Everything I Know About Business I Learned from Monopoly

I design games for a living. Not video games, but the traditional kinds of games played on boards or with cards—the kinds of games where what happens off the board is just as important to the experience as the physical game itself.

It’s a great job and often a challenging one. We game designers strive to engage people in strategic pursuits and compel them to want to win at them. We attempt to provide clear structures and objective ways to keep score. We try to create settings where people challenge each other in nonthreatening ways and come away feeling the better for it. More than anything, we want to convince people with little time that playing our games is the best way to spend it. On some level, these goals are the objectives of managers in business, too.

How much of what game designers do is applicable to management? In this article, I attempt to translate various facets of our craft, but you’ll probably find your own valuable connections as well. At the least, you’ll pick up some tips that will improve your chances of winning Monopoly. In addition to being a game designer, I’ve also been an executive for more than 20 years, first at Parker Brothers, where I led the R&D team, and more recently at Winning Moves Games, the company I founded in partnership with three other game designers. To the extent that I’ve been successful in business, it may well be because I’ve approached my work in a gamelike fashion.

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Principles of Great Game Design

The first thing to understand about games, and why people like them, is that they are structured entertainment experiences. This means that a game designer must do two things: provide an orderly environment and make sure that the environment generates fun. Over the course of my career, I’ve seen many successes and failures in both of those realms. These experiences have led me to a set of principles of great game design, which I share below. The first few of them deal with structure, the rest with providing entertainment.

Mind you, just knowing the rules of a game doesn’t guarantee a win. Each of these principles requires judgment and finesse. But the payoff that comes from successfully applying them is what keeps us all trying. Once a game becomes well established—like Monopoly or that great game of detective work, Clue—it’s very difficult for another game with a similar theme to succeed. And if a game endures for a generation, it can probably live forever.

Principle 1: Make the rules simple and unambiguous.

Providing the orderly environment required by a game might sound like a straightforward task, but in fact it has to be done with real creativity. By definition, a game is interactive; it’s not something you experience passively like scenes in a movie or words on the pages of a book. Thanks to that interactivity, a game can be far more engaging. People love to use their imaginations and concoct their own fantasies. But people can also find a game bewildering if they aren’t given a sound structure and clear guidance. Then their imaginations will be stifled, and the experience they’re seeking will never have the chance to unfold. The same is true, of course, in business. People engage most and their talents flourish best when job responsibilities, business objectives, and evaluation criteria are clearly understood.

In a game setting, structure and guidance come mainly from rules; a game will fail miserably if it doesn’t have clear rules that avoid controversy. This clarity, after all, is the essence of how games improve on the real world, which is very inconsistent and unpredictable—and therefore frustrating. In life, the rules always change: Banks suddenly increase the deposit levels required for free checking; schools alter the course requirements for graduation. By offering known and unvarying sets of options and outcomes, games can provide real comfort—especially when the rules are also kept simple. Which brings me to principle 2.

Principle 2:Don’t frustrate the casual player.

The problem with the rule to keep things simple is that designers can’t resist breaking it by trying to design something impressive and innovative. To use an analogy from publishing, they aim for literature in a market accustomed to pulp fiction; they want to create masterpieces. That impulse, if left unchecked, leads to failure. There are simply too few avid game players in this country. Their numbers continue to shrink because of the wealth of entertainment options available today compared with 20 years ago. If a game is to last more than a few months after its launch, it must appeal to a critical mass of casual game players, people who will rapidly comprehend and enjoy playing it. Complicated rules and subtle nuances make a game difficult to grasp and may make players feel stupid instead of empowered and enlightened.

Here’s a great example of a success and a subsequent failure by one design team. In the early 1980s, a new game called Trivial Pursuit took the market by storm. It was very simple to play; anybody could roll the dice, advance the spaces, and accept the challenge of answering a trivia question. But the appeal of its subject matter touched a responsive chord in millions of baby boomers. Trivial Pursuit achieved more sales in one year than any board game before or since. Naturally, the four inventors—who had not been professional game designers before that point—were suddenly major figures in the world of games. Demand mounted for them to design another hit, and they took that assignment very seriously. Perhaps too seriously. Their sophomore effort was a game called Ubi, which focused on world geography. The new game contained intricate rules and featured novel kinds of pieces. There was even a clever, unifying concept featuring triangles and groups of three. Do you remember Ubi? If not, you’re not alone. It was, as we say in the business, nailed to the shelf. Aiming for a masterpiece, the inventors lost sight of the simplicity and elegance that were the foundation of Trivial Pursuit’s success, and consumers rejected their efforts.

