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The harmful assumptions we make about tasks

What they cause and how to correct them

Most task managers make two assumptions. Do you make them too?

  1. A task manager needs to remember all of your tasks
    (Would you buy a task manager that lost data?)
  2. All tasks can use a similar creation workflow
    (You hit the 'create issue' button, and fill in some fields. Simple, obvious, how could it be better?)

It's not obvious that they're wrong—-they actually seem useful. But both at work, and at home, making these assumptions will reduce your effectiveness.

And if you have trouble context-switching, procrastinate tasks, or have an ever-growing task backlog that looms over your head, these assumptions have likely caused you unnecessary pain.

Here's how they hurt us, and how to stop it from happening.

Permanent tasks cause fatigue

Before starting Tandem, my manager Tim previously co-founded Astrid, a personal task manager, which he later sold to Yahoo.

At Astrid, Tim tried an interesting re-engagement email. Users who had been inactive for 6 weeks were asked: "want to delete all your tasks and start fresh?"

The hypothesis was that these inactive users had tasks that overwhelmed them. Either the amount, the complexity, or the low importance of backlogged tasks, caused users to put tasks off. So every time these users visited Astrid, they saw tasks they couldn't do, felt bad, and eventually stopped visiting—-procrastination in action. Astrid's re-engagement email offered the users a chance to start fresh.

It was impressively compelling. Most re-engagement emails get a 1% response rate. This email had about 5%.

I imagine those users had the same feeling you get when you move from one browser to another, or from one task manager to another, and leave your bookmarks, open tabs, backlogged tasks, to start fresh in the name of increased productivity.

But simply deleting the backlog doesn't end the cycle.


Nowadays, Tim uses a simpler task manager—-a notebook. He uses a page a day, adds some tasks from JIRA, and when tasks come in during the day, he writes them down and works on them when he's available. These are mostly small tasks, things that are easy to forget. If he gets a bug (important to track) or a task he can delegate, he puts it in JIRA.

The notebook isn't meant to store issues forever. The pages get turned, and previous information becomes less accessible. So the next day, if he needs to carry over something that hasn't been completed, he needs to make the conscious decision to do so.

This solution solves task-management fatigue. And incidentally, it solves another problem:

Not all tasks are created the same

There is a gap in task management. When we look at the tools used for tracking tasks and goals, there's something for every level of the company:


LevelGoalTool
Company quarter-levelQuarterly GoalsNotion/Gdocs
Org quarter-levelKPIsNotion/Gdocs, JIRA Epics
Team sprint-levelTicketsJIRA Tasks/Bugs
Personal day-level??????

Except at the personal day-level, where you're working on tickets, getting requests for feature updates from your PM, bug discoveries from QA, and breaking down your actual tickets into different tasks, which may require subtasks that weren't anticipated.

One proposal is that you should track all of these tasks, no matter how small, in JIRA. But the teams I see successful at implementing this are those that can afford to work at a slower, more "enterprise" pace. Which isn't a problem—-at least for engineering—-but it's often not an option at smaller startups, when learning cycles must be fast.

Even if you work at a larger company, at a slower pace, you may relate when it comes to personal life: tasks come from a variety of directions, at all times. You can't toss every minor task in a task manager.

You can't fix every task before the next one comes in. If you only use JIRA, you choose between possibly forgetting these small tasks, or breaking your train of thought to search, categorize, and fill out a form every time you get a small task.

On the flip side, quickly writing these down in a temporary place means that you don't need to:

  • Spend mental effort remembering minor tasks,
  • or take significant time to file minor issues.
  • Have your task manager filled with minor issues you've forgotten to close,
  • or leave hastily-written issues for later, when you forget what the vaguely titled issue is for.

Correcting for the mistakes

The solution is not complicated: use a temporary, personal task manager.

Don't go out and buy something new. You already have something you can use at home. Tim's notebook is a good example. I personally message myself on Slack (and iMessage, for personal use).

An example of how I Slack myself

Using Slack for daily personal tasks

When I'm working, and get a non-urgent task that would otherwise interrupt me, it goes in my Slack DMs. This is what it looks like:

}}{{

Some days are quiet

}}{{

And some are hectic

In the morning, to re-build yesterday's context, I just look at yesterday's list. If there are unfinished items, I can carry them over. But it's a conscious decision. I don't need to carry over optional, low-priority tasks.

And if you've got a bad memory, there's a huge benefit for team stand-ups. I used to write JQL filters to search JIRA (doesn't work—-and misses tasks), now I just take a look at Slack.

The important requirements are just that your task manager:

  1. Requires effort to carry over old tasks.
  2. Makes writing down tasks quick.
  3. Isn't used for notes (anecdotally, this adds noise, and forces you to parse notes from tasks).

If a task is critical, long term, or requires cooperation, file it in your normal issue tracker. Otherwise, it's probably a daily, personal task, and you can file it in here.

So take out a notebook, open Slack, pick what works for you. And see if you don't feel calmer and more in control of your tasks.





Relevant tools

I think these tools have interesting ideas to help individuals manage tasks.

Amna

Ravi, my old college roommate and friend since high school, left Microsoft to build Amna, a personal task manager with tight browser integration.

I resonate with the thesis: recently I switched away from Firefox Tree Style Tabs, because I noticed that by organizing my tabs (which were part of tasks), it inadvertently became a de-facto task manager. But it wasn't built for that!

Amna solves that exact problem: each task you do spawns a browser that keeps all of your relevant tabs.

}}{{

All the tabs in this browser window are related to the same task, and Amna keeps their state when I close the browser.

}}{{

After I'm done with a task, I can go back and look at the tabs I had open.

It helps prevent:

  • Muscle-memory opening HN, clicking an interesting blog post, and leaving it open "to read later" for several weeks
  • The pain of trawling through bookmarks and browser history, when you realize you forgot something
  • The clutter of leaving tabs open to prevent forgetting something

If you've forgotten a time when you had less than five tabs open, try using Amna.

Jam

Two of my ex-Cloudflare friends, Dani and Irtefa, started Jam. It's probably the fastest way for PMs/designers to directly make comments on a website. So you get less minor interruptions, and more clarity on the requested change.

}}{{

All you do is type jam on the page, click an element, and type the comment

But I don't include Jam here just for that. Jam also allows you to offload the actual copy changes to your PM, which flat-out decreases your minor tasks. If this sounds exciting, get on the waitlist here.


A big thank you to Calvin French-Owen, Zack Bloom, Tim Su, and Tejas Manohar for their thoughtful feedback on earlier drafts of this post.

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