Alan Webber: An interview by Bob Morris

Alan M. Webber


Alan M. Webber is an award-winning, nationally-recognized editor, author, and columnist. In 1995, he launched Fast Company magazine, a fresh, dynamic entry in the business magazine category. Headquartered in Boston, MA, the magazine became the fastest growing, most successful business magazine in history. Fast Company won two national magazine awards—one for general excellence, one for design—and Webber was named Adweek’s “Editor of the Year ” in 1999, along with co-founding editor William Taylor. Most recently, he wrote Rules of Thumb: 52 Truths for Winning at Business Without Losing Your Self. He has also been active at local, state, and national political levels, serving as policy advisor for the mayor of Portland, Oregon, writing speeches for several governors, and working as special assistant to the United States Secretary of Transportation.

Morris: Before discussing Rules of Thumb, a few general questions. First, when and why did you decide to pursue a career in journalism?

Webber: I’ve always been interested in reporting, writing, and the purposes that good journalism can serve. When I was in high school, I was editor of the high school newspaper, and we wrote editorials calling for our school (a private all-boy’s–and at the time all-white–prep school) to integrate, to accept black students. In college I became the chairman of our college newspaper. This was during the Vietnam War, and we used the newspaper to cover student attitudes to that war, but also to explore the issues on campus that went more deeply into the purposes of a liberal arts education. So I’ve always seen journalism and activism as closely linked.

Morris: Since then, what do you think have been the most significant changes in magazine publication that include both HBR and Fast Company?

Webber: The world of publishing, in general, has been changing dramatically for the last decade or more. It’s not just the web–although the web has served to disrupt the traditional business model of publishing. It’s also reading habits of different generations, attitudes toward the media and other large institutions, and the overall pace of change that people have to contend with in their daily lives. Obviously, HBR enjoys a privileged position in the magazine world, by virtue of its relationship with the Harvard Business School. The issue there is less one of economic survival, and more of relevance and impact with a business community that will always respect the HBR brand. But will the HBR brand be in touch with and in synch with the changing concerns and composition of the business community? Fast Company, because of its unique DNA as a business magazine devoted to the them of change and innovation, should be relevant forever! But it has to face the changing economic demands of publishing.

At the moment, I’m happy to say, both magazines seem to be meeting their respective challenges head-on.

Morris: Back to HBR, for a moment. What are your fondest memories of that association?

Webber: It’s always the people. When I took over as managing editor under Ted Levitt, we went about the work of re-inventing HBR. Ted was a brilliant marketer, mentor, and writer, so he provided the leadership and the vision to guide us. Then we recruited an almost entirely new team of people to re-invigorate HBR, to re-design the look and feel of the publication, to re-engineer the architecture, the structure of each issue, to bring in new ideas for presenting business thinking to the audience. For quite a few years, we had a terrific team that was excited about creating a new conversation about the direction that business was headed in. In many respects, I think those days helped foster an innovative culture at HBR and re-connected the publication with the larger business audience that was eager to be part of a fresh dialog about how business was changing, how the world was changing, and how the pieces fit together.

Morris: Please explain the process by which you and Bill Taylor co-founded Fast Company in November, 1995.

Webber: Bill and I met at HBR; I was the managing editor and he was the most talented, brilliant, energetic editor on the staff. We began exploring the idea for a new business magazine some time after I got back from a 3-month trip to Japan in 1989-90, where I was exposed to a set of powerful forces that were transforming the world of work. Some of the things I saw could be integrated into HBR, but because of the institutional limits of HBR, some were simply outside the legitimate boundaries of the publication at that time. So in the early 1990s Bill and I started talking informally about what a new magazine could be like. Bill left HBR first, and then when I left around 1993, we got serious about what a new magazine would be like: what it would look like, how it would perform as an editorial product, what we could create that would be exciting and useful, and speak to the dramatic changes going on in business: globalization, technology, the new opportunities for individuals to make a difference in work and through their work. We raised about $550,000 from a fantastic group of first round investors, and in 1993 we put out a “beta” issue. From the feedback we got from that issue, we wrote up a second-round business plan and then showed our work to different publishing companies, looking for a business partner with whom to launch Fast Company for real. Finally we were fortunate to make a deal with Mort Zuckerman and Fred Drasner, who owned U.S. News & World Report and The Atlantic Monthly at that time. The Atlantic was in Boston, where Bill and both lived, so to launch Fast Company we borrowed office space from The Atlantic and ad sales and business staff from U.S. News, making our launch very economical. We hired a small, dedicated staff to put together our first issues, and the first “real” issue of Fast Company came out in 1995. The rest, as they say, is history!

