Leading the Unleadable: How to Manage Mavericks, Cynics, Divas, and Other Difficult People

Leading the Unleadable: How to Manage Mavericks, Cynics, Divas, and Other Difficult People

by Alan Willett

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Difficult employees are by far the worst part of a manager’s job. Control freaks. Narcissists. Slackers. Cynics. Their outbursts, irrational demands, gripes, and countless other disruptions need to be dealt with, and you are the unlucky one with that job description. But every manager has to deal with these people. What separates the great managers is their ability to turn them into productive team players.Leading the Unleadable turns this seemingly difficult chore into a straight-forward process that gently, yet effectively, improves behaviors. And it begins with understanding a core truth: most people actually want to contribute results, not cause headaches. When the manager resets to that fundamental principle, the potential for change can reveal itself in even the most hopeless situations. Written by an insider in the tech industry, where personality issues routinely wreck projects, the book explains how to:• Master the necessary mindset• Explain the problem calmly in a short feedback session• Get a commitment to change, then follow up• Coach others to replicate the process• Develop the situational awareness required to spot future trouble before it hits Are you a great manager? Of course you believe you are. So don’t just put up with your difficult employees. Anyone can do that. Turn them into the tremendous team players everyone wants them to be!

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Product Details

ISBN-13: 9780814437612
Publisher: AMACOM
Publication date: 11/29/2016
Sold by: HarperCollins Publishing
Format: NOOK Book
Pages: 240
Sales rank: 487,006
File size: 1 MB

About the Author

ALAN WILLETT is president of Oxseeker, a leadership development and organizational culture change consultancy whose clients include Oracle, Microsoft, NASA, Intuit, and others.

Read an Excerpt

Leading the Unleadable

How to Manage Mavericks, Cynics, Divas, and Other Difficult People

By Alan Willett


Copyright © 2017 Alan Willett
All rights reserved.
ISBN: 978-0-8144-3761-2


The Leadership Crisis Point

In working with hundreds of leaders around the world, I have found that the greater the responsibilities of leadership, the greater the amount of trouble you must deal with. Recently, a division manager responsible for 100 million dollars in revenue and 500 employees distilled the situation perfectly to a roomful of colleagues.

He held his hands a few inches apart. "This," he said, "is how much good news I get to share with the upper management of this company." He then stretched his arms the full distance. "This," he said, "is how much bad news I get to share with upper management." The other leaders in the room nodded their heads in agreement.

This is why leaders often reach the point at which they wake up one morning and simply think, "I don't want to do this anymore." They have reached a leadership crisis point. There is a way forward, though.

Many managers have called me in the midst of this crisis, often ready to hear the most important message of their leadership careers. Leadership isn't just making a series of decisions (choices) on a daily basis. The very essence of being a leader and how you lead is itself a choice.

Achieving a long, enjoyable career in management is obviously a better alternative than viewing it as a trudge across a desolate landscape of leading people who do not want to be led. The difference between these two visions of leadership is a choice that one must actively make.

You must actively embrace the many good things that come with leadership. You are in the right place to have a positive influence on others. You will be able to accomplish bigger and better things than you could accomplish on your own. You will be able to grow your own skills and abilities as you work with others, and you will gain not just from your own experience but through other people's experiences as you work with them.

Choose not just the call to leadership; choose the call to exceptional leadership. This is a call to embrace the tremendous personal growth opportunity in learning about yourself, in growing your own career, and in contributing good to the world.

Before we can listen to the call we first must understand and accept the following facts about leadership:

• The call to leadership is a choice.

• Whatever you lead, leadership is about leading people.

• Leadership comes with a taxonomy of trouble.

• The trouble is your fault, even when it is not.

When we accept these facts, we are ready to learn how to lead the unleadable, including our own troublesome selves.

The Call to Leadership Is a Choice

To make the step from good manager to exceptional leader, the first step is to understand that however you have found yourself in a leadership position, you have made a choice to be a leader, even if that was not your intent!

There are a number of common reasons why people find themselves in leadership positions. Each of these examples offers a short origin story that illustrates how people had to grapple with what it means personally to take on the mantle of leadership.


Mary was superb technically, and the CEO wanted to reward her with a promotion. In Mary's company, as in many organizations, there was a ceiling to the career of the individual contributor. The only promotion available was to become a team leader. Mary happily took the promotion and the associated pay raise.

Mary had the sudden responsibility of doing work not with, but by leading, other people. She found herself doing things she had always thought of as overhead. Meanwhile, she was responsible for people doing the work she used to do. This transition was a shock to the very way Mary thought. She had to relearn how she would get meaning from her work in this new role.

