the bossbabe podcast - 462: My Biggest Leadership Mistakes + Regrets

Episode Date: May 8, 2025

No one talks enough about the hard parts of leadership — the moments you wish you could take back, the decisions that didn’t go as planned, and the lessons that only hindsight can teach. In this episode, Natalie pulls back the curtain on the biggest leadership mistakes she’s made over the years. From hiring too fast to ignoring gut instincts, and losing herself in the business, Natalie shares what she would do differently, what she’s learned the hard way, and how she’s leading now. Whether you’re building your first team or already leading one, this episode will give you the honest insights most people don’t share. Let’s dive in! TIMESTAMPS 00:00 Why we’re talking about leadership mistakes today + why more founders need to 03:05 The hard truth about hiring fast and leading without clarity 07:40 What happened when Natalie didn’t listen to her gut 11:20 The hidden cost of avoiding hard conversations 16:00 How people-pleasing led to a leadership identity crisis 20:45 A breakdown that forced a breakthrough in how she leads 25:10 The biggest regret — and what she’d do differently now 28:50 What “healthy leadership” looks like today inside Bossbabe 31:20 Natalie’s challenge to every founder who wants to grow with integrity RESOURCES + LINKS Join The Société: Our Exclusive Membership To Help You Build A Freedom-Based Business - start today for just $97.  Learn how to Start or Scale a Freedom-Based Business with this free training: bossbabe.com/class.  Sign Up For Our Free Weekly Newsletter & Get Insights From Natalie Every Single Week On All Things Strategy, Motherhood, Business Growth + More.  Drop Us A Review On The Podcast + Send Us A Screenshot & We’ll Send You Natalie’s 7-Figure Operating System Completely FREE (value $1,997).

Welcome to my seven part series on the biggest mistakes I've made in leadership to hopefully help you avoid them and shortcut your path to becoming a better leader. Hi, I'm Natalie Ellis, a multiple aid figure entrepreneur and CEO of Boss Babe, one of the world's largest media brands for female entrepreneurs. And here's the first mistake I made as a leader and a business owner. Let's talk about something that doesn't get said enough. Leading a team is a completely different skill set from building a business. Let me guess, you built a business, started growing a team, and now, instead of feeling lighter, it feels harder.

What no one tells you is building a team is not the same as building a business. The skill sets are completely different. And if you don't learn how to lead, your team, the thing that was supposed to give you freedom becomes the very thing that slows you down. I've seen it happen, I've lived it, and the worst part, most entrepreneurs don't even realize they're the bottleneck until it's too late. So today I'm

breaking down the seven biggest leadership mistakes entrepreneurs make. The ones that quietly kill momentum, crush morale, and cost you way more than you realize. This is from my own experience and also what I've seen by being in the CEO seat for a decade and I'm not here to sugarcoat it, but I'm also not here to make you feel like you're failing. Because guess what? The only way we actually learn is through experience. This is about helping you lead with more confidence, make smarter decisions and build the kind of team that actually gives you the freedom you started this business for.

Let's get into it. Let's start with a mistake I see all the time and honestly I've made it myself more times than I want to even admit. You've got someone on your team who's loyal. They work hard. They've been with you since the early days and you want to see them grow. So what do you do? You promote them. You give them the new title, the salary bump, and maybe even more responsibility,

hoping that they'll rise to the occasion. And listen, I get it. As a founder, there's nothing better than seeing someone you've invested in step into a bigger role. You want to reward their potential. But here's the hard truth. Potential doesn't always equal readiness. And when you promote someone before they've actually proven they can perform at that next level, it's not a strategic decision and it's an emotional one. And that's where the problems start. Because now you've created a gap between expectations and reality. If they struggle, and a lot of people do, you're stuck.

Demoting them feels like a punishment. Keeping them there creates resentment, both for them and the rest of your team who sees the gap. And here's what most people miss. Your A players, the ones you actually want to keep long term, don't want handouts. They thrive on earning their success. They want to know they're in the role because they deserve it, not because you're being nice or felt obligated.