Morris: Here’s a follow-up question. What was its original mission and to what extent has that mission since changed?

Webber: We said in our business plan that every great magazine needs a great purpose. Our purpose was to chronicle the massive changes undergoing in the world of business and to become a platform for describing those changes and for championing a wider conversation about the purposes, direction, ideas and practices that would make work meaningful for individuals and make business contribute to the world. We put our themes on the cover of the first issue of Fast Company: work is personal–and by that we meant that the individual was the most important factor in work, that one person could make a huge difference; computing is social–that the new technologies in the work place would connect us all in new and powerful ways, and create a new social context for people’s work; knowledge is power–that ideas were the source of competitive advantage, and that we were all living in a knowledge-driven economy; and break the rules–that the status quo was over, and that we all had to invent the new practices, strategies, techniques, and tactics that would make for success in business and in life. Looking back, I think we were spot on. Those were the themes then that people had to make sense of, and they’re still the dominant themes of our time.

Morris: As you reflect back over your life, other than a family, who has had the greatest influence on your personal development? Please explain.

Webber: Other than family? Teachers. Teachers at every level of school, both formal and informal. I was fortunate in that my mother and father were great believers in the power of education to shape a life. They fervently believed that education is the ladder of opportunity, and so they sacrificed to send my brother and me to good schools at every step of our lives. Along the way I was exposed to teachers who taught me how to read and write, how to think, how to make sense out of the world, and why it matters that we care deeply about the things going on around us.

Morris: The greatest impact on your professional development?

Webber: After I graduated from college, I went out to Oregon. I ended up getting a job in the office of then-City Commissioner Neil Goldschmidt, and one year later, Neil became mayor. For the next 6 or so years I was part of a team in the mayor’s office and in city government that was dedicated to creating a better future for Portland, Oregon. That was an incredibly dynamic time in the life of that city. Citizens were energized, the city government was an active partner, the whole region and state perceived that the future was at stake. I learned an enormous amount about how to make change, how to build and be part of a team, who to structure a strategy, how to communicate a larger vision–what it took to succeed in building an organization that could, in turn, build a movement. Then, when I was at HBR, I saw the same thing–only in the context of a magazine and a university, interacting with the larger business community. All of those lessons were the building blocks for what later took shape at Fast Company.

Morris: Here’s a hypothetical question. Let’s say that you are hosting a dinner party and can invite as your guests any five people throughout history. Who would they be? Please explain the selection of each.

Webber: Wow! That’s one of those questions where you’d like to have multiple sets of five, so you could build a variety of experiences to cover all the things you’re interested in! Let’s see: Julius Caesar–general, leader, author, and historical figure about whom I’m simply curious; Socrates–how much do we owe the Greeks in all respects, and who would you like for a better teacher? Thomas Jefferson–for his astounding scope of skills and talents, intellectual, political, artistic; James Joyce–just for the chance to hear him talk about writing; and then I’d save one slot for a last minute inspiration, for someone I haven’t been able to conjure up under the pressure of your question, but who I know I’ll think of once the dinner party actually approaches.

Morris: Despite have direct success to more and better sources of information than ever before, many executives have what Jeff Pfeffer and Bob Sutton characterize as a “knowing-doing gap.” In your opinion, why?

