Please describe for me your planning routines
June 23, 2017 11:15 AM   Subscribe

I've realized I need to get better at planning at work - especially for medium- and long-range projects and goals. I have no trouble finding suggested planning methodologies and documents online. Where I struggle is in understanding where and how this fits into daily working life. Can you share your planning hacks, techniques, systems and routines with me?

Not looking for "use Franklin Covey" or similar, but more things like "Every Monday I look at the week ahead, every three months I do a one-day planning retreat," etc. In other words, how do you structure your and your team's work time to create space for thoughtful planning?
posted by Miko to Work & Money (12 answers total) 63 users marked this as a favorite
I freelance, so this is a struggle for me. However I am also fairly organized and tidy so it's mostly ok. I also do not have to include other people most of the time so ymmv. I have a few guiding principles

- I have a big "year at a glance" wall calendar above my computer. Big travel and recurring deadlines go on there. I figure it's good to know there is a trip coming up in a few weeks, not that there is one, say, tomorrow.
- Anything scheduled goes on my digital calendar. I use the Mac Calendar thing and sync it to my phone and all my computers. I also sync it to Google Calendar so my partner can see it (he is a Google calendar guy). This is a little redundant with my printed calendar, I don't care.
- I have a clipboard with lists written on it. Keeping with the Discardia model I try to have no more than 5/6 "buckets" of things I am actively planning at any one time. I am not always successful.
- I break the day into chunks: email and phone activities in the morning (no unread email, no unreturned phone calls is the goal), maybe exercise or errands, lunch, work activities in the afternoon interspersed with home activities, unwind and reflect late afternoon coffee, little more work, dinner and offline time, social online time, check in with tomorrow's calendar and make sure I am all set.

I have gotten better at determining what needs advanced planning and what does not. So, like, some meetings need prep time so I would literally put "Prepare for meeting" on my calendar. Some do not. I find effective folks build in the prep, the event, the clean up and the recap/debrief as all parts of the event.

My work is often a combination of just "doing the thing" (i.e. writing an article, answering the email, picking up the stuff for the other thing) and "thinking about the thing" (i.e. figure out when and how to do the website redesign, work with the team to get updates happening better, chime in on the thread about the direction we're going in). I'm a thinking-while-writing person so I try to shuttle as much of the latter stuff to documentation or email as possible. I often have a small stack of papers with me with notes on projects and I'm usually trying to shuttle them into stuff that requires an email, requires me to do something, requires someone else to do something, basically moving them from ideas to something that can have a checkbox next to it.

And if it can't I try to untangle why not. Maybe it's five things masquerading as one thing. Maybe there is a "blocker" (which I see talked about more often in tech circles 'What is keeping us from getting this part of the project done?") which is good to know and identify. If you work with a team, trying to gently probe what their blockers are, see if you can help, see what help they might need, but trying to have everyone focused on what needs to happen. Ongoing blockers are not okay and become their own problem to be solved. Regular short meetings (i.e. stand-ups) that are basically status reports can help scoot something along if they're not also supposed to be team building or engagement exercises. Know when you need each.

And last, evaluate whatever system you have and see if it's working for you. As things change and people change, this may need to be adjusted, maybe an old boss liked things a certain way and a new one doesn't. Maybe a new staff member would prefer something different.

tl;dr I am calmed by routine, my life is astonishingly routinized but within the broad outlines of how this works, there is a lot of room for each day being a little different.
posted by jessamyn at 11:50 AM on June 23, 2017 [13 favorites]

