What a leader's calendar reveals about what she actually values.
A supervisor I once worked under spent hours across at least three separate admin meetings planning how we would celebrate the twelve days of Christmas as a staff. The decorations. The daily surprises. The reveal for each themed day. I remember the genuine enthusiasm in those planning sessions, the kind of energy usually reserved for something that actually mattered to the outcomes we were responsible for.
During that same stretch of weeks, almost no meaningful time was spent addressing our high staff turnover or the steadily declining data on student achievement. Both problems were named, occasionally, in passing, in the kind of tone reserved for acknowledged but unaddressed concerns. Neither one received the sustained, detailed planning attention that twelve days of Christmas received across three separate meetings.
The contrast was not subtle. It was simply never named out loud by anyone in the room, including me, for longer than it should have been. I remember sitting in those meetings, watching the whiteboard fill with decoration themes, feeling a quiet discomfort I did not yet have language for, a sense that something was misallocated without being able to articulate exactly what or why.
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I do not think she woke up choosing decorations over outcomes on purpose. I think, like most leaders who drift this way, the urgent and the pleasant crowded out the important one small decision at a time, until an entire season had passed with the wrong things getting the calendar's best hours. Planning a Christmas celebration is enjoyable. It produces visible, immediate goodwill. Addressing staff turnover is uncomfortable, slow, and often requires confronting decisions that are harder to reverse once named.
I understand that pull now in a way I did not understand it then, watching from the outside. The comfortable work always feels more urgent than it actually is, precisely because it is comfortable, and the uncomfortable work always feels less urgent than it actually is, precisely because avoiding it costs nothing immediate and visible.
There is an old saying about keeping the main thing the main thing. Watching that season unfold taught me that the saying is easy to agree with and remarkably easy to violate without ever noticing you are doing it, because violating it rarely looks like an active decision. It looks like a hundred small, individually reasonable choices about where to spend the next hour, none of which feel, on their own, like a betrayal of priorities.
A leader's calendar is a confession. It tells the truth about what she actually believes matters, regardless of what she says matters in a mission statement or a hallway conversation.
I have thought about that season often in my own leadership since, especially in weeks when I catch myself giving hours to something low-stakes and comfortable while something genuinely important sits untouched, quietly, in the background, waiting for attention I keep finding reasons to postpone.
I remember the first time I ran this exact audit on my own calendar, expecting to find it reasonably well aligned with what I claimed to value. I did not find that. I found meetings that existed out of habit rather than necessity, hours spent on tasks that felt productive without actually advancing anything that mattered most. It was a humbling exercise, more humbling than I expected, given how confidently I would have described my own priorities if you had simply asked me to list them from memory.
Here is the audit I now run on myself, and the one I would encourage any leader to run honestly. Pull your actual calendar from the last two weeks, not the one you intended to keep, the one you actually lived. Where did the hours go. Does that pattern match what you would say, out loud, in front of your team, actually matters most right now?
If it does not match, you do not have a time management problem. You have a values clarity problem wearing a scheduling disguise, and no amount of better time blocking will fix it until the actual priority gets named, out loud, specifically enough that it can be checked against the calendar honestly, week after week, rather than simply intended and quietly deprioritized again.
I think about that supervisor with more understanding now than I had at the time, watching her from the vantage point of my own leadership since. Staff turnover and declining achievement data are not comfortable problems to plan around. They resist tidy agendas. They often require conversations that risk conflict, decisions that might not work, timelines measured in months rather than the immediate gratification of a well-received holiday celebration. I understand, now, exactly why the comfortable planning won out for as long as it did.
I do not think naming this pattern once is enough to correct it permanently, in myself or in any leader. I run my own calendar audit quarterly now, not because I trust myself less than I once did, but because I trust the pull toward comfortable, visible work to reassert itself given enough unexamined time, in me as much as in anyone. Vigilance about this particular gap, I have learned, is not a one-time correction. It is an ongoing practice, closer to maintenance than to a cure.
I eventually left that particular role, and I do not know what became of the staff turnover or the achievement data in the years after I left. I hope someone finally gave them the sustained attention they deserved. What I carry forward from that season is not judgment of the supervisor who prioritized decorations. It is a standing question I now ask myself regularly, uncomfortable enough that I sometimes have to force myself to actually ask it. What is my current version of the twelve days of Christmas, the pleasant, visible work quietly displacing something harder that actually deserves my calendar's best hours.
I think most leaders have an answer to that question sitting somewhere just beneath conscious awareness, close enough to name if they are willing to sit still long enough to look. Mine changes by season. Some years it has been an ambitious content calendar substituting for the harder work of retention conversations. Other years it has been perfecting a system that did not yet need perfecting while a genuinely broken one sat untouched nearby. The specific answer matters less than the discipline of continuing to ask.
-- Dr. Rhonda
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