She’s That Founder
215 | Why Your Star Employee Won't Step Up (And It May Not Be a Performance Gap)
She got the bigger title, she got equity, and five years later, the thing she promised to build still didn't exist. I'm about to break this story down for you
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 using AI frameworks for faster delegation and decision-making.
This is for leaders. Let's do this. I'm Dawn Andrews, and today you'll discover why the longtime star in your business who just won't step up may not have a performance gap at all, and what's really going on underneath. We'll discuss the four things that leaders mash into one when they decide who grows with the company and who stays, and why pulling those things apart changes every people decision you're likely to make.
And we'll talk about how to run a future role conversation so you find out whether somebody wants the job, not just the title, before you build your growth plan around her.
So Hey, girly. If you're watching this instead of listening, you're getting worked on today.
I record these in my studio usually between my workout and actually beginning my workday. I know how to put on a blazer and armor up when a blazer is called for. This is not a blazer situation. This is you and me in my office, chilling, talking about business stuff, and I would rather spend that extra hour creating something valuable for you.
So enjoy the messy hair and drawn-on eyebrows.
Okay. Today, I wanna tell you about two women. I'm gonna call them Lena and June. Those aren't their names, and I blended a few stories from my practice together so nobody gets recognized, but every bit of this happened. Lena is our founder, so remember Lena's the founder, and June is one of the earliest employees in this service-based business.
June has been there from the beginning, before the systems, before the real office, before there was anything but Lena, June, and a whole lotta nerve. These are our first two [00:02:00] people through the door. And June is extraordinary. She is one of the best people I've ever seen at the core craft of this service business.
She carries the quality control. She carries the history. She knows why every little weird process in this business exists. And when a client gets June as her primary delivery person for the service, the client gets the very best.
So as the business grows, June wants more, which of course she does. More money, a bigger title, equity, more people reporting to her as the team grows. And Lena, the founder, isn't fighting any of it. She wants to reward June. She knows exactly what June has meant to this company. And the company is at a place where it needs something back.
Not more of what June already is good at, but something different at this age and stage of the company. And what it needs is to have June take everything that lives in her head and turn it into something that other people can use, a training system so that June can start to duplicate herself, documentation, a process somebody in another location could pick up and follow so that they can extend their business, like they can license and franchise their business.
So there needs to be a way to reproduce the quality that June creates with her own two hands. June says yes, and then it doesn't happen. So Lena, the founder, explains it again. She writes the expectations down and deadlines move.
The work gets chopped into smaller pieces. Eventually, Lena brings in an outside person just to help June get what she knows onto the page. That's the role that I played here. And June can explain the process beautifully, seriously, if you ask her how it works, and she'll walk you through it like poetry.
Still, she doesn't build it. So Lena, the founder, does what we do. She starts taking pieces back. She hands parts to other people. She builds workarounds. She gets irritated. She gets busy and comes back to it next quarter. Meanwhile, June has already gotten the bigger title, she's gotten equity, and the work has not fundamentally changed for five years.
Eventually, Lena, the founder, has to hire people around June and take responsibility away from her and step back into work she was supposed to have grown out of a long time ago, and the relationship ends badly. The kind of badly where two people who built something together can't really be in a room anymore.
If you're doing a little quiet math about someone on your team right now, stay with me. That's exactly what we're unpacking today. So what went wrong here? The obvious answer, June wasn't being held accountable, and I get it. It's true, and Lena would tell you that herself, but it's actually not deep enough.
So you look at everything that Lena tried, it's clear, obvious stuff, clear [00:05:00] expectations, more support, smaller steps, outside help, new deadlines. That's not a founder who ignored the thing. That's a founder who threw the entire kitchen sink at it. And here's where it gets really interesting. What if they were solving for the wrong thing the whole time?
Every one of those moves treats this as a performance gap. June needs more clarity. June needs more support. June needs coaching. June needs a smaller first step. But underneath all of it may have been something much simpler. June didn't want the new job. It's just that simple. She wanted a bigger role, she wanted equity, she wanted a bigger paycheck, but she may have not wanted different work.
She wanted to keep doing the thing she loved and was world-class at, and she wanted more recognition for how valuable that thing was, and those are legitimate desires. And I wanna be really clear about that because there's nothing about June wanting that that [00:06:00] makes her a bad employee. But it's not the same as wanting to become an executive, someone responsible for systems, for scale, for process, for developing other people, for building capability that doesn't run through her own hands.
