Monday, June 16, 2025

The Challenge of Self-Management

A long time ago, Price Pritchett wrote the following: “The first chore in managing change is the toughest: self-management. Handle that right, and you’re halfway home.” On the surface, this seems self-evident. But when one rereads it a couple of times, we realize that it has great depth. The challenge is that most leaders do not do this level of work. They avoid self-management, and instead focus on managing others first, organizational change second, and maybe themselves as a distant third. Still, if they were to do self-management first, they might discover that they are “halfway home.”


From my perspective, self-management begins with an understanding of how we choose to think about time. Once you choose the path of leadership and then organizational change, you will be constantly interrupted by some one. Most people new to leadership are surprised by this happening. Most experienced leaders understand that it comes with the job. 


Years ago, Peter Drucker shared two important insights about leadership and time. First, “The executive’s time tends to belong to everybody else.” Everybody and anybody can move in on your time and eventually does. How we deal with these interruptions sends a message about what is important, how people should treat each other, and how people should respect each other’s time. 


Second, “Executives are forced to keeping ‘operating’ unless they take positive action to change the reality in which they live.” As leaders, we can not let the flow of events completely determine the priorities we hold. Instead, we need to define what is important in spite of the flow of current events and current interruptions. We need to lead proactively rather than manage reactively. 


I have often reflected on Drucker’s insights since he published them in an article called “What is Our Business?” in the June 2001 issue of Executive Excellence magazine. However, I always struggled on one level to explain them in a practical, self-management kind of way. It was not until I read Cal Newport’s book, Slow Productivity: The Lost Art of Accomplishment Without Burnout (Portfolio/Penguin, 2024), that I discovered a key concept that explains a lot of about self-management.


In the book, Newport defines slow productivity as “a philosophy for organizing knowledge work efforts in a sustainable and meaningful manner, based on the following three principles: 1. Do fewer things. 2. Work at a natural pace. 3. Obsess over quality.” He defines “Pseudo-Productivity” as “the use of visible activity as the primary means of approximating actual productive effort.” Both of these definitions were helpful. They reminded me of an earlier book where he articulated the difference between deep work and shallow work. 


With this slow productivity framework in mind, Newport expands on the first principle called “Do Fewer Things.” As he writes, “Strive to reduce your obligations to the point where you can easily imagine accomplishing them with time to spare. Leverage this reduced load to more fully embrace and advance the small number of projects that matter most.” Then, for me, he adds a deeply insightful concept into the mix about leaders and time. As he writes, “In knowledge work, when you agree to a new commitment, be it a minor task or a large project, it brings with it a certain amount of ongoing administrative overhead: back-and-forth e-mail threads needed to gather information, for example, or meetings scheduled to synchronize with your collaborators. This overhead tax activates as soon as you take on a new responsibility. As your to-do list grows, so does the total amount of overhead tax you’re paying. Because the number of hours in the day is fixed, these administrative chores will take more and more time away from your core work, slowing down the rate at which these objectives are accomplished.” Later, he continues, “A key property of overhead tax is that it tends to expand to fill as much time as it’s provided. So long as a project is something that you’ve committed to, and it’s not yet complete, it will tend to generate a continual tax in the form of check-in meetings, impromptu email conversations, and plain old mental space.”


When I first read about the concept of an overhead tax, I had to stop reading, put down the book, and think. It was the key that unlocked so much for me as an executive coach. Over and over, I have worked with leaders who are willing to put in the deep work, i.e. the time, the focus, and the commitment, on a project, goal or strategy, and yet over time, they struggle with completing it. What I realized is that the problem is not effort or focus. Nor was the problem the lack of strategic perspective. The actual problem was the overhead tax. The more administrative details they had to manage, the less time they had for the actual work. Furthermore, if they were engaged in multiple projects, then there were multiple overhead taxes, all demanding time and attention. 


As I continued to read, I agreed with Newport that so many people are struggling with the overhead taxes that they have crossed a tipping point and therefore can not get to the actually key objectives, goals, or strategy that they were seeking to accomplish. Instead, they are swamped in administrative overhead. In short, their self-management is not self-management. They are actually just managing more and more administrative details with no time for self and actual work. 


Furthermore, as more and more of their time is consumed with the overhead taxes, they also do not have time for renewal or recharge. They just become consumed with minutia and the sinking feeling that life is nothing more than small details piled on small details. The outcome from this pattern of working and living always results in decision fatigue leading to decision burn-out. As Marshall Goldsmith in his book, Triggers: Creating Behavior That Lasts - Becoming the Person You Want to Be, (Crown Business, 2015), wrote: “Doing things that deplete us is not the same as doing things when we’re depleted.” And in the end, we always pay the overhead tax, resulting in careless choices, poor decisions, and ultimately a surrender to status quo. 


So, how does one do effective self-management when managing change?


First, sit down and evaluate how many current projects and priorities you are working on. Then, calculate how much overhead taxes you are paying per project. This may be an uncomfortable exercise, but the goal is to do fewer things well rather than many things poorly. And it is important to discern that doing fewer things well is not the same as accomplishing fewer things. The goal is to generate quality work by actually having real priorities rather than hopeful priorities. 


Second, improve your ability to delegate. When we choose to delegate something to another person, we are transferring the authority and responsibility from us to another person. The difficulty is that during the act of delegation we never clarify how much authority or responsibility the person has and can use. Furthermore, we assume that the person being delegated to understands the problem and has the skills and knowledge to solve the problem. Finally, we assume that they know how to measure their progress and know what a successful completion of the problem looks like over time. Nine times out of ten, poor delegation creates poor results, and in turn poor self-management. 


Third, schedule adequate transition time during each day. Our days are packed with back to back meetings and back to back check-in sessions. Often, we are shifting from operational issues to strategic issues to personnel issues. The result is reactive leadership and little time to process or complete anything. At some point, we just have to realize that this unceasing pace of work and life is unsustainable, and is detrimental to our health and our core relationships at work and at home. When we schedule transition time into our daily and weekly schedule, we are then moving from a place of clarity and alignment. 


Fourth, find and work with an executive coach, especially one who will ask you questions that you yourself would not ask. By creating time and space for structured unstructured time, we are building a foundation for resilience and capacity. This unique space gives us a chance to pause, share, and reflect. It also is a chance to think out loud in a safe and open environment. Here, we can zoom out to gain perspective or zoom in to gain understanding. We also can slow down so we can make wiser and more thoughtful choices. Then, we have a chance to check our default thinking and default reactions in order to not perpetuate unhealthy responses based on past unhealthy experiences. Over time, an experienced executive coach can offer unique insights and wisdom from their own years of working through problems of a similar nature, too. 


Fifth, discover or recover a why to live for that is greater than just getting all the office work done. As Jim Loehr and Tony Schwartz write: ”Purpose creates a destination." It is time to reclaim purpose and to reclaim destination in our life journey. It is time to figure out why we do what we do, and then use this to guide our life choices and decisions. Too often, we are living someone else’s definition of success. We also are trying to meet their expectations, and are not clear about what are our own priorities, hopes and dreams. When we create a purpose driven life, we are living and working from a place of great strength and deep inner alignment. We then move in a new and more grounded manner toward our desired destination. 


Self-management in the midst of change is hard and important work to do. It happens on a daily basis and is never completed in a single day. Still, by doing it consistently and thoughtfully, we can manage change in an effective manner. And then, we will be halfway home.


© Geery Howe 2025


Geery Howe, M.A. Executive Coach in Leadership, Strategic Planning, and Organizational Change

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