When Managers Help by Asking Questions
Cathie Leimbach • July 29, 2020
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How do you structure meetings with your direct reports? Do you give them their assignments for this week and then adjourn the meeting? Or, do you encourage two-way conversations by asking open-ended questions to learn about the successes, joys, and challenges in their personal life and their work responsibilities?
A manager's job is to serve the needs of their staff, to support them to be personally successful and contribute to the organization's success. Asking your employees open-ended questions is the best way to understand their needs.
Asking 'What would you like to talk about today?' or 'How can I help you be successful this week?' opens the door for your team members to share their bottlenecks. Open-ended questions, such as those that start with the '5 Ws' or 'How' allow your direct report to set the agenda for the discussion. When you know what is limiting their performance, you can help close their gaps in knowledge, skills, or tools so they can be more productive.
What open-ended questions could you ask your team members in your next one-on-one meetings?
Many leaders quietly carry the pressure that they are supposed to have every answer. Be decisive. Stay strong. Never show uncertainty. Keep pushing forward no matter what. The problem is that approach often creates distance inside organizations instead of trust. In The Imperfect CEO , which was released on May 19, Jim Brown challenges the idea that leadership effectiveness comes from appearing flawless. Instead, he makes the case that healthy organizations are built by leaders willing to lead with clarity, humility, accountability, and honesty. Larry Siff, CEO of Neptune Advisors and C-Level Community, shared this perspective: “In The Imperfect CEO , Jim Brown doesn’t shy away from the messy reality of being a real person in charge, yet he shows how that honesty becomes a source of organizational health.” Edna Lopez, former Senior Executive at Gateway and Amway, wrote: “In every organization I've led, one truth has been constant: culture determines whether strategy ever sees daylight. The Imperfect CEO gets to the heart of that reality.” That connection between leadership and culture is exactly why the ideas in this book matter. In Conversational Management, we often see organizations struggle , not because leaders lack intelligence or effort, but because communication patterns quietly create confusion, defensiveness, disengagement, or fear. The healthiest organizations usually are not led by leaders who are aiming for perfection. They are led by leaders who know perfection is elusive. They acknowledge their limitations and the benefits of team collaboration. They humbly create honest conversations, clear expectations, accountability, and trust — even when it feels uncomfortable. The wait is over for a down-to-earth book that dares to reveal common leadership imperfections and provides support for enhancing leadership impact! The Imperfect CEO is now available!
Many organizations assume their biggest challenges are rapidly changing technology, customer retention, and employee initiative. But quite often, the root cause is people leadership problems. That’s one reason The Imperfect CEO by Jim Brown is so timely. Releasing today, May 19, the book explores how leaders build healthier organizations not by pretending to have all the answers, but by creating cultures grounded in trust, clarity, accountability, and meaningful conversations. Brian Besanceney, Chair, Board of Orlando Health, Inc., described the book this way: “Through vivid stories, real-world examples, and a model grounded in collaborative culture, Jim Brown gives leaders permission to wrestle honestly with the generational divides, misaligned targets, and cultural fractures that can too often sabotage high-potential organizations.” Greg Apple, CEO of Amgine.ai, connected the book to leadership beyond business alone: “In a fast-moving company, culture is everything. Jim Brown’s principles have helped our team lead with greater clarity and alignment. The Imperfect CEO distills those lessons brilliantly. Every leader should read it.” What stands out to me is how closely this book aligns with the principles behind Conversational Management. Healthy cultures are rarely built through policies alone. They are built through the quality of everyday leadership conversations — how expectations are clarified, how accountability is handled, how feedback is delivered, and how trust is strengthened over time. That’s why leadership development cannot stay theoretical. Culture changes conversation by conversation. The Imperfect CEO is an easy-to-read business fable that illustrates common people leadership challenges and provides suggestions for overcoming them. Order your copy today and start building healthier leadership conversations inside your organization.