rocket of the week: Alan Willett, Author of 'Leading the Unleadable' - rocketMBA

rocket of the week: Alan Willett, Author of ‘...

rocket of the week: Alan Willett, Author of ‘Leading the Unleadable’

We are proudly presenting our next rocket of the week – Alan Willett, the author of Leading the Unleadable: How to Manage Mavericks, Cynics, Divas, and Other Difficult People. Alan describes himself as, “An expert consultant, an author, a speaker, a teacher, a husband, a father, a voracious writer, and reader, and enjoying the lifelong journey of adventure.“

Previous to Alan’s current activities, he has run across the country, was a member of the founding of “ecovillage at ithaca,” worked as software engineer, lead various product development efforts and worked at the world-wide think-tank, the Software Engineering Institute. Alan’s Master of Science degree was designed around innovation in the fast paced world of technology development.

Alan Willett is the master of the “friction points” where business needs meet engineering reality. Alan transforms the heat of the friction points into innovative results. You can learn more by visiting his website at

What inspired you to pick this topic for your new book?

In working with so many different organizations around the world, I have seen so much lost potential in both people — and in profit — in managers not being able to properly respond to difficult behaviors.

The worst outcome is when the manager doesn’t handle a problem situation in a timely manner and they feel they are forced to remove the person from the organization. This was especially discouraging to me because this managers confessed to me that in these situations they often ignored the problem until it was “too late.”

I have helped many managers work with people they deemed difficult. We have transformed the relationship and brought out the contributions of the individual in a very positive way. In doing this work we not only helped that person become a strong contributor to the organization, but also energized the whole group.

It is important to me that the pragmatic techniques in my book are known to everyone that has to lead the “unleadable.”

What is the biggest mistake people typically make when dealing with a difficult person?

The biggest mistake is that people too often miss the early opportunities to deal with emerging disruptive behaviors.  Sometimes they notice the early signs of trouble, but do not act until they feel forced.  The behavior is starting to do too much damage to the organization, to their teammates, and perhaps even to customers.

Leaders often miss those signs of trouble that are very obvious to the disruptive person’s peers.  It is important to develop the skill of noticing, and dealing with those early warnings.  In the book, a chapter is dedicated to “fine tuning your radar for trouble.” The chapter is filled with ideas on how to develop your personal early warning system.

Dealing with a difficult person can trigger a lot of internal feelings, including frustration, anger, and detachment. How do you suggest people deal with those internal feelings?

Feelings are so important. They are rich nuggets of information when properly explored!  Even the feelings of “this doesn’t’ feel right” needs attention.  It doesn’t have to be an intense feeling to warrant some introspection.

I encourage people to take the time to think about what the feelings is telling them.  Why are they feeling, for example, angry?   When people think about this, it is often because the disruptive behavior is doing harm to the organization, the project, or the team.  Often the anger is self-directed even if the manager doesn’t realize it. On examination they may realize they are angry because they should have noticed warning signs earlier and somehow prevented the problem.

Once you have an understanding of your feeling, you can hone in on the specifics of what that harm is and why the situation should be corrected for the good of others as well as the good of the disruptive person.

When a leader has a better understanding of their internal feelings, they are much better able to be able to provide feedback that the troublesome person can hear – and most importantly – positively act upon.

You have worked with many clients in the tech industry, and many of our readers also work in tech. Is there anything unique about “leading the unleadable” in that industry vs. others?

The short answer is Yes and No.

Let’s explore “no” first. People are just people across various types of organizations whether it be a high-technology development organization or a non-profit group of volunteers working on an important cause.  Each of these types of organization has people, and the opportunity for those people to be very difficult to lead.

However, there is also “yes” to this answer.  I find that each type of organization has their own cultures and special nuances that are important to recognize. The tech industry does have some special circumstances that can raise the “degree of difficulty” of dealing with the difficult situations.  For example, the managers in high-tech often do not know or understand all the details of the engineering work being done.  To be more specific,  a leader may know what a “client-server architecture” is but wouldn’t necessarily have the skill to provide feedback on the code being written.  This make an interesting power dynamic as engineers are sometimes treated as having “magic skills” and the leaders are afraid to intervene, afraid to anger the magician-like engineers.

Leaders in any industry must focus on the good of the overall group. If a person or group of people are becoming a focal point of trouble, the leader must act.

How do you know if you are an “unleadable” person yourself? What are some tips to become more “leadable” if that is the case?

The number one best way is to have a trusted third party observer that is not a direct part of the work you are doing. This trusted person can be an amplifying mirror to provide you with the feedback you need to know if you have crossed a redl ine on your own “unleadable” traits.

It is important to be clear that your “unleadable” traits are absolutely positive until a red line is crossed. The subtitle of my book is “How to Manage Mavericks, Cynics, Divas, and Other Difficult People.”  Let’s look at the positive attributes of these.

Mavericks are going to push against boundaries. They are going to question current practice. They are going to be looking at how to really push the performance envelop. These are great things to do.  You want these people in your organization.

Divas think they and their projects are the most important things. They work to ensure the success. You want these people in your organization.

Cynicism is viewed as a negative, but it very valuable. Edward de Bono dedicates one of his thinking hats to this very trait. He calls it “black hat thinking” and the description of this hat is to spot the difficulties of situations, of why it will fail.  This type of thinking is so important to successful projects when it is in balance!

The trouble is when one of these attributes becomes the dominant trait of the individual.  A red line is crossed and the behavior becomes harmful to the group.

Thus having the amplifying mirror of a third party is so important. The more powerful of a leader you are the more important it is that you have the feedback loop to know when you have personally crossed that red line. It has been a pleasure of mine to do this service for many of my best clients.

As you went through the writing process for the book and thought about these issues and/or talked to others, what surprised you the most?

This shouldn’t surprise me because I have seen it so often, yet it did.  Most leaders experiences years of reacting to trouble before they put serious thought and effort into how to prevent trouble.

I have seen managers with drama-rich groups accuse the low-drama group managers as being “lucky” as they have such easy going people with simple projects.  The fact is those group managers are often tackling much more difficult projects with the same kind of difficult people. However these leaders put so much work into the prevention activities, it makes it look effortless to those that are struggling.

In many ways this evolution makes sense. Going through the struggle and mastering how to react leads to a deep understanding of the roots of the problems. This deep understanding provides a basis to work on prevention.

You will notice the book is organized with Part 2 focused on “Dealing with Trouble” and Part 3 focused on “Preventing Trouble.”

We always like to ask…what is your life motto or favorite quote?

There are so many favorite quotes to choose from.  For today, I pick one of the best from Robert A. Heinlein.

“A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly.

Specialization is for insects.”

My other favorite is shorter.  “Do good in the world.”

Don't want to miss out on the best of rocketMBA?

Just type in your email address below and we will send you a monthly digest!

Before graduating from Stanford GSB with an MBA in 2016, Alex worked for three years in public equity investing. Born and raised in Los Angeles, Alex enjoys hanging out at the beach with friends, playing basketball, and learning about history. He currently works in Equity Research in Downtown LA.


Your email address will not be published. Required fields are marked *

Don't Miss Out!

We'd love to add a bit of inspiration to your inbox! Every month you'll receive our latests blog posts, along with insightful articles we read and motivational quotes. 


Finally a newsletter you look forward to!

You're Awesome!

Check your inbox to confirm the subscription and you're all set!