Leading by Screwing Up - Practical Lessons from Permission to Screw Up

Kristen Hadeed’s Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong is basically a long case study of a leader learning “on production.” No gloss, no heroic founder myth: just a college student who accidentally starts a cleaning company, has 45 employees walk out on her at once, and decides to turn that humiliation into an obsession with leadership.

What makes the book valuable is not just the stories, but the principles beneath them: how to build a culture where people are safe to fail and expected to grow.

Below I’ll walk through the core principles of the book and how to apply them in a practical, educational way for your own leadership.

1. Failure Is Your Leadership Classroom

The central message of the book is simple: you don’t become a better leader by avoiding mistakes, but by using them deliberately.

Hadeed frames her journey as a string of “screw-ups” that forced her to learn: bad hiring decisions, avoiding hard conversations, letting culture drift, overcontrolling, undercommunicating. Each failure becomes a feedback loop: what did I miss, what did this reveal about our system, and how do we design things differently next time?

This is echoed in later summaries of the book: failure is positioned as a learning tool, not a personal verdict.

How to apply it

• Name failures explicitly as learning events.
  Run short, blame-free debriefs: “What happened? What did we miss? What will we change in the system?”
• Separate the person from the mistake.
  Talk about the behavior and the process, not someone’s worth or identity.
• Build “learning margin” into your work.
  Don’t run everything at 100% capacity. If no one has space to experiment, no one has space to learn.

The shift is: from “don’t mess up” to “mess up fast, safely, and intelligently.”

2. Leadership Is Learned, Not Born

Hadeed calls herself an “accidental entrepreneur.” She didn’t intend to build a company; she just wanted money for jeans, posted a cleaning ad on Craigslist, and things snowballed.

Her point: she had no natural leadership credentials. She learned through:

• reading obsessively about leadership and culture
• finding mentors (often outside her industry)
• testing ideas in the messy reality of Student Maid

Leadership, in her view, is a skill stack: you build it through reps, reflection, and feedback—not through titles.

How to apply it

• Treat leadership development like a craft, not a reward.
  Schedule time to learn (books, podcasts, mentors) the same way you schedule time for operations.
• Explicitly tell your team “I am learning too.”
  This reduces pressure to be perfect and opens the door for others to grow with you.
• Run small leadership experiments.
  For example: “For the next two weeks, I’ll start every meeting with a check-in and see what changes.”

3. Trust and Psychological Safety Come First

A recurring theme is that trust is the foundation of everything else. Hadeed is explicit: vulnerability and psychological safety are not “soft” topics; they are prerequisites for performance and retention.

Practically, she does things like:

• regular “personal check-ins” at the start of meetings
• sharing her own mistakes and doubts openly
• making it safe to ask for help or admit “I don’t know”

This is how Student Maid—despite being in a low-prestige, high-turnover industry—became known for strong retention and loyalty. People stayed because they felt seen, safe, and growing, not because cleaning toilets was glamorous.

How to apply it

• Add a 2–3 minute “human check-in” to meetings.
  “What’s one thing on your mind—work or life?” It sounds small; it compounds massively over time.
• Model vulnerability first.
  Leaders go first: “I dropped the ball on X. Here’s what I’m changing.”
• Respond to bad news with curiosity, not blame.
  First questions: “What happened? What did we learn?” Only then: “What guardrails do we need?”

Trust is not a value on a poster; it’s the accumulated memory of how you reacted when things went wrong.

4. Empower People with Real Responsibility

One of the early lessons others distilled from the book is:

“Trust people with enormous responsibilities, allow room for mess-ups, then give them the chance to fix their mistakes so they can learn from them.”

In other words, ownership before perfection.

Hadeed shows that when you give people meaningful responsibility—owning clients, training others, leading teams—they rise to it if they know they’re allowed to learn in public. The mass walkout becomes a turning point where she realizes she must stop trying to control everything and start building leaders around her.

How to apply it

• Delegate outcomes, not tasks.
  Instead of “Do A, B, C,” try “Own this client experience end-to-end; I’m here as a safety net.”
• Let people feel the consequences—safely.
  If someone messes up, your first move should be: “How do you propose we fix this?”
• Design “stretch roles” on purpose.
  Create opportunities where people can lead a project, run a meeting, or mentor someone—even if they are still learning.

Empowerment is not “hands-off management”; it’s high support + high expectations.

5. Feedback that Cares: From Cheerleader to Truth-Teller

In the beginning, Hadeed saw herself as the “chief cheerleader.” She focused on keeping everyone happy and avoided hard conversations. She later realizes this is not kindness; it’s negligence.

She evolves toward a style that balances encouragement with honest, specific feedback—and one of her favorite tools is the FBI method:

• F – Feeling: how you felt
• B – Behavior: what the other person did
• I – Impact: what that behavior caused

Example (paraphrased from her writing):

“I felt disappointed when you arrived thirty minutes late to the meeting, and the impact is I’m not sure I can rely on you.”

