The Challenge of Leadership: Asking Some Key Questions

Posted May 12, 2016 in Business Technology & Digital Transformation Strategies

One of the hardest things to teach or learn is self-awareness. By self-awareness, I mean the capacity to evaluate oneself accurately from the perspective of others and the ability to detect differences between our behavior and our values. So many leaders are unaware of what others around them truly think about them, and at some point in these leaders’ careers, this inevitably leads to trouble. Usually these troubled leaders are constantly interpreting the world around them into their internal logic, thus preventing them from seeing the gap between their own internal understanding of themselves and what others think.

Managing these people can be maddening. It’s almost as if these leaders need a crucible moment that brings them to their knees and near the edge of despair. Most people do not challenge themselves until the world has overpowered them.

There is another way, however. That way lies in periodically challenging yourself, reflecting, and, better still, engaging a trusted mentor in critical questioning. A trusted mentor is one who can give you a mental whack upside the head and tell you very inconvenient, if not troubling, things about yourself. These days, leaders without adequate self-awareness pose a threat to themselves, their families, their organizations, and the world around them. None of us wants to be that threat, but some of us unfortunately become that at times.

Over the years, I have collected many questions from different people, which I regurgitate here, in no particular order and with no guarantees on their efficacy. All depends on the person asking themselves the questions. Not all these questions are about self-awareness, but about how much the leader is developing versus commanding those around. The impact of leaders on people tends to be more far-reaching and meaningful than our ephemeral impact of revenues, profits, and markets — all of which come and go like ocean shorelines.

Please read and certainly be challenged:

  • Who in my circle have I enabled to freely tell me the ugly truth about things I do that are incorrect? Do I proactively arrange for this review before I engage so I can receive it in time?
  • What skills am I missing? What are my strengths? What do others consistently say about me? What am I doing wrong?
  • What values are most important to me? How does my behavior reflect these?
  • Which employees or other people have I failed to reach?
  • Who in my staff has not advanced or developed? Have I told them? Have I affected them? Have I reached them?
  • Where have I connected someone to their passion? Where have I thrown cold water on their passion?
  • When have I been ahead of circumstances? When have circumstances gotten ahead of me?
  • How do I handle stress? Politics? Ethical conflict?
  • Do I address people early enough to prevent events from getting away from me?
  • Do I know when people are working against me? Do I know when people have the same interests as me? Have I ever been blindsided? What did I fail to see in others?
  • Do I know who is good at technical skills? How do I know?
  • Do I know who is good at staying ahead of events? How do I know?
  • Do I know who is better than me at detecting these things? Do I seek them out?
  • What have I learned recently? What is my lifelong learning plan? Who are my mentors?
  • Do I find reasons why things are difficult? Do I find traps?
  • Do I have the skills to manage these traps? Do I have doubts? How do I deal with my doubts?
  • Do I dislike what my fellow leaders are doing? How do I handle this?
  • What percent of my day is spent wondering why versus why not?
  • What is greatness/excellence for me? What does greatness/excellence demand from me? Do I want greatness/excellence? When will I know I have achieved greatness/excellence?
  • Do I have the perseverance for excellence?
  • How many outspoken and unbiased people have provided me feedback on where I am or am not in a path toward excellence?
  • What are the limits to my potential? How much can I endure?
  • Can I be better than anyone? Can I compete with anyone? Can I do whatever it takes? Can I change myself?
  • Can I overcome any obstacle? How do I do this? Can I trust and rely on others to help me?
  • How do I help others achieve greatness?
  • Am I in balance or out of balance?
  • Who have I profoundly influenced for the better? Who have I helped recently? Who is indebted to me?

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About The Author
Vince Kellen
Vince Kellen is a Fellow of Cutter's Business Technology & Digital Transformation Strategies and Data Analytics & Digital Technologies practices, a member of the Cutter Business Technology Council, and a Summit speaker. He is currently CIO at the University of California San Diego (UCSD), a member of UCSD’s Chancellor's Cabinet, and Vice Chancellor and CFO of the UCSD senior management team. Dr. Kellen brings a rare combination of… Read More