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

A pivotal moment for the author, the owner of a cleaning service called Student Maids, was when 45 of her employees walked out on her at once. In retrospect, she said it was this lesson that led her to become a better leader. In this book, she offers a candid account of her own screw-ups, and how she learned to give others permission to screw up.

Scroll down to see my video interview with the author, Kristen Hadeed.

Key points from the book:

Empower employees to solve problems. When employees continuously come to you with problems, ask for them to come up with their own solutions. If they don’t have any, ask them to think about it and get back to you. Eventually, employees will start to focus more on solutions than problems. If it’s not going to burn the place down, let them try their own ideas.

A leader guides and supports the team, not direct their actions, make their decisions and solve their problems for them.

Clarity must be established on the front end for employees to succeed in this environment. Employees must be clear on expectations and responsibilities.

Leaders who micromanage or always jump in to fix problems (even when well-intended) will never see the people on their team grow.

Giving people room to make mistakes doesn’t mean excusing bad behavior, ignoring poor decisions, or avoiding the feedback they need to hear. Teaching people to problem-solve on their own is important, but so is helping them grow from their mistakes. If they don’t realize they’re doing something wrong to begin with, someone has to tell them. If you’re a leader, that’s YOUR job!

Meet frequently with employees to go over two things: (1) where they need to improve and (2) what they are doing well.

While empowering employees to solve problems led to fewer calls from Student Maid employees about problems, it initially created a new set of problems. Customer complaints increased! With this came more frequent communication and timely feedback with employees. Most took it well, some didn’t. But over time, most employees came to realize these candid conversations were not intended to highlight weaknesses, but rather help them succeed.

A survey of millennials featured in a 2015 Forbes article reported that almost 90 percent said they would feel more confident if they received frequent or ongoing feedback at work. And a 2014 survey published in the Harvard Business Review showed that a whopping 72 percent of employees—from all generations—said they thought their careers would benefit from more corrective feedback as well. So, feedback is good!

Leaders need regular, constructive feedback also. Consider a tool like anonymous surveys or adopting the vulnerability to solicit and accept constructive feedback from your team.

F.B.I. (Feeling – Behavior – Impact). If you want to give truly effective feedback, you need to communicate three things: the way you feel, the specific behavior that made you feel that way, and the impact that behavior has—whether it’s on you, the company, your relationship with that person, or anything else.

Example of an FBI statement: “I feel disappointed that you were thirty minutes late to the meeting yesterday afternoon, and now I’m unsure if I can rely on you in the future.”

Research varies on the right balance of praise vs. critiquing, but there is a general agreement that there should be a little more clapping than critiquing.

To learn, grow, and be successful, people need feedback—the good, the bad, and the ugly. And to thrive, a company needs to provide its people with a system for communicating that feedback effectively at all levels.

The author is a strong advocate for reading to become a better leader. This may sound like a “Duh” observation, but on a personal note I find so few people in leadership positions invest time in learning and personal development.

What to do with a high performer with an ongoing performance issue (ie. constantly late)? Come up with a plan to improve the behavior that you both agree on. Commit to helping this employee improve and ask for his/her commitment in return. If improvement results, problem solved. If it doesn’t, problem solved. Time to let the employee go, but at least you know you made a strong effort.

How do you decide when to bend the rules or give someone a second chance, and when not to? The author called a team meeting and showed them a long piece of grey duct tape on the floor. She said both leadership and employees will stand at the line, giving and accepting feedback and growing from it. Show up every day wanting to invest in yourself. Try your very best and care about your team.

… “And if we see all that, we promise to let you screw up. We promise to give you the chance to improve when you mess up. That doesn’t mean you get unlimited chances; it means that when you stumble, we will help you make an improvement plan. When you stand at the Line, we promise to be flexible with our policies, to accommodate you, and to be fiercely loyal to you like you are fiercely loyal to us.”

…”We can’t make you stand there. We can’t help you if you aren’t willing to help yourself. We can’t make you care. We can’t make you try. We can’t control your actions. We can’t keep making self-improvement plan after self-improvement plan for you. If we don’t see you at the Line with us, we’re going to ask you to leave.”

Interview with author Kristen Hadeed

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