16 Questions Leaders Should Ask Themselves

Mary Poppins 3Just between you and the mirror…

1. Are you more motivated mostly by the drive to capture success or by a desire to serve others?

2. Do you use your grasp of internal politics as a weapon to get what you want? Or are you sensitive to the human dynamics at play in the organization, but work toward collaborative, empowering solutions that appeal to shared goals, values, and visions?

3. Do you rely completely on facts, logic, and proof? Or do you use intuition and foresight–gut and instinct–to balance those things?

4. Do you control information, knowing it makes you more valuable? Or do you freely and generously share your knowledge and know-how?

5. Are you highly competitive, independent, and primarily interested in the spotlight? Or are you more concerned about working closely with others, allowing yourself to be interdependent, and deflecting praise when it comes your way?

6. Do you place an over-emphasis on speed and fast action? Or do you focus on gaining understanding; adapting to organizational environments; and balancing the need for progress with the need for appropriate buy-in, input, and decentralized decision-making?

7. Do you spend more time telling or listening?

8. Do you equate patience with indecision? Or do you value listening and observation in order to make good decisions?

9. Do you act like you’re listening to those with whom you disagree? Or do you actually listen to those with whom you disagree?

10. Do you get annoyed when others won’t think or act the way you want them to? Or are you thankful for the variety and use it as an opportunity to examine your own thoughts, presuppositions, and conclusions?

11. Do you view your network as connections to be used to get you things or give you information when you want it? Or do you view them as other humans who have unique strengths, information, and perspectives that you could learn from?

12. Do you secretly relish being able to look down from atop the org chart? Or do you view your leadership position more as an immense privilege and responsibility to serve a larger group of people to a greater degree?

13. Do you use intimidation (in all its forms) over inspiration?

14. Which is more important: what benefits you or the good of the whole?

15. Do you believe leadership is about control? Or do you believe leadership is about finding ways not to have so much of it?

16. Do the people whose work you admire always happen to work exactly like you do? Or do you value the diverse and interesting ways people are wired to work?

No one’s judging anyone. At least I hope not, or I’m screwed. We’re all imperfect humans and consequently imperfect leaders. We all struggle with any of these things at given points. I know I have and do. But as leaders, I believe it’s important for us to look in the mirror, ask tough questions, and give vulnerable, honest answers.

17 thoughts on “16 Questions Leaders Should Ask Themselves

  • Great list Matt, thanks for sharing!

    I would like to propose 9a below, as a nuanced addition to #9-( “Do you act like you’re listening to those with whom you disagree? Or do you actually listen to those with whom you disagree?” )

    9a-Do you listen to understand or judge the perspectives, feelings or needs of others, that are different from your own?

    • I like it, Lori. The wise leader neither blindly accepts the ideas of others nor stubbornly refuses to consider opinions opposed to his or her own.

  • Another fantastic list Matt!

    Particularly useful for good leaders to become great leaders. As usual, those who would benefit the most from this information won’t even read it. Or if they do, won’t feel that it applies to them.

    • Thanks, David. Self-awareness and tough self-evaluation are key elements for a leader; I’m trying to get better at both.

  • I printed out this list and answered each question as truthfully as I could (as if I was taking a test!). I was really surprised at my answers…I think this is a valuable set of questions to help identify some areas in a person’s “leadership role” that may be lacking! I think another question to add to this list should be, “What method (if any) do you use to promote productivity and a sense of accomplishment in the workplace? Is this a method you use solely for an end result or because you genuinely believe in your staff and want them to succeed?…I think this kind of ties in to your question, Which is more important: what benefits you or the good of the whole?… As a new business owner myself (with not many employees) I want them to feel passion for their work! I want them to take pleasure in what they do and have a sense of accomplishment! This post really reminded me of a fantastic management book I just read on the subject of motivation (especially positive reinforcement in the workplace and at home!) called “Green Beans and Ice Cream” by author Bill Sims Jr. (http://greenbeanleadership.com/). The book is a fast paced read that delivers research and real life examples (I really feel like it reads like a conversation). What I like about it is that it’s well written and short enough that if you give it to someone, chances are that they are actually going to read it– and they are going to understand it. There are not many management books like that out there… Direct positive reinforcement with your staff helps to boost morale in the workplace and makes them feel like they’re apart of something meaningful, not just another boring job. I highly recommend it especially after reading these questions!! Thanks again

    • Leslie, thanks so much for the kind words and the your thoughtful post. I really appreciate how you position your philosophy within an employee-centric framework. It really does make a big difference! Kudos to you, and thanks again for commenting.

    • Thanks, Paul. Much of this stuff (and much of the other stuff you’ll find if you poke around the site) came from stuff I was thinking through myself. I didn’t like my answers to all of them. 🙂

  • Great list of questions Matt. I choose B.

    Thanks for sharing this – some great reminders and points that inspire reflection. Even when we want to be at our best it is easy to drift into old habits or patterns. I’ll use this to center myself on the kind of leader I want to be.

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