What was the turning point that transformed a young entrepreneur's rigid hiring checklist into a values-driven recruitment process? How did a cleaning company called 'Student Maid' balance growth and company culture, learning from their mistakes and celebrating their triumphs? Interested in how to handle goodbyes, support dreams, and grow from failures in leadership? Dive into the ups and downs of a leadership journey that began with a disastrous first cleaning job and evolved into a thriving business, built on trust, vulnerability, and empathy.

Permission to Screw Up

On a blistering summer day in Florida, Kristen Hadeed, the author, lounged in an air-conditioned clubhouse, scrolling through Facebook and texting friends. Meanwhile, just outside, sixty college students she had hired were scrubbing filthy apartments in sweltering heat. She didn't even think to check on them, assuming they knew what they signed up for. That was her first mistake.

Hours later, as Kristen was about to enjoy her Caesar salad, the clubhouse doors swung open, and forty-five of her employees stormed in, sweaty and scowling. "We quit," one of them declared, and they all marched out, leaving Kristen stunned and alone. That humiliating moment sparked her quest to become a better leader.

Starting a cleaning business in college wasn't Kristen's original plan. She was studying finance at the University of Florida, dreaming of Wall Street, but she needed quick cash for a pair of $99 jeans. So, she advertised house cleaning services on Craigslist. Her first job was a disaster—she spent seven hours cleaning a 4,000 square-foot house with just glass cleaner and a sponge. But the client was impressed enough to hire her weekly, and soon, word spread.

As demand grew, Kristen hired her first employee, Cacee. They faced some bizarre situations, like the petting zoo house with animal poop everywhere, but business boomed. Then came the opportunity of a lifetime: cleaning hundreds of apartments in a three-week span. She hired sixty students and thought she had everything under control—until forty-five of them walked out.

Desperate, Kristen gathered the remaining fifteen employees and called the quitters, begging them to meet at her house. With promises of early paychecks and pizza, they showed up. She apologized, admitting she had no clue what she was doing, and promised to clean alongside them. Surprisingly, they gave her another chance.

For the next two weeks, Kristen cleaned with her team, earning their respect and finishing the job early. The apartment managers were impressed and rehired her for the next year. She realized she wanted to continue this business, even if it meant giving up her Wall Street dream.

Over the years, her company has employed hundreds of students. Despite the challenges—low pay, grueling work, and high turnover—they've thrived. Their secret? Happy employees make happy customers. Many of her students stay long-term, turning down higher-paying jobs because they believe in what she does.

This journey has been filled with mistakes, but each failure taught Kristen valuable lessons. This book is about those lessons and how they shaped her into the leader she is today. It's for anyone who wants to improve as a leader, no matter the industry or challenges. Kristen hopes her story inspires you to persevere, even on the toughest days, and to see mistakes as opportunities for growth.

Can a Failed Leader Turn Into a Successful Entrepreneur?

Kristen woke up to her phone ringing at 2 A.M. One of her student employees was on the line, asking if he’d gotten a raise because his account showed a couple thousand dollars instead of a few hundred. Groggy, Kristen checked their bank’s website and realized they were tens of thousands of dollars short. Their HR intern, Lizzie, had mistakenly entered total amounts into the total hours column, overpaying 27 students by about $40,000.

Kristen called Lizzie, who was equally frantic. Together, they texted all the students to ask them not to spend the money and contacted their payroll rep, who promised to reverse the transactions within seven days. Miraculously, they got all their money back. Lizzie, despite the mess-up, handled the situation well and never made a payroll error again.

This incident taught Kristen a valuable lesson on leadership: trust people with big responsibilities, allow room for mistakes, and let them fix their errors. It reminded her of her dad’s tough-love approach during her high school calculus struggles and her early business missteps, like when she started her cleaning company, Student Maid. Her dad always pushed her to solve her own problems, which built her confidence and problem-solving skills.

Years later, as Student Maid grew, Kristen found herself overwhelmed with constant calls from employees asking basic questions. She realized she needed to empower them to solve problems independently. When she hired Erin and Abby to help run the business, she initially micromanaged them with detailed to-do lists. But a turning point came when she left for a short trip, and they had to handle a crisis without her. They managed brilliantly, proving they could solve problems on their own.

From then on, Kristen stepped back and let her team take more ownership. This shift in leadership style fostered independence and confidence among her employees. Stories like Monique’s, who turned down a prestigious job to stay with Student Maid because of the trust Kristen placed in her early on, and Lizzie’s, who used her learning experience to succeed in her career, showed Kristen the power of empowering others.

