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The Leadership Podcast

The Leadership Podcast

We Study Leaders

December 2, 2020

TLP231: Permission to Screw Up

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Kristen Hadeed is the founder of Student Maid, a successful cleaning company that has employed thousands of students over the last decade and that is known for building the next generation of leaders.

In 2017, she published her first book, “Permission To Screw Up”, in which she offers an unapologetic account of her biggest mistakes in leadership. She hopes that her vulnerability will give others the courage to open up about their own “perfectly imperfect” moments and proudly embrace them as the tremendous learning opportunities they are.

Kristen has been featured in news outlets including PBS, FOX, Inc., NBC, TIME, and Forbes. Her first TED Talk has more than three million views on YouTube. 

Key Takeaways

[4:10] In college, Kristen got a cleaning contract and within 3 days, 45 of the 60 people she hired walked off the job. She had no idea she was such a bad leader, but it was a defining moment for her to change.

[6:25] Instead of blaming others, Kristen took an introspective approach. That’s because she grew up in a household where failure is learning.

[9:55] People don’t trust people who are perfect.

[11:25] When Kristen was writing her book, she realized she had a fear of failure as well as a fear of success.

[14:20] If you keep people in bubble wrap to prevent them from making mistakes, the business will not be able to grow.

[14:50] Kristen defines “empowering” as trusting in someone before they’ve proven it. It’s about believing in someone’s potential.

[17:50] Kristen puts the responsibility on her staff to own their own performance plan and to take accountability for their actions.

[22:05] Kristen focuses on building leaders not simply hiring people to join a cleaning company. 

[25:20] Companies are hesitant to invest in their low-level employees if they know they’re just going to move on. Kristen invests in her employees because she cares about the people.

[25:50] People do so much for our organizations, so it’s only natural we give back and.

[26:50] Kristen used to be so focused on retention, but has since shifted her focus to investing in people.

[28:25] Empathy is really about hearing people, seeing them, and validating their feelings.

[30:35] The pandemic has been an excellent time for Kristen to reflect on her priorities as she now feels like she was on autopilot before.

[34:00] Kristen always ends her day on a daily reflection, so that she can both learn from the good and the bad that happened throughout her day.

[38:30] Listener challenge: When we look back on this time, what do you want to say about it? Live a proud life.


The Leadership Podcast is sponsored by W.S. Darley & Company.  

Founded in 1908, Darley remains a family owned and operated business, providing the highest quality equipment solutions to our country’s warfighters and firefighters.  

Learn more at darley.com and darleydefense.com


Quotable Quotes

“If you’re always trying to be perfect, you’re never going to take risks.” Share on X “In our effort to appear perfect, we lose a lot of trust.” Share on X “When human beings are in the equation, there’s probably some screwing up that’s going to happen.” Share on X

Resources Mentioned

  • Website: Kristenhadeed.com
  • Kristen on LinkedIn
  • Kristen on Facebook
  • Kristen on Instagram
  • Kristen on Twitter
Kristen Hadeed

These are the books mentioned in our discussion with Kristen.

Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong

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Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong
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Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong

Why is Everyone Smiling? The Secret Behind Passion, Productivity, and Profit

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Why is Everyone Smiling? The Secret Behind Passion, Productivity, and Profit
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Why is Everyone Smiling? The Secret Behind Passion, Productivity, and Profit

The Dream Manager: Acheive Results Beyond Your Dreams by Helping Your Employees Fulfill Theirs

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Buy from Amazon
The Dream Manager: Acheive Results Beyond Your Dreams by Helping Your Employees Fulfill Theirs
Buy now!
The Dream Manager: Acheive Results Beyond Your Dreams by Helping Your Employees Fulfill Theirs

The Now Habit: A Strategic Program for Overcoming Procrastination and Enjoying Guilt-Free Play

Buy This Book Online
Buy from Amazon
The Now Habit: A Strategic Program for Overcoming Procrastination and Enjoying Guilt-Free Play
Buy now!
The Now Habit: A Strategic Program for Overcoming Procrastination and Enjoying Guilt-Free Play

The Leadership Podcast is proud to announce a new initiative with thoughtLEADERS to provide very short podcasts called “chalk talks.” They’re “bitesize” hacks on common (but challenging) leadership issues. Interested in learning more? 

You can only access the Chalk Talks by subscribing to our newsletter at The Leadership Podcast.

Beyond the Uniform offers over 300 free episodes to help military Veterans succeed in their civilian career. This includes overviews of potential career paths, deep dives on necessary skills to succeed, and reviews of other free services that support the military Veteran community. You can find more info at BeyondTheUniform.org.

Filed Under: Podcast Tagged With: culture, entrepreneur, entrepreneurial, leadership, mistakes, vulnerability

TLP230: Lean Out
TLP232: Fall In Love With The Problem

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