The minute you skip that, you risk undermining their confidence, their motivation, and the culture you're trying to build. So what should you do instead? First, create a test period. Before making anything official, give them stretch projects, assign them leadership tasks, see how they can operate when the stakes are a lot higher. Do they take ownership? Do they problem solve? Do they inspire confidence in the rest of the team? Because that is what you're

promoting, not just their loyalty or tenure. Second, get crystal clear on what success looks like in the role. Like actually write it down. What specific outcomes would prove to you that they are ready? What metrics? What projects? What leadership behaviors? Because if they don't know what winning looks like, how can they ever hit that target? And third, use performance-based incentives instead of upfront raises. Make the raise the reward, not the gamble. Tie it to clear milestones when you hit X, Y, Z, that's when the role and raise becomes official.

And finally, have the conversation. Don't make it a surprise or a guessing game. Say it directly. I see you in this role and I believe you have what it takes and I want to set you up to win. So let's define success together and when you hit those targets the role and the raise are yours. That one shift can change everything. It can create a culture where promotions are earned not gifted and where your team knows exactly what it takes to grow. And the best part when they do step into that role they're ready.

They're confident and you're not crossing your fingers. You're rewarding performance that's already happening. That is how you build leaders, not just fill seats. Let's move to the next one. So if there's one leadership lesson that's changed everything, it's me. It's this. The conversations you avoid are usually the exact ones that would change everything. But for most of us, we convince ourselves it's better to wait. Maybe if we give it a little more time, things will magically get better. Maybe they'll notice they're dropping the ball and fix it on their own, but the truth

is they rarely do. And while you're avoiding it, the problem doesn't stay neutral. It grows. Resentment builds, both for you and for them. And the conversation, the longer it festers, the harder it becomes. Here's what I really want you to hear. Your A-players, they want the honesty. They do not want to guess where they stand. They do not want to feel like something's off but no one's saying it. And when you avoid those conversations you're not protecting them. You're actually making them question your leadership because people can feel it. They know when something's being left unsaid. And when leaders avoid hard conversations, teams start filling in

the blanks themselves and they rarely fill them in with anything positive. So what do you do instead? First, reframe it completely. Hard conversations aren't conflict. They're an investment in your people, your culture and your future success. The best leaders know this. Avoiding discomfort now only guarantees bigger problems later. When you approach the conversation, lead with honesty and care and say something like, listen, I care about you and because of that, I wanna have an honest conversation about something I think could help us both.

That one sentence lowers defenses. It reminds them you're coming from a place of care, not criticism, and then next you wanna get specific. So the fastest way to escalate a tough conversation is to lead with vague emotion. Telling someone you're not stepping up is subjective. It feels personal. But saying three deadlines have been missed in the last two weeks and it's starting to impact the team gives them something concrete to respond to. Facts ground

the conversation. They remove the emotion and focus it on outcomes on what needs to change. And here's the most important part. Do it early. Every week you avoid the conversation, you're adding months of frustration for you and for them. Because let's be real, the conversation is rarely as bad as the buildup in your head. Once you rip that bandaid off, most people are relieved you finally said what needed to be said.

And more often than not, they already knew it was coming. So the simple rule that I live by now, if a conversation feels uncomfortable but necessary, I have it sooner, not later. Because waiting doesn't make it easier, it just makes it messier. And the leaders who grow the fastest, who build the strongest teams, they're not the ones who avoid conflict. They're the ones who lean in, have the hard conversations early, and move forward with

clarity. Let's jump into the next mistake. One of the hardest parts of leadership is balancing trust with accountability. Because if you're like most entrepreneurs, you wanna believe the best in people. You wanna create a culture where your team feels empowered, trusted, and respected. But here's where a lot of leaders, myself included, go wrong.

We confuse being nice with being naive. We assume everyone is as aligned and bought in as we are, and that's where things start to break down. Here's what this looks like in real life. You delegate delivering a tough message to someone else on your team, maybe because you don't have capacity or maybe you're really trying to promote leadership

in the person you're delegating it to. But what happens next is where the real damage is done. That person either softens the message, misrepresents it or worse, throws you under the bus. This wasn't my decision. I don't agree with it, but it's what leadership wants. And just like that, you've created two problems. One, your team starts losing trust in you.

They don't know what's real, what's being filtered, or where you actually stand. And two, you've accidentally handed influence to the wrong person. The team starts looking to them for answers because they've positioned themselves as the approachable one, while you become the invisible decision maker

in the background. And that is a dangerous dynamic to play out. So what's the fix? It's simple, but it takes discipline. Deliver hard news yourself. Leadership is not something you can delegate. It is on you to communicate directly, especially when the message is tough.

