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5 Ways to Make ‘Intelligent Disobedience’ the CEO’s Best Friend

A CEO told me what keeps him up at night is the thought his people will tell him what they think he wants to hear. This is not an unreal fear.

Most of the world holds an image of the CEO as expecting and commanding obedience. Competent CEOs know they need good data, insightful analysis and candid feedback before they need compliance. There are only a few they can count on for this crucial support.

Enter the subject of Intelligent Disobedience. This may be the first time you have heard the expression. It is well known to those who train the best of man’s best friends: guide dogs for the blind.

For the first year and a half of the dog’s life it learns how to obey. Then it must learn when and how to disobey. Disobey? Yes, that is the crucial skill without which it cannot be a guide dog. If executing a command would harm the team of human and dog it must not obey, even if the command is repeated more insistently.

“The CEO has blinds spots  caused by poor data, wrong mental maps, time pressure, faulty analysis, distorted incentives, etc. The CEO needs a best friend.”

Think of this scenario: The person who is blind tells the dog to go forward at an intersection. A quiet vehicle is coming around the corner. If the dog obeys it endangers the safety and life of the team. If it disobeys, it can find a safe moment and way to achieve the task of crossing the street. That ability to differentiate between appropriate obedience and disobedience is the pivotal element that makes the guide dog’s service so valuable.

Transfer this to the C-suite. The easiest thing in the world is to obey the CEO’s orders. It may also be the most dangerous. Not because the CEO is evil, bad or even arrogant; but because the CEO also has blinds spots. This blindness is caused by poor data, wrong mental maps, time pressure, faulty analysis, distorted incentives, etc. The CEO needs a best friend.

Some CEOs make it exceedingly difficult for those around them to give candid guidance. Others work hard to create an atmosphere of professional candor; yet, they may still fall short of achieving this. They are up against the unspoken rules of culture and upbringing that their people are acting on.

An example may be what Tony Hsieh is experiencing in his attempt to recreate the culture at Zappos from hierarchical to a self-managing, bottoms-up organizational structure and processes. While welcome in theory, there are reports of discomfort and disaffection. To some degree, I believe this is a symptom of the deeply embedded programming of obedience to authority in which most cultures socialize their young, organize their schools, youth programs, law enforcement, military and business regimes. While I applaud Hsieh for his efforts, I view his situation as a visible case example of what CEOs are up against in creating cultures of candor and self-accountability.

How can a CEO change this? Here are 5 things a CEO, or other executive, can do.

  1. Don’t sell your ideas before they are tested. If you explain what you’re planning to do with enthusiasm, conviction or force and then ask for feedback, you won’t get it. Put your ideas forth as works in progress and ask what others see. Am I missing anything? Is there something I’m not seeing? Is there anything in my blind spot? Is there a better way to achieve this? Should we be doing this at all?
  2. Ask the lowest ranking person first. If you start at the bottom, those answering first do not have to tailor their thoughts to conform to remarks made by those who outrank them. This wrings out some of the distorting effects of hierarchy.
  3. Treat dissent as a golden opportunity. When a junior person offers a perspective that is known to diverge from the leader’s, there is a golden opportunity to prove you value dissent. Thank the staff publicly for his or her candor, acknowledge that the viewpoint differs from the one you are holding, ask for help in understanding the dissenter’s perspective. Only then decide if you will act on the dissenting perspective; if not, explain why and restate your thanks.
  4. Institutionalize dissent by appointing a devil’s advocate. Research shows a tendency for groups to value consensus that prematurely pushes robust dialogue toward agreement and conformity. Some groups contain a natural dissenter. If the group leaves the role of the dissenting voice entirely to this individual, the dissent begins to get screened out. “Him again!” Rotate the role. Tell the person playing the Devil’s Advocate for each meeting that you are counting on him or her to question assumptions the group and leader are making; to challenge the sufficiency of information and the interpretation of that information, to dare to question the sacred cows, to speak what has been held as undiscussable. Heap praise on that individual when this is done well and contributes to better decision making.
  5. Practice the practice of dissent. Leadership teams and management groups typically go on retreats once or twice a year to review their strategy. Team-building is often woven into the retreat. Weave in a different type of team strengthening activity—the practice of dissent. Exercises can be devised that prepare team members to offer constructive dissent. Draw on the experience of the aviation and medical sectors that formalize practicing dissent in simulations to reduce catastrophic mistakes. A little bit of practice goes a long way.

It takes more than an edict to change a culture. Regardless of how approachable and open-minded CEOs believe they are, they typically send micro-messages that the group quickly learns to read and interpret as the real wishes of authority. Take it from guide dog training—it is not just the dog that needs to be trained, so does the human that both leads the dog and is served by it. CEOs who want to earn a good night’s sleep need to occasionally put in a good day of training on creative and intelligent disobedience with their best friends.

Ira Chaleff is the author of The Courageous Follower: Standing Up To and For Our Leaders, now in its third edition, coeditor of The Art of Followership: How Great Followers Make Great Leaders and Organizations, part of the Warren Bennis Leadership Series, and his newest release, Intelligent Disobedience: Doing Right When What You’re Told To Do Is Wrong, which has been featured in the NY Times, Library Journal, and He is the founder of the International Leadership Association’s Followership Learning Community and a member of the ILA board of directors. He is a frequent speaker and workshop presenter, founder and president of Executive Coaching & Consulting Associates, and adjunct faculty at Georgetown University. Learn more at


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