Leadership Groups

Leading is Lonely 

Let’s face it, being a leader can really suck sometimes. You can’t really share those deep, dark emotions that keep you up at night. You know very well that sharing those feelings would only bring about fear in others and cause them to question your leadership. Not what you want.  So you hold it all in. And it eats away at you over time.


Imagine being able to really let it all go; imagine being able to release the burden that you’ve been carrying; imagine the freedom and lightness you might feel.  Imagine what creativity and intelligence can fill its place.


This is what can happen in a leadership group.   

Group Support is the Answer 

Each member of a Leadership Group works together to create an atmosphere where each person feels free to speak honestly and candidly about their emotional struggles. Rather than fix each other’s problems, they simply listen to the rawness of each others challenges. Members might lead with their curiosity, asking questions with appreciative inquiry. Members may make observations about what they are seeing or hearing.  Members might even directly challenge another member about an incongruence that they are seeing.  

To be clear, there is nothing easy about this for most leaders, who are used to tackling and handling the trickiest of problems. In a Leadership Group, leaders are asked to table this part of themselves in service of allowing authentic vulnerability to emerge among members. Problem solving and emotional vulnerability do not go hand-in-hand.  Mature Leadership Groups who are successful in learning the art of setting their problem-solvers aside are able to access a collective intelligence and wisdom that drives the group and their members to deeper levels of transformation.  

The role of the facilitator is to steer the group towards greater honesty and vulnerability and away from superficiality and a problem-solving mentality. The facilitator’s job is to reflect back what the group or a member is doing at any given moment. Their role is much like a curator, where they will bring the group’s attention to a certain aspect of the group’s experience and then step back to allow the group’s process to unfold.   

Paradoxically, while a Leadership Group isn’t set up to fix each other’s problems, the participant’s problems often do get solved. This is known as the paradoxical theory of change. It states that if we truly accept a person as they are, only then can they change. 

Leadership Groups are organized around members from similar leadership positions. This allows for authentic empathy, understanding and sharing.  For example, the emotional struggle that a CEO is experiencing is likely quite different than a first-time manager.  

Does this speak to something you’ve been wanting? I welcome you to reach out to learn more.  


I’ve been a member of Jeremy’s Leadership Group for years.  It has made all the difference in my personal and professional development. Learning to slow down, listen and reflect has been invaluable.  Acknowledging the stories I tell myself as just that, has freed me to go beyond the surface narrative to the emotional core of issues.  This has enabled me to make more sound decisions and to deal with difficult situations in life and at work more effectively.  You owe it to yourself to give it a try!

-DC, Small Business Owner, Portland OR

Groups are for the following roles:

Small Business Owners


First-Time Managers

Senior Executives

Mid-Level Managers

If you would like to learn more about joining one of these groups, I would love to hear from you.



[email protected]




0333 SW Flower St. Portland OR 97239