Pod Insights the bossbabe podcast 462: My Biggest Leadership Mistakes + Regrets About this episode 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 + 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
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Transcript 0:00 Speaker 00 We put out a lot of content, reels, carousels, YouTube and this podcast. And for every piece, someone on my team is hunting for the right clip or image to go with it. Storyblocks have made that part really easy. It's a 100% human-made stock library, which has footage, music, sound effects, templates and images, all made by professional filmmakers and artists, never AI-generated. We can grab visuals that actually look on-brand and everything is pre-licensed and ready to use. It's unlimited downloads under one subscription, so if you're creating content every week, you always have a library to pull from. You can head to storyblocks.com/bossbabe to access the human-made stock media library that is essential to our workflow.
0:45 Speaker 00 And for a limited time, they're offering 15% off any annual plan and that discount is only available through my link. Again, that's storyblocks.com/bossbabe for 15% off annual plans. 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 eight-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.
1:30 Speaker 00 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 realise 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 realise. 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.
2:17 Speaker 00 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
2:59 Speaker 00 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?
3:41 Speaker 00 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 behaviours? 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 XYZ. 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.
4:26 Speaker 00 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. Your reward and 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.
5:11 Speaker 00 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.
5:56 Speaker 00 When you approach the conversation, lead with honesty and care and say something like, "Listen, I care about you and because of that, I want to 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 want to 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.
6:36 Speaker 00 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 for real, the conversation is rarely as bad as the buildup in your head. Once you rip that Band-Aid 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.
7:19 Speaker 00 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 and 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.
8:00 Speaker 00 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.
8:41 Speaker 00 And if you ever catch misalignment, if you hear that someone on your team is misrepresenting your decision or your leader You address it immediately. No waiting, no hoping it resolves itself. You pull them aside and say, we are lined 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.
9:26 Speaker 00 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.
10:07 Speaker 00 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 are you doing 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.
10:46 Speaker 00 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. Part when you start leading this way, your team rises. They start 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. Boss Babe started as an Instagram account, quotes for women with big goals. That built the community, but then it became a business when we had a website for our products, because that's where people could actually buy from us. If you've built an audience and do not have that home yet, Hostinga makes it simple. Describe what you want, a sales page, a portfolio, an online store,
11:29 Speaker 00 and their AI builds a working version in minutes. No coding, no designer, no developer. And it doesn't stop at launch. Hostinga's AI agent works like built in specialists for SEO, website copy and email marketing. If you already have a site, they make moving it over quick and easy. Black Friday pricing is live now through December 14th. Snag Hostinga services at their lowest prices before the sale ends. Create your website today for just $1.99. Go to Hostinga.com/ bossbabe and use code BOSSBABE for an additional 10% off Black Friday and Cyber Monday pricing. Running a business rarely goes exactly as planned. Between insecurities, bad habits and even worse advice, founder stories are never really picture perfect.
12:12 Speaker 00 In this latest season of Amazon, This is Small Business, host Andrea Marquez sits down with the founders to unpack the moments that shaped their businesses. They get really honest about burnout, failure, identity, and the deeply personal reasons people choose to build something of their own. They talk about getting into stores, pitching on Shark Tank and dealing with copycats, bringing us closer to the products, ideas and experiences behind each story. Because there is no right way to be an entrepreneur. Check out Amazon's This is Small Business on YouTube, Apple Podcasts, Spotify and everywhere else you get your podcasts. 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.
12:54 Speaker 00 You interview someone, they look good on paper, the resume is stacked, 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've found the person who's going to 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 realise it's a culture misalignment, it's already costing you. That's why the shift here is so important. Hire for alignment first, skills 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?
13:39 Speaker 00 Do they see the bigger picture? Or they're 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 going to 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 good 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.
14:24 Speaker 00 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 realise, 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.
15:08 Speaker 00 Either they spin their wheels trying to guess, or they freeze because they were free 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 thirty days, sixty days, ninety 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 managing 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.
15:53 Speaker 00 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.
16:34 Speaker 00 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 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.
17:17 Speaker 00 They start working to look 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? Cause 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 smarter 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.
18:00 Speaker 00 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 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, where you're in that messy middle where leading people feels heavier than it should.
18:44 Speaker 00 I hope this gives you some clarity and honestly, a little permission to stop carrying the whole thing on your back. Cause 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.
19:17 Speaker 00 Wait, wait, wait, before you go, I would love to send you my seven-figure CEO operating system completely free as a gift. All you've got to do is leave us a review on this podcast because it really supports the growth of this show. This is my digital masterclass where I'll show you what my freedom-based daily, weekly and monthly schedule looks like as an eight-figure CEO, mama and high performer. And I'll walk you through step by step how to create this for yourself. It includes a full video training from me and a plug and play spreadsheet to literally create your own operating system. It's one of our best trainings and it's worth $1,997, but I will unlock access for you for free when you leave us a review.
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Previous 461: How to Trust Yourself Again After a Hard Season in Business Next 463: Why Most Entrepreneurs Stay Stuck at Six Figures (And How to Break Through) Page updated November 3, 2026 · transcript and summary are machine-generated