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[Review] What Keeps Leaders Up At Night


Here’s a truth that every leader needs to hear – you’re not perfect. You’re going to be making the occasional mistake, you’re going to suck, and things will go wrong. But that’s part and parcel of leadership, even for the most successful among us.

In fact, no matter how many initiatives you spearhead or how hard you think about decisions, you will make the occasional management misstep, says clinical and business psychologist Nicole Lipkin, as well as author of the book “What Keeps Leaders Up at Night: Recognizing and Resolving Your Most Troubling Management Issues“.

Lipkin points out in the book that there is such a thing called the Good Boss Gone Bad syndrome… and good bosses go bad for many reasons. But most often they go bad because of three reasons – (i) they’re too busy to win, (ii) too proud to see and (iii) too afraid to lose. Yes, a leader can be too busy – being busy is not bad, but there are times when excessive busyness can overwhelm your ability to cope, leading you to becoming tired, forgetful, and prone to poor decision making and problem solving. Or you can be too proud to see, when otherwise competent leaders get so caught up that they cannot receive or accept the information you need to make an informed decision, or biased towards the information being presented to you. Otherwise you can be too afraid to lose, when you shy away from certain risks and start hampering the team’s ability to function properly and productively.

In “What Keeps Leaders Up at Night“, Lipkin explores the underlying psychology and sociology principles around leadership and management in the workplace, answering various questions many leaders have, such as why some people resist change, why good teams turn bad, to losing your cool in certain situations or why people don’t heed good advice. She delves in deep into the issues of engagement, motivation, expectation, emotions, interpersonal and group dynamics – psychological triggers – that exist within the office context. Most of the examples she offers will sound familiar and strike a deep chord with leaders. And while many other leadership books tells you what to do in a certain situation, Lipkin tears apart the issue to find and make aware the underlying causes and triggers that has led the situation developing in the first place… and then offer sagely advice to deal with it accordingly.

What Keeps Leaders Up at Night” is going to be a very painful read for leaders, not because it’s poorly written but because it will cruelly expose you for the inadequate leader that you are. It will help you recognize your own leadership and management fallibility… and then help build you back up to be the better leader you can be.