Webber: I wrote it in Rules of Thumb: knowing it ain’t the same as doing it! Information can be a source of power–or paralysis. And, of course, there are lots of different ways of knowing. There’s theoretical knowledge–and there’s applied wisdom. I’ve witnessed business executives (and elected officials) who know a lot of things, but have a hard time moving from thinking to doing. They may lack decisiveness, or they may not trust their own judgment, or they may simply be frozen by the pace of change and the risk of failure in the face of so much external uncertainty. I don’t think you can teach courage. Or conviction. Top executives today are under enormous pressure to make money or lose their jobs; to feed the company’s stock price or lose the support of the board. Turnover rates are astronomical and tenures are short. The pressure drives people to make bad decisions–or no decisions at all. In some respects it’s an issue of individuals at the top and what they have inside of them. But in other respects it’s a system-wide problem–we’re creating conditions for failure. Failure by individuals and wider failure that reflects a flawed system, based on flawed assumptions that yield flawed practices.

Morris: Looking ahead (let’s say) 3-5 years, what do you expect to be the single greatest challenge that business leaders will face? Any advice for them?

Webber: Every where I’ve traveled recently–and I’ve been all over the world in the past year or two, from Tanzania to New Zealand, Finland to China–I see the same two challenges: change and leadership. Every day brings new surprises–in politics, economics, science, technology, business, you name it. The pace and trajectory of change is rapid and unpredictable. Any one who says he or she is actually “in charge” of their organization is fooling themselves. What they are, however, is responsible for providing leadership for their organization. Offering direction, articulating values, building a common culture of performance and integrity. And more than anything, making sense. Not just making decisions, but making sense of a world that is turbulent and uncertain. How do you do that? Listen and learn. Talk less and listen more. Read, travel, interact with people outside your own private circle. Get out of the bubble that is too often the reality of executive life. Think, for a change. Think about what matters to you and your organization. Think about what kind of team you want to build. Think less about your stock price and more about what you want to have as your legacy. Make decisions that you’ll be proud of, regardless of the outcome. Because the truth is, regardless of your illusions of power and money and position, you control a lot less than you think you do.

Morris: Now please shift your attention to Rules of Thumb. You state, “It’s time to rewrite the rules.” Which rules? Why rewrite them?

Webber: Whether we recognize it or not, our organizations, our systems, are governed by rules. Think of them as the default settings that define everyday life. Or the design specs that are embedded in our culture, in our society, in our companies and organizations. Usually the rules remain hidden, covered over by the outcomes they produce. We see the results, but ignore the rules. So we see that roughly half the kids who live in our big urban centers drop out of high school, fail to graduate with a high school diploma. That’s an outcome–but what was the design spec, the operating rule that produced that outcome? The unemployment rate in the U.S. is hovering around 10%; the richest 11,000 Americans have more wealth than the poorest 23 million Americans combined. Those are outcomes. What rules produced them? When we look at the operation of American business, we see that 70-80% of Americans get up every morning and trudge off to a job they hate! A job they hate!

And then we wonder about employee productivity, or morale, or the quality of service we get for our money. That’s a product of an operating rule, a rule that teaches business leaders how to run a company that may make money, but doesn’t make sense. We need to question the outcomes that we see around us every day in work and in life, and then unearth the operating rules that explain why we keep getting those same outcomes, year after year. Then we need to re-write the rules so we get different outcomes–better outcomes, more sustainable outcomes, more humane outcomes, more economically and socially viable outcomes.

Morris: To what extent (if any) is the book published by HarperBusiness significantly different from the book you originally envisioned?

Webber: Well, I was hoping it would have illustrations (but I didn’t produce any, so I guess that one’s on me). Other than that, the book HarperBusiness produced is totally faithful to what I was hoping for. In fact, I got nothing but fantastic encouragement and support from the publisher; I was enormously fortunate to have that kind of backing, as well as freedom, to do this book the way I wanted to do it.

Morris: Presumably your 52 rules came from a variety of sources. Was there any one source of special significance?

Webber: Work and family. Each of my “jobs” taught me a lot, from my years in Portland, Oregon in the mayor’s office, to HBR, to Bill Taylor and the team at Fast Company. And my family features in the book all along the way–I talk about my mother and father, my older brother, Mark, my wife, Frances, and my children, Adam and Amanda in the rules, and then underlying the rules. Influence tends to be cumulative, and then for a story, you have to pick a moment or an anecdote to create a narrative that encapsulates what is actually a much larger story.