Those are two different jobs, and one of them barely includes the work that June loves most. And this is something that happens so frequently in growing companies. I've watched so many brilliant founders miss this, and I get why. Because June never said no. She said yes every single time.
She agreed to the plan. She nodded in the meetings. She could describe the finished system in gorgeous detail, and it was all real. The yes was real. It just wasn't a yes to the job that the business needed her to do at this time and stage in its growth. It was a yes to the relationship, to the title, the money, being seen, and a yes to not disappointing Lena, the founder I don't know if this sounds familiar for you, because a lot of us are world-class at saying yes to things we have zero intention of doing.
Hello, my fellow people pleasers. I see you, and I am you. So here's the thing I want you to hold on from this part. When a great person keeps agreeing and keeps not doing, stop asking how to help her do it. Start asking whether she actually wants to. And that brings us to the part of the story that's really about Lena, the founder, and if I'm honest, it's about me and maybe about you.
But first, let's take a quick break so I can pay for this microphone. Quick pause. If a name popped into your head during that story, there's probably a conversation you've been putting off. And if you want it to be honest without being brutal, download The Feedback Fix. It'll help you give feedback that actually lands, even with the person you'd least like to lose.
You can find the link in the show notes. All right, let's get back to the good stuff
Okay, let's talk about the things that we mash into one that if we separated would make things a little bit easier. Lena, the founder, in this story is not weak. Nobody builds a company from nothing by being weak. She let this go on for five years because the alternative was terrifying. Because let's just take a minute and think about what June represents.
She might be close to impossible to replace. She carries knowledge nobody else has. She was there when there was nothing. Lena, the founder, feels like she owes her, and she does owe her something, and we'll get into what. And if June leaves, guess who picks that work back up? Lena does. And in your case, if you're dealing with something like this, you do. You pick up that work. So the thought becomes, surely I can develop her into this. And every time she doesn't do the thing, you adjust. One more conversation, one more deadline, one more coach, one more reorg, one more person hired around her.
And you can call that support, and sometimes it really is support. Sometimes it's the most generous leadership that there is. And sometimes support becomes avoidance dressed up as leadership development. I have done my own version of this. I kept developing someone because the honest conversation felt more expensive and impactful and even devastating than the workaround.
But it wasn't. It never is. The workaround just sends you the bill later with interest Founders don't struggle to hold mediocre people accountable. We struggle to hold valuable people accountable. Because with the mediocre person, there's nothing to lose. With June, there was everything to lose, and that's why the pattern can last five years.
It's not that nobody noticed, it's that noticing was too expensive. So how do you get out of it? You pull apart four things that we almost always squish into one.
The first is value. How important is this person to the company?
The second is capability. Can she actually do what the bigger role requires?
The third is aspiration. Does she want the bigger role and the work that comes with it? Not the title, but the work.
And the fourth is readiness. Is she prepared to do it now?
So if we could have a little bloop, bloop, like go backwards in time and run Lena and June through these questions, it gets clear really fast.
Value for June, off the charts. Capability, probably there or reachable with support. Remember, she could describe the whole system. Readiness, highly debatable. And aspiration, that is the one that nobody ever checked. A person can be sky high on value and low on aspiration for the next role, and that doesn't make her a bad employee.
It doesn't obligate you to redesign your next executive position around the work she'd prefer to do either. Which means you have to separate two questions that feel like the same question. What does this person deserve because of the value she's created and is currently creating, and what role does the company need filled next?
And those can produce totally different answers. Maybe June deserves more money, maybe equity, maybe a senior expert track where she's the undisputed master of the craft and nobody's asking her to run and create a training program. Maybe she deserves enormous respect out loud in front of everyone.
None of that automatically means she could run the next version of the function. So separate what this person deserves from what the company needs next. Honor the first, but hire for the second.
And so before this turns into an episode about a difficult employee, I have to turn the mirror around, because in a lot of ways, I'm June
Here's what I had to admit to myself while I was prepping this. I want the upside of growth without every piece of work that comes with it constantly. I want a bigger business. I do not want to manage a giant staff. I wanted leverage long before I was willing to document every repeatable thing I do. For years, documentation felt slow and painful, and honestly, kind of like a punishment for being good at my job.
