Everyone at Khan Academy received a plea recently:
I’m hoping to organize a blog post that joins together stories of how each of you manage your time, and lessons you’ve learned in your adventures so far. I’d love to learn from all of you, and I’d bet anything that a ton of other people feel the same way.
Here are four of the responses that came in (and stay tuned for the next fortnightly post where you’ll see Oliver’s full-length response)!
Each Monday, I make a to-do list in Trello with the most critical tasks I need to complete that week. This post isn’t about goal-setting, so I won’t go into too much detail about how I come up with my to-do list here, but on a high level, my weekly to-do list is derived from my yearly plan, which I create based on what I and my team are accountable for delivering to the company.
I make a new Trello card for each week and create a checklist for each day of the week. I tend to assign tasks that require long blocks of uninterrupted thinking time to Tuesdays and Wednesdays since I block Tuesday mornings and all day Wednesday for proactive work (no meetings). I also keep a couple hours Monday morning and all of Friday afternoon meeting-free when possible; that way I have time Monday morning to catch up on any emails or respond to any questions or docs that accumulated over the weekend and have time to wrap up any work from the week on Fridays before heading out.
After that initial respite Monday morning, the rest of Monday and all of Thursday tend to be filled with meetings, so I don’t assign tasks that require much uninterrupted work to those days. Whenever I complete a task, I check it off in Trello, which I find quite satisfying :). If I don’t finish a task I assigned to a particular day by the time I’m ready to wrap up work in the evening, I move it on Trello to another day that week.
I do my best thinking earlier in the day, so I try to do anything that requires me to generate original ideas in the morning or early afternoon and save things like providing feedback on others’ work, helping others make decisions, etc. for later in the day since critiquing others’ work is much easier than generating new work from scratch.
I get a lot of email, and I need to be pretty responsive since, as a manager, a big part of my job is helping others do their jobs more effectively; I also work with partner organizations so have to be responsive to their questions and needs as well. I could easily fill all of my working time in my email — responding to questions, providing feedback on docs, making decisions, etc. — but if I did that, I’d never make progress on bigger strategic questions or generate new ideas, plans, or processes for the company. In other words, I can’t ignore my email, but I also can’t let it dominate me.
Here’s how I try to navigate that balance: Whenever I check my email, I respond immediately to anything I can answer or deal with right away. If something can’t be dealt with immediately but isn’t pressing, I use Boomerang to make it disappear from my inbox until a later date. I think of Trello as my proactive to-do list and my email inbox as my reactive to-do list. I try to complete everything on my Trello checklists each day or at least complete everything I set out for the week by Friday afternoon, and the same is true for my ”reactive” to-do list: I try to get to inbox zero (no emails) every day or at least by the end of the week.
This is an important topic, but a broad one: people write books about time management! I’ll stick to two ideas that have particularly helped me.
From first principles
We’re all in crunch mode sometimes—one thing after another, churning through some list of tasks. Time management discussions often focus on this level (what task management system should I use?!), but the most valuable decisions and corrections I make are at higher fields of view. Good time management doesn’t matter if I’m not using that time to do what’s important.
As a first step: beyond the tasks on my list, what are the projects and outcomes I’m currently working towards? Do any need to be nudged along or rescoped? Have any become some kind of zombie that’s never going to end? Critically: are there projects missing given my areas of focus and responsibility? I generally review this level every Monday morning.
Then: I have to periodically review those areas of focus and responsibility. Given my couple-year goals, am I focusing on the right spheres in my life? Are my accountabilities working for my goals or against them? In the last couple years, I’ve often found myself answering ”no” here, and that’s driven valuable evolution of my role at Khan Academy.
Reviewed less frequently, but crucially: given the vision I’m pursuing in my life, do I have the right couple-year goals? Or even higher: does that current vision align with what I consider to be my purpose? (Thankfully, that last one changes less frequently).
