Unwrapping The Gifts of The Unleadable

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Have you ever worked with people who seemed to you to be difficult, and perhaps in the worst moments, unleadable?

I pondered this question often when writing the book Leading the Unleadable: “How to Manage Mavericks, Cynics, Divas, and Other Difficult People.”  I reflected on my career where I have worked with, often in a leadership role, over 2,000 people. In my career as an expert consultant working with organizations around the world this number has at least quintupled. I also interviewed many executives in writing the book.

Unwrapping The Gifts of The UnleadableThe answer will not surprise you that everyone has worked with people who they consider difficult.  Indeed, leadership comes with taxonomy of trouble.  Consider projects that you’ve lead that were ambiguous and filled with unrealistic expectations; projects that are late and projects rife with quality problems, for example, and those are just the short list. However the worst part of leadership often comes with the taxonomy of trouble that comes with the people.  This list can be expanded to include as the subtitle of my book says, the maverick, the cynic, the diva, and other troublesome character roles.

I will talk about how to unwrap the gifts those people bring, but first let’s take a peek inside those boxes and see what presents await inside.


The Maverick 

Mavericks push against boundaries. They question the status quo. They are seeking to go beyond whatever the performance expectations seem to be. While this sounds like a desirable trait, the problem is when they cross a redline and instead of pushing groups to greater heights, they are hiding themselves and their team members in wrapping paper made of trouble.  I have seen mavericks show disdain for other people’s work in ways that causes harm to them and to the group.  Morale drops, productivity drops and attrition can increase. However, this gift is still there but it is too bad if no-one can see it.


The Diva

Divas believe so strongly that they and their projects are the most important things in the entire organization. Like the movie diva who wants their dressing room to be just perfect for their needs, the diva project star wants that same perfect, egocentric image for their project. This passion for perfection is also a gift as you want people that are really focused on the success of their project, even obsessed by it.

However this gift can be completely masked when the diva loses all perspective of the needs of others on the team, or for other projects in the organization.  They stay completely focused on the tactics of the project and will not work strategically with management to make strong changes quickly when needed. It’s their baby come hell or high water!


The Cynic

The poor cynic!  Cynicism is so often viewed in a negative light. However, a healthy dose of cynicism is needed on most projects! Edward de Bono even dedicates one of his thinking hats to this very trait. He calls it “black hat thinking” and the description of this concept is to spot the potential difficulties and anticipate the why things might fail.  This is what cynics do!

This type of thinking is so important to successful projects BUT only when it is in balance and not overdone. When balance is lost a red line is crossed and the behavior becomes harmful to the group effort.  Rampant cynicism leads to low risk taking, a draining of group energy, and a very frustrated leader!


Three Ways to Unwrap the Gifts

Provide Mountains for the Team to Climb

I find the worst behaviors arise when organizations and teams do not have a compelling mission to achieve. Without a difficult challenge the team believes in, they are more likely to wander and lose focus. They are more likely to have arguments arise that can lead to destructive conflict.

When teams are faced with something compelling, something that all believe in, something that is difficult and, with strong thinking and teamwork, achievable, the team will work together to climb that mountain. Be assured, there will still be some types of conflict, but with proper leadership pointing towards that mountain peak, the conflict will be constructive and lead to innovation.

Expect Excellence Everyday

I have seen many managers ask one question so often that most team members believe that is all they care about. You know the question:  “When will it be done?”

Exceptional leaders have clear expectations of what excellence looks like, that its vision becomes an essential part of the fabric of how they lead. They work to ensure what they focus on first is the customer and the value provided to the customer.  They focus on quality because they know that is the key driver to value and to schedule.  They work on ensuring everyone knows what behavior is expected to be successful in climbing the mountain challenge given.

Managers with drama-rich groups have accused the low-drama group managers as being “lucky” as they have when enjoying easy going people with simple projects.  The fact is those managers may be tackling much more difficult projects with the same kind of difficult people. However these leaders who take the time to know who they are working with and plan strategies to avoid drama that it makes it look effortless to those that are struggling.

Provide Powerful Feedback That Leads to a Powerful Positive Difference

Too many managers stay quiet for too long about the behavior problems they see. They hope it will just “work itself out.”  However, too often they come to me and in the analysis we realize the damage being done to the overall team is too much and is unrecoverable.  (Note: There is a chapter in the book dedicated to this called “Decision Time: Remove or Improve.”)

So, managers are advised not to staying quiet just hope things will work themselves out. That should not be an option.  The other, and best option, is to provide feedback.  However: too often the feedback doesn’t lead to a positive difference.

In the book, the chapter, “Take Action: Transforming the Troublesome,” details the steps to provide feedback that leads to a positive difference.  By the way, this skill comes with the bonus of the unexpected gifts:  the messenger doesn’t get shot and the receiver of the information says “THANK YOU!”

The first two actions I suggested in this article are: First, establish a strong foundation that makes this action easier; moreover, this skill can also stand alone. Setting a tone of honest and constructive communication paves the way for a constructive feel to any feedback.

In summary, developing the ability to deliver constructive feedback allows managers to transform the potential gifts and unwrap the benefits that the unleadable normally sabotage.


Additional Reading

Developing Leadership in the Digital Age

Evolution In Leadership: A Discussion with Shawne Duperon

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