PMPM Execution -- Organization

Sometimes, the kid comes home from sleepovers with other kid's clothes. It's usually because the original owner outgrew it or didn't like it and my kid did. Or it could be a swap of clothes. I usually only discover this when I catch it in the laundry (the kid sometimes does laundry, but when I do it, I'll grab whatever's dirty, so it's a mix). I long ago stopped worrying about this sort of thing. As long as the garment is cleanable and generally suitable for age and weather, the kid can wear whatever, so I don't stress too much. This is in part because I'm a cool parent (ask anyone) but also in part because I just don't have my shit together enough when it comes to laundry.

Not being organized about laundry doesn't cause me too much woe in my life. Enough gets done so that we have clean things to wear and I'm always conscientious about dress clothes and dry cleaning. Beyond that, if the laundry room is a mess and we're usually about four loads behind (where in gods' name did all these towels come from!) well, it's not the end of the world.

However, there are other areas of my life where being organized is much more critical. Work, for example. Clearly as a project manager, it's really important that I be organized. In fact a part of my role is really being organized for other people (I organize so you don't have to!). Being disorganized is bad, bad, bad in my line of work.

Expert Project Manager for hire...

I find that when I have a personal project or working I want to launch, being organized is just as critical. This is different from a place where I've already got my systems sorted and my habits set. There, the organization is more organic. But it takes work to get to that point. So my advice is to be organized about your workings -- particularly if they involve big changes or new processes. Documenting a project charter and plan and so forth is a part of that. In Part Two of the Project Planning post, we talked about creating a project schedule including deadlines, milestones, and repeating tasks.

However, having an organized list of stuff that you don't actually get organized enough to do isn't really helpful. When it comes to project execution, it's organizing your time and activities that means the difference between getting your shit done and not. This is one of the key components of making your plan actionable.

Since being organized is important for my work, you'd think I'd be really good at it. But what I've discovered over the years is that I often rely on raw brainpower in order to stay organized. That is, I remember the things I need to do and track. However, I've noticed a couple of issues with this plan.

First, there's only so much I can remember, and since work is where the money is, I will remember stuff at work in lieu of at home. So I can remember the details of my three different projects, but I can't remember that we need milk. Second, as I get more responsibility at work, there's more to remember. The sheer number of moving parts and integrated dependencies and so forth means it's harder to just remember everything. This was brought home to me painfully when I forgot an important deadline about 18 months ago. Just remembering everything wasn't going to work anymore. Third, as I wend my way through my 40s, I find that my brain isn't as limber at it once was. It still works generally fine. I don't have any medical concerns. But I'm less likely to have rapid recall of tons of facts. What I am better at instead is synthesizing facts into theory, pattern, and strategy... not a bad trade off, but only if I get better about logging the details I need to track.

After the missed deadline, I took stock and reevaluated the gaps in my current system and filled those gaps with techniques and tools. A lot of the rest of this is a little bit organization porn, I admit. But it's based on things that really work for me and may be helpful for you.

The Hierarchy of Organization
I tend to track items in the following general hierarchy:

This is the high-level container that everything else live in. Examples include work, home, and so on. For me, there's enough difference in tools and processes (and requirements for information privacy) between the two that it makes sense to track them separately. For you, the areas might be Business/Personal, Family/Personal, Day Job/Business/Creative. Or everything just blends together and you don't really have distinct areas at all. What I don't recommend is separating Magic/Mundane, since you should be making every effort to integrate those into throughout your life.

Two different types:

Projects: As you well know by now, projects are driven by a common goal and require multiple different activities to complete. They also have at least one deadline. From delivering a new software release (work) to planning a vacation (home), projects have some kind of end goal or target and a deadline. We'll get back to the deadline issue in a bit because it was one of the flaws in my project tracking that I had to fix.

Operations: We touched on ops before when we discussed risk. An operation is a group of related activities with a common goal, but without a specific deadline. Operations are ongoing efforts. For example, Clean Garage is a project. The goal is to be able to park a car in your garage and the deadline is October, before the weather gets bad. Keep the Garage Clean, however, is an operation. It has a goal, but there's no end to it. It's ongoing and you have to keep up with it. Meeting the goal of the project isn't a one time event, but a status that's constantly being tracked or judged. This is why websites track uptime. Because getting up and running is important, but staying up and running is even more important. You can see how completing a project can spin off a regular maintenance operation that follows. So project Adopt a Dog is then followed by operation Dog Care (including training, vet visits, regular upkeep like baths and nail clipping, keeping them supplied and so on). When taking on a new project, you should always consider what the ongoing operations will be and compare that ongoing cost to the benefit of meeting the project goal.