Morris: In the first chapter, you suggest, “The best way to create the future we want is to share what we know with each other.” I agree and am convinced that social media offer unprecedented opportunities to do that with ever-increasing speed, scale, and impact. What do you think?

Webber: Absolutely! We’re all in this together! And if you look at what social media offers, we’re finding new ways of connecting every day. Now the boundaries of time and space, of geography and organizations are all permeable. That means we can all help each other, learn from each other, teach each other, share what we’re learning and what we care most about. Of course, it also means we can fritter away our time and energy on endless amounts of twaddle! In the end, the technology is neutral and what we do with it is everything.

Morris: When creating the future, what should its foundation consist of?

Webber: Great question! I’ve been thinking lately: in a world of change, what isn’t changeable? A number of things have occurred to me, some when I was in Tanzania with a tribe of hunter-gatherers: how have they survived for 70,000 years? What are the deep well-springs of sustainability? Things like a deep regard for nature. An understanding of what works, what actually works in nature, and what doesn’t work. Adaptability to certain kinds of forces that are larger than you are, and then deep attachment to values and practices that define what you stand for. Ultimately, it’s some combination of profound values that have guided humans for a long time–equity, justice, dignity, kindness–and the application of Darwinian principles of adaptability and pragmatism.

Morris: To what extent (if any) do technologies dehumanize people?

Webber: When the technology becomes an end in itself, then we’ve lost our perspective on what it means to be human. It happens when we let it; what’s the old saying: FIrst we make our tools, then our tools make us. It’s easy to get lost in your technology. But most of our machines come equipped with off buttons. As long as we retain the old skills of drawing by hand, writing by hand, hiking on foot, singing, talking, and listening, we can cure ourselves of technology overload. Just stay in touch!

Morris: I am a father of three sons and a daughter as well as a grandfather of ten. It will come as no surprise that I have learned a great deal of practical value from all of them, especially when they were small children. Picasso claimed that he spent most of his adult life trying to see the world the same way he did as a child. What do you make of all that?

Webber: I’m old enough to think that life runs like electrical currents. It runs one direction when you’re raising your kids, and then, magically, at some point it the current reverses direction and your kids raise you! It’s a beautiful and scary thing when it happens–and also a part of the nature of life, I suspect.

Morris: Which of the 52 rules seems to be the most difficult for most people to follow? Why?

Webber: The soft stuff is the hard stuff. Tom Peters wrote about that rule in In Search of Excellence and Jim Collins made it the cornerstone of Good to Great. But when you look at what American business actually practices, the hard stuff is still the hard stuff. Creating shareholder value is the mantra of American business, and finance is the temple where most business leaders go to worship. What continues to get overlooked is that people are the foundation of performance. Hiring great people, giving them the culture and the tools they need to do great work, rewarding them for their great work, promoting them, developing them, advancing them, creating a climate of trust and loyalty–that’s what makes great companies. And produces great results, including financial results. But for some reason, American business leaders focus on the end–the financial results–and skip over the people part of the equation. It’s a lesson that seems to elude the thinking of too many business leaders, perhaps because it doesn’t feel macho enough.

Morris: Here’s a related question. Which of them have you found most difficult to follow? Why?

Webber: Rule #33: Everything is a performance. I admire great performers, some of my old Fast Company colleagues who have evolved into brilliant speakers on stage, with advanced multi-media presentations that carry their messages onto the web and gain them great followings. But for some reason, when I go to put on a performance, I get short-tempered and impatient! I just want to cut to the message and get to the point! So my performances tend to be, um, non-performances, at least in my eyes. I’ve got great stories to tell, and lots of anecdotes to back up my presentations and the thoughts I’m trying to get across. But for some reason, I’ve avoided (or perhaps refused to learn) the real art of performance, of putting on a show. Tough to teach an old dog new tricks, I guess.

Morris: During the course of writing Rules of Thumb, were there any head-snapping revelations?

