Permission to Screw Up

1. Embrace failure as a powerful learning tool

"Fail and figure it out yourself"

Learning through experience. Allowing employees to make mistakes and solve problems independently fosters growth and self-reliance. This approach builds confidence and problem-solving skills, ultimately creating a stronger, more capable team.

Creating a safe environment. Establish a culture where failure is seen as an opportunity for growth rather than a reason for punishment. This encourages innovation and risk-taking, leading to better solutions and a more resilient organization.

Leading by example. As a leader, share your own failures and lessons learned. This vulnerability builds trust and shows that mistakes are a natural part of the learning process, encouraging others to be open about their challenges and seek help when needed.

2. Build a culture of trust and empowerment

"I trust you, and I believe you are capable."

Delegating responsibility. Empower employees by giving them ownership of tasks and projects. This demonstrates trust in their abilities and encourages them to take initiative and think creatively.

Providing support. While empowering employees, ensure they have the necessary resources and guidance to succeed. Offer mentorship and be available for questions or concerns without micromanaging.

Recognizing achievements. Celebrate successes, both big and small, to reinforce the value of employee contributions and build confidence in their abilities. This positive reinforcement encourages continued growth and engagement.

3. Hire for cultural fit, not just skills

"A company's culture isn't defined by its perks at all. It's defined by its people."

Values-based hiring. Focus on finding candidates whose personal values align with the company's core values. This ensures a cohesive team that works well together and maintains the desired company culture.

Looking beyond qualifications. While skills are important, prioritize character traits such as adaptability, willingness to learn, and teamwork. These qualities often contribute more to long-term success than technical skills alone.

Involving the team. Include current employees in the hiring process to assess cultural fit and gain diverse perspectives. This also helps new hires integrate more smoothly into the existing team dynamic.

4. Foster open communication and vulnerability

"Being vulnerable and open and allowing people to feel at work isn't about crying with someone. It's about understanding what they're going through so you can work better together."

Creating psychological safety. Establish an environment where employees feel comfortable sharing their thoughts, concerns, and personal challenges without fear of judgment or repercussion.

Leading with transparency. As a leader, be open about company challenges, decisions, and your own struggles. This encourages others to do the same and builds trust within the organization.

Encouraging feedback. Implement regular check-ins and feedback sessions to ensure open lines of communication. Use tools like the FBI (Feeling, Behavior, Impact) method to provide constructive feedback and recognition effectively.

5. Balance praise with constructive feedback

"To learn, grow, and be successful, people need feedback—the good, the bad, and the ugly."

Providing timely feedback. Address both positive and negative behaviors promptly to reinforce good habits and correct issues before they become ingrained.

Using specific examples. When giving feedback, use concrete examples to illustrate your points. This helps the recipient understand exactly what they did well or where they need improvement.

Maintaining a positive ratio. Aim for a balance of positive and constructive feedback, with more emphasis on recognition. This helps maintain motivation while still addressing areas for growth.

6. Invest in relationships beyond the workplace

"When we bring our humanity to work, so do our people."

Building personal connections. Take time to get to know employees on a personal level, understanding their interests, challenges, and aspirations outside of work.

Creating shared experiences. Organize team-building activities and retreats that allow employees to connect in a more relaxed setting, fostering stronger relationships and trust.

Showing empathy. Be understanding of personal circumstances that may affect work performance, and offer support when appropriate. This demonstrates genuine care for employees as individuals, not just workers.

7. Know when to let go for growth

"Turns out losing her job at Student Maid was the best thing to ever happen to her."

Recognizing limitations. Acknowledge when an employee's growth is limited within the current role or organization, and be willing to have difficult conversations about their future.

Facilitating transitions. When it's time for an employee to move on, support their transition by offering resources, references, or connections to other opportunities that may be a better fit.

Learning from departures. Use employee departures as opportunities to reflect on the organization's strengths and weaknesses, and implement changes to improve retention and employee satisfaction.

8. Lead with empathy and compassion

"We can't expect people to just leave their feelings, worries, and hardships at the door and then pick them up again when they leave work."

Understanding individual circumstances. Take the time to learn about employees' personal challenges and how they may impact their work performance.

Offering support. Provide resources and flexibility to help employees navigate difficult times, such as flexible work arrangements or access to counseling services.

Adjusting expectations. Be willing to temporarily adjust workloads or deadlines when employees are facing significant personal challenges, demonstrating that their well-being is a priority.

9. Create a framework for accountability and fairness

"The Line is based on one overarching philosophy: If someone's good qualities outweigh the bad, we will fight for that person."

Establishing clear expectations. Develop and communicate guidelines for behavior and performance that align with company values and goals.

Implementing consistent consequences. Create a system for addressing violations of company policies or expectations that is fair and consistently applied across the organization.

Allowing for context. While maintaining consistency, consider individual circumstances and intentions when making decisions about disciplinary actions or second chances.

10. Adapt leadership style as the company grows

"I had to think about our people and our culture and what something like move-out season did to both."

Recognizing changing needs. As the company expands, be willing to reassess and adjust leadership approaches, policies, and structures to accommodate growth.

Balancing scalability and culture. Find ways to maintain the core values and culture that made the company successful while implementing necessary changes to support growth.

Empowering others. Delegate more responsibility to trusted team members as the organization grows, allowing for more efficient decision-making and freeing up time for strategic planning.

Last updated: August 7, 2024