AI changed a lot of that for me. Like, being able to talk my thinking out loud and have it captured, organized, and turned into something that my team can actually use made systematizing my brain dramatically easier. I just decided to step into being an idiot using AI until I became passively proficient.
That is why we're early adopters over here. And none of this makes me a hypocrite for telling Lena's story. It makes the challenge really human.
We often want the result at the next level before we've decided whether we actually want the job required to produce it. Employees do it, founders do it, I do it. We all do this.
We want that next pop, that next level of excitement, that next achievement, that next revenue goal. But getting where you want to go requires doing something that got you to where you are. So how do you find out early whether someone wants the job, not five years in, before you build your whole growth plan on their shoulders?
You have what I call a future role conversation, and you have it from the same side of the table. You're not evaluating her. You're sitting on the same side of the table looking at the future of the company together as teammates.
So you don't open with, "Do you want more responsibility?" Almost everybody is gonna say yes to that, even if they really don't want it.
It's like asking someone if they'd like to be appreciated, and they're gonna be like, "Hell yeah, let's do it."
So ask things like this instead: What do you want to spend more time doing, and what do you want to spend less time doing? What kind of problems do you want to own? Do you want to manage people, or do you want deeper authority in your expertise?
Do you want to build systems other people will use? Do you want to be accountable for outcomes produced by people other than you? What parts of this next role sound exciting, and which parts sound miserable? And that last one is gold. Like, give your person, this senior person that you've been building with, permission to say miserable out loud, because that's where the truth lives.
And then once you have those, you can start to create the actual job, not the title, the salary, not the box on the org chart, but what Tuesday at 4:30 looks like, the actual work. And that Tuesday at 4:30 work is the call where someone in the other location got the process wrong again, and you have to figure out whether the process is broken or the training is, or it's the documentation that nobody applauds, or it's measuring your success by how good other people get at the thing that you used to be the best at.
Show her that, and then believe her answer Now the harder question, because I know some of you are thinking, "Girl, I did all that. She said she wants it, and it's still not happening." When does this stop being a coaching challenge? Well, here is where I have landed. When the expectations are clear, when she has the capability or access to support, when the obstacles have been dealt with and the same commitment keeps failing to become behavior, at that point, stop asking, how do I make this easier for her?
Ask, are we still dealing with a development gap, or are we dealing with a choice? That's a very different conversation. A development gap you coach, a choice you respect, and then you get to make yours. Show her the job, not the title, then believe what she tells you
So here's where we've been today. A great person can keep saying yes and keep not doing, and it may not be a performance gap at all. She may want a bigger role, but not different work. We hang onto that mismatch for years because valuable people are the hardest ones to hold accountable because there's something real to lose, and the way out is to pull apart value, capability, aspiration, and readiness, and to separate what she deserves from what the company needs next.
The way you find out early is a future role conversation where you show her what work would actually look like at 4:30 PM on a Tuesday, and then believe what she tells you about potentially doing that work.
So here's your try this for the week. Pick one person you're quietly counting on for the next stage of your company. Ask yourself, " Has she actually told me she wants the job I'm imagining for her, or have I built that future in my own head and not communicated it to her?" Then have the conversation, same side of the table, because you don't owe a great employee the next job, and she doesn't owe you an appetite for becoming the person your growth plan requires.
What you do owe each other is honesty. You owe her the chance to see the future you're imagining, to understand what the role actually requires, to tell you whether she actually wants it, and if she does, to build the path to get there together.
And if she doesn't want it, believe her, because the company you're building is supposed to be a place where women can tell the truth about what they want and not get punished for it.
That includes June. That includes you. Five years of trying to force alignment will cost both of you far more than telling the truth early, and sometimes the most respectful thing you can do for a great employee is stop trying to turn her into someone she never asked to become. And if someone came to mind while you listened, not on your team, but a founder or senior leader wrestling with this exact thing, a longtime star and a quiet question about whether she needs more development or just wants a different future, send her this episode. It might be the nudge to have that conversation.
That's it for today's episode of She's That Founder. I'll see you on Thursday, and until then, you've got this. Tell the truth early because it's so much kinder than it feels like it is. Take care, Lovey.
