Most leadership mistakes don’t result from a lack of intelligence or experience. They occur because of unexamined assumptions, unrecognized fears, unchallenged self-interest, or unbridled enthusiasm.
While seeking outside perspectives can help leaders understand what they may be overlooking, looking inward is also an essential part of the discovery process. Asking hard, self-directed questions is how the best leaders improve their thinking, judgment, and decision-making.
Good leaders assume their awareness is incomplete, so they use self-directed questions to surface the limits and constraints of their thinking and understanding. They treat their own thinking and judgment as something to improve, not something to defend.
Self-directed questions help leaders to audit their thinking and reflect upon why they believe what they do. By looking inward and asking the tough questions most others don’t, they uncover biases and blind spots they wouldn’t otherwise see.
Powerful self-directed questions push past simple reflection — “What did I learn from this experience?” or “What are the risks involved?” — and ask leaders to challenge their own thinking.
Some examples:
- “What evidence am I discounting?”
- “What behavior am I unintentionally discouraging?”
- “What conversation am I postponing?”
- “What answer would be uncomfortable for me to discover?”
- “What would my successor do differently?”
Tough self-directed questions require leaders to audit their own thinking. They often reframe how leaders see a situation by exposing the unexamined assumptions they’re making and revealing the shadow side of what they believe to be their strengths. They challenge who leaders think they are and the quality of their decision-making.
Self-directed questions come in many forms, but the hardest ones generally fall into four categories:
- Assumption: “What am I presuming?”
- Fear: “What am I avoiding?”
- Identity: “What am I protecting?”
- Blind spot: “What am I missing?”
Consider asking all four questions in any situation you are working through, crafting each one to fit the specifics.
For example, you might ask, “What performance conversations am I avoiding?” or “Why do I react defensively when people ask me to explain my reasoning?” Questions from these four categories will shake things up and force you to take a fresh look at how you think.
Of the many questions leaders ask, perhaps the most impactful ones for personal growth and improvement are self-directed.
Self-directed questions turn passive thinking into purposeful insight, helping you learn, decide, and grow more effectively. They are the leadership engine of self-awareness and better decision-making.
Hard questions turned inward often lead to the biggest breakthroughs outward.