Nomination Accepted

This situation happens more often than the bestowal of formal titles of leadership. There are significant issues that cut across normal boundaries in which no official leader is clearly responsible. A combination of forces happens whereby (a) someone has the skill to handle it, (b) that someone has little tolerance for the current situation, and (c) the group urges that someone to take the lead. This person may be an individual with no title but suddenly is leading.

This was actually how I became a leader. I went to college to become great at software development. Within six months in my first job, I found myself doing very little development because I was organizing and leading multiple teams that cut across organizational boundaries. I was nominated, and I accepted. Within a few months I was given the title of manager. It did take me some time before I noticed the real implications of leading people.

Business Owner

Many leaders became leaders because they had a good idea and started a business around that idea. Simon is typical of many business owners. He had a great technical idea and started a business around the idea as a business of one — just himself. However, he soon found that his idea needed other people.

Although it took a few years, Simon found himself responsible for an organization of over 300 people and growing.

Many business owners did not realize when they began their business journeys that they would be leading so many people.

A Desire for a Title

This category represents just a small percentage of all the leaders I have worked with. However, some people really want the prestige of the title that is associated with leadership. They have often received business-specific college degrees and are hungry to be part of making significant business decisions.

They reach for and achieve their desire to have the title of manager. They find much of what they expected, such as the joy of looking at the returns on significant investments they made in the course of leading their organizations. However, they are often surprised to find that there is a world of people problems that comes with leadership. They were not prepared.

The Expert Becomes Leader

This happens frequently in the field of high technology development. "The expert" has been focused on a very specialized field of the technology. Everyone begins to look to "the expert" for guidance on anything to do with that technology.

Soon, "the expert" finds himself leading a group of people who follow him easily, based on the vast knowledge he possesses. The expert is able to do his own work and guide others in theirs. The rest of the team is often essentially a pair of hands for the expert's deep understanding and vision of where the technology, and thus the team, need to go.

The trouble begins for the expert when a new technology replaces his area of expertise. This will eventually happen. Now "the expert" has been typecast as a leader but is a novice at this new technology. He is no longer the expert but still the leader and not prepared.

Dynastic Transition

This is often true in family-run organizations. The daughter or son has worked in the organization for years and now the parents step out and suddenly the heir is in charge.

For example, a friend of mine worked in his parents' company and knew that he always would. He went to college to learn about the business, then came back and was his father's go-to person for any special tasks. He worked in many areas, even on the manufacturing line when the work was so intense that his hands would help meet deadlines.

His father ran the company for another twenty years and continued to make all the important leadership decisions throughout that time.

His father retired and immediately moved to Florida, handing my friend the complete responsibility of running the company.

He was suddenly in charge.

In talking to people about their leadership origin stories, there are common experiences regardless of how they became leaders. They come to a point where they realize that the work of leadership is different. They come to the point where they realize that the work of leadership is all about people.

Further, they realize that even if they didn't mean to do so, they each made a choice to be a leader. If they faced the leadership crisis referred to in the first section and continued leading, they again made a choice.

Whatever You Lead It Is All About People

This book is written for managers and leaders of all stripes. But what do they lead?

Leading a Group of Leaders Within a Company

This is a generic category that can include, for example, the COO (Chief Operating Officer) or a division leader of a cast of hundreds. Or it can include a manager of a group of thirty. The common characteristic is that they are leading other leaders.

These leaders report to at least one other person and often have a cast of stakeholders who have high expectations of results.

Leading Projects

The leader here may have a very large project team. There are teams as large as a thousand people dedicated to developing and delivering a single product to the marketplace. There are also teams as small as just two people.

The project leader must deliver results, whether anyone reports to her directly or not. She may have a single sponsor who is paying for the project. It is, however, more likely that the project has many stakeholders who care about those results, and they often have conflicting priorities they are presenting to that project leader.

Leading a Company

This can range from leading a famous company such as Apple to helming a small restaurant with a staff of three. It can also include a company the size of one person where individuals must lead themselves but also a virtual team of everyone who helps support that company, such as lawyers and accountants.

Even CEOs who are in charge of an entire company, small or large, have a number of stakeholders outside their direct lines of command. This can include the board of directors, a board of advisers, and investors in the company. It also always includes the customers of the business.

Leading a Cause

Gandhi, Martin Luther King, Jr., and many others are examples of people who had no official position but are yet considered great leaders.

I have a number of friends who are activists. One person is specifically working to protect the fresh water in our local lakes. She has put many hours into speaking, writing, and organizing to achieve this mission. She has suddenly found herself a leader of many people, none of whom are paid. Nor does anyone officially work for her. Yet all of these people look to her for leadership.

* * *

The common thread all the examples have is that leaders are leading other people to accomplish a shared set of objectives. The objectives vary immensely across the various roles of leadership and the context within which the leaders work, but what they all have is a set of responsibilities that comes with leadership.