I too have learned this principle from personal experience. Years ago, I invented a business game called Cartel, in which players competed to acquire many companies and build up huge conglomerates. To this day, it shows up on the “desert island” lists of dedicated game players, which gives me real pride. (You might find it offered on eBay, likely at several times its original price.) Cartel failed with casual game players because it required a comfort level and fascination with financial strategy not found outside Wall Street or the economics departments of leading universities. (Ironically, Monopoly was initially criticized for similar failings—later I’ll explain why that criticism was misplaced.)

Am I claiming that, as H. L. Mencken is quoted as saying, “the masses are asses”? Absolutely not. But digesting complicated game rules isn’t how people today want to apply their overstressed intellects and spend their time. I suspect it’s not much different in most businesses: Not every employee wants to think like an executive. It’s important that a business’s environment be structured so that people at all levels can feel like a part of a team and contribute to the company’s success.

Principle 3: Establish a rhythm.

Just as important as effective rules is an intuitive sense of rhythm in a game. One aspect of rhythm comes from the number of players involved. Most successful games are designed for three to six players, but the ideal number is usually four because everyone’s turn arrives often enough to maintain interest. It’s probably a good guideline for business, too, to give everyone a turn, early and often, and even better if the “turns” involve rotating assignments. Many companies find it useful for their rank and file to experience the pressures and rewards of the jobs of their colleagues.

The rhythm of a good game, moreover, comes from a clear beginning, middle, and end. In a well-structured game, players can feel the shift occurring from one of these segments to the next. When a game begins, the mood is tentative as players start to position themselves in a hierarchy. Monopoly’s beginning phase, for example, focuses on contending with the luck of the throw and on buying indiscriminately. In this phase, accumulating property is a must in order to be a player in future negotiations. As the opening phase evolves, players grow aware of who’s in the lead, who’s in the pack, and who’s behind. As the game shifts to its middle segment, play becomes more intense. Players are jockeying for a clear advantage and trying to overcome any bad luck suffered in the opening phase. At this point, experienced Monopoly players become highly focused on acquiring at least one significant color group and rapidly developing it. The endgame of Monopoly usually occurs with the first bankruptcy. Now the game becomes a race for survival by the trailing players while the leader hopes the odds will continue in his or her favor. Inevitably, one winner emerges and takes all the money. Monopoly’s race to the financial finish is akin to other games where a token reaches an end space (Parcheesi) or a specified point total is accumulated (canasta). In the best games, the end comes with a bang, not a whimper. If a game paces itself effectively, people will instinctively know which phase they are in. If the pace doesn’t build, it’s not much of a game. It’s more like a lesson.

Is there an analogy for business to the beginning, middle, and end rhythm in games? I think so. A good manager might engineer these types of shifts over the course of a critical project—and be prepared for different moods and levels of motivation from people. An experienced manager, too, knows the difficulties that can arise in hand-offs between teams working sequentially. Think, for instance, of a group of product developers putting its latest innovation into the hands of the marketing department. The developers’ work on the product is in its breathless endgame while the work of the marketers is in the more tentative, less intense, beginning phase. No wonder it’s hard for the two sides to relate to each other and feel like they’re on the same team.

Principle 4: Focus on what’s happening off the board.

So far, the principles I’ve outlined have focused on providing structure. But structure isn’t everything. A game with a perfect set of rules and a sense of building throughout its phases won’t be played again if it doesn’t also entertain. Players are not going to come back unless they experience pleasurable emotions (which, in the context of a game at least, might even mean stress and fear).

The second challenge for game designers is to maximize the entertainment value. During a game, in addition to the actual play, people are affected by and participating in what’s happening off the board. That’s a function not so much of the game’s components but of how the players interact because of them. A well-designed game makes people feel better afterward—and for many players, that’s due to the larger social experience, of which the game is only the core activity. I believe this is why card and board games endure despite the onslaught of computer games. Computer games, as technically astonishing and adrenaline stimulating as they can be, are essentially solitary experiences. Even multiplayer computer games only support interaction about the games themselves. When three or four people sit around a table and play a traditional game, interaction is happening on many levels that cannot, at least yet, be replicated electronically.

Of course, I don’t mean to suggest that every traditional game enriches people’s experience off the board. In fact, two of the world’s most revered games are in marked decline today, which I would say is largely due to their antisocial nature. I’m referring to bridge and chess.

Both of these games require real applications of brainpower to win, and the norms that have grown up around them discourage players from making comments or betraying emotion during the course of play. Chitchat is distracting, and emotions cloud decision making. But I suspect the real reason for this quiet stoicism is that, because these games establish intellectual superiority, losers can feel humiliated, and emotions can turn ugly. Some of my least favorite memories of game playing are of evenings at bridge tables. I’ve been embarrassed to witness a loving husband or significant other berating his otherwise adored partner after each imperfect bid made and card played. Such a scene does not beg for an encore.

