Before I was a campaign manager for Brian Garry, I ran my own small business (and I still do). Before that I was the principal of a medium-sized urban high school and I had two school-age children. 

My calendar needs have changed over time, but the main point remained the same. I depended on my calendar. If I was not keeping up with my calendar, I was not meeting all of my responsibilities.

I’ve tried a lot of approaches. I have Franklin-Coveyed, I’ve bullet journalled, I’ve paper desk-calendared, I’ve gone fully electronic. Each approach had strengths and weaknesses, advantages and pitfalls.

This shift to campaign manager has changed my scheduling and calendaring needs tremendously. First, I am no longer primarily concerned with creating my own schedule. Instead, I am managing someone else’s schedule.

As David Plouffe said in The Audacity to Win, his account of being campaign manager for Barack Obama’s 2008 Presidential campaign, “How the candidate is spending time, day in and day out, ought to be the clearest reflection of the campaign’s strategy and priorities.”

So managing his schedule on top of managing my own, means having to commit to a full online calendar. There’s no way to constantly access and manage another person’s paper calendar. I’m still keeping my bullet journal (because Google hasn’t fully integrated to-do and journal with calendar, as near as I can tell) but that’s for me.

I’d like to share some things I have learned along the way, and I invite you to offer your feedback about any and all of the information below.

The best system is the one you use

What system works best? The one you use.

I sometimes get asked how I managed my time as I was writing a book as a principal. I usually answer, “poorly.” This is because I depended on “quantity time” over “quality time.” That is, I just worked a LOT.

Perhaps too much.

I’m going to credit the GTD system for emphasizing this important point, but I am certain that I read it in Covey, or Duhigg, or in any of dozens of other great leadership and time management books I’ve studied over the years. 

There is not one best system. That is, the best system is one that matches your needs, keeps you engaged, and fits the work you need to do. If you use it, and it helps you manage the work you have to do, that is the right system for you. The one you will use is the best system. Period.

I found visuals like this one from Moehrbetter.com to be very helpful to me as I conceptualized the work flow process.

Visit this link to download a PDF of this chart or its less cluttered predecessor.

In this image, a calendar is a place to “defer” work. I don’t love that term. Let’s use the word “schedule” instead. Because scheduling something shows that it is important.

The “big rocks” system works

In his massively best-selling and widely imitated and used system, Stephen Covey describes a calendar habit where you put the most important items on the calendar first. 

For instance, family milestones, children’s recitals and games, or large social commitments go on the calendar first, and then you fill everything in around it.

To show how this works, he used the metaphor of putting rocks, stones, pebbles, and sand in a jar. The size of the items is related to its importance in your life. Rocks are big events – weddings, an anniversary weekend escape, interviews. Sand is just all the little things that need to be done – laundry, watering the plants, and such. 

As part of a lesson to show how important it is to get it right, I used to sit in front of my students with an empty jar and a pile of rocks, stones, pebbles, and sand. We’d label the big rocks with events that students felt were the most important things – a date with a special person, a big game, a performance at church. Then we’d label the rocks as less important events, and so on until the sand was identified generally as a lot of little things.

There was always a debate about whether homework was sand. I argued it was rocks, but not big ones. That is, it was important, but not the most important thing.

 I’d pour in the sand first, then the pebbles, and then stones, telling a story about how I wanted to listen to this new song, and play my video game and stay up late and go out with my one friend. Social media posts and responses. I’d try to work in all the things that come up in a teenager’s life. 

Finally I tried to put the big rocks. And they didn’t fit.

Photo by Bruno Braghini from Pexels

“When are you going on that date?” I’d ask.

Invariably someone would say to their classmate, “You’re NEVER going on that date!” And we would laugh about the lost possibilities.

Then I would dump out the jar and start over, by putting the date with someone special in first. Then the other big rocks, and then we’d put in the rocks next, then pebbles. Finally I would pour the sand in. If some of the sand didn’t fit, no big deal. It was just sand.

By using this approach, though, we were accomplishing the things that were important to us in our life. These were the things that only we could define, but they were the things that mattered most for our happiness, our success, our joy.

For my candidate, this means protected time with his grandson. And some time where he can be *not* on campaign time. Sure, he still spends it campaigning, but that is just who he is.

The big rocks system works until it doesn’t 

Things come up. 

You can maintain your system brilliantly and get to most of your big rocks, but things come up. 

