094 | 3 Signs Your Loyal Employee Is Now Holding Your Business Back — And How To Use AI To Fix It Fast

What happens when the employee who once saved your business is now the one holding it back? 

In this episode, you’ll learn how to separate gratitude from strategy, spot the signs that loyalty has become a bottleneck, and use AI to make confident decisions without the guilt spiral.

In this episode, you’ll learn:

• Why loyal employees sometimes can’t scale with your vision
• The Growth or Go filter: capability, curiosity, and courage
• How AI helps you assess performance objectively
• A conversation framework that protects both your business and your team member’s dignity
  
  

Episode at a glance:
[00:00] – When loyalty becomes the bottleneck
[01:30] – Client story: gratitude vs. growth
[04:00] – The 3 signs loyalty is holding you back: [06:00] – The Growth or Go filter explained
[08:00] – Using AI prompts to get clarity without guilt
[10:00] – The Growth or Go conversation framework

Resource:

• Loyalty Reality Check + AI Prompt – Free Assessment

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Transcript

She's That Founder
094 | 3 Signs Your Loyal Employee Is Now Holding Your Business Back — And How To Use AI To Fix It Fast

Quick question. What do you do when the person who saved your ass is now the reason it's getting kicked? 

I'm talking about that ride or die employee who worked weekends for equity dreams and on ramen budgets. Who now can't handle a Tuesday without three check-ins and a pep talk. Who feels like family, but is actually the bottleneck, keeping your business stuck in startup mode. If you're sitting there thinking, oh yeah, this is my situation, this episode is for you.

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 the help of a little AI magic. I'm Dawn Andrews, and today we're talking about the hardest leadership decision you'll ever make. What to do when loyalty and business growth are at war. 

By the end of this episode, you'll have CEO level clarity for separating gratitude from business strategy. You'll have a conversation structure I use when clients face this situation and an AI tool that cuts through the emotional noise so you can see patterns objectively.

So let me set the scene for you, first of all, hi everybody, and we are in the process of bringing this podcast to YouTube. So if you end up catching this episode, I am in a messy bun in my sweaty workout clothes, just making this happen because progress over perfection, right? we do not have a big old budget to create some fancy YouTube studio. 

This is just me sitting in my office getting it done, passing on all of my wisdom and compassion and heartfelt goodness to you. So you're just gonna see me as is when onscreen on YouTube, and we'll get fancier with it as we go, because I want it to be really useful and helpful for you.

But mostly I just wanna get you the information that I get asked, you know. The answers to the questions that I get asked all the time. 

Okay, so let's get back to topic. What to do when. Business growth and loyalty are at war. So last week I was coaching Rachel who runs a wealth management firm. Think a-List Money, the kind where one's client's, monthly investments moves probably equal your annual revenue.

Her first hire, Maya knew every client's dog's name their favorite coffee order, but when Rachel landed a $50 million portfolio client, Maya spent three weeks researching and came back with questions that sounded like she Googled what is fiduciary responsibility the night before. 

And this is really tough because Maya is smart. She's loyal as hell, and completely overwhelmed by the altitude that Rachel's business had reached, and Rachel was trapped between gratitude and growth. She said to me, "Dawn, I feel terrible, but I think Maya is the reason I can't take on bigger clients and I don't know how to fix it without destroying her." 

And even more than that. Maya is an integral part of what the future of the business looks like next. So Rachel's already contemplating a potential legacy plan, what her exit plan is, and Maya's standing in the way of that as well. And in entertainment, we call this a first ad problem. 

Your first assistant director was amazing for you when you were shooting short films, but now that you're directing a hundred million dollar feature, they're still asking if they should call lunch. The stakes have changed. The role has changed, and most of the time, that key person for you has to change too. 

Does it sound familiar if it's hitting home? I created a simple checklist assessment called the loyalty reality check. That walks you through the framework that we're gonna talk about today in the podcast, and it includes an AI prompt that helps you analyze the situation in this person's performance objectively without all the emotional noise.

You can grab it free at Dawn Andrews at hellodawn.live/loyalty. And I just wanna say real quick about that, if you suspect. Something needs to change with this key person that you're hanging onto. It needs to change so. I love my AI prompt that I'm passing on to you, and I know it will help.

The thing that it will most likely help with is giving you the words that you're trying to find to be able to have a very difficult conversation.

 So trust your gut. 

Let's talk about why good people, great people, loyal people, stop being the right people.

Here's what I see. After 23 years of watching female founders build teams, we promote loyalty over capability. Nearly every damn time, and especially in the early days of growing our teams.

And then we wonder why our $2 million vision is being executed by someone who's still thinking in $200,000 terms. Businesses are very different at each stage of growth and development, and we need different functions to be fulfilled. So after working literally with hundreds of founders. I do see this pattern quite consistently and we mistake tenure for leadership potential and we confuse gratitude with strategy.

So here's what you need now. You need clarity, not another guilt spiral. Your vision outpacing their capacity and skills does not make you a bad person. It makes you a CEO. Rachel told me, "But Maya sacrificed for me when I couldn't pay her market rate", and I said that was then. What sacrifices your business making now to keep her in a role that she's not equipped for and what is it doing to her as a person?

Her confidence, her ability to move forward and grow. 

So if you're sitting there and you're thinking, okay, Dawn Maya feels like family. Family doesn't send invoices. Family doesn't generate revenue unless it's a family business, and that's a whole different podcast. This is business and in business.