Today’s players don’t want emotional or social restraint from their games. Quite the opposite. Over the past few decades, what happens off the board has gained new emphasis. And so we’ve seen a new class of games arise, known in the industry as social games. Trivial Pursuit was the groundbreaker in this category and arrived on the scene at the perfect time. The TV-happy boomers, enamored of the kind of trivia knowledge this game tested, reached adulthood and were looking for new ways to socialize. With busy lives and often both halves of a couple working outside the home, they had little time for active involvement in the bridge clubs or social organizations their parents had favored. Instead, they became the first generation that graduated from childhood and still had a purpose to play “childish” games.

A striking feature of many successful social games is that they are based on ones that a lot of people have known for a long time. For example, Pictionary is just a 1984 commercial adaptation of a game known as picture charades, which had been played at parties for probably 20 years. Clearly, the important thing for a social game is not that it offer innovative play but that it make the play accessible and entertaining to the maximum number of people.

What’s the management analogy to focusing off the board? For one thing, a good manager thinks not only about whether an employee is challenged appropriately by an assignment but also about whether the person relates well to other team members and finds fulfillment in work. More broadly, of course, a manager must consider people’s work-life balance. An executive with a broad perspective will, for example, refrain from assigning the best project manager in the Houston office to a client in Winnipeg at the same time that the manager is planning her Texas wedding.

Principle 5: Give ’em chances to come from behind.

One of the trickiest aspects of game design is achieving just the right balance of skill and luck. If a game uses only skill, you have chess. And if it involves only luck, you have a child’s game—something like Uncle Wiggly or Chutes and Ladders. As this implies, different proportions of chance work for different levels of player maturity and intellectual involvement.

It’s very tough to make a game that can satisfy both those who prefer casual games of luck and those who prefer to use their heads. In 1999, my company developed Monopoly: The Card Game with the aim of providing the emotional high points of the original game but in much less time. Given Monopoly’s wide appeal, we knew we had to design a game that kids could find fun to play but that adults could also approach with sophisticated reasoning and decision making. I think we succeeded, despite having such a tough act to follow. A friend of mine once commented, “The reason Monopoly endures is that it’s 75% skill and 75% luck.” What he meant was, if you lose, you can blame it on luck, and if you win, you can claim to be a great negotiator and cunning strategist. (For more on how to win at Monopoly, see the sidebar “Confessions of a Monopolist.”)

Managers may benefit from learning some of the rules of games and game design. Undeniably, though, game players benefit from learning the disciplines of management. In particular, the spoils in Monopoly routinely go to the players who…

take a close look at return on investment. Casual players don’t know this, but the 28 properties around the Monopoly board are not equally valuable in terms of ROI. Boardwalk and Park Place, which many people regard as the most precious, actually are not. It turns out that the oranges and reds have the highest ROI and are the best properties to own. In part, it’s because there are three of each rather than two, so the odds of landing on these color groups are better. But these reasonably priced properties have something even stronger going for them: They’re perfectly positioned beyond the corner where jail is located. The odds of any player’s going to jail are reasonably high over the course of the game—and when that player comes out of jail, the chances of landing on an orange or a red are good. By contrast, the green properties, which lie just after the “Go to Jail” space, are far less likely to be landed on during the game. And they’re expensive to boot.

know the art of the deal. A player rarely acquires all the properties of a color group by actually landing on them. So a trade is frequently required to own a complete color group. This fact alone proves the merit of buying every unowned property you land upon. Then you’ll have property to trade to get what you want. Cash alone is insufficient to get a good deal. The first monopoly is a big event in the game. It skews the expected cash flow in favor of its owner. If the monopoly lies on the second or third side of the board, it may be enough to bankrupt opponents who haven’t faced reality and traded among themselves to establish competing monopolies.

make no enemies. Having material to trade is essential, but so is your conduct if you are to come out ahead in a trade. There’s an adage in game playing: Be the kind of player to whom others won’t mind losing. No one wants to lose, but if you’re going to, it might as well be to someone who’s gracious, considerate, diplomatic, and knowledgeable. Nobody likes to lose to a browbeater, a player quick with insults, or a know-it-all.

A casual player of Monopoly might think that it’s a game of chance and that the winner is determined by rolls of the dice. Watching the best players in the world in tournament play has shown me it’s not. The winners are actually masters of strategy and negotiation. They know how to minimize the impact of bad luck—and to put themselves in the way of an undue share of lucky breaks.