Trusting people with responsibilities, supporting them through mistakes, and encouraging self-reliance can transform a team. It’s about making them feel capable and confident, just as her dad did for her.

Empowering Leadership: Transforming Teams through Trust and Independence

Kristen stormed into her office, fuming about one of the student, Courtney's latest antics. This time, Courtney was caught playing "Mary Had a Little Lamb" on a client's off-limits antique piano. Kristen was determined to confront her, but the moment Courtney walked in with her sweet, misleading smile, Kristen caved and ended up helping her carry supplies to her car instead.

Kristen's leadership style has always leaned towards cheerleading rather than confrontation. She recalls turning around Bill's demotivation by giving him an enthusiastic pep talk that even got him dancing while cleaning a toilet. This knack for boosting morale was crucial during the summer of The 45 when Kristen nearly lost her entire team. She cheered them on, and they stuck around, but she knew deep down that she was avoiding necessary tough conversations.

One infamous incident was with Courtney and her "BLOW ME" car window message. Kristen tried to address it via email, but Courtney quit shortly after, leaving Kristen to realize her avoidance of conflict was unsustainable. Her mentor, Eva, urged Kristen to implement regular evaluations, which terrified her. She eventually gave in, alternating between praise and constructive feedback using what she dubbed the "shit sandwich" method.

Despite initial reluctance, these evaluations worked, but not without causing some tears and complaints. The feedback became essential in maintaining standards and morale. Yet, as Student Maid grew, Kristen's absence from daily cheerleading duties led to a dip in team spirit. Enter Rich Blaser, who introduced Kristen to the concept of combating job misery by ensuring employees felt measured, recognized, and understood their work's relevance.

Inspired, they created a survey system for client feedback and a "WOW Wall" to celebrate perfect scores. But it led to new issues; top performers didn't want to work with those who dragged them down. This internal drama made Kristen realize they needed a better system for peer feedback.

They introduced 360-degree reviews, allowing everyone to evaluate each other anonymously. The results were eye-opening, especially for Kristen, as she learned she was perceived as "too nice." This feedback pushed her to adopt a more balanced approach.

Years later, Kristen attended a workshop by Barry-Wehmiller that revolutionized her feedback method with the FBI (Feeling-Behavior-Impact) approach. This method of giving and receiving feedback has transformed their company culture, making it more transparent and supportive.

FBIs have replaced the sandwich method, empowering their team to handle conflicts directly and positively, even extending this approach beyond work. It’s not a perfect balance, but it’s a step towards creating a thriving, appreciative work environment.

To sum up, effective leadership requires both cheerleading and honest feedback. While it’s tempting to avoid conflict, addressing issues head-on can lead to growth and a stronger team. So, next time Kristen faces a Courtney or a Bill, she'll remember: a balanced approach of appreciation and constructive feedback can work wonders.

Can a Balanced Approach of Cheerleading and Honest Feedback Revolutionize Your Leadership Style?

Kristen remembers the day Jade walked into her office for an interview. Jade was early, confident, and well-researched—everything Kristen could hope for in a candidate. Jade aced every question, even Kristen's quirky one about her spirit animal. Jade was perfect until she revealed she didn't have a car, a dealbreaker for Kristen's cleaning company, Student Maid. Regrettably, Kristen turned her down because of this rigid rule.

That night, Kristen couldn't sleep, haunted by the decision. Jade had walked miles to get to the interview. She had shown dedication and integrity—qualities money can't buy. The next morning, Kristen decided to hire her, but Jade had already accepted another offer, showcasing her loyalty and commitment.

This experience was a wake-up call for Kristen. Her hiring checklist, including requirements like being a student with a 3.5 GPA and having a car, was too rigid. Kristen knew she had to adapt. A few months later, she met Andrew. He wasn't a student, but he was eager and reliable. Trusting her gut, Kristen hired him, and he became a stellar team member.

Inspired by Tony Hsieh's book "Delivering Happiness," Kristen realized that company culture is about people, not perks. To preserve Student Maid's culture, Kristen created their own set of core values, their "Commandments," based on input from her team. These values became their new hiring criteria, ensuring they selected people who truly fit their culture.

Things weren’t always smooth for Kristen. One time, she ignored a team member, Morgan, who reported a colleague stealing time, fearing confrontation. Months later, the same colleague committed another offense, costing the company money and trust. Morgan lost respect for Kristen, and she learned the hard way that protecting their culture means taking immediate action against those who violate it.

