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This groundbreaking book provides a framework and set of key concepts enabling leaders to exert their influence over the difficult choices and competing priorities they confront. Compelling stories and vivid case studies help to deliver a serious game plan to any leader who is grappling with burnout caused by the manager's dilemma.



Embrace The Dilemma



THE MANAGER’S DILEMMA EXPLORES THE widening gap between the increasing demands we face and the shrinking resources we have available to meet them. However, this is not a time management book to deal with the avalanche of e-mails, meetings, and tasks dropped on your plate. Nor does it offer a packaged set of clever work-arounds to deal with the overflowing and stressful priorities you face. As you will see, it is time for managers to take off their capes once and for all; the superhuman notion of getting more and better work done with fewer resources is a profoundly damaging myth whose time has passed.

Jesse Sostrin

Chapter 1. The Evolution of A Dilemma

It begins when our overloaded working lives tilt us into the Danger Zone where counterproductive habits accelerate the dilemma’s undermining effect

THIS IS A BOOK THAT COULD HAVE BEEN written 35 years ago with nearly the same urgency and poignancy. While the reference points may be different and the jargon dated, the tinderbox has been building for several generations. The modern-day origin story of the dilemma goes back as early as 1981 when the Harvard Business Review began publishing articles that dealt with the growing concerns of managers who were overwhelmed by the struggle to cope with increasing demands and rapidly changing conditions.1 And although this building pressure finally exploded at the inflection point of the Great Recession, the manager’s dilemma was already embedded in our way of working.

Jesse Sostrin

Chapter 2. Know Your Dilemma

Because what you are unaware of controls you, and the dilemma has nearly imperceptible ways of constricting your performance and fulfillment on the job

ARE YOU STUCK IN THE MANAGER’S DILEMMA? If you manage people, priorities, and projects, then the chances are good that you have encountered the dilemma at some point or may even be struggling with its consequences right now.

Jesse Sostrin

Balance the Equation


Chapter 3. Follow The Contradiction

Because the chink in any dilemma’s armor is the subtle-but-powerful contradiction that loosens its absolute grip

THE MANAGER’S DILEMMA LEAVES US feeling trapped, with unwanted options on all sides. The trade-offs inevitably create an alignment problem that reduces our capacity to think and act in ways that are consistent with our values and priorities. This fracture is one of the dilemma’s most perilous effects. Over time, the worn-out, off-course way of working ties us in knots and leaves us unsure about how to find our way back. Once inside the manager’s dilemma, the fastest way out is to follow the contradiction.

Jesse Sostrin

Chapter 4. Determine Your Line of Sight

Because the dilemma’s noise and clutter will keep you chasing your tail and following shiny objects while your true priorities remain elusive

THE DILEMMA TURNS US AROUND and distorts our priorities. As a result, we end up pursuing goals and outcomes that are not necessarily important, valuable, or consistent with what we care about. Accelerating this “creep and drift” is one of the dilemma’s specialties.

Jesse Sostrin

Chapter 5. Distinguish Your Contribution

Because the dilemma knows how to keep you occupied with unimportant things that leave your distinctive value and impact on the sidelines

A DAY IN THE LIFE OF MANAGERS is marked by constant demands that push and pull them in many directions. Whether from bosses, peers, or direct reports, they are called upon to contribute in numerous, often conflicting, ways. The predominant effect of this scattered state is a diluted contribution with diminished impact both to the team and to the organization at large.

Jesse Sostrin

Chapter 6. Plug The Leaks

Because the worst kind of problem is the one you don’t know you have until it silently drains your resources and erodes the things you value

THE DILEMMA RELENTLESSLY PUNCHES small leaks into our already fragile TERF. These slow drips could be fixed in the moment with less time and effort; however, because we are overloaded and distracted by other concerns, we often fail to notice and address them. As leaks linger, they require an even greater effort to repair once the damage is done. Another classic dilemma calling card, the initial challenge of the leak is nothing compared to the compounding, secondary damage created by the delay in repairing it.

Jesse Sostrin

Flip the Scales


Chapter 7. Create Your Conditions

Because knowing what to do and even how to do it is not enough: You have to know how to generate the required circumstances to make it all happen

THE HECTIC PACE OF THE MANAGER’S dilemma can make us think things are random, but behind every experience and outcome there is always a set of specific conditions that made it possible. The dilemma delivers unwanted conditions that undermine our capacity to achieve what we want, but to flip the scales you have to intentionally craft your own.

Jesse Sostrin

Chapter 8. Find The Pocket Of Influence

Because there is only one best chance to get it right and that exists inside your pocket of influence

WHETHER IT IS A NEW PROGRAM YOU want to launch, a sensitive personnel decision you need to make, a bold new initiative you’d like others to support, or a controversial change that requires carefully coordinated execution, there are critical moments when the attitudes, motivation, and decision-making powers align to make things happen. I call these moments the pocket of influence.

Jesse Sostrin

Chapter 9. Convert Challenges To Fuel

Because the dilemma will bury you in obstacles unless you flip the scales and find the path to performance hidden inside every barrier

IF OUR EVERYDAY HEADACHES AND challenges at work were a form of fuel, we would never run out of energy. As anyone who has spent even five minutes on the job can tell you, fuel is everywhere. However, for most of us these lingering obstacles are anything but small twigs and dry leaves that can be conveniently collected and used to start a productive fire. Instead, they take, take, and take from us in both direct and subtle ways.

Jesse Sostrin

Chapter 10. Make Your Goals Their Priorities

Because in the space between what matters to you and what your team and organization need, there is a mutual agenda that keeps you first

THE MANAGER’S DILEMMA THREATENS us with scarcity. The unending cycle of “never enough” time, energy, resources, or focus to meet the increasing demands we face can produce a destructive competition between individuals and organizations, with managers stuck in the middle.

Jesse Sostrin



An inevitable, self-sustaining bind suppresses your capacity to perform at your best when the inverse equation of shrinking resources and increasing demands takes hold in your working life.

Jesse Sostrin


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