What Keeps Leaders Up at Night Book Summary



“The ability to summon positive emotions during periods of intense stress lies at the heart of effective leadership.” — Jim Loehr

John Wooden lived his life with “peace of mind.”  His philosophy was simple — give your best where you can.

But easier said than done.

What happens when you give your best, but the worst things happen at the worst times?  And, when you stop behaving like your better self, how do you get back on track?

When you’re a bundle of nerves and all you want to do is curl up into a little ball in the corner, how do you summon positive emotions and show the world what you’re capable of?

Or, how do you at least get a good night’s sleep.

In our “always on,” 24×7, connected world of ultra-competition and extreme change, it’s easy to let stress get the best of us.  Especially, if you don’t have tools and techniques for dealing with your worst setbacks.

Enter What Keeps Leaders Up at Night: Recognizing and Resolving Your Most Troubling Management Issues, by Nicole Lipkin

This is one of those books.

It’s a MUST read.

It’s that good.

It’s the perfect answer for today’s world.  It will fill your toolbox with leadership skills that take your leadership effectiveness to another level.

Nicole Lipkin is a psychologist and business consultant that knows how to deal with the most troubling management issues facing leaders today.

Some of the hot leadership issues include:  mis-communication, stress, change, unhealthy competition, damaging group dynamics, loss of motivation and engagement, elusive success, and common leadership pitfalls that make us temporarily go from good bosses to bad bosses.

With that in mind, let’s dive in …

What’s In it For You?

Here is a sampling of some of the challenges that What Keeps Leaders Up at Night helps you with:

  • How to resolve conflict or personality clashes
  • How to ensure workplace harmony and engagement
  • How to stimulate high performance and productivity
  • How to win approval of a major shift in strategy
  • How to create and manage effective teams
  • How to deal with extreme stress in the worst scenarios
  • How to get back on track when you get into a slump or spiral down
  • How to develop excellent leadership skills
  • How to develop rapport to influence others
  • How to perform effective self-reflection
  • How to perform highly effective active listening

Chapters at a Glance

  • Chapter 1 – I’m a Good Boss.  So Why Do I Sometimes Act Like a Bad One?
  • Chapter 2 – Why Don’t People Heed My Sage Advice?
  • Chapter 3 – Why Do I Lose My Cool in Hot Situations?
  • Chapter 4 – Why Does a Good Fight Sometimes Turn Bad?
  • Chapter 5 – Why Can Ambition Sabotage Success?
  • Chapter 6 – Why Do People Resist Change?
  • Chapter 7 – Why Do Good Teams Go Bad?
  • Chapter 8 – What Causes a Star to Fade?

Key Features

Here are some of the key features of What Keeps Leaders Up at Night:

  • Actionable.  The book is extremely actionable.   In fact, every few pages you turn, you’ll likely want to try something.
  • Applied research.  Throughout the book, Lipkin cites theories and research and includes references to the work, so you can explore for more.
  • Easy to read.   This is a big deal, especially for this book because it’s jam-packed with hard-core information, insight, and action.
  • Psychology terms and concepts.    As a leader, you can change your game if you have psychology on your side.  You’ll quickly expand your vocabulary and knowledge base of psychology that you can use on a daily basis.  Lipkin went to town in packing a wealth of psychology-related terms and concepts throughout the book.  If you’re a seasoned psychologist, you’ll enjoy seeing how the research is applied.   If you dabble in psychology as a hobby, you’ll appreciate the breadth and depth of the research that Lipkin covers.  Here are some of the theories, terms and concepts she includes:  Confirmation Bias, Transactional Model of Stress, Social Exchange Theory, Norm of Reciprocity, Extrinsic Motivation, Intrinsic Motivation, Cognitive Dissonance, Group Conformity, Social Identity Theory (SIT), Social Loafing, Collective Effort Model (CEM), Polarization, Groupthink, Shadenfreude.
  • Stories and examples.  Lipkin includes many quick stories and examples throughout her book that make the ideas real and turn the theories into things you can easily relate to.

Here is a sampling of some of my favorite nuggets from the book …

Others Just See Our Behavior

You know what’s going on in the inside.  Other people just see what happens on the outside.

Lipkin writes:

“To paraphrase an old adage, ‘We see ourselves as a combination of our thoughts, fears, and intentions, but others just see our behaviors.’”

3 Causes of Good Boss Gone Bad

Why do some great leaders, end up not so great?