Within these two groups are all the activities that need to get done in order to meet (or in the case of operations, keep meeting) the goal. I distinguish between types of activities because they have different characteristics that require different management. This hadn't been clear to me in the past, which is why I was having issues getting stuff done at home. For each of these items, I'm going to briefly note the solution I use, issues I've had in the past, and how to tell if this is a problem for you.

Events -- If it lasts a whole day or more and you can't schedule anything else... that's an event. This became especially important when I started traveling for work. The key to tracking events is advanced visibility. If I look at my regular calendar in the morning and see that I have a meeting at 1, that's usually not a big deal. But can you image waking up and realizing you need to be at the airport in half an hour? Yeah, not so much. Or more likely, I haven't forgotten a trip, but I forgot the trip when I scheduled another critical meeting, class, appointment, etc. At this point, that can happen months in advance.

This visibility is so critical that events are the only things that I actually track in multiple places (something I usually try to avoid). I note them on my Outlook calendar at work so that I appear unavailable when people try to schedule meetings. They also appear on our home calendars that we use to track household schedules. In addition, I track all major events on a vis-a-vis wall calendar in my office. That's so I can see availability many months in advance. I know that sounds a bit crazy, but in fact, I just hung my 2016 calendar so I can start to visualize next year's stuff as well. A non-electronic solution would just be the annual wall calendar. A monthly calendar doesn't work nearly as well because you only see this month (which means that by the end of the month, you are completely unprepared for what's next).

If you find you can never plan anything between all the classes, camps, trips, etc. going on in your household, this is where to focus your efforts.

Appointments -- An activity that includes a start and end time (duration), affects availability, and needs a reminder. From meetings at work, to your ritual on the full moon, to the typical Dr./Dentist kind of stuff, these are tracked on the same electronic calendars as above. No double-tracking required. A date book is a perfectly acceptable paper solution to this. One with day and time slots where you can see at least the current week all at once. If that datebook also includes all your events, you will never over schedule.

If you are always forgetting about appointments or meetings or constantly end up double-booked, this is the place to concentrate on.

Todos -- An activity with a rough timeframe (today, this morning, this week, etc,), no duration, doesn't affect availability, usually repeats, needs a reminder. These are items like give the dog a heartworm tablet, put the trash out (bi-monthly), make an offering to the spirits of your city, refill a prescription, etc. They don't really fit into a calendar slot like an appointment because they don't have a specific timeframe. But they do have a rough time they need to be completed by. They typically repeat and are infrequent enough that a reminder is necessary. These also include all the cyclical items in your PMPM workings, like regular reviews of your project plan, check-ins with stakeholders, and so on.

I tend to forget these things, so some kind of in-my-face appearance is critical. I don't want to stare at them every day (because I will train myself to ignore them and then never see them again), but need them to magically appear when the time comes. There are a host of tools and apps that work great for this kind of stuff and no reason to overthink it. Pick one that works for your platforms and allows you to get an email, txt, or phone reminder when they are due. If you prefer paper, then putting them in a side column in your date book works. You can mark them for a particular day or just for the week and then rewrite them into future weeks as your reminder. Or you can use the Getting Things Done tickler file method (Google for more on this).

Before I got a tool with reminders, I was always letting this kind of stuff slide. I mean, I don't stare at my calendar every minute of the day. I needed something that would poke me. If you keep losing track of your repeating activities, this is the place you need to improve.

Tasks -- An activity with no timeframe, unknown duration, no auto-repeat, and no reminder. If you make a list of all the small tasks you need to do to accomplish a big goal, there will be a ton of things you have to crank through. But while they may all have to be completed by a certain date, they don't each have to be completed on a particular date. This is the key difference from a todo.

I know this sounds like a subtle distinction, but it was totally screwing me up. Date driven tools like calendars didn't work because it wasn't like each item had an obvious day attached, let alone a timeframe. For tracking these the best tool is a good old fashioned checklist. Many of the todo-type tools and apps will also allow you to create checklists that don't have dates attached. And for paper, nothing beats a notebook where you write down everything you need to do and then check or strike them off. However, I found that an outliner worked really well for rapidly capturing items and then easily reordering and grouping them.

