Permission to Speak Freely

How the Best Leaders Cultivate a Culture of Candor

Matt Kincaid (Author) | Doug Crandall (Author)

Publication date: 03/20/2017

Permission to Speak Freely
Lead So Your People Speak Freely

Candid communication enhances innovation, ownership, engagement, and performance. The benefits of hearing questions and uncertainties, good and bad ideas, and honest feedback are game-changing. Yet research shows that most of the time, people never share their true thoughts with each other—and especially not with their leaders.

But what if they did? What if everyone could confidently communicate without fearing a negative response? In
Permission to Speak Freely, highly acclaimed leader developers Doug Crandall and Matt Kincaid illustrate the benefits of candor, explain the inhibitors that cause it to feel unsafe, and provide tools for leaders to encourage their people and embed trust and openness into the foundation of their organizational culture.

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Lead So Your People Speak Freely

Candid communication enhances innovation, ownership, engagement, and performance. The benefits of hearing questions and uncertainties, good and bad ideas, and honest feedback are game-changing. Yet research shows that most of the time, people never share their true thoughts with each other—and especially not with their leaders.

But what if they did? What if everyone could confidently communicate without fearing a negative response? In
Permission to Speak Freely, highly acclaimed leader developers Doug Crandall and Matt Kincaid illustrate the benefits of candor, explain the inhibitors that cause it to feel unsafe, and provide tools for leaders to encourage their people and embed trust and openness into the foundation of their organizational culture.

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Meet the Authors

Visit Author Page - Matt Kincaid
Matthew Kincaid, PhD, is the managing partner of Blue Rudder, a leadership development consultancy. His work has been published in multiple international scientific journals, and he has been featured in two widely distributed business textbooks. Dr. Kincaid has led the efforts of four start-up companies and worked as a strategic planning consultant for an array of Fortune 500 companies.

Visit Author Page - Doug Crandall
Doug Crandall is the founding partner of Blue Rudder. He has led multiple units in the US Army, and spent time in operations at For five years, Crandall taught Leadership, Advanced Leadership, and Leading Organizations through Change at West Point, where he won the Excellence in Teaching Award. He is the coauthor of two other books, Hope Unseen and Leadership Lessons from West Point, which have sold over 50,000 copies worldwide.

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Permission to Speak Freely



There are naïve questions, tedious questions, ill-phrased questions. . . . But every question is a cry to understand the world. There is no such thing as a dumb question.


WE HAD A STUDENT, Paul, who was investigating a given career path and needed some help. One of us reached out to Micah—a friend in that field. Micah suggested that our student talk to a woman named Lisa, and we passed this info on to Paul via email. Shortly after, a text exchange followed:

PAUL: So email both of those two people?

US: Email Lisa and copy Micah.

PAUL: Like copy his email? Sorry I probably sound dumb.

US: When you send an email you can “copy” someone by putting them in the “cc” address. This means you’re sending it to Lisa but letting Micah know what’s going on.

PAUL: Oh, okay.

US: You don’t sound dumb.

When people expose themselves as unknowing, they immediately feel vulnerable. If they speak up and ask a question, they will search for the right way to ask—a way that doesn’t sound “dumb.” The leader’s response to their questions will have a significant impact on whether or not they ask again. And a culture of candor or a culture of silence will have been reinforced. It happens that quickly.

As leader developers, we’ve seen the boundless benefits of people speaking freely—and embracing a culture of candor. It happens when you release people from the burden of saying things the right way. As leaders, we should be cultivating questions, doubts, uncertainties, and other variations of not knowing. When people have permission to speak freely, they will put forth their perspectives, ask when they don’t understand, and seek guidance when they need help. So ask yourself:

Do I welcome a spirit of speaking freely?
Do I really welcome it?

Let those questions echo within you for a few seconds. Do you want to hear the questions and uncertainties that the people you lead wish they could say, want to say, aren’t sure they should say, feel vulnerable saying, and hold back from bringing up simply because they can’t find the right words? We believe all leaders need to hear the unfiltered thoughts and ideas from their people. What we’re proposing in this book is that you hear everything. Literally everything. You may be thinking, “I don’t want to hear everything. I don’t have time.” We hope this book will change your mind. The benefits of candid communication are immense and often life altering. Let’s look at a simple example of speaking up in confusion.

One Sunday afternoon, ten-year-old Timmy appeared to halfheartedly play through the first two quarters of a youth basketball game. He was jogging up and down the court, and his defense lacked intensity. Few things will accelerate the pulse of a basketball coach (or an overbearing father) more quickly than lackadaisical defense. In this case, the spectating father turned to his daughter midway through the first half and grumbled, “What’s the deal with your brother? Look at him. He has his back to the ball and he’s completely lost his man.” If you’re unfamiliar with basketball, one of the most important defensive principles is that every player should have his or her “head on a swivel” and be able to see both the person he or she is guarding and the basketball, at the same time, at all times. Timmy wasn’t doing this.

