Permission to screw up: building a culture of failure and growth

Executive overview

Most leaders know failure is valuable, but default to hiding mistakes. Admitting errors publicly is the fastest way to build trust and give others permission to do the same.

Kristen Hadeed built StudentMaid — a cleaning company employing college students — into a leadership development program by modelling vulnerability, investing in soft skills, and redefining success on her own terms.

The moment that changed everything

• Hired 60 students for a large apartment-cleaning contract with no leadership experience
• Sat in the air-conditioned clubhouse while students did gruelling work — assumed that was what a boss did
• 45 of 60 quit on the spot, day two
• Won them back by admitting she had no idea what she was doing
• That moment triggered an obsession with leadership and set the direction of the company

Creating a culture where failure is safe

• Leaders who say "I messed up — can we talk about it?" give everyone else permission to do the same
• People model behaviour they see; vulnerability from the top unlocks vulnerability below
• Admitting weakness doesn't make people feel unsafe — hiding problems does
• Silence breeds rumours; transparency about challenges builds trust
• The goal shifts from "keep everyone" to "prepare people to succeed anywhere"

Building a leadership development program inside a cleaning company

• Started organically: sharing books, discussing lessons from difficult situations
• Workshops cover soft skills — listening, empathy, networking, feedback, relationship-building — not cleaning
• Low overhead: a quarterly gathering of 8–10 people sharing wins, challenges, and lessons is enough
• The program became a recruitment draw; people referred friends specifically for the leadership development
• Key insight: overcomplicated it at first by chasing perfect curriculum; the best content came from their own experiences

Leading and teaching the next generation

• Soft skills are underdeveloped across generations, not just millennials — phone use at dinner spans all ages
• Leaders must stop assuming people know how to give feedback, communicate, or handle conflict
• Rule at StudentMaid: no texting about anything that matters — important conversations must be face to face
• Bring people into the conversation: ask what they fear, what they want, how they want to feel at work
• Don't generalise by generation; everyone wants to feel valued and significant

Redefining success on your own terms

• Early goal was to franchise StudentMaid into every college town — adopted because others said she should
• Writing the book prompted a reassessment; closed a location to focus on systematising the leadership curriculum
• Resisting external pressure to grow in a direction that didn't fit required deliberate courage
• Success is now: students graduate, carry the skills elsewhere, and make a positive impact