462: My Biggest Leadership Mistakes + Regrets

the bossbabe podcast

Natalie Ellis

Education, Entrepreneurship, Marketing, Business, Self-improvement

4.9 • 2.3K Ratings

🗓️ 8 May 2025

⏱️ 18 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 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: www.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).

Transcript

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0:00.0	Welcome to my seven-part series on the biggest mistakes I've made in leadership to hopefully
0:04.7	help you avoid them and shortcut your path to becoming a better leader. Hi, I'm Natalie Ellis, a multiple
0:09.6	eight-figure entrepreneur and CEO of Boss Babe, one of the world's largest media brands for female
0:14.3	entrepreneurs. And here's the first mistake I made as a leader and a business owner. Let's talk about
0:19.7	something that doesn't get said enough.
0:21.3	Leading a team is a completely different skill set from building a business. Let me guess.
0:25.5	You built a business, started growing a team, and now, instead of feeling lighter, it feels harder.
0:30.5	What no one tells you is building a team is not the same as building a business. The skill sets
0:34.3	are completely different. And if you don't learn how to lead, your team,
0:37.7	the thing that was supposed to give you freedom, becomes the very thing that slows you down.
0:41.9	I've seen it happen. I've lived it. And the worst part, most entrepreneurs don't even realize
0:46.7	they're the bottleneck until it's too late. So today I'm breaking down the seven biggest
0:50.9	leadership mistakes entrepreneurs make, the ones that quietly kill momentum,
0:54.9	crush morale and cost you way more than you realize. This is from my own experience and also
0:59.6	what I've seen by being in the CEO seat for a decade. And I'm not here to sugarcoat it. But I'm
1:04.1	also not here to make you feel like you're failing. Because guess what? The only way we actually
1:07.8	learn is to experience. This is about helping you lead with more
1:11.4	confidence, make smarter decisions and build the kind of team that actually gives you the
1:16.0	freedom you start at this business for. Let's get into it. Let's start with a mistake I see all
1:23.1	the time. And honestly, I've made it myself more times than I want to even admit. You've got someone on your
1:28.2	team who's loyal, they work hard, they've been with you since the early days and you want to see them
1:32.7	grow. So what do you do? You promote them. You give them the new title, the salary bump and maybe
	...

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