Webber: Not so much head-snapping as heart-warming. It was an excuse to go back and get in touch with people I’d worked with and known over a 40-year period, so the book served as a wonderful device for researching what happened “back then” and catching up with old friends by reliving things we’d done together. That made the experience even richer for me.

Morris: You assert that Rule #1, “When the Going Gets Tough, the Tough Relax,” touches every other rule. How so?

Webber: Everything I’ve ever done has shown me that the biggest enemy we all need to learn to confront is fear. Fear of failure, fear of criticism, fear of being shown up in public, fear of not living up to your own expectations, you name it, humans have learned how to be afraid of some aspect of it. It’s what freezes us in place, what stops us from growing, what takes our dreams and hopes and aspirations and sticks them in the deep freezer. So if you really want to work on living a fully life at work and at home, start by recognizing, acknowledging, and confronting whatever your fears happen to be.

When I’m talking with young people about their work lives, I always ask, What’s the worst thing that could happen? It usually turns out that what they’re imagining as a horrible disaster isn’t horrible or a disaster. It might look like failure. It might feel like a setback. But it is usually not life-threatening, and when they hold it up and look at, they learn to laugh about what could go wrong. And, of course, we all know that the truth is, failure is how we learn and how we grow. Pain is required; suffering is optional. So learning to deal with your fears is how it all starts.

Morris: Have you formulated any additional rules since the book was published?

Webber: Absolutely! And I’ve had readers send me their rules. Rule #52 says “Stay alert! There are teachers everywhere!” That’s undoubtedly true. The more I travel and meet people who aren’t like me, the more I learn what they use for rules. People don’t always formulate their “inner design specs” as rules of thumb. But when you read an op-ed in a newspaper or a column on the web, you’re encountering somebody’s version of a rule of thumb.

Morris: Is there any one rule among the 52 that you think is of greatest importance to those who have only recently embarked on a career in business?

Webber: Rule #23: Keep two lists. What gets you up in the morning? What keeps you up at night? If you’re just starting off, it’s the best time to do a serious inventory of your own inner self. What really gets you excited in the morning? What can’t you wait to do? When you’re headed off to work, what are you looking forward to? Is it working with a terrific colleague? Interacting with interesting customers? Solving difficult problems? Coming up with new ideas? Proving how dependable you are? Keep a close watch on yourself–monitor what makes you tick. And the same when you turn off the light and call it a day. What is the last thing you’re thinking about? What keeps asserting itself in your mind as something you just can’t shake? Maybe the thing in the back of your head during the day comes to the front at night, and reminds you that you’ve got a deep personal feeling about the lack of parks in your neighborhood. Or the way your community deals with recycling. Who knows? It could be anything. But pay attention to those signals, and try to find a way to bring those signals and your own life into some working arrangement. I’d say, listen to what you’re trying to tell yourself, and start now, because it only gets more difficult over time.

Morris: What about those who are underemployed or unemployed?

Webber: Same thing. It’s easy to get discouraged and start to think that there’s something wrong with you, or that you need to take short-cuts to find a path to the future. You can always try harder, of course. But first, see if you can try softer. Listen to what you want to do, how you want to spend your time, what would really tap into your passions and your talents. You may have to make a sacrifice to do it, but you’ll be working on something that matters to you, and it could lead to opportunities you’ve never even thought of. What amazes me, frankly, is how many people are willing to tolerate a really crappy job or a bad work situation, just because they have no other option. In my view, life is way too short and way too valuable to be “tolerated.” At a minimum, if you’re work isn’t satisfying, make sure you have a hobby or do volunteer work or make some kind of a contribution that gives you a sense of satisfaction and participation in something that matters to you and to others.

Morris: Your chapter titles are brilliant. I’ll cite a few in sequence. Please explain the key idea for each. Let’s begin with “Ask the Last Question First.”

Webber: As usual, a story goes with it! In this case, in the beta issue of Fast Company we had a brilliant essay by Mark Fuller, one of the founders of Monitor and a devotee of military strategy. Mark wrote an essay called “Business As War,” and in it he raised a fascinating question: How did the United States manage to win every battle in the Vietnam War, and yet lose the war? The answer he provided, which applies equally well to business or military strategy is, the U.S. failed to “ask the last question first.”