If you are having a hard time focusing on the things you need to get done to reach your goals, or if you are surprised when a deadline arrives and not everything is complete, this is the place you need to improve.

This was the big weakness of my previous project planning (hence the missed deliverable). Unlike operations (which tend to have repeating schedules), projects have one or more deadlines. Each deadline not only has a due date, but also contains a number of activities that have to be completed by that deadline. However because this date was in the future I had no way of "seeing" it coming. Here's where my system fell down.

Let's say you have a PMPM working with a six month duration. In order to accomplish the goal of the working, you need to complete a bunch of different activities. Some of those activities will have dates (like meetings) or timeframes (like todos), but plenty of others will just be tasks attached to the deadline. That deadline is far enough away in time that you can't really see it coming. It's easy to forget that it's out there, looming, until it gets close enough and then you're rushing around trying to finish everything at the last minute.

Calendars aren't very good at this sort of thing. They only show you the month or week or day ahead. And reminders don't help because, well, when do you remind yourself? Reminding yourself right before its due doesn't help. And reminding yourself right at the start doesn't do much good either. If it's an important deadline, you'll want to remind yourself every single day, but not in a way that's annoying or that will -- Pavlov like -- train you to ignore it. And checklists aren't very good either. After all, a deadline isn't a thing that you do and check off. It's a thing that you meet, by doing all the other components.

I chewed on this for a while (nothing will motivate you to focus on a weakness like having fucked up based on that weakness in the past) and came up with several ideas:

If you don't have many projects or deadlines, you can track it manually right in your PMPM planning write up. I talked a bit about this in the deeper content portion of project planning. So if you want more details, sign up  (it's even free!).

Another idea is to put the deadline on your annual wall calendar. This gives you visibility many months in advance, but the weakness is that it doesn't do anything to tie that deadline to the activities it contains. That means you risk thinking you met the deadline, but actually forgetting a component. It's also only works if you don't have too many deadlines.

Since I do have a ton of deadlines, I leveraged the outliner for that as well, and I have to say it really helped me keep much closer track of everything I needed to do. I should point out that this switch occurred before I took on a new and much more complex and demanding role and I'm sure I wouldn't have been as successful without it. I simply list all my deadlines in date order and then put all the tasks a level below. When a task requires a event, meeting, or todo, I schedule those things in their respective tools and then cross off the task. I can easily scan down the list of deadlines and see what's coming.

If you think this is all a bit insane, well there's a reason that not everyone is a project manager for a living. But ask yourself this: are your own personal projects any less important than those of your company? Are the initiatives and goals you set for yourself any less critical?

If you want to make changes in your life toward a goal -- and make them stick -- you will have to get organized. Flailing your way to success or happiness is rare -- like winning the lottery. If you'd like better odds than that, you will have to get your shit together. If you want to leverage magic to increase your odds even more, your shit needs to be even more together. Unlike a company, you can't just hire a someone like me to organize your stuff (well, you can, but it would probably be cost prohibitive -- if you have lots of cash and need organizational help, email me, I'd be happy to hire on as your personal consulting project manager).

The truth is that planning is easy (however esoteric it can seem to the uninitiated). Doing is what's hard.

Those of you on the deeper content list will be receiving a nifty set of Project Planning and Execution worksheets. For those of you who enjoy working on paper, these printables will allow you to document a charter, plan, and track execution activities. There's even a calendar for 2016 and a weekly activity tracker.


  1. Hmmm. you've given me a lot to think about here. I mean, one of the things that I'm running up against these days is that I did a major project (completed on time and under budget) last spring... and now the operations are bogging me down a bit, especially since (in an academic setting, at least), there are start-and-end points to course loads and projects and programs... but then in a year or six months you have to do those same or similar projects/programs/operations again.

    1. In the corporate world, projects and operations are considered different enough to have their own specialties -- particularly in manufacturing or research. I think you should focus on automating your operations (in an organic way, so you don't introduce fragility) so that you aren't always reinventing the wheel. I do this with magic. I have standard processes that I use for offerings, ancestor work, etc. I get creative around those things of course, but by automating the basics, I make it easier to keep it up.


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