Eye-opening Self-Reflection Questions for Leaders
Growth requires self-reflection. Do you actually deliver the goods? Could you have blind spots?
Structured self-reflection questions keep leaders on track.
Eye-opening self-reflection questions:
Initiative:
- How frequently do you step up when help is needed?
- What is your track record for taking on new challenges?
- How frequently are you seeking permission to act?
Vulnerability/Courage:
- What do you say when you screw up?
- What personal stories do others know about you?
- How good are you at confronting tough issues?
Open-mindedness:
- How well do I adapt when situations change?
- What’s my ratio of questions to statements?
- What do I do when situations are confusing or ambiguous?

Humility:
- How freely do you honor others?
- How well do you seek and receive help?
- How frequently do you express gratitude?
Influence:
- How do people feel after spending time with you?
- Who is better because of your influence?
- What do you see in yourself that others might emulate?
Energy:
- Are you an energizer or an energy suck?
- Do you make life easier or harder for others?
- How well do you practice self-care (energy management)?
Learning:
- What are you learning from books, conversations, experiences?
- How do you respond to new ideas?
- What are you learning from failure?

Trust:
- How much authority do you give others?
- How frequently do you expect people to solve their own problems?
- Do you establish accountability without being up in everyone’s business?
Insight:
- How well do you understand your colleagues and team members?
- Can you see a connection between day-to-day operations and long-term vision?
- Do you have an idea of what makes your team members light up?
Tip: Adapt these questions for meeting openers.
What new categories can you add to the above self-reflection questions?
What self-reflection questions would you add to the above lists?
A little book about humility.
John David Mann and I give readers an opportunity for structured self-reflection in our new book, The Vagrant. There’s hope for you if you occasionally see yourself in the story.

Dan
I’m proud to be able to say I could positively answer all those questions. Obviously still personal reflection and improvement to grow more – life is a journey not a destination.
I’ve been a long time subscriber and I’m sure that is big part of why I’ve already progressed far along my leadership journey.
I warmly recommend new subscribers to review back over the years of dans posts which often challenge your own perceptions about yourself, relationships, family, leaders, teams, colleagues and purpose. That includes the countless leaders that contribute with comments – thoughts – reflection – questions. You may not always agree with the post or comment but that’s the beauty of curiosity and understanding the world through others perceptions.
Rob mc
Thanks, Rob. What a delightful comment. Growth over the long-term pays off. I appreciate your support and feel honored to be part of your journey. Best wishes, Dan
“Life can only be understood backward, but it must be lived forwards.”
– Søren Kierkegaard
Wonderful quote, Melanie. Thanks for leaving it.
Great list.
I’m also thinking about Clarity as a category.
Questions could include:
Do I understand the key priorities of my role right now?
Do I understand who else cares about those priorities and why?
Am I meeting my own standards for proactivity, quality and appropriate speed?
Wonderful, Jenny. That one is so important. It’s frustrating to work hard doing something that doesn’t matter.
Great insights! While I was quite happy to be “checking boxes” along the way, I found a few within which I am comfortable, but am employing further introspection. Glad I read this!