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time is short, this period may be brief, but often you have
several days. Few important management decisions are made
under acute time pressure, and good organizations and good
managers make sure there is enough time for decisions that
matter. And the reason, as before, involves process. For a final
decision, however, the process that matters takes place in your
mind and heart. And, fortunately, there are several steps you
can rely on because, for centuries, they have guided the intui-
tive judgments of men and women facing hard decisions.
Get Off the Merry-Go-Round
Shakespeare’s Macbeth is a dark, turbulent story of ambition,
treachery, and moral collapse. So it is easy, while watching or
reading the play, to overlook the three-word phrase in which
Shakespeare distills a crucial piece of guidance—something
Macbeth failed to follow in his headlong rush to disaster. The
phrase is “the pauser, reason.”
14
The first step in testing and tempering your intuition is
as much physical as intellectual or psychological. It is taking
time out. This means you ending your conversations with
others about the problem, closing the door, muting the elec-
tronics, and then looking out the window or gazing at the
wall. It means finding a convenient and comfortable way
for you to step back, if only temporarily and partially, from
everything going on around you.
As Shakespeare emphasized, reason involves pausing—
as do imagination, feelings, convictions, and the other ele-
ments of a tempered intuition. The first four questions and
the humanist perspective they represent are crucial ways to
slow down and look carefully at a situation or problem. And
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132
the deeper suggestion in Shakespeare’s phrase is that those
who haven’t paused probably haven’t reasoned or deliberated.
They may instead be plunging ahead, missing important
insights, courting danger, or doing damage, because they
are the unwitting puppets of the emotions, drives, and biases
compressed in their unexamined instincts.
Use All Five Questions and
Don’t Pick Your Favorite
There are two ways to view the long-standing and apparently
permanent disagreement among serious thinkers about the
right way to make hard decisions. One is the skeptical or cynical
view. It sees the whole effort as the intellectual version of a circu-
lar firing squad: each way of thinking undermines and discred-
its the others, no single, sound approach emerges, and all we
have left is disagreement and confusion. As a widely respected
political theorist put it, “The substructure of the ethical world is
a subject of deep and apparently unending controversy.”
15
The other approach is the one in this book: seeing these
powerful arguments and their insights about decision mak-
ing as a long and illuminating conversation about a real-
ity—the essence of judgment and sound decisions—that is
intrinsically multifaceted. There is no single, final, simple
insight that comes in a nice little box with a bow on top.
In this great conversation, no one view of ethics or decision
making has won out—because human beings and our lives
together are simply too varied, subtle, and complex. Each
voice in the great conversation provides valuable, if partial
insights for men and women facing difficult decisions. This
is why William James, one of the founders of American
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133
pragmatism, wrote, “Facts are good, of course—give us lots
of facts. Principles are good—give us plenty of principles.”
16
An old saying tells us that we see the world, not as it is,
but as we are. In other words, thoughtful, intelligent peo-
ple, looking at the same situation, will differ about what the
situation is and what to do about it. The four questions are
antidotes to the hazards of this reality. They can help us to
some extent see the world as it actually is or at least see it
as others see it. Sound deliberation counters the temptation
to grasp hold of a single grand principle and use it to dom-
inate other ways of thinking. This means viewing the five
questions, not as majestic, final truths, but as useful, every-
day tools. Carpenters work with toolboxes. They don’t try to
do everything with a saw or a screwdriver. The same, sensi-
ble approach works for the great humanist questions. This
means desanctifying and demystifying them, seeing them as
implements, and using them all.
This approach improves deliberation and judgment because
the questions complement, correct, and strengthen each other.
To see this, think about people you know. Some think natu-
rally in terms of consequences, some feel strongly obligated
by their duties, others are naturally or even disturbingly prag-
matic, and some seem to embody, in what they say and do, the
important values of a community or organization. Each of us
has natural grooves in our thinking, and this can lead to prob-
lems. People who think only about consequences can trample
on basic human duties. Pragmatism alone can be amoral or
worse. And a preoccupation with the values that bind a group
together can obscure serious consequences for people outside
the group and strong duties to them.
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134
The fifth question—What can I live with?—is danger-
ous if someone uses it as the only question, rather than the
final question. That is because the first four questions serve,
in effect, as border guards policing a territory. Within this
territory, managers can trust themselves to make sound deci-
sions—on the basis of their convictions, their judgment, and
their sense of what is right for their organization in a partic-
ular set of circumstances. But the border guards limit this
freedom. Its exercise can’t impose significant hardships on
others, violate basic duties, or ignore the values that define an
organization. That is why the second piece of guidance for
final reflection says to use all five of the questions, rather than
rely on your favorite one.
Expect to Struggle
Notice how the fifth question is phrased. It doesn’t ask about
what is best or what is right. Instead, it suggests a more mod-
est and realistic standard: simply being able to live with and
accept a decision. Put differently, the fifth question recog-
nizes that what managers have to struggle with are often
questions like these: Which option am I least uncomfortable
with? Which option will lead to the fewest regrets?
These questions reflect the basic nature of gray areas.
Discomfort and misgivings come with the territory. Gray
area problems have no easy answers. They involve hard
choices and difficult trade-offs. And, even when managers
do all they can to get these decisions right, they often have to
live with troubling uncertainty about whether they made the
right decision and whether their efforts will accomplish what
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135
they want. In a gray area, struggle is usually a sign of serious
thought and effort.
For example, Alisha Wilson said she lost “a fair amount
of sleep” as she tried to decide what to do about Kathy
Thompson. Wilson’s main concern was that whatever prob-
lem was causing Thompson’s failure at work would also keep
her from getting the help she needed after she lost her job. In
the end, Wilson met with Thompson several times. The con-
versations were awkward because Wilson was walking a fine
line between her duty to respect her assistant’s privacy and
the potentially dire consequences of simply terminating her.
Wilson wanted to help Thompson but, as her boss, she felt
she had no right to intrude into her employee’s personal life.
Finally and reluctantly, Wilson told Thompson she was
likely to lose her job and that she needed to look into getting
long-term disability coverage before this happened. Thompson
eventually followed this advice and, later on, Wilson helped
her find an attorney to assist with the complicated applica-
tion process, because Wilson didn’t think Thompson could
handle it on her own. However, despite all her efforts, Wilson
was never sure she had done the right thing. Perhaps she
pushed too hard; perhaps she didn’t do enough. All Wilson
knew for sure was that, several years later, no bad news about
Thompson was circulating through the grapevine.
Two lessons about reflection and expectations emerge from
this incident. One is that reflection on gray areas often means
feeling anxiety, hesitating, going back and forth, and losing
sleep. None of these reactions are signs of failure. In all likeli-
hood, they show that someone really understands a situation,
grasps what is at stake, and sees the challenges of resolving
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