What Keeps Leaders Up at Night
Recognizing and Resolving Your Most Troubling Management Issues
Author: Nicole Lipkin
Pub Date: June 2013
Print Edition: $21.95
Print ISBN: 9780814432112
Page Count: 288
e-Book ISBN: 9780814432143
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I N T R O D U C T I O N
What Was I Thinking?
I LEFT CORPORATE AMERICA IN 2005 to put my full energy into
growing a psychological and consultation services practice. To build the
practice I tried to hire only well-balanced mental health clinicians who require
minimal management. These self-motivated, down-to-earth, easygoing
people have built their own practices under my company’s umbrella.
As the company grew and I started building my leadership consulting
business, I needed to hire someone to take care of routine functions in the
practice. I had composed, in my head, a job description that included handling
client referrals, medical billing, accounts payable and receivable, and
other general office procedures. I hired a young woman, Hope, who had
never actually managed an office but who wanted to become a psychologist.
Hope brought to the job what seemed like useful experience in customer
relations, recruiting, and marketing. And she seemed like a quick learner,
someone who could pick up the other skills she needed in a flash.
From day one, I taught Hope the business side of psychology, a valuable
lesson for someone starting a career in the field because you don’t learn this
in school. In addition to the basic office medical procedures, I tried to coax
her gently toward the two important qualities she would need in order to
pursue her chosen career: professionalism and poise. Hope was a Millennial
and typical of her generation. She possessed both a lot of idealism about her
future and a sense of entitlement to the good things in life. Despite my best
efforts, she gradually became my worst nightmare. She made careless and
costly mistakes in billing and bookkeeping. She treated both patients and
clinicians with a supercilious attitude. Unable or unwilling to pay attention
to the details of her job, she rarely followed through on important tasks without
several reminders. The clinicians constantly complained about her and
often just threw up their hands and did the work she should have done.
My patience wore thin. I was spending more time micromanaging Hope
than I would have spent doing the work myself. With the practice suffering,
thousands of dollars lost in billing mistakes, and office tension growing
alarmingly, I sat Hope down for a performance review. Because I still
thought I could get her on track, I did not consider firing her. I simply could
not accept the idea that I had made a mistake by hiring her in the first place.
As I critiqued her work, I told her I could not possibly give her a raise, but
would like to work with her to set goals that would improve her performance
over the next three months. A crestfallen Hope finally said, “Nicole, I
wasn’t really expecting a raise. I know I keep making mistakes. But I need
you to know how difficult it is to be my age and still rely on my parents to
pay for my cellphone, credit cards, and vacations.” Huh? When I suggested
she do a better job to earn a raise or take on another part-time job, or even
find a better paying one, she tearfully responded, “But, Nicole, this is supposed
to be my FUN year!”
I should have fired her that day (or three months after she started), but
I clung to the hope (no pun intended) that she would change, thereby proving
I was a good boss. As you’ve probably guessed, the situation only got
worse. I was drowning in a sea of frustration, stress, and anger. I was mired
in the mud of the status quo, unwilling to consider change and cut my
losses. My cognitive biases were running amuck, interfering with my beliefs,
attitudes, thoughts, behaviors, and decision making. My mounting stress
rendered me deaf, dumb, and blind. All I did was complain behind Hope’s
back and treat her inconsistently. In a weird way, I was paying her to torment
me and just couldn’t snap out of it. I finally had to admit I was, in fact, a
One day, Hope strolled into my office and handed me her two weeks’
notice. Her father had offered to pay for a month-long vacation to Europe.
After her paid holiday, she told me matter-of-factly, she would come home
and find a “real job.”
Finally I was “Hope-less,” and loving every minute of it. Nevertheless,
the experience kept nagging at me and ultimately became the inspiration
for this book. How could I—a well-trained psychologist with a doctorate
in psychology and an MBA, a “corporate shrink” who coaches others to become
better leaders and managers, and the author of a book on managing
Generation Y folks—screw up so badly? How could I let my clinicians and
company culture down? How could I let our clients down? How could I let
myself down? What, in short, was I thinking? If I could unwittingly go from
good boss to bad boss in the blink of an eye, couldn’t anyone?
I crossed the line from good boss to bad boss because I didn’t do what
I’ve spent my career helping others do. I didn’t pay attention to what makes
our brains tick, to the basic principles of psychology, and to the age-old
tenets of human nature.
The philosopher Jean-Paul Sartre famously wrote about the “gooeyness”
of human nature. Whether we sit at the top of the corporate pyramid, ensconced
in C-suite splendor, or spend our long days delivering goods coast
to coast in an eighteen-wheeler, we are all human beings. Being human is a
messy, quirky, complicated, frustrating, perplexing, and sometimes frightening
All leaders and managers should invest as much time mastering the soft,
human, mental side of business as they do the hard financial side. The more
we know about the tiny firings and misfirings of our brain chemistry, the
power of environmental conditions, the inner workings of group dynamics,
the nature of deeply rooted and firmly fortified psychological defenses and
biases, and the function of cognitive processes, the fewer mistakes we will
make with our people and the more quickly we will correct the mistakes we
Over the years I’ve helped clients, business leaders, and would-be leaders
solve the challenging problems that nag at them and keep them up at
night. In this book we will explore ways to recognize and resolve eight of
the most troubling management issues leaders face today: the leadership
snafus that make us temporarily go from good to bad, miscommunication,
debilitating stress, unhealthy competition, elusive success, scary change,
damaging group dynamics, and loss of motivation and engagement.
The solutions, as the saying goes, “are in your head.” You may not permanently
solve your most perplexing leadership problems, but you can
learn to deal with them more effectively. You will screw up, you will regret
something you said, you will engage in a bad fight, you will feel unsatisfied
with a success, you will fight change, you will do something in a group you
would never do on your own, and you will think your company or your
people don’t give a damn about you. But, and this is a very big but, you can
gain greater awareness of what causes these recurring problems and find
better solutions by recognizing and addressing those causes more quickly
The advice I’ve assembled in this book comes from a lifelong study of
human nature, psychology, and neuroscience, both in and out of business.
I’ve learned that two “ups” can make a “down,” and when we do screw up,
it makes no sense to beat ourselves up. You can’t change what’s already happened,
but you can change what you do next. That became my motto, as
I’ve learned to pause and consider the psychological and physiological reasons
I or someone else did what they did. I’ve learned that the solutions always
begin with raising my self-awareness and helping others raise theirs.
In this book, I offer some fresh ways of looking at and thinking about
some of the most troublesome people problems that leaders encounter
every minute of every day (and night). Such problems have sometimes kept
me up at night. I’m willing to bet they’ve also disturbed your sleep from
time to time. Nothing would make me happier than to help you get a good
night’s sleep for the rest of your life.
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