On the way home from the game, Timmy’s father broached the subject of proper defensive technique. His sermon lasted for about three minutes, during which he told Timmy, “Don’t turn your back to the ball,” six or seven times. “It’s about giving it 100 percent. You’re capable of playing great defense. Stuff like turning your back to the ball is all about effort,” huffed his father. The conversation stifled, and Timmy slowly grew more and more agitated. Finally his anger and frustration boiled over and he screamed out with tears in his eyes, “I don’t even know what you mean! I don’t know what you’re talking about when you say ‘Don’t turn your back on the ball’!”

There’s so much power in speaking freely, whether it’s a ten-year-old after a basketball game, a school janitor, a new manager, a rookie baseball player, a private first class in the military, or a commercial airline copilot. If Timmy doesn’t speak up in that moment, his dad assumes that he got the message. And because he had no idea what his father meant, his silence means that everything his dad said has been lost on him. Nobody benefits. The next time his father sees Timmy turn his back to the ball, he will assume that Timmy blew him off. And because he told Timmy six or seven times during the car ride, he concludes that his son lacks respect or just doesn’t care. The situation spirals downward at an accelerated rate. Three months later, he fires him. And while a dad can’t fire a son from the family, you get the point—this isn’t just a youth basketball story. It’s a story about leadership and communication. Leaders often mistake a lack of clarity for defiance. Timmy was confused, but his willingness to speak up saved the moment.

The reason that a permission to speak freely leadership orientation is so critical is because it’s so different. We all recognize organizational silence as a problem. It’s not a novel idea. But collectively, we’ve attempted to solve this problem in the wrong way. There are a handful of best-selling books aimed at teaching followers how to articulate their thoughts effectively, or how to speak courageously, or how to speak persuasively in an upward direction. Millions of dollars are spent on communication training each year. Timmy had neither read any of these books nor been trained in how to see things from his dad’s perspective. He just boiled over and spoke freely: “I don’t even know what you mean!” And truthfully, his dad was lucky that he spoke up at all. As leaders, we can’t rely on luck. It’s our job to initiate these conversations and build a culture where speaking freely is the norm and where people never ask for permission to speak freely—they simply know it’s been granted.

Dan Lovallo, from the University of Sydney, and Olivier Sibony, from McKinsey and Company—who’ve done extensive research on the role of inclusion and voice in decision-making—observe, “The culture of many organizations suppresses uncertainty and rewards behavior that ignores it . . . seldom do we see confidence as a warning sign—a hint that overconfidence, overoptimism, and other action-oriented biases may be at work.”1 Whether because of culture, incentive structures, insecurity, or inexperience, Jeff Gaines found himself in a situation where he needed help but forged on with “confidence.”

Gaines started out as an hourly associate at one of the world’s largest retailers. He earned a college degree on the side and then rapidly worked his way through the company’s merchandising ranks to become one of its youngest directors. Identified as “top talent,” Gaines earned a nomination to the company’s high-potential leadership program and a promotion to senior director. The original pilot of the leadership development course included an exercise designed to place front-line leaders and headquarters executives in the shoes of their own constituents: the Core Customer Challenge. Because of the emotional impact of the event, it has maintained its place in the curriculum through multiple years of revisions.

Per the challenge, Gaines and his cohort of eight colleagues set out one afternoon to purchase a week’s worth of groceries for a family of four living just above the poverty line. The budget was just under $70 (yes, for the entire week). Thirty minutes later, with milk, breakfast cereal, and a loaf of bread loaded in their shopping cart, Gaines and his group stood in front of the canned vegetables looking for the least expensive offering of green beans. Situated prominently on the middle shelf, the company’s private label was the best bargain at $0.68. A woman on Gaines’s team grabbed two cans and tossed them in the cart. Gaines, though, stopped the group before they could move on. “Just a second,” he murmured, “there are some cheaper ones down there.”