The other thing I forgot about until I just did it. When I have something that needs to happen "In a few hours" but maybe isn't calendarable for various reasons, like a thing I need to do at the computer but I am not there, or a thing that I need to do when businesses are open and its 11 pm, I have my phone set a reminder. Literally I just talk into it "Remind me at 2 pm tomorrow that I need to call the dentist." or "Email mom tomorrow about that house I just saw for sale" This gets it completely out of my psychic load, is viewable on my phone if I need it to be, and will not only remind me but it will NAG me until it's done. This is helpful. I can also set up these nags to show up on my computer if I want, or not. And sometimes it's good for things that need to happen in advance but that need nags not just calendar entries. The phone reminds me a few days before rent is due. It reminds me to get the generator serviced in mid-November, that sort of thing.
posted by jessamyn at 2:02 PM on June 23, 2017 [5 favorites]

Jessamyn's is solid.
One thing to notice is when she says something like "I've gotten better" or "this may need to be adjusted." I found that when I started intentionally organizing myself, even organization felt like a mess! I still missed deadlines, and didn't acknowledge that it happened less often. Years later (yes, years!) people assume I'm naturally organized. I'm not, but now I know when something needs special planning or how to identify where a plan could fall through and how to prevent that. It came through just trying a bunch of different little techniques and finding that some are easy for me to stick to and also yield results.

For planning with teams, the number one thing I do is understand where someone needs support from someone else. I ask the members of my team several times a week what they are working toward, what they are working on, and what they need from others. Then I help make that happen. Often people don't realize they have a gap until they are asked to talk about it. Often people don't know they should ask for help until they are asked how they can be helped.
posted by jander03 at 2:19 PM on June 23, 2017 [5 favorites]

Response by poster: Thanks for these great responses so far. I realized it may help to say what I do do.
-Google calendar for personal life
-Outlook calendar at work - live religiously by it.
-Schedule in "work times" to get things done - could get better at this
-Try to start the week with a look ahead and make schedule adjustments
-Try to end the week with another look ahead, clean-up and wrap-up
-Bullet journal for personal tasks, day planning and major work events

What I am struggling most with is the kind of longer-range planning that's about setting in time for visioning, looking at the year and taking big six-month to one-year sort-of vague goals and turning them into a work plan. Not so much getting things done/knocking off a list, but creating regular time for referring back to the big plans and moving them forward - and the structures that do so. Not sure if what I need is some sort of quarterly or bimonthly process to plan the year ahead, slot in time well in advance on the calendar to work on just those goals, etc.

I find I get super sidelined by things that pop up in the short term that claim some sort of urgency - often a legitimate urgency. But how to build in routines that keep me on track for the long term, big stuff?

I'd love to chunk out my day better where I save mornings for brain work, afternoons for meetings, but unfortunately in a very team-based workplace I don't quite have that kind of freedom, as it would inconvenience everyone else.

Love the notion of 'blockers' and helping others identify them.
posted by Miko at 2:37 PM on June 23, 2017

I wrote this before your update, though I think paragraphs 2+4 are still helpful (but I’d schedule more check-ins for a longer project). I’d also put in reminders every two weeks nagging me to be more accountable to my long-term projects. If I still don’t make progress, then I'll re-evaluate what these long-term projects mean to me/the team, or if it's too nebulous, or what exactly is hamstringing its progress.

When starting a project, I write out a general list of things that need to happen. The act of writing it out is more important to me than the accuracy of what I’ve written. The items on the list don’t need to be extremely concrete if I don’t have exact knowledge yet, but writing it out makes the project seem less nebulous to me and gives me a way to be accountable to myself. Then I order the list into two columns. The left column is for tasks that are crucial to the progress of the overall project. It might go X-> Y-> Z. That means task Y can only be done after I’ve complete task X, and so on. The right column is for tasks that can be done in a general timeframe. I take about 15-60 min to roughly do this after an important meeting or something.

Every four to seven working days I block out swathes of time for the different types of tasks I’ll be doing on Google Calendar. I’ll have time blocks for procedural tasks, research/reading/ideation-based tasks, and skilled tasks that require more energy or careful thinking. It’s important that I have a balance so I don’t burn out. For blocks for procedural-type tasks, I’ll have a concrete list of things I need to do that day that I’ve generated in my head during the morning.