Move-out season posed another challenge for Kristen. They hired hundreds of temporary workers quickly, sacrificing their values for profit. This led to a toxic environment, demoralizing their best team members. Finally, they decided to scale back, prioritizing their culture over profit, and Student Maid thrived.

Jade and Andrew taught Kristen that flexibility and gut feelings often lead to the best hires, while Tony Hsieh showed her that values should be the ultimate dealbreaker. Balancing growth and culture is tough, but it’s essential for long-term success.

Redefining Hiring Practices: Lessons from Student Maid's Journey Towards a Values-Driven Culture

Imagine a raucous college party, music blaring, red Solo cups everywhere, and a girl doing an upside-down keg stand. That girl was Kristen. It was a wild scene, one she wouldn’t exactly call a proud moment. But it happened before Kristen learned the true essence of leadership and team building.

Back then, Kristen thought bonding with her team at Student Maid meant partying together. She was just out of college, and blurring the lines between boss and friend seemed harmless. But as time went on, Kristen realized there was a deeper, more meaningful way to build relationships: through trust, vulnerability, and empathy.

A turning point came when her mentor, Rich, introduced Kristen to a group where they shared their deepest fears and challenges. Initially, Kristen held back, but seeing Josh, a tough-as-nails entrepreneur, openly share his struggles gave her the courage to do the same. This vulnerability created a supportive environment that profoundly impacted Kristen.

Inspired, Kristen started bonding deeply with her colleague Abby. They went on retreats, shared personal stories, and built a strong partnership. This closeness made them better leaders and helped them support their team more effectively.

When they expanded Student Maid, Kristen knew they needed a leader who embodied their values. Rachel, a loyal team member, stepped up to the challenge despite her lack of formal business training. With support and training, she thrived, proving that passion and dedication often outweigh credentials.

Their leadership team also grew closer through annual retreats and monthly workshops. They took personality assessments, shared personal stories, and learned to appreciate each other's strengths and quirks. Kristen's own vulnerability, like sharing a childhood story about her dad's job loss, helped create an environment where others felt safe to open up.

One of the most touching examples of the power of these bonds was Meghan, a student who formed a deep connection with an elderly client, Ms. Byron. When Ms. Byron was on her deathbed, her last wish was to see Meghan, highlighting the profound impact of genuine relationships.

Ultimately, building a team isn’t about wild parties; it’s about creating a supportive, empathetic environment where people feel valued and understood. It’s about being there for each other, both in good times and bad, and fostering connections that go beyond the workplace. That’s the kind of trust that truly makes a team strong.

Can Vulnerability and Empathy Transform You Into a Better Leader?

Kristen was in Michigan for a long-awaited vacation when her phone buzzed incessantly during Sunday dinner. She finally answered to hear Sam, Josh's business partner, sobbing as he delivered the unbearable news: Josh had passed away in his sleep. 

Josh, only 28, was full of life and energy. The next few hours were a blur for Kristen as she informed friends, colleagues, and their software development team. Josh was an honorary member of their Student Maid family, and the shock and grief were overwhelming.

The days leading up to Josh's funeral were dark. Rich, a close friend, suggested a group meeting to cope. They shared how Josh had impacted each of them, feeling his absence acutely. Josh’s death was sudden and mysterious, but knowing he lived fully brought some comfort. Kristen vowed to make her time count, just as Josh had.

Not all goodbyes are tragic. Some are necessary for growth. Kayla, a resilient member of their team, joined during a busy move-out season. Despite her impeccable cleaning skills, she was perpetually late. Kristen learned of her troubled background and wanted to support her, but Abby, Kristen's partner, insisted her tardiness was unfair to others. Their arguments strained their relationship, but Kristen continued to believe in Kayla.

Marty Schaffel, a mentor, shared a story about giving a second chance to his employee. Inspired, Kristen devised a plan to help Kayla improve her punctuality. For thirty days, Kayla had to call Kristen an hour before her shift. She succeeded, but on day 31, she was late. Kristen broke her promise to Abby and gave Kayla another chance, which only worsened the situation. Eventually, Kristen discovered Kayla struggled with substance abuse and let her go, urging her to seek professional help. Kayla later thanked Kristen, saying losing her job was the best thing that ever happened to her.

Abby and Kristen often disagreed on HR issues, but they knew they needed structure. They created a Guidebook, but it felt too rigid. They introduced "the Line," a philosophy where leaders and team members meet halfway, committing to mutual growth and support. If someone’s good qualities outweighed the bad, they’d fight for them. Otherwise, they had to leave. This approach helped them handle goodbyes with compassion and fairness.

