Leaders Make the Future

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Dilemma Flipping

Ability to turn dilemmas —

which, unlike problems, cannot be solved —

into advantages and opportunities.

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The test of a fi rst-rate intelligence is to hold two opposing ideas

in mind at the same time and still retain the ability to function.

One should . . . be able to see that things are hopeless yet

be determined to make them otherwise.

F. SCOTT FITZGERALD

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LEADERS MAKE THE FUTURE

Holding “two opposing ideas” in mind will be even more

important in the future than it was when Fitzgerald observed this

in 1936. In fact, there will sometimes be more than two opposing

ideas

—all of which have some validity. Leaders will need to learn to

like this space and make decisions, even when they cannot succeed

by problem solving.

More volatility, uncertainty, complexity, and ambiguity means it

will be harder to see through the mess. The dilemmas of the future

will be more grating, more gnawing, and more likely to induce feel-

ings of hopelessness. Leaders must be able to fl ip dilemmas over and

fi nd the hidden opportunities. They must avoid oversimplifying or

pretending that dilemmas are problems that can be solved. Dilemma

fl ipping is the recurrent skill that leaders (many of whom were trained

as problem solvers) will need in order to win in a world dominated by

problems that nobody can solve.

Many people will fi nd it hopeless. Certainly, we all have those

moments

—and looking ahead ten years may spark more of them—

but the lesson for future leaders: nurture the ability to engage with

hopelessness, learn how to wade through it to the other side, and fl ip

it in a more positive direction. Dilemma fl ippers turn hopelessness

into hope.

My defi nition of a dilemma is a problem that cannot be solved

and will not go away. The traditional defi nition of a dilemma was

the choice between two equally bad options (often referred to as a

“Hobson’s Choice”). The challenge for leaders is to fl ip the dilemma

into an opportunity. At Walt Disney World in Orlando, for example,

standing in lines has always been a dilemma. Nobody likes to stand in

line, and there is strong evidence that the guests are less patient than

ever. Still, Disney doesn’t want long downtimes when there is nobody

ready to ride, so they make the waiting experience as pleasant as

possible. They have made a number of attempts to fl ip the waiting

dilemma, including video entertainment and indicators about how

long the wait will be from a particular point. Another interesting

innovation is Pal Mickey, a stuffed Mickey Mouse doll that entertains