Why it works: it’s specific, it’s about observable behavior, and it’s rooted in your experience, not an attack on the other person’s character.

How to apply it

• Use the FBI formula for tough feedback.
  “I felt [feeling] when you [behavior], and the impact is [impact].”
• Give “keeps” and “considers.”
  • Keeps: what they should continue doing
  • Considers: what they might do differently next time
• Ask for feedback in return.
  “What’s one thing I did that helped, and one thing I could have done better?”

You move from “being nice” to being genuinely helpful.

6. Hire, Fire, and Promote Based on Values

Another big pattern in the book: the people decisions that hurt most were rarely about skill—they were about values and culture.

Later summaries of the book highlight:

• hiring for cultural fit, not just skills
• trusting your intuition in hiring decisions
• knowing when to let people go so both they and the company can grow

Hadeed learns to treat Student Maid as a leadership development environment. If someone doesn’t align with the culture of trust, growth, and ownership, keeping them—no matter how talented—undermines everything.

How to apply it

• Write down 3–5 non-negotiable behaviors.
  For example: “owns mistakes,” “respects feedback,” “treats clients with dignity.”
• Hire for behavior, not just résumé.
  Ask for concrete stories that demonstrate your values.
• Be honest when it’s not a fit.
  Letting someone go kindly can be more respectful than keeping them in a role where they and the team suffer.

“Permission to screw up” does not mean “no standards”; it means “high standards, human process.”

7. Relationships Are the Real Retention Strategy

The cleaning industry typically has a 75% turnover rate. Hadeed’s response is not to raise wages endlessly or micromanage; it’s to give people a reason to show up that goes beyond the task.

She invests in:

• personal check-ins
• development opportunities
• building a sense of belonging and shared growth

That’s how Student Maid becomes known for unusual retention in an industry where employees usually churn fast.

How to apply it

• Make growth part of the deal.
  “If you work here, you’ll learn X, Y, Z about leadership, not just task A.”
• Protect time for human connection.
  Short rituals (check-ins, shout-outs, 1:1s) are more powerful than rare “big events.”
• Know your people beyond their roles.
  Career goals, personal stresses, what excites them—these are retention levers.

People stay where they feel they’re becoming someone better, not just doing something useful.

8. Let Go to Grow

As Student Maid grows, Hadeed bumps into a classic founder problem: her old leadership style doesn’t scale. She has to:

• delegate more
• trust other leaders
• accept that some people will move on
• adapt her leadership as the company changes

The book emphasizes that leadership is dynamic. The behaviors that worked with a small student crew don’t work with a larger organization and senior staff. She has to keep reinventing herself.

How to apply it

• Regularly ask: “What version of me does this stage need?”
  Starter, builder, scaler, coach—these are different hats.
• Create space for new leaders.
  Give others scope, authority, and visibility.
• Release people with gratitude when their season ends.
  Not every great team member is meant to stay forever; the way you handle exits shapes your culture.

Letting go—of control, of certain people, of old habits—is part of honoring growth.

9. The Tension Inside “Permission to Screw Up”

There’s an important tension in the book’s message:

• If you over-index on “permission to screw up,” you risk complacency.
• If you under-index on it, you create fear, secrecy, and stagnation.

Hadeed navigates this by pairing grace with structure:

• culture of psychological safety and vulnerability
• plus clear expectations, fair consequences, and accountability frameworks

The mature version of her philosophy is not “anything goes”; it’s:

“You’re allowed to screw up. You’re also responsible for learning from it and helping us build something stronger because of it.”

That’s a powerful stance for any team.

10. Turning the Book into Your Own Practice

If you want to turn the book’s ideas into action, you can think in a simple sequence:

1. Define your stance on mistakes.

   • Write a one-sentence “failure philosophy” for your team:
     “We don’t hide mistakes; we use them to redesign how we work.”

2. Install one safety ritual.

   • Personal check-ins, “oops of the week,” or a simple rule: “Bad news travels fast and is rewarded.”

3. Teach the FBI feedback method.

   • Run a short workshop: practice “Feeling–Behavior–Impact” in pairs for real scenarios.

4. Delegate one real, slightly scary responsibility.

   • Let someone else lead a project, call a client, or run a critical meeting—with your support.

5. Review and refine.

   • After 4–6 weeks, ask: “What changed? Where did we screw up? What did we learn about our leadership?”

Final Thought

Permission to Screw Up is not a permission slip to be sloppy. It’s an invitation to lead in a more human, learning-centered way: to admit that you don’t know everything, that your team won’t get everything right, and that this is precisely how you all become better.

If you treat every misstep as data, protect your people with psychological safety, and hold them (and yourself) to clear, fair standards, you’ll be living the core principles of Hadeed’s book—whether you run a student cleaning company or a high-scale tech product.