And from day one, you've got to create a culture of transparency. Your team should know if they have a question, if they're confused, if something doesn't sit right, they come to you. Not through back channels, not through whispers or middlemen. And if you ever catch misalignment, not through whispers or middlemen.

And if you ever catch misalignment, if you hear that someone on your team is misrepresenting your decision or your leadership, you address it immediately. No waiting, no hoping it resolves itself. You pull them aside and say, we aligned on this. If there's a concern, you bring it to me directly before it gets communicated.

We are on the same team and our alignment is non-negotiable. Because that's what this is really about. Trust is earned. But alignment, alignment is required. You cannot afford to have people on your team playing both sides. It erodes trust, it creates silos and ultimately it puts you right back in the bottleneck. The best teams operate with clear communication, full transparency and absolute alignment at every level and that starts with you modeling it every single day. Now this next one hits home for a lot of founders, especially if you're used to being the person

who get things done. One of the fastest ways to burn out as a founder is falling into what I call the fixer trap. It happens when you jump in every single time there's a problem, because it feels easier, it feels faster, and honestly, it feels good. You solve the problem, you feel useful, and for a moment you feel like the hero.

But here's the problem. Every time you swoop in to fix something, you're training your team not to think for themselves. You're unintentionally reinforcing this unspoken rule. If it gets hard, just wait, the boss will handle it. And what happens next is predictable. You become the bottleneck. Your team stops coming to you with solutions

and starts coming to you with problems. They stop growing because you've never given them the space or the expectation to solve things on their own. And then you, you're stuck in the weeds spending your days putting out fires instead of driving the business forward. This is exactly how founders end up feeling like employees inside their own companies. You're working harder than everyone else, but the business isn't growing because you are the system and the system breaks the second you step away. So what do you do instead? You coach, you don't fix. The next time someone comes to you with a problem, resist the urge to jump straight into solution mode. Instead, ask them one question. What do you think we should do? Then stop talking,

give them the space to think even if it's uncomfortable because growth doesn't happen in comfort. And yeah, sometimes they'll stumble. Sometimes they won't have the answer, but that's the point. You're building that critical thinking muscle. You're training them to take ownership. You're showing them that you're not there to be the hero. You're there to build other leaders because the real job of a CEO isn't to solve every single problem. It is to build a team

that knows how to solve problems without you. That is how you scale. That's how you actually create freedom in your business. And the best part, when you start leading this way, your team rises. They stop bringing you solutions, not problems. They grow, they get better. And for the first time you actually feel what it's like to have a team that can run without you. That is

real leadership and that is how you break out of the fixer trap for good. The next, if you've been hiring for any length of time chances are you've made this mistake because almost every entrepreneur I know has. You interview someone, they look good on paper, the resumes stack, the experience checks every box, they know the tools, they've done the job before, on paper it feels like a no-brainer. So you hire them, you're excited. For a minute it feels like you found the person who's gonna take this entire department off your plate and then six months later you're

sitting here wondering why it's just not working. Because the truth is, skills can be taught, tools can be learned, but values, values are baked in. You can't train someone to care about the mission. You can't teach someone to take ownership or to genuinely collaborate with the team. And by the time you realize it's a culture misalignment, it's already costing you. That's why the shift here is so important. Higher for alignment first, skill second. Now that doesn't mean you ignore skills.

Of course it doesn't, but what it does mean is it matters more how someone shows up. Do they take ownership? Are they adaptable? Do they see the bigger picture? Are they just checking boxes? The way you figure that out is by changing how you interview. Don't just walk through their resume or ask about technical skills. Those are easy. Instead, test for the things that actually make someone successful in your company. Ask, tell me about a time you solved a problem without being asked. Or walk me through a moment where you disagreed with leadership.

How did you handle it? These answers are gonna tell you so much more than a certification or software knowledge will. And here's the part that took me a while to trust. If your gut is telling you they're not a fit, listen. Every time I've ignored that little voice because I was too excited about someone's skills, it came back to bite me.

Every single time. Because here's what I've learned. Skill gaps can be closed, but culture gaps, they only get wider. And the longer you wait to fix it the more damage it does. Hiring the right person isn't about finding the smartest resume in the pile, it's about finding the person who will thrive inside the way you run your company. That's what keeps your culture strong. That's what creates a team that moves fast, solves problem and actually cares about the mission and that's the

kind of team that builds businesses without you carrying the whole thing on your back. This next one is sneakier than most people realize, but it shows up everywhere. And it's one of the biggest reasons teams underperform. Your team often isn't failing because they're lazy or unmotivated. More often than not, they're failing because they don't actually know what success looks like.