I also put time for re-evaluating the project and/or a self-check-in on a calendar. I schedule these at around 10%, 40%, and 80% project completion. So if I estimate that a project will take 12 weeks, I’ll schedule time for processing mid-way through week 2, and at the end of week 4 and 8. I ask myself if I’m happy with my role in the project, what I’ve learned, what I hope will happen, how I can do better, and what I’m doing right. If it’s a larger project I’ll think about how it figures into or (mis)aligns with my overall career goals. I take the time to think about the project and how it’s changed, and how this change factors into future tasks. I try to clearly outline general changes so that planning for future/other projects will be more realistic. This takes me 1-2 hours, and I mostly do this at home.
posted by typify at 2:48 PM on June 23, 2017 [3 favorites]

It seems like you actually know what you need to do, but feel like you can't do it.

Option 1)
Ignore that feeling. Pick a day where you are simply unavailable to your team for a few hours each week. Hit a coffee shop or a bar and maybe even leave your laptop behind.
I had a boss who dedicated Friday afternoons to testing the software we build (or that of our competitors).

Option 2)
Do your reflection and planning early in the morning before everyone gets in. Or on the weekend.

And then once a quarter just take a day off. Hang out someplace cool and hopefully out of town. Get up early and work your ass off until lunchtime and then go do something fun. Like take a nap on a park bench or play mini golf or buy your friends some drinks.

David Seah's been doing something kind of neat for years. He takes a few hours every year to set commitments and then reviews them every month in an interesting way. (1, 2)

Buster Benson does a yearly reflection. Probably not as work-related as you want, but interesting...

posted by jander03 at 5:28 PM on June 23, 2017 [1 favorite]

I work from home one day a month to do deep planning and thinky work. It's scheduled on my calendar, visible to everyone that I am out of office that day. I send a reminder a few days before to my boss and my team. They can get ahold of me for emergencies, but otherwise I have that time to focus and plan. I keep a list of things to work on during that time so I don't waste the morning trying to remember what to focus on. I also schedule twice yearly planning days with my team so it's not just me. We are trying to work further out so we are all thinking about it but it's so easy to push off on a daily basis.
posted by peanut_mcgillicuty at 6:00 PM on June 23, 2017 [1 favorite]

For me it scales by time and scale of the task.

I start the work day by listing the immediate things that need to be done -- things like "call Sue" or "submit invoice." I use paper because that way it can sit out in the open always visible, but my phone or Outlook would work equally well.

For larger projects, I almost always build a Gantt chart. Even a simple hand-scrawled one on paper or a white board lets you see the critical path and how the pieces interrelate; larger or more complex projects are easier to chart in MS Projects or whatever software you prefer.

Putting it on paper also gives a good tool for coordinating and planning, like being able to tell someone that they need to schedule in time to review the draft before a deadline.

For larger planning that involves more people, we schedule it just like any other admin task, and whenever possible formalize it by developing a plan or schedule that can be shared and revised as things progress.

Trying to keep it all in your head is how things get missed; when you do even a little planning up front then you have deadlines, checklists, and ways to hold people accountable.
posted by Dip Flash at 11:37 AM on June 24, 2017

This is an admittedly minor suggestion, but one thing I do sometimes is block my calendar off—basically put in a calendar event that looks like a meeting on a quick glance—whenever I have something I know is going to take uninterrupted time.

I also put calendar events (15-30 mins) at the end of significant meetings so that I can take notes, set up tasks and due dates, delegate things, etc., without having one meeting start immediately following.