Everyone needs to grow, including you. The loyalty trap works both ways. You think you're protecting them, but actually you're setting them up to fail in a role they're not equipped for While your business suffers. 

In Rachel's case, when she gave Maya a high value client, weeks went by with zero progress. The client wasn't getting white glove service they expected Maya couldn't even explain what the delay was, and Rachel had been considering her for a partnership. And that's not partner behavior. That's a bottleneck with good intentions. 

Okay, let's talk about the next thing, the growth or go filter. So how do you know if someone can grow with your business or if it's time for a transition?

You can use the growth or go filter three areas that you're looking at. Capability, curiosity, and courage. And I'm giving extra weight to courage, like capability with a capital C, curiosity with a capital C, and COURAGE in all caps. 

So let's define those real quick. 

Capability. Can they do the bigger role? Not could they learn with six months of handholding. Can they do it now or within 90 days of clear support. And do you have the resources to give that to them to uplevel them? 

Curiosity. Are they asking questions about the business that match where the business is headed, or are they still focused on the tasks that they've always done?

Like do they understand that they're still stuck in your business of a year ago, two years ago, five years ago, and they're willing to. Look to the present day into the future, or are they just still stuck? 

And then finally, the COURAGE in all caps. When you give them stretch assignments, first of all, do you give them stretch assignments? And when you do, do they lean in or lean back? 

So, like I said, I created an AI prompt that cuts through all this emotional noise and shows you the patterns that you're probably too close to see, because sometimes you need a computer to tell you what your gut already knows, and especially I think as female founders having a neutral third party, if you will, to help us get our words around it and point out to us what it is that we're feeling, but can't seem to say.

So Rachel used it and realized something crucial when she mentioned expanding into estate planning services, Maya seemed more worried about her workload than excited about the opportunity. When she asked about tax research, something that should be in her wheelhouse, Maya's answer was consistently, "I don't think I can handle more."

She was protecting her comfort zone, not scaling with Rachel's vision and what we'd be looking for. Even if Maya didn't think she could handle more, what we're looking for is for her to be able to say, "I wanna be able to take that on, but here's what needs to change."  That shows that she's thinking about the future of the business and the future of her position. Not just shutting it down entirely. 

So here's a quick version that you can try right now with your own AI tool. And then you can grab the prompt and then you can grab the prompts from the download. Okay, so remember we said capability, curiosity, and courage.

So the first thing, capability check. These are questions for you to answer and then put the answers into your LLM In the last six months, when you've given your person stretch assignments or new challenges, did they rise to meet them or struggle to keep up? And what did that look like? 

Two, the curiosity test, when you talk about where your business is headed, new services, bigger clients, strategic changes, do they ask engaged questions or seem more concerned about how it affects their current workload?

And then finally, the courage factor. When problems arise with clients or projects, do they bring you solutions? Do they proactively come to you to make things better, or do you just discover the problems and have to go to them to fix them? 

If you're getting a lot of struggle concerned about workload and just problems, you have your answer.

The full assessment with the detailed prompts will be in the guide. 

So here is the conversation that can change everything. If your assessment shows that they can't or won't grow into what's needed for the business, you have to have what I call the growth or go conversation.

And here's the framework that I teach. Start with appreciation and your vision for the future. "Maya, you have been crucial to getting us to where we are today, and we could not be more excited for you to grow into what's next." Then, state the reality as we scale. "Every role is evolving, including yours", and then you present the choice.

I see two paths forward and I want your input on what feels right to you. 

And then you outline path A, what growth looks like with specific expectations in the timeline and path B, what a respectful transition looks like. Cool. This is where the magic happens because you're letting them choose instead of making them feel chosen against.

So here's what happened with Rachel. When she finally had this conversation, Maya got emotional and said, "my friends and family love me just the way I am." And she walked out. When Maya said that, Rachel finally heard what I'd been trying to tell her. Maya wasn't talking about the business. She was talking about her comfort zone and comfort zones don't scale businesses, vision does. 

If you're ready to stop letting guilt run your personal decisions, grab the assessment guide. It includes the AI prompt I mentioned that helps you see your situation clearly, and you can find it at hellodawn.live/loyalty. 

So, just a quick kind of wrap up here.

I feel getting all emotional. I feel your heart over there because starting and growing a business is no joke, and that little group of people that you started with in the foxhole are everything to you, but your vision for the future of your business, outpacing someone's capacity, isn't a failure.

It's growth. It does not make you ungrateful. It makes you responsible, responsible to your vision, your clients, your future employees, and honestly responsible to that loyal person who deserves to be in a role where they can actually succeed. 

So here's your action step. Stop letting loyalty override strategy.

Download the assessment. Pick one of those loyalty members that you know you've been thinking about, and get honest about whether they're growing with you or holding you back and get honest about their capacity for growth in the current circumstances of your business. 

Here's what great CEOs know, the kindest thing you can do for someone whose role has outgrown them is to help them find where they can actually win. And the smartest thing you can do for your business is make room for people who can match your vision's altitude. 

In future episodes. I'm diving into the mindset shift that makes these conversations easier because honestly, the real work is internal. 

And until then, be patient. Be strong, be patient, be brave, and have those conversations because the next level of growth for your business and for yourself is on the other side.

Okay, love. I'll see you then.