The Questions Leaders Need to Be Asking Themselves
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What truly sets an effective leader apart? Is it their ability to craft a strategic vision, juggle time management, or exude decision-making confidence? According to renowned expert Robert Kaplan, the magic lies in asking the tough questions that pave the way for sound decisions.
As a senior fellow and esteemed professor emeritus at Harvard Business School, Kaplan is a thought leader whose wisdom shines in his book, What to Ask the Person in the Mirror: Critical Questions for Becoming a More Effective Leader and Reaching Your Potential.
In this eye-opening episode, you’ll discover how to formulate better questions that lead to the answers you crave for impactful decision-making. Get ready to clarify your four key priorities and ensure your time is dedicated to what truly matters.
This episode first aired in August 2011, and while the audio may be a bit rough around the edges (we recorded it via phone), trust us—the conversation is worth it. Let’s dive right in!
SARAH GREEN: Hello and welcome to Leadership Insights. I’m your host, Sarah Green. Today, we’re exploring the familiar yet often overlooked topic of leadership—yet with a refreshingly unique perspective.
I’m thrilled to introduce Robert Kaplan, a distinguished professor at Harvard Business School and the author of the insightful book, What To Ask The Person In The Mirror: Critical Questions For Becoming A More Effective Leader And Reaching Your Potential. Rob, it’s a pleasure to have you with us today.
ROBERT KAPLAN: Thank you for having me, Sarah!
SARAH GREEN: One of the standout aspects of your book is its focus on questioning, a departure from the usual answer-driven approach. What inspired you to take this route?
ROBERT KAPLAN: My extensive experience managing businesses and coaching leaders has led me to a startling revelation: at the heart of the toughest management challenges, it all boils down to questions. I’ve engaged with countless leaders, and what I’ve learned is that the most effective ones are masters of inquiry.
Surprisingly, the same questions often resurface. When someone encounters a challenge, their perceived issue might just be a symptom rather than the root cause. So, rather than charging ahead with solutions, I advocate stepping back and asking the vital questions.
SARAH GREEN: The book includes a valuable arsenal of questions beneficial for leaders at all levels. Let’s get into the nitty-gritty—how can questions improve time management, which is a struggle for so many of us?
ROBERT KAPLAN: Absolutely! The book features eight chapters exploring essential areas of questioning. We begin with overarching strategic inquiries—defining our vision and pinpointing our key priorities. This sets the stage for digging deeper into personal strengths and weaknesses, passions, and how effectively we align our time with what truly matters.
For example, let’s say you’re working 60 hours a week—do you really know how you’re spending that time? Tracking it can reveal mismatches between your actions and your priorities. When many leaders examine their time distribution, they often find surprising disparities. It’s all about jarring yourself into awareness!
As a Harvard professor, I constantly reassess: what should occupy my focus? You’d be amazed at the habits I’ve unconsciously hung onto even as circumstances evolve. By asking pointed questions, I can challenge outdated practices and ensure my efforts align with current priorities.
SARAH GREEN: You also touch on a compelling concept of looking at your business with a “clean sheet of paper.” Could you elaborate on that?
ROBERT KAPLAN: Certainly! This straightforward question—if you were to start your business from scratch, would you structure it the same way?—can provoke profound insights. It’s challenging because it forces leaders to confront uncomfortable truths about their operations and structures, but it’s vital for continual growth.
Here’s a strategy: engage your upcoming talent. Assignment them the task of evaluating your business as if they were establishing it anew. Their fresh perspective often uncovers incredible recommendations, freeing you from emotional biases.
Ultimately, leaders must confront reality or risk being overtaken by it. If we neglect this self-examination, the market will impose its own verdict.
SARAH GREEN: That surely keeps leaders on their toes!
ROBERT KAPLAN: Absolutely. A misconception is that leadership is solely about direction—proclaiming, “This is where we’re heading!” It’s equally about acknowledging uncertainty and encouraging open discussion. Effective leaders embrace vulnerability, asking the right questions rather than guaranteeing they hold all the answers.
This shift in focus not only alleviates pressure but also fosters collaboration in searching for solutions, leading to richer, more informed decisions.
SARAH GREEN: So, the crux of the matter is, if you’re not asking the right questions, you won’t uncover the right answers.
ROBERT KAPLAN: You’ve got it! Leaders must define their beliefs and act upon them. Cultivating the skill of framing questions and orchestrating conversations is crucial. Listening—one of the most potent tools at a leader’s disposal—enables respect and sparks innovation.
SARAH GREEN: Great insights, Rob. Thank you so much for sharing your thoughts with us today!
ROBERT KAPLAN: My pleasure, Sarah!
HANNAH BATES: That was Robert Kaplan sharing his wisdom with Sarah Green. Kaplan’s book, What to Ask the Person in the Mirror: Critical Questions for Becoming a More Effective Leader and Reaching Your Potential, offers invaluable expertise.
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