Two weeks ago we had an important strategy meeting with a crucial advisor, but my candidate was late. His business partner’s wife had died suddenly, and the funeral was happening that morning. His morning had been thrown into disarray, of course. 

These things happen. 

Another time we were driving between shots for an upcoming series of advertisements when we passed the location where a woman had been struck and killed by a driver of a car. This pregnant woman was temporarily housed at a shelter and was standing outside when the driver lost control and his car went over the curb, the sidewalk, and down a short embankment and hit the shelter. 

At the hospital they delivered her baby but it was stillborn. 

Brian made me stop the car. 

We had somewhere to go, but he needed to pay his respects. Too often in our society we associate people’s work with people’s worth. That’s not a mistake he makes. We walked the scene, and he told me the history of the shelter, and he paused for a moment at the impromptu memorial, saying a short prayer for the woman and her child. 

We were late to our next shot. 

So the best laid plans can often go awry, to paraphrase Robert Burns. But the best chance at success comes from having laid plans in the first place. 

Calendaring and holding space on a calendar

From my first day on board Brian’s campaign, I saw massive differences in how his calendar looked and how I managed mine.

First, several members of the campaign had access to his calendar. This alarmed me. This meant there was not one central decision-making person. Well, actually, we now had one decision-maker on the calendar, and it was the candidate. But without a clear plan for what made the calendar and what didn’t, the sudden default was that he had to choose on the fly which priorities were being met and which were not. The goal was to not force him to make too many decisions.

So I reduced access to his calendar, and worked on a system where only the two of us could add to or take away from the calendar and the daily schedule.

Second, he had multiple calendars. This was alarming too, because of the first rule: the system that works is the one you use, and the system you use is the one that works. I worried that Brian having too many calendars meant that he wasn’t using any of them. It is easy to get overwhelmed, especially when you are in a political campaign.

I encouraged him to use only one calendar, and I refused to look at any calendar other than the campaign calendar. In this way I hope to nudge him in the direction of a single calendar (or at least just one personal and one campaign calendar).

Third, there was no process for dealing with conflicts in the calendar. Some items had been added as recurring events, some items were “understood” to be recurring events. This happened whether they were important items / big rocks that needed to be there (like protected time with his grandson) or weekly online meetings that he could tune in to whenever he liked. 

I started putting items in with “??” at the end to indicate they were just space holders.

This is how I used to schedule with others, holding two or no more than three possibilities. Then, when I confirmed, I replaced the “??” with “!!” and deleted the other one or two options.

And then we had recurring “big rocks” which were Brian’s call time to potential donors. This is an unnervingly large part of a candidate’s time. It is even moreso the case when a candidate like Brian has spent decades working with people experiencing poverty and homelessness. If we knew 100 people who would donate the maximum $1,100 dollars, we could quickly sprint toward our fundraising goal. However, Brian’s average donor is giving about $85 dollars. So he will need to make more than a hundred calls each week. This time can’t be compromised often without long-lasting ill effects on the campaign. So, “big rock.”

The “??” approach would work with multiple users, so I started it, but the calendar could get very cluttered very quickly, again leading to the problem of the calendar not getting used.

Enter the spreadsheet.

Turning emails into calendar items

By far the handiest tool I ever used was an integrated email program that allowed me to import emails as calendar items. This was through the internal email and system offered through GroupWise by Novell. Similar systems are offered through Microsoft and Oracle.

Gmail has recently taken a good step in this direction, by offering some tools on the side of the screen. Ideally, the system will allow you to create a calendar item and then keep the email – and thus the associated Zoom link, attachments like agendas and handouts, and more.

Spreadsheets, here we come

As in so many things in this world, the correct answer was finally a spreadsheet. 

Here, multiple users could add events, sorted by date. We could then look together at the week ahead and make decisions, or even delegate people to attend in Brian’s place if he couldn’t make it. 

With two campaign interns, and a lot of help from everyone on the campaign to search for events and ideas, we began to populate a spreadsheet so we could make decisions about the week ahead as a group, keeping an eye on our priorities. In this way we knew what we were up against days in advance, instead of having to make on-the-fly calls.

This is where we are currently. I manage my own calendar and Brian’s, and I have a team working to populate the spreadsheet from which we draw our events.

If you have any ideas, tips, or tricks for managing a calendar, especially if it is someone else’s calendar, I’d love a link or a comment in the space below.