What Reading 500 Pages of Monday Musings Helped Me Rethink about Leadership
Over the last couple of months, I’ve been playing around with AI. As part of that project, I put all my Monday Musings posts into one file—it’s almost 500 pages long! The length made sense once I realized that I’ve been writing the newsletter weekly for over five years, but it still caught me off guard to see it in that format.
Before unleashing the AI on the compilation, I decided to re-read and manually categorize the posts. I was having trouble making all the categories work until I realized the missing one was simply “Humans Are Tricky.” That’s probably the most important category!
Once the compilation was ready, the first thing I asked ChatGPT to do was “summarize my perspective on leadership in about 100 words.”
What ChatGPT Told Me
“Your view of leadership centers on clarity, courage, and disciplined simplicity. A leader’s job is to focus attention—cutting through noise, setting priorities, and repeating key messages until they stick. Culture is shaped by behaviors, not slogans: what leaders model and reward becomes the organization’s truth. Committees and complexity diffuse ownership; clear routines and direct engagement drive progress. You see leadership as a daily practice of focus, example, and conversation—less about charisma, more about helping others align on what matters most and sustaining that focus through uncertainty.”
Reflections on the Synthesis
That summary sounds about right. It looks like AI knows what it’s doing!
The main thing I would have underlined in that summary—and what stood out as the major refinement of my thinking on leadership as I’ve worked with executives and organizations over the last five years—is the emphasis on the “daily practice of focus, example, and conversation.” This is, after all, why I wrote Everyday Strategic Leadership.
In particular, good leadership is fuzzy when thought of at a conceptual level. But when you drive it to daily practices, it’s much clearer.
How do I convince people to align their work with the strategy? You have as many conversations as possible. How do I develop the culture we need? You focus on setting an example and reinforcing the right behaviors in every forum possible. How can I help the team be more effective? You give as much praise and constructive feedback as you can.
It’s both complicated and not complicated.
Another thing I’ve come to realize is just how often technical challenges at work get mistaken for leadership challenges. For example, I’ve been in coaching meetings with clients who are stuck on how best to solve knotty issues on their teams. Partly because many take ownership of the challenges, they start by analyzing their own leadership behaviors, believing that if they were somehow leading more effectively, the challenge would be overcome.
In those instances, they’re finding leadership to be hard—and judging themselves for it—only because they’re applying the wrong tool. It’s like they’re responding to a door not opening by pushing harder (lead better!), rather than examining whether the door might just be locked.
However, the path forward often becomes clear when considering questions that help them realize that it’s not their leadership that’s the problem.
Are those two goals even achievable at the same time?
How does the organization’s structure contribute to the conflict?
Even if your team members had Superman-level skills, would they be able to reach the goal in time?
Mistaking a leadership challenge for a technical one also happens because many people get vague feedback. I’ve often talked with prospective clients, usually after a performance review that did not go as well as they hoped, who believe leadership coaching is the solution for getting a better review next time.
More often than not, however, I end up asking whether their leadership approach is the primary challenge. It usually sounds like, If you hadn’t missed the revenue target, would they have mentioned any of the issues with your performance?
Of course, great leadership supports achieving greater results, but the time scale is the challenge. When executives put too much effort into becoming better leaders, they risk putting too little effort into grinding out the results that others are looking for. It’s an 18-month effort to solve a six-month problem.
This dynamic highlights a somewhat uncomfortable truth: great results provide the space for great leadership—even though we'd like to believe great leadership always comes first. Yes, it’s worth doing things the right way, but there’s typically little patience for great leaders whose results are poor, and few nitpick the leadership qualities of those who get great results.
What’s Interesting to Me Now
The other goal of exploring my past writing was to spark thoughts about what’s interesting to explore about leadership going forward. I kept coming back to this: How will AI change the practice of leadership?
Artificial intelligence will obviously have a significant impact on workplaces, but I suspect the first challenge leaders will face is how to generate the pace of change that the moment requires while recognizing the natural inertia of the humans on their teams. Most directly, leaders will have to decide whether to be patient with the change process, force people to change against their will, or replace significant parts of their teams.
There’s probably not one right answer to that choice—and what’s right for the organization may differ from what’s right from a moral perspective—but I suspect leaders will need to clarify their personal and leadership values to both navigate the change and sleep at night.
Moreover, I imagine that artificial intelligence will force leaders to analyze which parts of their role are management (e.g., the information processing of project management, decision-making, and providing expertise) and which are leadership (i.e., attending to the human challenges of driving results). The sharp edge of that dynamic is that, as AI takes over much of the information-processing part of the role, it will leave some managers with the core question: What do I do all day? That’s not just a question of how they should spend their time, but more fundamentally, how they justify their paycheck to their employer and justify the person in the mirror that they are making a contribution.