Although I took meetings on my laptop (mostly using Emacs' org-mode) for years, recently I've tried going back to using legal pads and a pen. I find the notes are higher-quality, because I can make diagrams and other complex annotations, and it's harder to get distracted when you're staring at a legal pad full of notes, compared to a laptop. I just scan the notes afterwards with a phone app, then shred the paper.
posted by Kadin2048 at 8:52 PM on June 24, 2017

For me, I have regularly scheduled meetings when I need to provide updates on the plan. So upper management or my team or my internal customers need to know what is the plan, what are our milestones, where are we in regard to those milestones - and there is a weekly update meeting for the internal customers and for my team, and a monthly update for upper management. That all helps keep things from getting too far out of control. And if something comes up that takes half the time in a week that I was going to spend on Project X, I need a proper decision on whether to prioritize that new thing over Project X or not. Because we all can see the costs of working on the urgent thing, it means project X milestone A is now at risk.

The other trick is learning to build in some "everything will not be perfect" time. A new task that should take an experienced person 3 days? I need 2 weeks because I also have to learn how to do it and validate my results. The work takes 2 days but requires scheduled time on a shared resource? It usually takes a couple of days to get time on that resource, too. People will take sick days and that needs to be accounted for. All that.
posted by Lady Li at 1:15 AM on June 25, 2017

I haven't yet managed to work this into my routine, but a co-worker mentioned an intriguing idea. Every time he schedules something in his calendar, he also looks a month in advance. So, meeting on Friday? What will he be doing a month from Friday? He says he plans much better and fewer things hit him by surprise since he started this. I would imagine you could do this for 3 or 6 months out instead, if you want a longer view.
posted by greermahoney at 11:27 PM on June 27, 2017

I'm part of a small bureau/team (all except one in the same building, less than 20 people total) in a large government org (statewide, thousands). My team has weekly meetings, with the one other person calling in, and people in-office take turns writing meeting notes. We go through our list of active projects by reviewing and updating the project and activity list on a large white board. There are some quarterly meetings, and we list agenda items for those meetings, but the most of the space is full of color-coded projects: responsible staff, project title/summary, and the next project deadline.

Individuals submit weekly reports to their direct supervisor on Friday afternoon or Monday morning. Everyone uses this to submit a summary of activities and issues from the past week, and days out of office (meetings and vacation) next week and farther out. The big issues get taken up the chain for weekly management meetings with the head of our division and the different bureau chiefs and managers. I structure my individual reports on activities and projects as follows:
Project/activity title - summary of activities in the past week, including who I talked to/worked with - action item or next steps: final summary.

And for personal reminders, I use Outlook. I have a list of things to get done soon saved in a numbered list as a daily reminder. I delete things I complete, add new tasks and activities, then re-save the item as an event for the next day at the start of the day, and re-set the reminder to 5 minutes. This allows me to remember all the things I need to be doing and prioritize as necessary.

On the topic of using Outlook for things other than meetings, I had a co-worker who scheduled in self-care reminders, like "take a walk" every day at the same time, or he never would.

The quarterly meetings are with associated groups, who sort of report to us. We update them on rules, regulations, guidelines and processes, and discuss all that.

In the past, we've had "all hands" meetings of our division, but that was a one-off here. It's good to know who's who, what they do, and potentially how your work relates to theirs. We've also had a small bureau/team Annual Planning meeting, to discuss more lofty goals for our group in the next year and the years to follow. We identified the 3 or so major bureau things we wanted to accomplish, in addition to our other projects and activities. Unfortunately, our management changed, and we lost staff, so we went back to focusing on the daily activities and duties, as we didn't have any spare time for loftier goals.

recently I've tried going back to using legal pads and a pen. I find the notes are higher-quality, because I can make diagrams and other complex annotations, and it's harder to get distracted when you're staring at a legal pad full of notes, compared to a laptop. I just scan the notes afterwards with a phone app, then shred the paper.

There are a number of digital platforms where you can do all this, to step the scan and shred steps. I use Evernote, which allows syncing between devices (currently free to use on 2 devices), allows written and drawn notes, as well as photos, check-lists, reminders, and a ton of other features I haven't even gotten into. If you have a tablet, you can use it as your virtual note pad, as phones are generally a bit small for drawing anything but small diagrams.
posted by filthy light thief at 11:01 AM on June 30, 2017 [1 favorite]

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