100 Self-Assessment Questions for Leaders
One Hundred Self-Assessment Questions for Business Leaders
A Reflective Tool for Leaders Who Want to Lead with More Awareness, Purpose, and Impact
Strong leadership begins with asking the right questions—especially the hard ones. One Hundred Self-Assessment Questions for Business Leaders from Capacity Building Solutions is designed for business owners and executives who are serious about personal growth, organizational health, and leadership integrity.
This tool isn’t about checking boxes—it’s about digging beneath the surface, challenging assumptions, and helping leaders reconnect with the “why,” “how,” and “what” behind their leadership journey.
Why This Tool Matters
Most business owners are so busy leading others that they rarely stop to evaluate how they’re leading themselves. This document gives them permission—and a structure—to do just that. It’s designed to help leaders:
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Build greater self-awareness and emotional intelligence
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Examine their leadership habits, mindset, and values
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Reassess priorities, direction, and blind spots
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Foster personal alignment with professional strategy
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Spark meaningful coaching conversations or strategic retreats
It’s ideal for executive coaching, performance reviews, off-site planning, or solo reflection.
What’s Inside
Organized into key leadership domains, the 100 questions challenge leaders to explore:
About You
Purpose, mindset, energy, habits, focus, and emotional regulation
“What is your ‘Why’? Are you having fun at work? How do you manage fear, doubt, and inner dialogue?”
About Your Leadership Performance
Accountability, decision-making, priorities, feedback, and succession
“Are you operating at your highest and best use? Are you grooming a successor? Do your people tell you the truth?”
About the Business
Vision, strategy, innovation, risk, culture, and sustainability
“Is your business model still viable? What are your blind spots? How would a competitor beat you tomorrow?”
About Your Team
Trust, delegation, loyalty vs. performance, coaching, and team dynamics
“Would you rehire your leadership team? Are you investing in their development? Do you truly know and support them?”
About Life
Well-being, relationships, balance, regret, fulfillment, and legacy
“Are you an attentive spouse or friend? Are you choosing your trade-offs intentionally? What advice would your older, wiser self give you today?”
Each section provides space for leaders to pause, reflect, and ultimately lead with greater clarity and conviction.
