Rohit Malekar

May 7, 2021

Why Do Careers Get Stuck in Middle Management?

Hypothesis: Most high-performing careers hit a wall in middle management because practitioners shy away from taking risks to address high-quality problems, thus unable to develop skills to create clarity and define playbooks as a leader.

Shifting a career from an individual contributor to a leader requires the ability to establish the why (clarity) and the expertise to determine the how (playbook). If we plot these two capabilities on a graph, it is easier to see this journey in the form of milestones.

Seeks clarity.png

This progression is best achieved as a by-product of working on high-quality problems. A high-quality problem requires self-discovery of a first principle that brings a shift in how you view your challenges. It is based on intrinsic motivation (recognition, challenge, collaboration) and needs you to embrace your weaknesses. If done right, such an experience can help you expand your worldview.

A good number of careers get stuck in middle management because of the comfort of solving low-quality problems efficiently. Low-quality problems use your strengths and do not influence who you are as a person. They are mostly triggered by extrinsic motivation (milestone, pay, title) and often lead to strong non-productive biases.

There is a lot still to uncover here with examples. I will follow up with a slightly detailed post in a few. Stay safe out there!

Update: The follow-ups to this post are below -
Part II: Common traps in seeking high quality problems
Part III: How can you expand your circle of influence?