If you’re tired of reading cliché “fail forward” or “failing is succeeding” stories, you’re in luck. This isn’t one of those.
This is about the mistakes — big ones — that my professional speaker colleague Kristen Hadeed, entrepreneur and CEO of Student Maid, made over her last 10 years in business. She recently gathered these experiences into her book, Permission to Screw Up.
Her book caught my attention because it’s not what you might expect from a CEO and nationally recognized speaker. On the contrary, the book is about screw-ups, setbacks, and the kind of mistakes you think the leaders you idolize would never make.
She turns these not into a story of success and how to achieve it, but rather how to become the kind of leader and build the kind of company you’d always imagined.
Here are three of her biggest mistakes and the lessons she took away.
1. Find confidence in fixing mistakes
In the early days of Student Maid, Hadeed hired an intern to help with HR. From the start, the intern impressed Hadeed by how quickly she picked things up. So, Hadeed decided to give the intern an enormous responsibility: She put her in charge of payroll. The payroll company thought Hadeed was crazy for putting something so important in the hands of an intern, but Hadeed believed in the intern and wanted to give her something significant to put on her resume.
Long story short, the intern messed up big time. The first time she submitted payroll on her own, she mistakenly overpaid 27 people by $40,000.
Typically, you would’ve expected things to go pretty badly for the intern after that. However, Hadeed called the intern and asked if she knew how to fix the problem. She did. Several days later the $40,000 was returned.
Even though the intern had made this terrible mistake, she was also empowered to know she was capable of turning it around. As a result, the intern continued to do payroll until the end of her internship, and she never made the same mistake again. In turn, Hadeed didn’t see trusting the intern as a mistake — rather, she learned to guide good employees up front and give them a chance to fix their own errors.
2. Build trust through sincere apologies
Hadeed was pretty clueless about leadership when she first started Student Maid. Instead of checking in on her team and making sure they had everything they needed, she sat in an air-conditioned office while her people were out in the Florida summer heat scrubbing filthy apartments, many of which had broken AC units. It was no surprise then, that 45 of the 60 people on her team quit.
When they quit, Hadeed panicked. Promising them early paychecks and lots of pizza, she persuaded each of the 45 — plus the 15 who hadn’t quit — to meet for an emergency meeting. At the meeting, Hadeed admitted that she screwed up and asked for their help.
All 45 of her team members came back. This helped to establish a culture of mutual respect. From that point on, Hadeed tried to always admit her failures out loud. The more honest she is, she said, the more her people trust her as their leader — and the safer they feel admitting their own mistakes.
3. Turn to your team for solutions and support
Early on, Hadeed found herself in a situation that no business owner ever wants to experience: they didn’t have enough money in the bank to cover payroll.
It was a situation Hadeed knew she could’ve prevented if she had paid closer attention to the company cash flow and outstanding invoices. It was a dicey situation and she knew that pushing a paycheck back a couple weeks could mean that her staff would not have enough money for food or rent.
When Hadeed got to the office, she explained the situation to the executive team. One of the team members suggested her solution before she did: The entire executive team, including Hadeed, would hold off on getting their paychecks so there would be enough in the account to pay the student employees.
What started as a massive failure quickly turned into remarkable teamwork and sacrifice.
These experiences serve as a reminder that while screwing up can be painful, stressful, and even humiliating, it can also guide us to become better leaders.
In a mid-career slump? Then this is for you.