Mistakes: The Real MVPs of Leadership
Introduction: Celebrate the “Oh No” Moments
Ask any seasoned leader about their defining victories and you will hear proud stories. Dig a little deeper and they will confess the truth: the big wins rest on a mountain of smaller missteps—missed deadlines, botched rollouts, and hires that looked perfect on paper but fizzled on day three.
Those blunders are not blemishes on your résumé. They are the raw material of growth. When handled with intention, each “Oh no” teaches humility, sparks innovation, and strengthens culture faster than any playbook or seminar ever could.
Three Classic Multifamily Misfires (and the Lessons They Teach)
Swiss-Cheese File Submission
What Went Wrong: A compliance packet you swore was airtight returns with a page of findings.
Leadership Lesson: Build feedback loops that surface errors early, not after audit day.
The “Game-Changing” Software Rollout
What Went Wrong: The new platform technically works, yet adoption stalls and workflows break.
Leadership Lesson: Never launch tech without a change-management plan that includes training, champions, and contingency paths.
The “Perfect” Hire Gone Sideways
What Went Wrong: Stellar résumé, bad cultural fit; team morale dips within weeks.
Leadership Lesson: Hire for values first, skills second. A strong onboarding program reveals misalignments quickly.
Why Mistakes Trump Manuals
They Trigger Real-Time Learning
Manuals outline the ideal. Mistakes expose reality, forcing teams to solve the problem in front of them.They Build Psychological Safety
When leaders own their slip-ups, teams feel safe raising issues early instead of burying them.They Fuel Process Innovation
Each post-mortem becomes a lab. What failed? Why? How do we prevent a repeat? Continuous improvement thrives in this cycle.
Turning Stumbles into Strategy
Normalize Failure in Your Language
Swap blame for curiosity. Try, “What did we learn?” instead of “Who dropped the ball?”Design Systems That Learn
Incident Logs: Track missteps with context, root cause, and corrective action.
After-Action Reviews: Hold a 15-minute debrief within 48 hours of any critical error.
Process Updates: Document and broadcast improvements so every property benefits.
Coach Forward, Not Backward
Focus feedback on the future state: “Next time, here’s how we test file completeness before submission.”Reward Transparent Risk-Taking
Celebrate thoughtful experiments—even those that miss the mark—so innovation keeps flowing.
Building a Culture That “Fails Up”
Lead with Vulnerability
Share a personal misstep at the next all-hands meeting. Model the behavior you expect.Institute Micro-Pivots
Encourage teams to run small-scale pilots before full deployment. Mistakes stay manageable and learning accelerates.Invest in Cross-Training
When leasing agents shadow maintenance or compliance partners sit in on resident service meetings, empathy grows and blind spots shrink.Measure Learning, Not Just Output
Add a KPI that tracks implemented improvements from post-mortems to underscore the value of iteration.
The Bottom Line
Perfection is a mirage. Progress is real—and it is powered by the misfires most leaders try to hide. Embrace those stumbles, extract the lessons, and you will build organizations that:
Adapt faster than competitors
Retain talent that values growth over ego
Deliver sustainable NOI through continuous improvement
The next time something blows up, resist the urge to sweep it under the rug. Instead, call it what it is: a Masterclass in Leadership, courtesy of real life.
Ready to Turn Setbacks into Springboards?
At Weishaar Strategic Partners, we help multifamily leaders create learning cultures where mistakes become assets. Let’s talk about how coaching, process design, and team training can turn your “Oh no” moments into “A-ha” breakthroughs.
About the Author
With more than twenty years in property management and operations, I guide organizations to align people, process, and performance—one lesson learned at a time.
