calendar hacks. Prioritization systems. Creative boosters. Scheduling techniques. Weekly workflows. The internet (and, honestly, this column) is full of ideas on how to better organize your work to get more meaningful stuff done in less time with less pain. All of these ideas solve some problems for some people, but it’s rare to get a glimpse of the whole suite of systems, documents, and tricks an individual high performer leans on to scaffold her success.
Which is what makes a recent First Round Review article from startup veteran and now Kool-Aid Factory founder Brie Wolfson so fascinating. In the in-depth piece she lays out her whole productivity system in meticulous detail, including all the documents she relies on for annual and quarterly planning, as well as organizing her day-to-day work.
If the chaotic workflow from running your business could use a bit of an overhaul, the whole thing is well worth a read. But perhaps the most useful part of the article is immediately the five documents Wolfson uses daily to remind her of her priorities, boost her energy, and maximize her learning. Helpfully, she even offers templates when needed. Here, in brief, are these five success-boosting documents.
1. Ongoing Stack Rank (OSR)
To-do lists are a simple and popular way to organize your work, but they have a fatal flaw. The essential gets mixed in with the simple urgent or the genuinely trivial. When you’re dreading writing that sales email, it can be tempting to just move down your list and check off ‘pick up dry cleaning’ instead. You accomplished a to-do list item, but did you really advance your work?
What you need is not just a list of things you need to get done sometime, but also a system that shows you what you should be prioritizing now. That’s what Wolfson’s ‘Ongoing Stack Rank’ is designed to accomplish. Like a to-do list, an OSR lists “things I’m working on or could be working on over a given time period,” Wolfson explains. But with three key differences:
An OSR lists only outputs, not constituent tasks. “Outputs are defined as shippable units work,” Wolfson explains. “Phrasing them as such will also help remind you that you can only check it off once it’s completed. For example, ‘hosted dinner for startups’ can show up on your list, while ‘booked restaurant for startup dinner’ shouldn’t.”
Include status. Is this in progress? Awaiting approval? Deprioritized until a particular future date? Your OSR should tell you at a glance.
Ordered by priority. Your OSR should tell you not just what you could be working on, but what you should work on first.
“Things might move up and down on this list or get added to or removed from it. That’s okay! Record it all. This simplified list will provide clarity when things get especially messy and keep those higher-order goals top-of mind,” Wolfson insists. Here’s a template.
2. “It’s Only The Weekend When” Post-It
If the OSR is a little complicated, the “It’s Only The Weekend When” Post-It is so dead simple you can review it at a glance. Which is the point. This list of three things you want to accomplish within a given week should follow you everywhere, gently (or not not so gently) reminding you of your key priorities. Then, at the end of the week you get the joy of physically checking them off.
“Throughout the week, I’ll move it around and stick it various places–in my notebook alongside my daily to-do list, on the cover of my notebook, in the corner of my monitor, at the bottom of the keyboard, or even on my bathroom mirror if I’m getting really desperate as the weekend nears!” reports Wolfson. No template required for this one.
3. “What I’m Proud Of” Scrapbook
Knowing what to work on is only half the battle. You also need the energy and confidence to actually do those things. That’s where the “What I’m Proud Of” Scrapbook comes in.
“This is exactly what it sounds like; a collection of things I’m proud of. It’s a running list and hodgepodge of formats (screenshots, emails, pings, feedback, etc.) with no real organizational structure, but over time, it will turn into a fantastic raw data set for the things that give you energy and make you tick,” explains Wolfson.
This scrapbook of success not only acts as your personal energy pack, it is also a learning tool. “Lining my Things I’m Proud of Scrapbook with my OSR side-by-side helps me figure out what work truly satisfies me,” Wolfson notes. You may think number crunching is important or your strong suit, but if it never makes it to your scrapbook you can be pretty sure it still doesn’t bring you personal joy. You can check out a screenshot of Wolfson’s scrapbook here.
4. Snag Log
Knowing what brings you happiness is useful, but so is knowing what makes you miserable. Use this document, in Wolfson’s words, to write down “the things that give me the ickies.”
“You know what these things are–the things that made your tummy turn or maybe made you want to throw your laptop out the window or scream into a pillow,” she writes. All you need to do is be honest and diligent about recording them.
This catalog of miseries not only gives you a private place to exorcize negative emotions, it also helps you identify patterns. If that same meeting, colleague, or type of work pops up again and again, maybe you need to take action to avoid this pain in the future.
5. “Today, I Learned”
“This document is also relatively straightforward. It’s a list of things I learned, usually in bullet form,” Wolfson explains. These can be technical details (how to do things or where to find them), insights about colleagues (Andrea like a written weekly update, for instance), personal details (John has a birthday next week), or self insights (this kind of work goes a lot better if I do it first thing in the morning).
It’s a straightforward idea, but Wolfson claims this simple doc has brought her plenty of benefits. It helps her remember details, provides a searchable archive of lessons learned, and saves her from pestering colleagues with the same question multiple times.
Referencing all five of these documents each day might seem likely to make your desktop a bit crowded (though, be honest, how many browser tabs do you currently have open?), but Wolfson insists they keep her on track and growing as a professional. Surely, that’s worth a little organizational effort. Why not give these docs a try and see if they can help you be more successful too?