Kristen Hadeed: Millennial expert writes book giving leaders “Permission to Screw Up”

Kristen Hadeed: Millennial expert writes book giving leaders “Permission to Screw Up”

If you aren’t familiar with Kristen Hadeed’s work yet, that’s okay, but understand she won’t be America’s best kept secret for much longer.

Hadeed started Student Maid, a Florida-based cleaning company recognized for a high-retention rate and positive work culture.

Using the lessons she learned as CEO and a viral Tedx talk, Hadeed then launched a successful speaking career, traveling the country and positioning herself as a Millennial expert.


I first heard Kristen speak in 2015 and have kept in touch ever since.

She’s genuine.



Oh, and uber talented.

Now, just as she promised, she’s releasing her first book: Permission to Screw Up. It’s available for pre-order this week before it hits bookstores everywhere on Tuesday, Oct. 10.

Hadeed was generous enough to answer a few questions about the book, which she says is a departure from the usual “leaders-should-be-perfect-before-they-lead-and-if-they-aren’t-they-can’t-lead” mindset.

1. What is your goal with this book?

As I grew my business, I read dozens and dozens of leadership and business books by people who seemed to have it all figured out. Though those books offered wonderful advice and had a major role in shaping me as a leader, none of them gave me any indication of exactly how hard leadership is. As an inexperienced leader, I needed to hear that I wasn’t alone: that other people messed up along the way just as bad as I was messing up. I needed to hear that I wasn’t the only one who didn’t get it right on the first try every time.

This book is my whole story, warts and all. I didn’t want to write only about the good stuff, or just gloss over my mistakes and share only the lessons I learned in the hopes that they would be useful to someone else. I want leaders just starting out to read this book and think, “Wow. If she got it wrong that many times and she’s still managed to be successful, maybe I have a chance after all.”

I also want to inspire others to share their “whole stories” so we can ditch the idea that everyone has to be perfect. I used to think that asking for help or telling someone that hey, actually, things aren’t going so great was frowned upon. But it shouldn’t be: Leaders need help and support, too. I want people to be honest about where they went wrong so others feel more comfortable with being vulnerable and asking for help when they need it.


2. Why do you think leaders feel the pressure to be perfect, have it all figured out, mistake-free?

Leaders feel that pressure because perfect stories are all we hear. Even though it’s become more common for leaders who have succeeded to say, “It’s OK to fail! It’s OK to make mistakes!” not enough of those leaders talk about their mistakes. It’s uncomfortable. It’s not fun to admit you handled something poorly, or made a decision that negatively impacted people. You fear that people will judge you or look at you differently.

There’s also a pressure to make people feel safe. Success and perfection–we think–are what make our people feel secure in their jobs and in their own futures.

But I’ve found that when I admit that I’m struggling, or when I tell my team that I don’t know how to solve something, it actually builds trust because I’m being vulnerable. My people know that I’m not putting on an act. And most of all, they want to help me.

Unfortunately, when leaders aren’t vulnerable and they pretend they have it all together, they make leadership seem less attainable to everyone around them. Their “perfection” makes people think, “I could never be a leader because I’m not like that person. I must not have what it takes because I don’t know what I’m doing.” We need to break the illusion that leaders must be perfect so that more people will step up.

3. How does it feel to see your name on the cover?! What did you learn about yourself writing it?

It’s still sinking in! I just got my first physical copy, and it’s just . . . amazing. I’m proud of it because I know I poured my heart onto every page. It took two and half years to finish (and I might have missed my deadline a few times).

When I first started writing, it was about getting the book done and hitting the deadline. But then it became about writing the right book, the one I wish I would have found on the shelf when I started my business. I realized that kind of book was really hard to write, but I stuck with it.

I became a perfectionist, which is kind of ironic for a book about screwing up, but I had to get the stories right. I would tell myself I wasn’t being vulnerable enough, and I’d challenge myself to take a story further and give more of the not-so-nice details. And sometimes, that meant painting myself in not the best light. But in the end, I’m glad I wrote the book that was hard to write instead of one that made me look good.

I’m a speaker and have been giving talks for years, but writing made me realize I could do so much better in my speaking. Before I started writing, I would always talk about success and all the lessons I learned. I wasn’t talking about my struggles or what I had to get wrong to learn those lessons. Writing this book helped me find the courage to be the real, imperfect me–and I like her way better!

Ready to buy the book? Pre-order it here!