In other words, the U.S. never asked, “What’s the point of the exercise?” “What’s our definition of victory?” Usually that question comes last; but before you embark on any campaign, you need to have asked it, and answered it. So “ask the last question first,” has become for me a shorthand way of saying, be sure you know why you’re doing something before you try to do it. Why are you trying to launch that company? Why are you trying to entrepreneur a new product or service? What’s the point of the exercise? And what’s your definition of victory?

Morris: “The Difference Between a Crisis and an Opportunity Is When You Learn About It”

Webber: Another story! My friend Leif Edvinsson, a Swedish knowledge guru, told me the story of Ragusa, a town that for centuries flourished in the Mediterranean as an independent republic despite being surrounded by more powerful, larger, and more aggressive empires. So the question Leif was interested in was, how did Ragusa keep its independence and also thrive commercially. When you go back and look at history, the answer is that the Ragusan Senate had a highly developed system of ambassadors who were deployed to the various power centers around the world.

Every month the Ragusan ambassadors would send back dispatches, answering questions asked by the Senate. Think of it as the world’s first knowledge sharing system, a version of the web before there was a web. Through the dispatches from the ambassadors, the Ragusan Senate knew more about what was going on around the world than any other body. They had more information, and they had it sooner. Knowing what the different empires were planning gave the Ragusans a huge advantage: time. They had an early warning system that gave them time to develop a strategy. So, it turned out, what would have been a crisis if they’d learned about it later, became an opportunity because they learned about it sooner.

Morris: “Good Design Is Table Stakes. Great Design Wins.”

Webber: We are living in an era that is marked by design. Product design, process design, organizational design, business model design, web design, social media design, human factors design–you name it, design is being used to address it. But there’s good design, and then there’s great design. You know brilliant design when you see it, whether it’s in a consumer product or a business strategy. Today, design is the solution to every problem–but too often we get superficial design solutions. Design that’s only good or fair won’t win. If you want to use design to differentiate your offering, or to create extra value, or to provoke your community to respond, or to build a closer relationship with a customer, whatever your goal, you’ve got to shoot for great design. Which is hard work, lots of iterations and patience, and a healthy dose of inspiration! But don’t settle for good design. Go for great design.

Morris: “Simplicity Is the New Necessity”

Webber: I don’t know about you, but for me, the world is filled with complexity. Things that were supposed to make our lives easier only seem to make them more complicated. So if you go back to what I just said about design, one question could be, “How can you use design to make your customer’s lives simpler?” If you can find a way to reduce the friction of daily life by whatever you offer your customers, I can guarantee you a large and growing base of stark raving fans! But be warned! Like great design, simplicity is hard to achieve! It takes real work to refine something down so that it’s as simple as possible, but no simpler than that. We all want choice, but we don’t want useless choice or stupid choice or unnecessary choice. So figuring out how simple you can make something is a real art.

Morris: “If You Want to Think Big, Start Small”

Webber: The Silicon Valley mantra has long been, “Get big or go home.” But when I look at brilliant innovations that I admire the most, they tend not to follow that iron law. They tend to have started as small, tentative startups, very modest, and driven not by the need to get big, but by the need to be authentic. Think of a social change program like When it was started, its founders simply took the plunge after getting years of advice from VC types on what they needed to have a business that would grow. All they knew was, there was a great need to help poor people in Africa and that micro-finance over the web could help. So they did it. It was a “Petri-dish startup.” Very small and very authentic. Today it’s a huge success, but not because the founders devised a dramatic growth strategy. But because they stayed close to the ground, paid attention to what worked and what didn’t, and followed an authentic path that was true to their mission. These days, social media and iPhone apps often start as “Petri-dish sized” experiments. If they work, they can grow. If they don’t work, they can pivot, adapt, or, sometimes, give it up and try something else.

