Craig Groeschel Leadership Podcast

Episode: 5 Times I Was Wrong and What It Taught Me | 10-Year Anniversary Edition
Host: Craig Groeschel
Release Date: January 1, 2026

Overview

In this special 10-Year Anniversary episode, Craig Groeschel reflects on a decade of sharing leadership lessons and personal growth with listeners. He discusses five significant beliefs he held as a leader that proved to be wrong over time, what he learned from these mistakes, and how embracing change and humility can transform both leadership and organizational impact. The episode is filled with candid stories, actionable insights, and compelling questions for self-reflection, all delivered with Craig’s sincere and encouraging tone.

Key Discussion Points & Insights

1. The Willingness to Be Wrong is Essential to Growth

• Old Belief: Great leaders must always be confident and right.
• New Insight: Real growth happens when leaders are willing—often—to admit when they're wrong.
  • Early in his journey, Craig realized youthful passion led to absolute statements (“We’ll always do this” or “We will never do that”), which quickly became limiting as conditions changed.
  • “The promises you make early can become the limitations you live under later.” (03:15)
• Advice: Get comfortable with being wrong, and be willing to change often.
  • “If you want to grow fast, you have to change often. Be wrong fast.” (05:23)
  • The areas where a leader feels most certain are often the areas where they're most vulnerable to lacking perspective.

2. Lead with Purpose, Not Preference

• Old Belief: The organization should reflect the leader’s preferences.
• New Insight: Leading by preference is limiting; lead by purpose instead.
  • Craig shares that expecting everyone to think, decide, and work like him stifled diversity and organizational growth.
  • “If everything has to match your preference, nothing will ever outgrow your leadership.” (11:39)
• Advice: Tolerate styles, workflows, and methods you wouldn’t personally choose to expand the organization’s impact.
  • “Get good at letting great people do things their way—not just your way.” (15:48)
• Key Thought: If nothing in your organization rubs you the wrong way, you’re building for yourself, not for a broader mission.

3. Keep Standards High, Expectations Fair

• Old Belief: Everyone should meet the same high standards the leader sets for themselves.
• New Insight: While holding oneself to high standards, expectations for others must be fair and context-aware.
  • Team members can care deeply, but they don’t have the same information, support, or capacity as the leader.
  • “You can have world-class standards for yourself, and still be fair with what you expect from the team that you love.” (25:14)
• Advice: Help people excel in their unique season and situation, rather than pushing them to meet your personal standards.
• Result: Compassion and fairness lead to people thriving and often surpassing expectations—not by pressure, but by empowerment.

4. Success Creates Options, but Options Create Distractions

• Old Belief: More options and opportunities are always good.
• New Insight: While success brings options, unchecked options breed distractions which threaten core priorities.
  • “Success creates options, options create distractions, and distractions diminish success.” (32:48)
• Advice: Fight for focus and simplicity. Discipline yourself to say no to good ideas that do not serve the main thing.
  • “Just because we could doesn’t mean we should. Every yes costs you something. Too many yeses cost you everything.” (35:10)
• Key Thought: Some of the best leaders lost their edge by saying yes too often; guard your focus relentlessly.

5. Leadership Never Gets Easier: Embrace Discomfort

• Old Belief: The longer you lead, the easier it gets.
• New Insight: The journey only gets more challenging; increased impact means increased complexity and discomfort.
  • “You must become comfortable being uncomfortable… growth and comfort never coexist.” (40:25)
• Advice: Don’t expect leadership to get easier. Instead, step toward discomfort, difficult conversations, failures, and new risks.
  • “Don’t worry when you’re uncomfortable. Worry when you’re not.” (43:23)
• Key Thought: The difference between where you are and where you could be is often the discomfort you’re unwilling to embrace.

Memorable Quotes

• “The promises you make early can become the limitations you live under later.”
  — Craig Groeschel (03:15)
• “If everything has to match your preference, nothing will ever outgrow your leadership.”
  — Craig Groeschel (11:39)
• “Get good at letting great people do things their way—not just your way.”
  — Craig Groeschel (15:48)
• “You can have world-class standards for yourself, and still be fair with what you expect from the team that you love.”
  — Craig Groeschel (25:14)
• “Success creates options, options create distractions, and distractions diminish success.”
  — Craig Groeschel (32:48)
• “Just because we could doesn’t mean we should. Every yes costs you something. Too many yeses cost you everything.”
  — Craig Groeschel (35:10)
• “Growth and comfort never coexist.”
  — Craig Groeschel (40:25)
• “Don’t worry when you’re uncomfortable. Worry when you’re not.”
  — Craig Groeschel (43:23)

Timestamps for Key Segments

• Intro & 10-Year Reflection — 00:06
• 1. Willingness to Be Wrong — 02:15
• 2. Purpose Over Preference — 10:10
• 3. High Standards, Fair Expectations — 20:57
• 4. Guarding Focus Amid Success — 30:30
• 5. Comfortable Being Uncomfortable — 39:10
• Reflection Questions for Team Discussion — 45:15

Reflection Questions (For Application & Teams)

Craig concludes with five practical leadership questions (45:15):

1. What leadership belief do you need to admit is wrong?
2. Where are your preferences limiting your impact or your people?
3. Are you expecting something unreasonable from someone based on their role, season, or capacity?
4. What good thing is distracting you from the main thing?
5. What discomfort are you avoiding that you need to face and embrace?

Final Encouragement

Craig emphasizes gratitude for his listeners, reiterates the importance of transparent leadership, and shares a prayer for courage, character, and influence in the new year. He encourages all leaders to keep growing, keep showing up, and remember:

“Everyone wins when the leader gets better.” (48:50)

Resources Mentioned

• Leader Guide & Reflection Questions: cglp.com
• Recommended Leadership Books List: cglp.com/leadershipbooks

Stay tuned for the next episode, where Craig will dive deeper into more advanced leadership adjustments for growth.