Tools for Judgment
5
of severance and support will she get? Can you treat her with
respect and compassion, when you are taking away her live-
lihood? These are all hard management questions, and you
have to answer them one way or another. And behind these
decisions is a profound social decision that society has del-
egated to you: given this employee’s age and failing perfor-
mance, you may be deciding that her work life has come to an
end. In short, when you do a good job of resolving a gray area
issue like this one, you are doing the heavy lifting—not just
for your organization, but for other people and the society in
which you live.
At the same time, when you grapple successfully with a
gray area problem, you are testing and developing your skills
as a manager. A basic test of whether you are ready for more
responsibility in an organization isn’t how well you manage
routine situations; it is how well you handle really hard, uncer-
tain, important challenges. This is because gray area problems
are the core of a manager’s work. As you meet these challenges,
you build your experience and confidence, and you add lines
to the informal, unwritten résumé that circulates inside orga-
nizations and determines who gets promotions. Good bosses
recognize and reward people who handle the tough, gray area
problems well. And, when you meet these challenges, you
are also becoming a good boss yourself—by serving as a role
model for the people who work for you.
Gray areas are basically organizational versions of the clas-
sic Gordian knot: that is, they are dense tangles of important,
complicated, and uncertain considerations. As such, they can
be some of the hardest work you have to do as a manager, and
they can feel like a serious burden. At the same time, like the
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