“Down there” was on the bottom right, out of the sight line of the average-sized human. Jeff spotted the Three Charms–brand beans—priced at $0.52 per can—because he had put them on the bottom shelf two years earlier while fighting his way up the merchandising ranks as a canned-vegetable buyer.* When Three Charms came to Jeff with their original pitch, he was hesitant to make the beans part of his assortment. Although doing so would be consistent with company strategy (offering the lowest price point of any retailer), the company’s mission (helping people save money), and Gaines’s own values, it conflicted with his incentive structure. His target for the year was a 4 percent revenue increase in his category. His performance review and bonus depended on it. At the point when he met Three Charms, he was trending just above 3 percent growth and working hard to improve. Placing Three Charms beans on the shelf—in a prominent position—would reduce sales of more expensive beans, slowing Gaines’s revenue growth. In the end, it wasn’t his conscience or his concern for the customer that put those beans on the shelf. From a strategy standpoint, he simply knew that he needed to introduce the lowest-priced option. So if he had to do it, he’d protect his revenues in the process. Hiding Three Charms in the bottom right solved the problem. Gaines never shared his concerns with his boss. When the two of them went through his display plan, he justified the placement of Three Charms beans through a number of logical arguments. None of them included what he was really thinking: I’m trying to hide them.

Most will empathize with the push and pull of Gaines’s competing interests: customers, strategy, and his own job performance. In his mid-twenties, trying to launch a long-term career with the company, he had three reasonable options:

1. reject Three Charms;

2. put the new brand of beans on the shelf; or

3. make Three Charms available, but in a place where customers probably wouldn’t see the beans.

In the world in which many of us reside—the one where people measure their words, hide their thoughts, and speak only when they know it’s safe—Gaines settled on the hide-and-seek-the-beans option. Speak Freely leadership creates a fourth possibility: Jeff Gaines shares his uncertainty with his leader and asks for help:

You know, boss, if I put the Three Charms beans right in the middle, it will cannibalize my other sales. My revenues will drop below target, and I won’t get my bonus. I’ll look like I’m failing. But I can’t not offer them. They are the lowest price on the market. I want to do what’s right for the customer and company, but I’m not going to make 4 percent if I do that. I don’t know what to do. I need your help.

We’ve queried thousands of leaders regarding scenarios similar to Three Charms beans. Literally no one has ever stood up in one of our classrooms and suggested that they wouldn’t want to hear Gaines’s vulnerable admission and request for guidance. The benefits of this type of candor are immediate and self-evident: instead of his placing the product below the normal customer’s sight line, he uncovers a different solution with his boss. The company benefits. The customer benefits. Gaines does the right thing. Trust ensues, and he opens up a little more confidently the next time he faces a dilemma. And to be clear, this story is not about retail strategy, Jeff Gaines, beans, or even values and mission. It’s simpler than that. It’s about open communication in an upward direction. If you’re Gaines’s leader, you should want to know what he’s actually thinking. You should want him to come to you for help if he needs it. You should want him to speak freely.

Permission to speak freely means, first and foremost, that the people you lead trust you enough to tell you they need help, to ask when they don’t understand, and to be bold with their lack of clarity. When these thoughts start to pour out, others will follow.

*We’ve omitted the company’s name and changed the brand to “Three Charms” on the advice of counsel (their counsel).

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Permission to Speak Freely is a rare leadership book that entertains and educates. The stories are memorable, the research is meaningful, and the takeaways are immediately actionable.”
—Adam Grant, Wharton professor and New York Times bestselling author of Give and Take and Originals

“We simply cannot figure out what is essential as leaders without people sharing what they are seeing, hearing, and experiencing. This takes powerful listening on the part of the leader. These truths—and how to make them a reality—are beautifully illustrated in 
Permission to Speak Freely.”
—Greg McKeown, New York Times bestselling author of Essentialism

“This book tackles the most important problem in organizations today—leaders do not know how to encourage their subordinates to speak up.
Permission to Speak Freely not only identifies the problem with powerful stories but offers suggestions that are important to leaders at every level, especially those at the very tops of their organization.”
—Edgar H. Schein, Professor Emeritus, MIT Sloan School of Management, and author of Humble Consulting and Humble Inquiry

“Incredible writing. Edible lessons. I set out to read a chapter of
Permission to Speak Freely and then couldn't put it down. Devour this book and learn from it.”
—Scott Snook, Harvard Business School Senior Lecturer and coauthor of The Discover Your True North Fieldbook and The Handbook for Teaching Leadership

“Crandall and Kincaid adroitly reveal how leaders inadvertently derail creativity and commitment, and deliver keen insights on how to avoid that trap.
Permission to Speak Freely is a powerful reminder to leaders that they aren't necessarily the smartest people in the room.”
—Tom Kolditz, Founding Director, Ann and John Doerr Institute for New Leaders, Rice University; retired Brigadier General; and former Professor and Leadership Development Program Director, Yale School of Management

“The tenets illustrated in
Permission to Speak Freely are already shaping the way I operate my business, build my team, and consult on matters of organization change management. This book is a remarkable tool for diverse leaders worldwide. ”
—Tyler Borders, cofounder and Principal, Dartlet

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