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Upside-Down Leadership: 30 Days to Lasting ImpactSample

Upside-Down Leadership: 30 Days to Lasting Impact

DAY 14 OF 30

Day 14: Character Flaws vs. Mistakes

The idea of redemption and reconciliation is profound. Forgiving someone who’s made a mistake makes me feel great, especially knowing I’ve likely made the same or worse. But what about those situations where we know it wasn’t just a mistake?

You know what I mean…like when you “accidentally” smacked your brother as a kid. Or as adults, when we cut corners, lie, or manipulate to get ahead.

That’s not an honest mistake. That’s a character flaw.

So today, we’re asking two important leadership questions:

  1. How do you identify character flaws?
  2. How do you address them?

Mistakes vs. Character Flaws

I mentioned “honest mistakes”—those made from good intentions or a lack of knowledge. In leadership terms, these are training deficiencies, and that makes them our problem to help solve.

In Luke 6:40 (NIV), Jesus reminds us:

The student is not above the teacher, but everyone who is fully trained will be like their teacher.

When someone lacks the skills to succeed, they need clear guidance, repetition, and feedback. A training deficiency is an opportunity to teach and develop.

But not all deficiencies are training-related. Sometimes, you’re dealing with something deeper—a character flaw.

Oxford Languages defines “character” as “the mental and moral qualities distinctive to an individual.” Character flaws are the internal traits that consistently lead someone to act against the vision, values, and integrity of the team or family they belong to.

Example: Judas vs. Peter

Let’s look at two key figures in John 13: Judas and Peter.

Judas was called a thief (John 12:6), led by Satan (John 13:2), and ultimately betrayed Jesus. He had proximity to greatness but never surrendered his heart.

Peter, on the other hand, wasn’t perfect either. He was impulsive and prideful and even denied Jesus three times. But his failures stemmed from fear and misplaced loyalty, not rebellion.

The difference? Intent and heart posture.

Jesus continued to invest in Peter because Peter was teachable. He corrected him (Luke 22:61), restored him (John 21:15–17), and empowered him to lead (Acts 2).

With Judas, Jesus still washed his feet, but He did not correct him in the same way. Why? Because Judas’ heart was already hardened.

How to Address Character Flaws

Let’s start with a tough, upside-down truth:
Jesus still washed Judas’ feet.

He knew Judas would betray Him, and He even told the disciples as much (John 13:21). Yet, He still knelt and served him. That’s agape love—unconditional, sacrificial, and undeserved.

Jesus said in Matthew 5:44 (NLT):

But I say, love your enemies! Pray for those who persecute you!

So yes, as leaders, we’re called to love and serve even those who may intentionally hurt us. But love doesn’t mean ignoring misconduct. Accountability is still our responsibility.

Love Enough to Lead: Practical Tips

Customize your training and mentorship.

Each person has different motivations, needs, and learning styles. Meet them where they are, challenge them to grow, and equip them to rise.

Don’t outsource key leadership opportunities.

Don’t pass off every tough conversation to HR, a counselor, or someone else. Yes, use those tools, but don’t let them replace relationships. The best leaders engage personally.

Know when to set boundaries.

When someone’s character is out of alignment with your core values—and they show no signs of change—leadership requires hard decisions. In business, that might mean letting them go. In a family, it means establishing firm boundaries.

Family Application: You Can’t Fire Your Kids, But You Can Still Lead

So, what do we do when our child or family member exhibits a character flaw?

  • Call it out with love. “I love you, but this behavior doesn’t align with who God created you to be.”
  • Connect actions to consequences. Not as punishment, but as natural accountability.
  • Mentor through it. Read Scripture together. Find a mentor or trusted adult to help guide them.
  • Affirm growth. Celebrate character wins just as much as academic or sports success.
  • Stay consistent. Kids learn through repetition and reflection. Let them know the standard doesn’t change with your mood.

Final Thought: Righteous Leaders Restore the Repentant and Hold the Proud Accountable

Jesus restored Peter because Peter was repentant. He didn’t rescue Judas because Judas was resistant. As leaders, we’re not called to control outcomes but to mirror Christ’s love and integrity.

Lead with grace and truth, and when you have to make the hard call, do it in love.

About this Plan

Upside-Down Leadership: 30 Days to Lasting Impact

"Upside-Down Leadership" by author and U.S. Marine Olaolu Ogunyemi is a 30-day Bible plan that challenges conventional leadership. Through Scripture, stories, and practical insights, you'll learn to lead with humility, serve boldly, and leave a lasting legacy at home, work, or wherever you're called. Drawing from his "Lead Last" philosophy, Olaolu's guide will teach you to lead from the bottom up, just like Jesus.

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We would like to thank Parent-Child-Connect for providing this plan. For more information, please visit: https://parent-child-connect.com