Book Review - Leading the Unleadable


Leading the Unleadable is really more about generic leadership principles than it is about dealing with difficult employees or other challenging interpersonal issues at work. But that does not diminish the value of the book overall, and I would suggest that the relatively short time it takes to read this book is well worth it.

Technology is Easy; People are Hard

We know some technology is hard (distributed systems I’m looking at you) but generally speaking as an industry I think we actually are pretty good at getting technology in place and working…eventually. Sure, usually it takes awhile and is more expensive than we’d like, but ultimately it gets done.

However, if the DevOps paradigm has showed us anything, it’s that of the triumvirate of people, process, and tools, people are the most difficult. Then comes process (because it’s so related to people) and finally, technology.

Leading the Unleadable

Leading the Unleadable (LtU), by Alan Willett, is a management and leadership book about dealing with difficult people. Interestingly the preface of this book, ie. the very first page, contains the following sentence:

Sometimes leaders terminate difficult people too quickly, which harms the group by giving it no chance to change the difficult people and reclaim them.

There is a lot to unpack in that sentence. Perhaps the most interesting part is the idea that leadership is often about helping a team integrate and deal with difficult people, as opposed to having a “leader” deal with them. Later on in the book (pg. 35) we get a supporting quote:

Exceptional leaders know that when encountering some behaviour or action that appears unacceptable their first thought should be to wonder what they don’t understand about the person and the communication process.

The book suggests that more often than not difficult people can be understood and reclaimed or integrated by understanding their personal story; that overall people are good and should be approached as such. It is certainly a positive view on difficult people. Troublesome Individuals

The book lays out a few archetypes of challenging people:

A couple of examples are given in terms of dealing with the above archetypes, specifically Divas and Mavericks. However, while the examples are good, I don’t feel that they in depth enough, nor do the archetypes cover enough possibilities, especially for a book that is supposed to deal with a specific subject: dealing with difficult people. Actually, not just “difficult” but “unleadable.”

However, LtU does give an interesting model for determining whether or not to “remove or improve” an employee or team member (chpt 7). Leaders could adopt that model to help determine what to do with challenging employees. Leadership Advice

The book does provide great leadership advice. For people who want to be leaders, it puts the following points in order of importance:

  1. Provide a great return on investment to your employer
  2. Improve yourself
  3. Reduce your labour while dramatically improving the value you provide

LtU also constantly reinforces the need for leadership to set the bar high in terms of what the organization can accomplish. Willett also discusses how exceptional leaders accept reality but don’t let it define them. He is definitely a proponent of “the need for mountains” and setting audacious goals. It would seem that Willett believes that many issues in the workplace are caused when people, teams, and even the organization itself, aren’t challenged.


I do recommend the book. It is a quick read and there is valuable information that can be gleaned from it, especially about general leadership.

There are a couple of useful chapters on processes for dealing with difficult people, especially chapters 5 and 6. If the difficult people are really misunderstood people, then these ideas, tools, and processes should help.

If there is any specific message that I took from the book, it’s that setting the bar high is important. Often people, teams, and organizations don’t give themselves enough credit in terms of what they can accomplish.