What Keeps Leaders Up At Night

What Keeps Leaders Up At Night

Recognizing and Resolving Your Most Troubling
Management Issues.

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About the Book

Whether you preside over a global manufacturer of insomnia medicine, a regional chain of mattress stores, or a three-person sleep counseling service, you make the occasional leadership misstep with people. Most of your screw-ups don’t cost you market share, drive valued employees out the door or send your share price tumbling. But some of them do. And those stupid mistakes not only rob you of sleep, they can cost you your job or even your company.

Most leadership and management gurus preach perfection, urging you to lead “straight from the gut” and to make all the moves that will propel your company from “good to great.” Yet you know in your heart that no matter how many Six Sigma programs you launch, no matter how many lean initiatives you install and no matter how much careful thought you give to your major decisions, you will mess up. We all do. But what do you do then? Do you lie awake at night, rocking back and forth in the fetal position as you wrestle over your predicament? Or do you open your dog-eared copy of What Keeps Leaders Up At Night: Recognizing and Resolving Your Most Troubling Management Issues.


Business psychologist Dr. Nicole Lipkin has written this book to provide sleep-deprived leaders and managers the understanding they need to prevent or resolve the inevitable leadership mistakes they make with their people. She answers such tough questions as:

Why Does a Good Boss Like Me Sometimes Act Like a Bad Boss?

Why Can’t I Develop My People’s Full Potential?

How Can I Keep Smart Individuals from Making Dumb Team Decisions?

How Do I Remain Cool in Hot Situations?

How Can I Deal with Change More Effectively?

When it comes to effective leadership, “It’s all in your head.” It’s all about the messy, complicated, illogical and fallible human variables. That’s why busy leaders in high-pressure jobs can benefit from an occasional visit to the corporate shrink, an expert who has spent her career examining the underlying psychology and neuroscience that plays a bigger role in the workplace than all the whiz-bang software and management fads in the world. She knows all about the “gooey stuff”: engagement, motivation, expectations, emotions, interpersonal dynamics, and all the rest of the fundamental psychology that plays itself out in the workplace. Her insights into neuroscience, psychology and group dynamics shine a bright light into the dark corners where all leaders struggle with their own shortcomings.

Switch off your computer, fluff up your pillow, lie back with your arms folded under your head, and let Dr. Lipkin illuminate the basic principles that have guided human interactions for millions of years. You may not solve all your leadership problems, but you will sleep better at night.

Table of Contents


Chapter One

Chapter Two

Chapter Three

Chapter Four

Chapter Five

Chapter Six

Chapter Seven

Chapter Eight


What Was I Thinking?

I’m A Good Boss. So Why Do I Sometimes Act Like A Bad One?

Why Don’t People Heed My Sage Advice?

Why Do I Lose My Cool in Hot Situations?

Why Does a Good Fight Sometimes Go Bad?

Why Can Ambition Sabotage Success?

Why Do People Resist Change?

Why Do Good Teams Go Bad?

What Causes a Star to Fade?

The A-Ha Moment

What People Are Saying

Reading this book was something of a light-bulb moment for me. Suddenly, long held thoughts, concerns and curiosities about how and why we operate as we do, have been explained in a thought provoking, intelligently written and highly readable way. This book enables everyone to consider their own prejudices, opinions and professional behaviours. How they inform their own agendas and judgments, and indeed the judgments and behaviours of others, over whom they have influence. This should be compulsory reading and reference guide for anyone leading, or with aspirations to lead, any team, group or business.

Andrew Williams, Head of Security EMEA
Nomura International, PLC

Anyone who manages people – and tries to do it well – will benefit from the sage advice that executive coach and consultant Nicole Lipkin offers in What Keeps Leaders Up At Night. Nicole brings together social science, compelling examples, easy-to-remember frameworks, and her own extensive management experience to isolate eight key problems that real leaders face in the messy world of organizational life. She then helps readers solve these problems in honest and authentic ways that will lead to many, many more nights of sound sleep.

G. Richard Shell, Thomas Gerrity Professor
Wharton School of Business
Author of Bargaining for Advantage and The Art of Woo.

Very interesting! The analysis by a shrink to improving management and leadership performance is a perfect marriage. Discovering the psychological theory between success and failure from an expert psychologist is very powerful . These imminently implementable learning lessons are supported by stories from the ages that illuminate basic “how to’s” that can make virtually any leader more effective. If you’re a leader of a department or an organization this is the book for you.

Mark Rikess, CEO, The Rikess Group
Founder, Digital Air Strike and Green Dealer Support

Nicole Lipkin is a new, witty and refreshing voice in the world of Leadership Development. While she has the PhD and clinical background to back up her psychological theories and her guidance for leaders, her writing is hip, edgy and spot on when it comes to describing the joys and challenges of leading people. Nicole doesn’t just discuss theory and share illustrative stories. She has an uncanny way of providing suggestions and tools that encourage and motivate you to apply what you have learned and find ways to change your leadership behavior for the better. The wrap-up sections at the end of each chapter provide a roadmap for success.
However experienced or successful you may be, you will find yourself reading this book and thinking “Oh no, I do that!” Luckily for all of us, the book is rich with advice on how to avoid the perils and pitfalls of our own thinking and how to embrace change for the better. In particular, Chapter 6, which focuses on our response to change and the neuroscience behind it, provides readers with practical advice anyone can use to challenge their biases, reframe the challenges they are facing and recoup their financial, emotional and physical costs. Nicole’s books on Gen Y have changed the way I approach generational differences in the workplace and this new book is already influencing my approach to coaching and advising senior leaders.

Shari Ekelchik, VP of Organizational Development

Understanding how and why people do what they do and what makes them tick is at the heart of leadership, negotiation and working together effectively. When you add self-awareness to the mix, you have a powerful combination. What Keeps Leaders Up At Night, written by business psychologist and consultant Nicole Lipkin, helps leaders and managers understand the dynamic interplay between the workplace, psychology and neuroscience and forces readers to take a hard look at their own leadership behaviors, beliefs and thoughts to enhance their leadership impact. Written in a fun, witty way, this is a must read for anyone interested in developing their own leadership capabilities and the capabilities of others.

Jon Benjamin, UK ambassador to Chile

Extremely Introspective! Dr. Lipkin’s book has placed me in front of the mirror and explained in a very understandable manner how my actions/reactions impact my leadership abilities/inabilities. I will be applying the valuable insights and techniques I have learned from this book in both my role as a CEO and as a head Collegiate Softball Coach.”

Michael Smigocki, Founder and CEO
Federal Strategies Group

Dr. Lipkin has an uncanny ability to delve into the minds of business leaders and their charges; consider everyone’s intentions, anxieties, and potential; and analyze the foundations of all of these things in a way that is disciplined, empathetic, and insightful. Thanks to Dr. Lipkin’s engaging writing style and pragmatic advice, What Keeps Leaders Up at Night has encouraged me to think about key leadership topics – both in general and personally – in a way that has enabled me to make the types of personal commitments that will help me be a better leader and, of course, sleep better at night.

Steven L. Pessagno
Alliance Management, Worldwide Business
Development, GlaxoSmithKline

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