Inspiringly Horrible Bosses

Over the last few years, I’ve been fortunate enough to provide coaching & leadership development workshops to new and emerging leaders. These half/full day sessions have been hugely rewarding and a great learning experience. Being able to listen to and understand so many perspectives on leadership and help deeper thinking around it is a privilege.

One specific exercise I love to use and always brings up very interesting views is to give the attendees space and time to think about what makes up a great leader? What are the attributes, traits, competencies and habits they’ve experienced, or would like to experience from an inspiring leader? It gets the conversation started, helps the group open up and connect better.

Interestingly though, when the question ‘what makes up a horrible boss?’ is posed, the energy changes. There is more laughter, greater enthusiasm, and one flip chart page per group to list out the traits never seems to be enough! Everyone has a few words to contribute about their horrible boss experience over the years and the sharing within the group goes up a few notches. All in a confidential way, of course.

Next the real interesting work happens. When the group is asked to come up a leadership philosophy of their own (in 25 words or less) first using the words identified in a great leader, it can be difficult.

However, when asked to do this same task by thinking of the words to identified for the horrible boss traits and flipping these to be opposite (e.g. flipping micromanagement to autonomy), to be the leader they DO NOT want to be come, the philosophy starts to flow onto the page much quicker.

What are the great inspiring lessons you’ve learned from a horrible boss? You have a lot to thank them for as are their bad habits are helping you grow into exactly the leader they aren’t.

Till tomorrow.


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Rob is a qualified Executive Coach (ICF) and has been Mentoring and Coaching over the last decade in various roles held during his career. In 2017, Rob launched the Rob of the Green Platform which hosts the 1% Better Podcast. Rob currently is a director of Project Management and Leadership Coaching at Dell in Cork, Ireland. Rob also publishes articles on productivity, leadership, goal setting, meditation, and other topics, like this one!

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