The Power Of Hard Questions: Why Every CEO Needs Someone Who Pushes Back
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The Power Of Hard Questions: Why Every CEO Needs Someone Who Pushes Back
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As leaders rise, honest feedback gets harder to find—not because people don’t care, but because questioning the boss can feel risky, disrespectful, or emotionally charged. In this episode of The Business You Really Want, Gwen Bortner and Tonya Kubo explain why every CEO needs at least one trusted person who will push back, ask the tough questions, and reveal what they can’t see alone. They unpack what makes a question “hard” (hint: it’s rarely the words—it’s the emotional discomfort, blind spots, and hidden assumptions) and why accountability often breaks down when the power gap is too wide. They also share a practical roadmap for finding real pushback—whether through a true #2 internally, the right peer group, a coach, or an experienced advisor—and show how to create a culture where your team feels safe challenging you without fear of fallout. If you want better decisions, clearer priorities, fewer preventable crises, and a team that solves problems instead of nodding along, this conversation will transform how you think about leadership—and the questions you’re willing to face.
Mentioned in this episode: Subscribe to Gwen’s weekly email, One REALLY Good Question, at everydayeffectiveness.com/question.