Even for mature players, a component of luck adds a valuable emotional payoff to a game by allowing for come-from-behind opportunities. Most of us love thinking, “The odds may be stacked against me, but just one great stroke and I’m right back in it.” A good manager holds out the same hope for a struggling employee. Of course, an employee should not be expected to rely on luck for a turnaround but instead should be given clear, attainable goals for improvement. In some instances, though, a recognition of the role luck plays is healthy. It can keep a trailing team from becoming demoralized and keep a winning team from resting on its laurels.

Principle 6: Provide outlets for latent talents.

Great games, and great workplaces, also offer outlets for skills that people would like to express but don’t use during their normal routines. And again, for game designers at least, a shift has occurred over time in how this principle is applied.

Chess and bridge had their heyday in the United States in the 1930s and 1940s, when wide-ranging opportunities to exercise intellectual powers or gain intellectual stimulation on the job simply didn’t exist. Then, the typical laborer’s job required doing essentially the same thing all day long. Not surprisingly, in their off-hours, people sought ways to sharpen and show off their analytical abilities. Now, however, people have so much complexity in their work and personal lives that they don’t often seek it in games. Instead, what appear to be missing are alternate forms of self-expression and ways to connect socially—chances to let down one’s hair, laugh, and have a good time. And people probably need outlets in business as much as in games.

The theme of a game can also provide escapist pleasure by tying into current interests or worlds people enjoy dreaming about. Certainly, that was the great appeal of Monopoly when it exploded onto the scene in the midst of the Great Depression. The game was initially thought to be too complicated for most players because of its reliance on financial calculations. It succeeded, though, because it arrived at a time when most people could only dream of handling large amounts of money, let alone acquiring property. Because it forced players to calculate like landlords, the game offered them much-needed vicarious pleasure.

Sometimes, game designers make the mistake of thinking they can improve on “games” found in real life. But there’s an industry axiom about stock market and horse-racing games, in particular: They never sell. The people who are attracted to those worlds generally have access to the real things. By contrast, the industry has produced many successful games with football themes. That’s a world (at least at the professional level) where most of us can only pretend to play.

Managers as Game Players

Many of the best Monopoly players come from business backgrounds; I observed this truth time and again over years of officiating at U.S. and world championships for Parker Brothers. For example, the 1983 world championship was held in Palm Beach, Florida. The grand prize was a substantial amount of money, but it carried a stipulation: It could only be spent in one afternoon on Worth Avenue, a tony district of shops in Palm Beach. Greg Jacobs, a real estate developer from Australia, won that year. Winnings in hand, he went first to one of the avenue’s fashionable boutiques and bought a souvenir scarf for his wife. Then, knowing that Parker Brothers was owned by General Mills at the time, Jacobs walked down the street to a brokerage and invested all the rest of his winnings in General Mills stock. I’ve always admired that coup. It was simultaneously a tough-minded decision to preserve his gain and a gracious nod to his generous host. Now, that’s a great player.

But if business training makes for a better game player, game playing also trains one for better business judgment. Maybe this is why companies are increasingly bringing game playing into the workplace. At the very least, an afternoon of playing games builds relationships among workers and increases the social capital within an organization. I remember just such an afternoon at Parker Brothers, when the HR department sponsored a business-simulation game for our factory workers. Afterward, camaraderie, mutual understanding, and cooperation improved markedly.

But workplace games can go further to combat small-mindedness and to help people recognize that they are part of a larger whole. Some excellent games are explicitly modeled after the very businesses using them. Andromeda Training is one company that designs and markets this type of simulation. Its managerial game Income/Outcome has been adapted for small companies as well as large corporations like Hewlett-Packard and AT&T. Employees playing the game become department leaders who must quickly learn the fundamentals of finance within their own type of business. Among other benefits, they experience the impact of profits versus cash flow and the importance of different departments working together to achieve success.

Finally, game playing in the work-place might teach managers to appreciate that the success of a game depends on how well it is designed—and that many design challenges have their equivalents in the art of management. I mentioned earlier that my managerial success is probably due to my game-like approach to my work. Does this mean that I think management is trivial or that it should be left to chance? Not at all. Playing games and designing them has conditioned me to play the game of business by the kinds of rules I’ve outlined here.

In many ways, workplaces are like games. Both can be structured to avoid controversy and even to sweep us up in exciting rhythms of activity. Both can engage us in challenging tasks while supporting rich experiences off the board. And ultimately, a great game or a great workplace can produce the same sentiments: If we’re challenged by and challenging others in nonthreatening ways, if we’re using pent-up skills that we’d love to express, and if we’re experiencing an emotional trip that ends on a high note—well, our time was well spent. And we’ll look forward to coming back for another round.

A version of this article appeared in the March 2002 issue of Harvard Business Review.