According to Lipkin, there are three fundamental ways good leaders go bad:

  1. Too busy to win.
  2. Too proud to see.
  3. Too afraid to lose.

Too Busy to Win

Are you crazy busy?  It’s easy to get too busy.  And, when we get too busy, we become ineffective.

Lipkin writes:

Keeping busy may make you happy, but at some point excessive business can overwhelm your coping capabilities. 

That’s when we become too busy to win. 

Excessive busyness can impair performance and productivity, making you increasingly forgetful, fatigues, and prone to poor decision making and problem solving. 

Feelings of isolation abound as communication with others breaks down. 

The resulting frustration, anger, and impatience can lead to physical ailments, job loss, and, in some cases, mental health problems.”

Too Proud to See

When a leader is too proud to see, it’s like the emperor who wears no clothes.  According to Lipkin, the three ways you show you are too proud to see are:

  1. Letting yourself get so tied to an idea that you won’t let it go.
  2. Refusing to heed the advice of others.
  3. Relying on your past successes at the expense of weighing different patterns, options, or solutions.

Too Afraid to Lose

If you can’t lose, the problem is then you can’t win, or go out on a limb.  According to Lipkin, here are the signs that you are too afraid to lose:

  1. Worry excessively about failing to get the right result.
  2. Question and second-guess every step along the way.
  3. Avoid decisions and commitments that might cause mistakes.
  4. Get involved in every detail, particularly as deadlines loom.

Three Simple Rules to Get Back on Track

How do you get back on track when you start to suck as a leader?  Lipkin shares three rules and a formula that leaders can use to get back on track.

Three Rules:

  1. Seek self-awareness.
  2. Help others gain self-awareness.
  3. Remember we’re only human after all.

The Formula:

  1. Admit the problem.
  2. Recognize that my thoughts and actions contributed to the problem.
  3. Identify the causes of those thoughts and actions.
  4. Detect the cognitive biases involved.
  5. Think up new ways to manage the causes and biases.
  6. Adjust my leadership approach accordingly.
  7. Make amends with the people I hurt.
  8. Expect to make more mistakes but strive to deal with them differently.

How Does the Marathoner Scale the Wall?

I really enjoyed this little reminder of how to take baby steps when the going gets really tough, and you need to keep on going.

Lipkin writes:

“How does the marathoner scale the wall?  She sets small, incremental goals she can accomplish: left foot, right foot.  Ten more steps.  Just to that next step sign.  Okay, now to that bend in the road. 

The enables her to cover the last mile and throw herself across the finish line.  Leaders can learn a lot from that response to acute physical stress by breaking down the accumulation of stressors at work into bite-sized, manageable bits.”

What Excellent Leaders Do

Lipkin says, “The mindset of an excellent leader spreads throughout the organization to all the stakeholders.”  Here is what excellent leaders do:

  1. Think and behave panoramically.
  2. Eliminate myopic attitudes and behavior.
  3. Close their mouths and open their ears to learn what their people feel and need.
  4. Create safe cultures where people freely ask for help and never fear making a mistake.
  5. Develop emotional intelligence, self- and social awareness, and relationships skills.
  6. Encourage others to do the same.
  7. Remain visible, present, and open to all feedback.
  8. Model the attitudes and behaviors they expect of others.
  9. Create and maintain a culture of pure transparency.
  10. Align people with the organization’s values.
  11. Stress how every job fits into the organization’s strategy and goals.
  12. Follow through on promises and commitments and all psychological contracts.
  13. Restore broken contracts.
  14. Practice the highest levels of ethics and integrity.
  15. Welcome and share input, feedback, and ideas from all levels.
  16. Establish and manage expectations.

The Building Blocks of Self-Perception

How unshakeable is your foundation?   According to Lipkin, our self-perception is rooted in how we answer the following questions:

  1. Who am I?
  2. What can and can’t I do?
  3. What belongs to me?
  4. What way should I react to people, experiences, and situations?
  5. What do I expect from myself and of others?
  6. What is my measure of success?

Destructive and Constructive Core Beliefs

According to Lipkin, positive core beliefs can keep you in control of your emotions, while the negative ones can undermine your ability to handle stress effectively.

