71
4
What Will Work in
the World as It Is?
Georges Frederic Doriot was an extraordinary individual.
He was French by birth, became an American citizen, taught
at Harvard Business School, served as a Brigadier General
in the US Army during World War II and worked on mil-
itary planning, and then founded the American Research
and Development Corporation. This was the first important
American venture capital firm, and Doriot is widely regarded
as “the father of venture capital.”
1
He was also known for his
practical wisdom. For example, Doriot often gave managers
this advice: if you have to choose between a great strategy
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Managing in the Gray
72
with a good action plan and a good strategy with a great
action plan, you should pick the second option.
2
In short, what mattered for Doriot was what worked.
“Without actions,” he once said, “the world would still be an
idea.”
3
This way of thinking is the basic premise of the third
crucial question. It asks: What will work in the world as it is?
And that is, of course, an utterly unsurprising question for a
manager—except for the phrase at the end, “in the world as
it is.” Those are the words of Niccolò Machiavelli. They were
his way of saying that leaders who faced hard decisions had
to be, above all, realistic and pragmatic and not let idealistic
notions distort their thinking.
Machiavelli can seem like a very odd choice for a humanist
perspective on hard decisions. He was, indeed, a humanist,
but his ideas are widely reviled. Machiavelli lived in Florence
during the late Renaissance and served the Medici as a senior
government official, so he understood politics and leader-
ship from the inside. He was also a prolific writer and is best
known for his handbook of political leadership, The Prince,
which is still widely read and discussed—and condemned.
Machiavelli is also known, fairly or unfairly, for saying that
the ends justify the means and believing that the means could
be deceit, treachery, a poisoned chalice, or a stiletto between
the ribs. The British historian Thomas Babington Macaulay
began his account of Machiavelli’s thinking with the warn-
ing, “We doubt whether any name in literary history be so
generally odious as that of the man whose character and
writings we now propose to consider.”
4
So should Machiavelli be mentioned with John Stuart
Mill, Confucius, Aristotle, and Thomas Jefferson? How can
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73
a reprobate of historic proportions serve as a guide to effective
and responsible decisions? These questions seem serious—
until we ask something else: Would we know Machiavelli’s
name today, if all he said was that you can get ahead in life
by being sleazy? This observation hardly merits five hun-
dred years of renown. All the ancients—Greek, Roman, and
Chinese—understood that power-hungry, savvy, unscru-
pulous people could do quite well in life. Almost all of us
think we know a few people who succeeded because they
were fairly smart, worked reasonably hard, had some luck,
and were willing to cut corners or worse.
Machiavelli must be telling us something more. That
would explain why his guidance endured for centuries. So
what does his voice contribute to the long conversation about
power, decision making, and responsibility? And what advice
does he have for managers working on gray area problems?
The World as It Is
The basic answer to this question is that Machiavelli believed
that, if you have serious responsibilities, you must avoid the
trap of seeing the world as you want it to be. You have to
keep your eyes wide open and see the world as it is. That
means Machiavelli would discourage you from relying on the
guidance in the last two chapters because it is optimistic and
naive.
5
The first question asks us to do what is best for every-
one. The second says to focus sharply on our basic duties. In
a virtuous, stable, predictable world, those sentiments would
be fine, but that isn’t our world.
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Managing in the Gray
74
The world we live in, as Machiavelli sees it, has three fea-
tures. First, it is unpredictable. Sound plans can turn out
badly, and bad plans sometimes work. Second, the world
is often a very tough place. Much of what happens is sim-
ply outside our control. Leaders often have few degrees of
freedom, limited resources, and can’t avoid hard, sometimes
painful choices. Third, the world as it is can be hazardous
and dangerous, because it is heavily shaped by individuals
and groups pursuing their own interests, sometimes clum-
sily and sometimes with sharply honed strategic skills. In the
world as it is, Machiavelli warned, “Any man who under all
conditions insists on making it his business to be good will
surely be destroyed among so many who are not good.”
6
This is an ominous picture, yet it describes situations most
managers have experienced. Several years ago, for example, a
twenty-seven-year-old manager at an online retailer was under
pressure from her bosses to change a performance evaluation
she was about to submit for someone on her staff. The man-
ager, Becky Friedman, was responsible for a small, highly pro-
ductive group of fourteen people who handled online clothing
sales. The team was under intense performance pressure, but
one individual, Terry Fletcher, wasn’t doing his part.
Fletcher had been hired when the company was growing
fast and its prospects seemed strong. He was a good friend of
several senior executives and was teaching scuba diving to some
of them. Fletcher had done badly in his hiring interviews, but
his connections got him a job anyway. Friedman’s predecessor
had given him scores of 3.5 on the company’s five-point perfor-
mance scale. This supposedly meant he was a solid performer,
but it probably meant his boss was playing it safe.
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What Will Work in the World as It Is?
75
When Friedman took over, she gave Fletcher several
opportunities to develop his skills and contribute to her
unit, but nothing came of them. Most of the other team
members had strong software skills or in-depth industry
experience, and there was no quick way for Fletcher to
acquire either.
Friedman decided to give Fletcher the performance rating
she thought he deserved. This was a 2.5. And she planned to
put him on a PIP, a so-called performance improvement plan.
Many companies use PIPs, but Friedman’s company used it
as a greased chute for getting rid of employees. Fletcher’s
work would be scrutinized intensely for the next six months.
If he made a single mistake during this period, he would be
fired. A 2.5 rating accompanied by a PIP was basically an
organizational death sentence.
When they heard about Friedman’s tentative decision, two
of the company’s vice presidents paid her a visit. She later
reported that they asked, “What’s going on?” and “Are you
sure about this rating, since Fletcher’s been getting 3.5s?” and
“Do you really know what you’re doing?” When Friedman
told them Fletcher simply wasn’t qualified for the job, they
suggested the real problem might be her management skills
and not his background. After the meeting, Friedman had
no doubt about the high-stakes politics of her situation.
She also had other concerns. Fletcher was fifteen years older
than her, which made their whole relationship awkward. She
later said, “Fletcher just didn’t seem well balanced. He had a
lot of things in his life that weren’t good.” She knew he had
a rifle in his car because he sometimes went target shooting
after work and on weekends. For Friedman, the only positive
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