Their Pensacola branch faced challenges. Rachel and Sara, incredible team members but not salespeople, struggled to grow the business. Abby suggested hiring a new team, but Kristen couldn’t let them go. Eventually, both Rachel and Sara moved on, and they sold the branch. Their departures taught Kristen the importance of aligning strengths with roles and preparing for transitions.

As their leadership team grew, they encouraged open discussions about future plans. This transparency helped them plan for departures and support each other’s dreams. But the hardest goodbye was yet to come. Abby, Kristen's confidante and partner, decided to leave for a new opportunity. Her departure was a significant loss, but Kristen found peace knowing they gave each other their all.

Investing in people is always worth it. Even when they leave, they leave a positive mark. Leadership isn't just about retention; it’s about helping people grow, whether they stay or move on. Goodbyes are tough, but they’re a part of growth and leadership.

Leadership and Loss: The Power of Goodbyes in Personal and Professional Growth

Kristen's heels clacked down the hallway to the green room, catching her reflection in a giant mirror. She hardly recognized the polished, airbrushed woman staring back at her. The dark circles from a sleepless night worrying about loan payments were miraculously gone, thanks to a professional makeup artist. Her sister, there for moral support, reassured her, "You’ve got this."

Minutes later, Kristen was on a national TV set, blinded by bright studio lights. The famous anchor began, "So, Kristen, you now have a cleaning empire, and it all started with a pair of jeans?" The interview was a blur, but it was a game-changer. Her phone blew up with messages from friends, family, and even former employees, all amazed by her journey.

Despite the accolades—TEDx talk, Forbes feature—the pride was fleeting. The media painted a picture of "rags to riches," making it seem like Kristen always knew what she was doing, never messed up. But that wasn’t the whole story. Her speeches highlighted lessons learned, not the struggles behind them.

It wasn’t until Kristen started writing this book that she realized the importance of sharing her failures. She scrapped her initial chapters, which read like a glossy success story, and began anew. Writing about her mistakes—like spending $1,000 on sushi—was tough but necessary.

Kristen began incorporating these honest anecdotes into her speeches, and it felt liberating. Admitting her imperfections made her feel more alive and connected to her audience. She wished she had been this open from the start, as her filtered stories likely made others feel inadequate.

Leadership is hard, filled with mistakes and setbacks. Kristen's early blunders—like telling people what to do instead of empowering them—taught her valuable lessons. Sharing these experiences is crucial because it makes leadership more relatable and attainable.

Kristen recalls the night 45 employees walked out. She was hurt and confused but called an emergency meeting at her home. Admitting her uncertainty won back her team's trust. They rebuilt Student Maid together, creating a supportive, genuine culture.

Kristen is proud of Student Maid and the journey it took to get there, full of hard times and mistakes. Wherever the future takes her, she knows she'll continue to screw up and learn from it. By sharing her imperfect story, Kristen hopes to inspire others to embrace their own.

Can Sharing Your Failures and Imperfections Make You a More Authentic Leader?

Florida-based entrepreneur, Kristen Hadeed, shares her personal journey of founding her company, Student Maid, and the leadership lessons she learned in the process. The company began as a way for her to earn quick cash during college, but it grew into a business employing hundreds of students.
 
Kristen initially struggled with leadership, which led to a mass walkout of 45 employees. However, she learned from her mistakes, apologized, and worked alongside her team to regain their trust.

Kristen emphasizes the importance of a supportive company culture, learning from failure, and treating employees with respect. She found that giving her employees ownership and responsibilities, and allowing them to learn from their mistakes, fostered independence and improved their problem-solving skills.

She also realized that she needed to balance cheerleading and constructive feedback in her leadership style. Addressing issues directly, she discovered, could lead to team growth and strength. She also learned that company culture is about people, not perks, and that hiring should be based on alignment with company values, rather than rigid checklists.

Kristen also shares the importance of building deep, meaningful relationships with her team through trust, vulnerability, and empathy. She found that dealing with goodbyes and staff departures were part of the leadership journey, and that it was best to handle such scenarios with compassion and fairness.

Finally, Kristen stresses the importance of embracing and learning from failures. She believes in sharing her mistakes openly to make leadership more relatable and attainable. Despite the challenges, she is proud of what Student Maid has become and hopes her story will inspire others to embrace their own imperfect journeys.

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