Lipkin shares a summary of destructive and constructive core beliefs:

Destructive Core Beliefs Constructive Core Beliefs
I always get the short end of the stick. I know that there is both gain and loss in life.
I must be perfect at all times. I try to do my best.
I can never change. I will constantly evolve.
I must only look out for myself because no one else will. I care for myself and others.
I am not a people person. I like and enjoy other people.
I am never listened to or respected. I feel respected and appreciated.
I must strictly adhere to my plans. I know the best-laid plans require adjustments.


2 Reasons Why You Lose Influential Power

According to Lipkin, there are two reasons why you lose influential power:

  1. People do not buy into you.
  2. People do not buy into your message.

3 Levels of Buy-In

According to Lipkin, there are three levels of buy-in:

  1. At Level One, the most basic level where persuasion holds sway, people buy into your idea intellectually.  Here you put facts and figures to work.
  2. At Level Two, emotions come into play and begin to influence the outcomes.  The facts weave themselves into a verbal or visual tapestry, triggering the emotional centers of our brains.  The message is now more powerful, more memorable, and more influential.
  3. At Level Three, a story told from personal experience by another person, carries the greatest influence.

4 Primary Styles of Communication

Directness and sociability are the cornerstones of our communication styles.  Lipkin shares a generalized model based on research that helps us see the key points of difference in communication styles:

  1. Direct, with High Sociability
  2. Direct, with Low Sociability
  3. Indirect, with High Sociability
  4. Indirect, with Low Sociability

We can communicate more effectively when we are aware of our own communication styles and the styles of others.  We can match, blend, or bridge styles to accommodate the differences and improve our ability to communicate more effectively.

7 Ways to Build Rapport

Rapport is the key to influence.  When you have rapport, it’s easier to get on the same page.  Lipkin shares the secrets of building rapport:

  1. Engage in mirroring behavior.
  2. Make eye contact.
  3. Match tonality and rate of speech.
  4. Listen carefully to sum up what the other person has said.
  5. Breathe at the same rate.
  6. Learn the other person’s name and use it throughout the conversation.
  7. Find common ground and engage in small talk.

Telling Stories

One of the most powerful ways for a leader to become more convincing is to couple an important message with an unforgettable story.

Lipkin writes:

“Why do stories carry so much weight? First, they make a dry or boring topic more interesting.  They create pictures in people’s minds.  You can’t really picture ‘John loves Mary’ in your mind, but you can see John sweeping Mary off her feet and kissing her passionately. 

People could not ‘see’ an emergency, but they could picture zombies attacking. 

The CDC posting relied on the fact that in emergency situations, our brains often freeze up, preventing us from logical thought.  The moral of a good story, like the point of a parable in a fairytale, becomes deeply ingrained and helps us remember what do do.  The DDEC posting offered advice on coping with a pandemic flu, but tacking it onto the compelling picture of hungry zombies made the point harder to forget.”

Why Learn Stress Coping Skills?

Stress can be your downfall, either in your job, your relationships, your happiness, or your health.

Lipkin writes:

“Why should you learn stress-coping skills?  Because unmanaged stress — the most underestimated constant in the workplace today — can strangle your company to death.  Leaders who do not manage it will make more mistakes under pressure and tend to rationalize their mistakes with the old, familiar excuse, ‘Oh, I was under a lot of stress at the time.’  Make that excuse often enough and it soon becomes an addictive habit.  You earn a reputation as a stressed boss or a boss who cracks under pressure, labels that, in the end, will cost you the respect of your people, and potentially, your job.”

What Can Stress Do To You?

What can stress do to you?  A lot, if you let it.  Stress can be devastating.   Long-term stress takes its toll.  The good news is that how we see things, and how we respond, changes how our bodies respond to stress.

Lipkin writes:

“The long-term response depends on hormone secretion (especially mood-altering cortisol).  Our perceptions of a given threat determine the type and amount of hormones that endocrine system will dispense.  A steady bombardment of blinking lights, phone beeps, email alerts, and personal and professional obligations builds a chemical cocktail that keeps our bodies in a constant state of edginess, impairing memory and learning.

Left untreated, this blockage increases the odds that we will end up with serious mental health problems like severe anxiety or clinical depression. 

In addition to memory and mental health problems, prolonged exposure to stress hormones stimulates the liver to elevate glucose levels.  The body cannot sustain these high levels for long periods of time without suffering an adverse reaction, such as diabetes.  In addition, long-term stress can cause narrowing of the arteries and elevate cholesterol levels, boosting the chances of succumbing to heart disease, heart attack, and stroke.  It can wreak havoc with the reproductive system and weaken the immune system.”

