What Keeps Leaders Up at Night

Recognizing and Resolving Your Most Troubling Management Issues

 What Keeps Leaders Up at Night

Author: Nicole Lipkin
Pub Date: June 2013
Print Edition: $21.95
Print ISBN: 9780814432112
Page Count: 288
Format: Hardback
e-Book ISBN: 9780814432143

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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

bad boss.

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

do make.

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

and effectively.

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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