For example, my professed purpose is ”expand the reach of human knowledge and ability”; my current vision is ”do that by making powerful ideas more learnable and by helping more people become life-long learners”; my couple-year goals on that path are to establish a successful research practice while supporting others in picking off lower-hanging fruit in the space.
For now, at least, these answers seem reasonably well aligned, but that’s only because I often review my work from first principles in the way I’ve described. That vigilance is essential: I’ve certainly thrown out plenty of older answers to these questions.
Reliability without anxiety
Reliability is a hallmark of professionalism. It helps organizations scale because it allows work to be truly handed off. I can rest easy knowing that a reliable colleague will either complete their work as expected or will raise warning flags early if that won’t happen.
As my responsibilities multiply, anxiety often accompanies my quest for reliability—not because the actual work is too difficult, but because I’m constantly afraid I’m forgetting something that’s going to screw me.
Peace of mind here comes from a trusted source of truth. What are all my obligations? All of them? This isn’t so hard in principle: get a task manager; do weekly ”mental sweeps” to add everything that’s missing; sleep easy.
But such a list quickly stops being a trusted source of truth because it’s overwhelming and anxiety-inducing in itself! I might notice myself wincing away from it in the morning, letting my eyes glaze over the sprawling contents, only pretending to study it instead of thoughtfully prioritizing. Then when that really important task comes in, I won’t simply add it to the list because I don’t trust myself to reliably prioritize and complete work from it anymore—instead, I write it on the whiteboard behind me, or use a sticky note, or start another list… and that’s when it’s clear I’ve failed!
The hard part about making a ”trusted source of truth” is the ”trusted” bit. I find trust requires regular maintenance: reviewing my tasks often to ensure that they’re actionable and relevant; delegating, deferring, and removing tasks which I’m not going to complete; slicing and filtering so that I’m only seeing usable information. I have to watch my own reaction when something important comes up, and when I feel wary of my own source of truth, I dig to find out why.
Reliability doesn’t stop at the task level. As our scope increases, we become responsible not only for completing all our projects reliably, but also for choosing the right projects in the first place, and so on, all the way up the reflection ladder discussed in the previous section. One defining attribute of successful executive and senior executive roles is reliability at the couple-year-goal through vision levels. But first, my notes tell me this essay is due tomorrow…
[These ideas perhaps primarily adapted from practices I learned from David Allen’s ”Getting Things Done”, influenced by Tim Urban, Merlin Mann, and various others.]
- I work from 9:30 – 6:30
- I start by journalling 1 page on: why, what, and how. I come up with 1 “wildly important goal” that I schedule my day around.
- I spend 10 mins on my morning checklist — scheduling the day, checking calendar, quick check of Slack, status update.
- I’ll spend two solid 2-hour blocks, one in the morning, and one in the afternoon, on the wildly important goal. I close Slack and email during this time. Sometimes, I’ll go to a cafe too.
- I use the Pomodoro technique — 25 min working, 5 min break. I meditate during breaks to calm and re-center.
- I keep a spreadsheet of how focused I was on each Pomodoro work session. I ask my manager to look at that spreadsheet each week to keep me accountable.
- I spend 5-10 mins at end of day reflecting — what I’m happy about, what I’m worried about.
Responsibilities pile up after you’re at a company for a little while. I’ve been working at Khan Academy for a couple years, so regardless of the project I’m on, there’s always unrelated things competing for my attention.
My system for dealing with this is dead simple, and fairly effective: between 2 PM to 6 PM every day I work on my current project only, and I strongly resist any attempts at pulling me away from that work. Outside of that 2-6 block, I let myself be distracted by anything else that’s demanding my attention.
This lets me estimate my projects more effectively (I know each day is going to be 4 hours of focussed work on the project, no less, and probably not much more), and also allows me to be pretty trustworthy when I say ”I’m busy and can’t do that right now, but I’ll take a look at it tomorrow morning”.