Ankle-Biting Chihuahua Dogs

Beware the ankle-biting Chihuahua dogs in the workplace.

Lipkin writes:

“Our prehistoric ancestors faced the occasional marauding saber-toothed tiger.  Today, not many saber-toothed tigers pop up in the office, but a bewildering array of ankle-biting Chihuahua dogs attack us throughout the workday.

Ongoing psychological, social, and financial problems, constant and accelerated change, overwork, job dissatisfaction, information overload, and all the other ‘low-grade fevers’ characterize today’s business environment. 

Our physiological response, although amazingly suited to deal with the sudden onslaught of acute stress, does not fare so well with chronic stress, the endless little yipping Chihuahuas that prompt what psychologists call the long-term fight/flight response.”

You Take Action If You Know How To

It’s one thing to be motivated.  It’s another to know which action to take.  Sometimes, even just knowing what to do, motivates us to action.

Lipkin writes:

“Psychologists know that people perform well under stress if they possess the information they need to take effective action.  Under stress they feel they can take control of, or at least strongly influence, what happens next. 

In order to learn how to do that, you must gain some understanding of the neurological and psychological fire alarms that start blaring inside your mind and body whenever you experience the negative effects of stress and pressure.”

Rise Above Envy

Is there a way to rise above envy and schadenfreude?  Lipkin provides the following steps:

  • Pinpoint the cause of your schadenfreude or envy.
  • Measure the strength of your relationship with that person.
  • List your emotions: resentment, anger, shame, regret, disdain, frustration, etc..
  • Describe your expected outcome before you felt these emotions.
  • Pinpoint the events that led up to your feeling out of control.
  • Identify the people (intended and unintended) who might suffer from your actions.
  • Rate your current sense of self-worth on a scale of 1 (ashamed) to 10 (proud).
  • Place your behavior on a continuum from mild to outrageous.
  • Consider advice you would give to a trusted friend about coping with similar emotions and behaviors.
  • Identify one or two steps you can take right now to rise above your circumstances, take ownership of your situation, and achieve your desired results.

16 Cognitive Distortions

Cognitive distortions warp our world by changing how we see and experience it.  They get in the way of our objective reasoning, logical conclusions, and keeping perspective  Lipkin shares a consolidated set of common cognitive distortions:

  1. Asking “What if?.”  You worry about all sorts of problems that probably won’t occur.
  2. Assigning False Control (Fallacy of Control.)  Externally, you think your happiness depends on outside forces (external control).  Internally, you feel totally responsible for other people’s happiness (internal control.)
  3. Dreaming of Future Rewards (Heaven’s Reward Fallacy).  You expect your sacrifice and self-denial to pay off later, and you feel bitter when the reward doesn’t come.
  4. Expecting Others to Change First (Fallacy of Change).  You think other people should change to suit your needs, usually through blaming, demanding, withholding, or trading.
  5. Expecting the Worst-Case Scenario (Catastrophizing).  You automatically think the worst will happen.
  6. Filtering.  You magnify the negatives and downplay all of the positives of a situation.
  7. Global Labeling.  You extrapolate one or two qualities into a negative global judgment.
  8. Jumping to Conclusions (Mind Reading).  Lacking sufficient information, you assume that you know how someone feels and why they act the way they do (specifically toward us.)
  9. Insisting That You Are Always Right.  You demand that people never question your judgment and do not question it yourself.
  10. Letting Emotions Overrule Logic (Emotional Reasoning)  You believe what you feel must be true.
  11. Making Unfair Comparisons.  You feel you always fall short when you put yourself up against others.
  12. Overgeneralization.  You draw very broad conclusions based on a single, negative event.
  13. Personalizing the Situation (Personalizing) You assume that everything people do or say represents a reaction to you, which makes you think you cause events in which you actually played no big role.
  14. Thinking Egocentrically.  You rarely put yourself in other people’s shoes but expect them to walk in yours.
  15. Thinking in terms of Black or White.  You see people, yourself, and things as either all good or all bad, with no in between.
  16. Using Fairness as an Excuse (Fairness Error).  You judge other people’s actions according to personal rules of fairness and get upset when people do not follow your rules.