As founders, we assume it's obvious. We think, of course they know what good looks like. Why else would I have hired them? But the reality is what's obvious in your head is not obvious to your team, especially when you're moving fast. Priorities shift and people are working remotely or in creative roles where the outcome isn't black and white.

And when people don't know what winning looks like, two things happen. Either they spin their wheels trying to guess or they freeze because they're afraid to get it wrong. Either way, you're losing momentum. The fix here is actually quite simple, but it takes intentionality. You have to define success at every level.

What does winning look like in this role? In the next 30 days, 60 days, 90 days? What outcomes would tell both of us, yes, you're on track, yes, you're crushing it. And this isn't just about big revenue goals or team KPIs, it's about getting specific with each person's role. For example, if your manager in social media is winning, hitting engagement targets, growing the audience by a certain percentage, driving X

number of leads, because if the only direction they get is grow the account, you're leaving way too much for interpretation. So the clearer you get, the faster your team will move because now they're not guessing. They know what matters. They know what great looks like and they know exactly what they're working toward. And here's the part most leaders miss. You don't define this once and then walk away. You revisit really often. Priorities shift.

The business evolves. Your team deserves to know what success looks like at each stage. When people know what winning looks like, they show up differently. They take ownership. They get creative. They push for results because they know where the target is. But if you don't define it, don't be surprised when they miss it, because you can't hold people accountable to expectations you never set.

So define it, measure it, talk about it. That's how you build a team that knows how to win and actually wants to. This is one of the easiest traps to fall into as a leader, especially when your business starts growing and things feel chaotic. You see people busy, slack is buzzing, there's a million tasks in motion, and it feels like progress. But here's the reality, just because someone's busy doesn't mean they're driving the business forward.

And if you're not careful, you start rewarding the wrong thing. You start rewarding the person who looks the busiest, the one who's always on, always in meetings, always talking about how much they got going on instead of the person quietly moving the needle where it matters. And here's when that dynamic sets in.

You promote the wrong people. You start elevating the ones who seem the most essential, but in reality, they're just the loudest or the most reactive. You lose sight of what's really driving impact because when everyone's running around busy, it's hard to tell what's actually working. And worst of all, your team starts performing for optics instead of outcomes. They start working to look busy busy not to solve real problems. This is how you end up with a bloated team, bloated payroll, and a business that feels

like it's running fast but going nowhere. So what's the fix? You have to get crystal clear on what actually drives the business forward. What are the needle moving activities that create revenue, build assets, or solve real problems? Because that's what should be rewarded. Not how many hours someone's logs or how many meetings are in.

As a leader, you've got to measure impact, not effort. I don't care if someone's working 10 hours a day. If they're not producing results, that's not productivity. That's motion. And once you have that clarity, you build a culture where working smart and not harder is what gets recognized. Why the people who get results without creating chaos

are the ones who rise. Cause at the end of the day, your business doesn't grow because people are busy. It grows because people are focused on the right things and they know the difference. That's how you create a team that performs for outcomes, not just for show. And that's how you make sure your leadership is scaling the business, not just fueling the busyness. Here's the thing, leadership is a skill. It's not something you're either naturally good at or not.

It's something you build, refine, and get better at over time, just like every other part of running a skill. It's not something you're either naturally good at or not. It's something you build, refine, and get better at over time, just like every other part of running a business. And the entrepreneurs who scale the fastest, it's not because they never make these mistakes. It's because they learn to spot them early, adjust quickly, and lead better the next time around. They stop seeing leadership as this innate talent

and start treating it like it really is. It's a learned skill set that determines how far and how fast their business can grow. So if you're building a team right now, we're in that messy middle where leading people feels heavier than it should, I hope this gives you some clarity and honestly a little permission to stop carrying the whole thing on your back. Because your job isn't to have all the answers, it's not to fix every problem or to be the hero every time something breaks. Your real job is to build leaders who build the business with you,

to create a team that solves problems, takes ownership and drives the thing forward without you needing to be in every room, every decision, every moment. And that's how you scale. That's how you create freedom. And that's how you build a business that lasts. I'll see you in the next episode.

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