Morris: “Tough Leaders Wear Their Hearts on Their Sleeves”

Webber: My friends, Dev Patniak and Peter Mortenson at Jump, wrote a terrific book about the power of empathy. It’s powerful, I suspect, because it’s counter-intuitive. In the world of Wall Street and big business, leaders are supposed to be stoic. Never let them see you sweat! Check your emotions at the door! My experience tells me, real leaders have strong emotions, great hearts, and the capacity for real empathy. If you want people to follow you, you have to care about them. You have to care about your customers. You have to care about a lot of things that are a lot more important, a lot more vital, than just making money. If you want people to see you as a real person, show them that you care. Then they’ll follow you wherever you lead them.

Morris: Why should aspiring leaders “disarm their border guards”?

Webber: This rule starts with a story about my brother, Mark. Years ago, back in the late 1960s, he and I were traveling together through Europe in a VW that he’d bought as a student in Germany. We went to Prague, but to get back to West Germany, we had to cross through East Germany (I told you it was a long time ago). We went to an East German check point and there the border guards decided to have a little fun at the expense of two young Americans. So they made us sit for hours while they pretended to go over our papers.

Finally, Mark had had enough. He signaled for one of the East German border guards to come over and then said, in perfect German (since he was on his way to becoming a German professor), “I think one of the other guards took our papers and has probably run off to West Germany by now!” The guard, who was huge and carried an automatic weapon, turned on his heel, went to the guard booth, got our passports, and waved us through. It made a huge impression on me. We all have border guards, especially when we’re in leadership positions in business. The border guards are supposed to keep us secure. But most of the time, they don’t keep us secure–they keep us in the dark. They keep out unwelcome information. They prevent us from dealing with unpleasant news or difficult developments. If you want to be a leader today, you’ve got to disarm your own border guards. You’ve got to let in the news–especially the news that’s hard, unpleasant, or upsetting. Because if you stay in the dark, you’re bound for failure, in the end. Border guards don’t make you safer; they make you more vulnerable when change happens.

Morris: Almost 20 years ago in a commencement address at Stanford as well as in an article for Harvard Business Review, Teresa Amabile affirmed the importance of doing what you love and loving what you do. In your opinion, what sacrifices must be made for that to happen?

Webber: You have to sacrifice the approval of others. You have to sacrifice the need for external validation. You have to put your own convictions ahead of other people’s judgments. In America, because we measure success in dollars, you have to let go of that metric and substitute your own. But it’s only a sacrifice in the sense that other’s look at you from the outside and feel you’ve given up something valuable. Once you’re on the inside, living with your own convictions, you realize that they’re the ones making the sacrifice. They’re sacrificing an independent life for a life of dependence and the pursuit of financial rewards. But what happens? People make a lot of money in America–and don’t find what they’re looking for. In some respects, that’s the key lesson from the last crash on Wall Street. The investment banks and bankers got rich, but the way they went about it destroyed the global economy, produced the equivalent of national bankruptcies in Europe, demolished the lives and savings of millions of Americans, and garnered the mistrust and profound anger of most Americans. They sacrificed their integrity and the well-being of millions of people for the sake of the pursuit of personal wealth. Why is that a good deal for any one to make?

Morris: What’s your next adventure in the vineyards of free enterprise? A book, perhaps?

Webber: These days I’m a “global detective”–perhaps the world’s only global detective–traveling and looking to unlock mysteries in the way the world works, and how to make it work better. I’m studying how change actually happens, how solutions emerge to problems that appear to confound us. There may be a book that comes out of, or a conference–we’ll see.

Morris: Which question had you hoped to be asked during this interview – but weren’t – and what is your response to it?

Webber: Thanks for the great interview! And thanks for giving me the chance to be part of your own adventures! Now: What’s the point of the exercise for me? Well, I suspect it has to do with work and family, with the wonderful people I’ve met and worked with and continue to meet and work with as I travel and write and speak all over the world. It’s a joy to watch my two children grow up and learn their own rules, and teach them to me. My wife continues to pursue her own work and demonstrate great design thinking and grounded ways of living. And I’m always made optimistic when I encounter people who are working at the grass roots level to bring about change, inventing solutions that work for problems that matter. That keeps me learning and growing and having more than my share of fun in the world!

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Alan Webber invites you to check out these websites:


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