The SLAM Model for Engagement

How do you create and maintain engagement in the workplace?  Lipkin developed a model for thinking about engagement:

  • S – Social Connection
  • L – Leadership Excellence
  • A – Aligned Culture
  • M – Meaningful Work and Life

It’s a holistic view and includes psychology, physiology, emotions, attitudes, and behaviors.

6 Factors that Govern Group Dynamics

Lipkin says there are six factors that govern group dynamics.  You need to manage them, or they manage you.  The six factors are:

  1. The inevitability of groups
  2. The “us” vs. “them” mentality
  3. Group conformity
  4. Social loafing
  5. Emotional contagion
  6. Smart people, dumb group decisions

Groupthink Undermines Long-Term Viability

According to Lipkin, group think undermines the long-term viability of the team because bad decisions pile up over time.

Lipkin writes:

”You can recognize groupthink by its typical symptoms: close-mindedness, lock-step conformity, self-censorship, overestimation or stereotyping of outsiders, and a sense of invulnerability and moral superiority. 

When members feel compelled to agree with the leader and with one another, they do not express reservations openly and offer little criticism. 

This self-censorship bolsters the fictional belief that everyone wholeheartedly backs what the group thinks, says, and does.”

Three Main Theories to Explain Polarization

When people join groups, they can be more willing to accept, rationalize, and embrace extreme views.  Group decision making can increasingly polarize and strengthen initial preferences.  And, those people who hold dissimilar preferences can often end up changing their mind and accepting the majority opinion.

Why is that?

Lipkin shares three theories that psychologists use to explain polarization in groups:

  1. Persuasion.  People change their minds when they pay attention to what they deem rational arguments offered by other group members.
  2. Comparison.  People change their minds to conform to the group, especially when they accept those norms as socially desirable.
  3. Differentiation.  People change their minds to accommodate a decision they think the group should take.

7 Ways to Counteract the Traps of Groups

Can you defeat the downsides of groups and group decision making?  Yes, you can.  Lipkin shares some specific ways to help counteract some of the problems that can make a good team go bad:

  1. Establish group diversity.
  2. Define expectations.
  3. Emphasize collective awareness.
  4. Provide the right training.
  5. Stress freedom of thought.
  6. Insist on information sharing.
  7. Promote innovation.

Self-Reflection and the Learning Leader

Effective leaders keep learning.  Self-reflection is a powerful tool.  As a leader, you should make conducting a reality check an ongoing process.  Lipkin shares how to perform some simple self-reflection you can use after every project, sale, presentation, review, difficult conversation, or any other potentially stressful incident..

The questions are:

  1. What worked?
  2. What did not work?
  3. What got in the way of getting desired results?
  4. What helped me/us achieve desired results?
  5. What other, perhaps better, ways could I/we have approached the situation?
  6. What have I/we learned from this situation?

Get the Book

What Keeps Leaders Up at Night: Recognizing and Resolving Your Most Troubling Management Issues is available on Amazon:

What Keeps Leaders Up at Night: Recognizing and Resolving Your Most Troubling Management Issues, by Nicole Lipkin

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  1. Sounds like a good read. I have a question though: How much adjustments can you make to your plans, if any at all, and still appear decisive of the vision you’re trying to sell? Maybe it’s just me, but I thought good leadership requires one to stick to their plans, which sometimes involve bearing the brunt of some decisions made.

    • Hey Viv,

      Great question.

      The more stable and durable parts are the mission/vision/strategy.

      On the execution side, this is where the changes really happen.

      I think timelines are key here. I’ve seen businesses change from annual reviews of their plans to bi-annual, to quarterly, to monthly. The changes here are not the mission/vision/strategy, but rather the investment, resourcing, and tactics based on what’s working and what’s not.

      The other big shift is away from plans that promise results a year from now, to quarterly results. Businesses are looking for accelerated payback.

      Business agility is the name of the game, while strategy helps you rise above the noise and provides the North Star. In today’s changing landscape, the customer is the North Star. You choice of customer is a strategic decision.

  2. Viv, one thing that’s helped me is to know the big picture and realize that there might be different avenues to achieving that big picture. Be decisive about the big picture but flexible on the approach. I also read a good book by Chris Argyris about Double Loop Learning vs Single Loop Learning which suggests that to truly learn and be effective sometimes you have to change your assumptions and “global variables” at times instead of just changing your behavior. I think if you stay anchored in the big picture and realize that even the big picture might change if you learn something new about your assumptions or “global variables” then you will walk the tight-rope more successfully.

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