socialized since we were five or younger, to accommodate to be nice, to make people comfortable. We've been taught that boundaries make us difficult. That saying, no makes us a bad guy. 

So we sit there calculating in our heads, can I afford to lose this person? Will they think I'm inflexible? What if they leave a bad Glassdoor review? What if I'm just being unreasonable? Meanwhile, your male counterparts are good at saying no without a second thought and sleeping like babies.

Can I get an amen? 

Here's what I need you to hear. Boundaries aren't mean they're strategic. Being clear doesn't mean you're being cold. And your team will actually respect you more, not less when you stop trying to be everyone's favorite person and start trying to be their leader. Now, stay with me here because this is important.

Here is where most people get this wrong. They think boundaries are all or nothing. You're either the cool boss or you're the dictator, and that is garbage. You need three categories of boundaries, and I'm inviting you to think of them like this. 

Category one is the line in the sand boundaries. These are the non-negotiables, client deadlines, non-negotiable revenue generating activities, non-negotiable. This is the stuff that keeps your business running. Those don't move, period. 

Category two. The how, not the what boundaries. These are flexible, the work gets done. But how and when has some wiggle room. Maybe they work remote, maybe they shift their hours, maybe they batch their work differently. You're generous with the how, but that what is still happening.

And then category three is the gift that you choose. These are genuine gifts that you choose to give. Not because someone asked, not because you feel guilty, but because you decided to. Maybe it's a half day on Christmas Eve. Maybe it's a surprise bonus.

Maybe it's closing the week between Christmas and New Year, but it's your choice. Your choice, because you've reviewed. Whether or not that it's possible to make that decision, it's not a response to pressure. 

So can you feel the difference? I hope that airing these out is giving you a little bit of like, ooh, looseness in your neck, right?

So here's where it gets really interesting. Most of us avoid these conversations because we don't know what to say exactly. We don't wanna sound harsh, we don't wanna be misunderstood, so we just avoid it and keep going, staying up till 2:00 AM or we say yes, and then we resent everyone. 

So this is where AI can become your boundary translator.

And listen, I want you to use AI to draft warm, clear boundary communications before you send them. Think of it like having a communications coach in your pocket. 

Here's an exact prompt you can use. 

“I need to communicate specific boundaries to a specific person or team in a way that's warm, clear, and non-negotiable. Here's the context [and then explain the situation]. Draft three options that sound like me that are direct, but kind.” 

So I'm gonna give you three real scenarios to hopefully give you some freedom around this time of year. 

Scenario one, the time off request that you just can't approve. So someone on your team asks for December 23rd to 30th off, but you have a client deadline on December 27th. Your prompt. I need to tell Sarah I can't approve her December 23rd to 30th time off because we have a client deadline December 27th. She has been a great performer all year and I wanna be fair, but this deadline is non-negotiable. Draft three responses that acknowledge her request, explain the constraint and offer an alternative.

And AI will give you options. Then you can pick the one that sounds most like you, adjust it, send it, and done. Now, you may already be saying, well, what if Sarah figures out some way to get the work done by December 27th so that she can leave on the 23rd?

Look, if your employee can hustle and arrange things so that can get taken care of, and you truly know that she doesn't need to be there for that December 27th deadline, then great. But just remember that if she doesn't do it, it's still on you. 

Scenario two. A client request for December 31st revisions. Oh my gosh, I can't tell you how many times people try to slide in, like under the midnight deadline on December 31st with me. So client emails asking for quick revisions due December 31st after you already said your team is off the 26th through the 31st, so your prompt. I need to push back on a client requesting revisions due December 31st when I've already communicated that we're closed December 26th through 30.

First, I wanna maintain the relationship, but hold my boundary. Draft three responses that are professional, firm, and offer an alternative timeline. I know. Does it make your stomach quiver? You're just hearing me say that. I don't know if it does, but I know that it does for some folks. But imagine having three potential options that you can choose from that test well and make a difference for you that have that client rethink the options.

That's freedom, right? You don't wanna be up all day and then up all night celebrating your new year. 

Scenario three. The, Can we push this to January request? This is when your team wants to push a deliverable from December 20th to January 10th, but your client is expecting it before year end, so your prompt;

“My team wants to push a December 20th client deliverable to January 10th, but the client needs it before the year end for their own planning. I need to explain why this deadline matters and can't move. Draft three ways to communicate this, that show. I understand their request, but hold the line on the deadline.”

Real talk. The first time you do this, it'll feel weird, first of all, collaborating with AI. But by the third time, you'll wonder how you ever did it without it. And here is the key. Train your AI tool in your communication style. Feed it examples of emails you've written that felt really good. Tell it your values, tell it. You want it to be warm, but direct and make it sound like you. Because boundaries delivered in someone else's voice don't land, but boundaries delivered in your voice with clarity and warmth, those stick. 

Okay, so to recap quickly, one December, boundaries are strategic, not selfish. Yes. In December equals resentment in January every time. Two. You need three categories of boundaries. The line in the sand, the how, not the what, and the gift you choose. Know which is which before someone asks. Three. Use AI to draft your boundary scripts. Warm, clear, non-negotiable. Train it in your voice so it sounds like you.

And four, your team will respect you more, not less. When you stop trying to be everyone's favorite person and start being their leader. 

So if this hits home and you realize you're needing more help communicating boundaries that actually land, you can download the feedback fix. Right now, it's free. It's in the show notes, and it's full of scripts for giving feedback and setting boundaries without sounding like a robot or a tyrant, because the difference between a boundary that sticks and one that gets ignored.

It's just how you say it. Grab it, use it, and I hope you'll thank me later. Whew. All right. Until then, stop being Santa and start being strategic. I'll see you next time. Lovey.