These responsibilities are not to just get things done, but to lead others to accomplish great tasks.

All leaders know that it is truly all about leading people, and that comes with a taxonomy of trouble.

Leadership Comes with a Host of Trouble

A friend of mine once said, "Everything was fine until there was more than just me in the room." That evoked my laughter because he was talking about me entering the room — a great joke!

However, I often remember his quote when I find myself in a room full of discord. Yet, we absolutely need others if we wish to achieve the bigger things we desire to accomplish.

The following is a taxonomy of difficult challenges that leaders, even those with just a few years of leadership experience, are likely to encounter.

Troublesome Project Teams

If a project is truly striving for exceptional impact, there is a level of stress on the team and natural barriers in the way of success. This is normal. The problem occurs when the project's troubles start negatively impacting the whole organization. Consider these three examples.

1. Teams that are always late and have quality issues. This occurs when the project team says they are "almost done" and then announces to management that they need another three months. When that time is almost up, they say that they need yet another three months. This delays the revenue expected from this project repeatedly and does not allow the organization to plan. Quality issues exacerbate these delays. Further, this impacts the ability of leadership to start other projects and thus delays the revenue achieved from these other projects.

2. The "firefighting" projects. These teams are constantly battling fires. They release their products to their customers, but there are always significant problems that the team must deal with. The problems are multiplicative, typically starting with phone calls from customers. Further, the team is spending so much time fighting fires that the time to build new services or features is greatly diminished.

3. The divided team. There will be stress on any team striving for excellence, and that often leads to conflict. The key is that conflict must be constructive such that arguments produce better solutions and improved trust. With the wrong chemistry, the opposite occurs, resulting in damaged trust and team drama. The worst variant of this situation is when that drama leaks from the project in trouble and divides other parts of the organization as well. The damage done has many ripple effects, as leaders have to deal with drama instead of progress.

Troublesome Individuals

Projects such as the ones just mentioned can get in trouble because of things like technology issues or incorrect requirements. However, those are often excuses. Projects are successfully completed by people — not by methodology or technology. If a project is in trouble it is most likely to be a people issue.

The following is a sample of people issues that leaders commonly must address.

The cynic. Sarcasm, cynicism, pessimism, whining, and general sniping are all common negative attitudes that, when delivered in the right-sized doses, can provide relief to difficult situations. However, many leaders have faced situations where individuals bring too much of that attitude to the team and it breaks down the fabric of the team culture.

The slacker. Many times, managers face the problem of an individual not living up to teamwork standards. There can be many causes for this, but the main problem facing the leader is that there is a team member who is not contributing sufficient value. This is sometimes a competence problem, sometimes a bad fit of skill to task, and sometimes an attitude problem where someone just doesn't seem to care. The appearance may be "slacking," but the causes behind it are often hidden.

The diva. Some people are experts at narcissism. It appears that they believe that everything that is going on is all about them. In fact, with the most extreme divas, if things happen that distract from the diva being the center, the diva will raise enough trouble to bring the spotlight firmly back to his or her own personal center-stage performance. This is often a difficult leadership challenge, as most people develop their diva personalities because they are actually very good at what they do.

The pebble in the shoe. These people are the teammates who provide persistent annoyance to other teammates. The types of annoyances vary. Sometimes a person has a ready excuse that is actually plausible, but it seems there is always an excuse. Another example is the person who is a little critical of other teammates, with comments ranging from their clothes to how the work is done. It isn't quite enough to challenge them on it; it is the persistence of it. These slights observed by an outsider for one day would seem to be just mildly annoying if noticed at all. Yet these little "bug bites" being repeated daily have a cumulative negative effect.


Excerpted from Leading the Unleadable by Alan Willett. Copyright © 2017 Alan Willett. Excerpted by permission of AMACOM.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents


PREFACE, xiii,
1. The Leadership Crisis Point, 3,
2. Accept the Call of Exceptional Leadership, 19,
3. The Mindset to Lead the Unleadable, 33,
4. Fine-Tune Your Radar for Trouble, 53,
5. Take Action: Transforming the Troublesome, 69,
6. Follow Through: A Bridge to Enduring Improvement, 83,
7. Decision Time: Remove or Improve?, 101,
8. The Need for Mountains, 115,
9. Set Expectations of Excellence, 125,
10. Expecting Excellence Every Day, 137,
11. Exceptional Starts Lead to Exceptional Results, 157,
12. Lead Leaders: Growing Proven Ability, 179,
13. Leader, Lead Thyself: Exceptional Self-Leadership, 195,
14. Closing Notes on Transforming the Troublesome to the Tremendous, 213,
INDEX, 215,

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