Project management (to-do lists) software with time estimation?
March 4, 2022 10:42 AM

Asana, Trello, Monday, whatever you want: Do any of these project management / team collaboration make it (easy to make it) automatic to ask for time estimation when adding/editing tasks, or in some kind of post-just-make-a-list now-add-time-estimates step? Deadlines do not do it for me.

I'm facing an overwhelming number of large projects/tasks and a teammate who wants everything now. I sympathize -- they're important and urgent -- but I need to keep things sane.

Also, this is a way of working that I plan to apply in other contexts too.

FWIW my team is currently two people.

Time estimates seem like they would be central to project management, but I have never used one of these tools, so I don't know how they work. I watched a couple of short intro videos and didn't see anything about time estimation, searched the text of a couple of pages for [estimat] -- this is taking a long time and not getting me what I want yet.

Anybody know of one of these that will make time estimation easy/automatic? (I know time estimation is hard, super hard, but I figure something is better than nothing).

Thanks!
posted by amtho to Grab Bag (12 answers total) 4 users marked this as a favorite
Trello has add-ons that you can use to assign estimations, but that would require a paid account. It's been a few years since I messed around with using Trello add-ons, but this article gives you an idea.
posted by Medieval Maven at 10:54 AM on March 4, 2022


This is software focused (no idea what your projects actually are), but the embedded.fm podcast had a discussion recently on how to get better at estimating time for projects and the philosophy around making good time estimates.

As software for time tracking goes, most of them seem focused on deadline based time management rather than "how long will this take". we end up using a fucked up combination of JIRA, MS Project and a wall full of sticky notes to manage projects because we've never found one tool that works well for us.
posted by Dr. Twist at 11:21 AM on March 4, 2022


I use and like teamwork.com for my job that is a mix of client project work and internal projects at a software company. I am not an admin of Teamwork so not sure if you can require an estimate on a task, but I can vouch that estimates are easy to add and easy to see.
posted by paradeofblimps at 11:40 AM on March 4, 2022


OMG why is this not common for every single tool? Urgh.

I'm open to a spreadsheet centered solution since there are only two of us. Anybody have one? It's OK if it's old as long as it's not too complex.

On edit: Sorry, Teamwork.com might be fine -- I got excited and didn't read closely. I don't mean to absolutely require time estimates -- I think it's probably helpful to be able to add/list tasks and then add estimates in a second step.
posted by amtho at 12:12 PM on March 4, 2022


I'm down to pay for something good as long as it's not > $20/month (prefer something less expensive since THIS SHOULD BE NORMAL).
posted by amtho at 12:13 PM on March 4, 2022


Jira? That's what I use at work.
posted by deezil at 12:50 PM on March 4, 2022


Jira is used in many software teams for tracking tasks and bugs. Jira is highly customisable, you can certainly set it up so that all freshly created tickets have a mandatory effort estimate field. Many people I work with who must use Jira at their jobs hate it, but this is usually because they work in very large organisations (100s, 1000s, 10,000s of staff..), where the organisation has customised Jira to serve the needs of people in other roles (audit, finance, ...) at the expense of making it usable for the people working on the tasks being tracked. If you can set it up to have a workflow customised for your team's needs, maybe it'll be quite pleasant. They're pricing it at $0 for up to 10 users, then $5 / (user month).

What's much harder is filling in a reasonably accurate estimate into the box, none of these general purpose industry-agnostic project management tools can do that. People doing the work need to estimate based on their experience, and when trying to underestimate a task that they haven't exactly done before, will usually underestimate the complexity and individual tasks and steps involved, and underestimate the total effort.
posted by are-coral-made at 12:55 PM on March 4, 2022


> when trying to underestimate a task

i intended to write "estimate a task", but this is an apt description of how it actually plays out
posted by are-coral-made at 1:01 PM on March 4, 2022


Trello has gotten way more complex and harder to use since it was bought by Atlassian (creators of Jira). Just FYI.
posted by sixswitch at 1:03 PM on March 4, 2022


> time estimation

in case you're not aware, there's a whole ecosystem of "Agile" project management, often mentioning "Scrum" or "Kanban", rich with jargon. One frequent characteristic is that instead of trying to directly estimate time to complete a task, they focus on trying to assess relative effort only -- the difference between small, medium, large, very large. or 1 point, 2 points, 3 points, 5 points. Sometimes the former get called "T shirt sizes" and the latter "story points" -- every task is a story, how many points of effort does it take. So it is possible you might find some hits for free add-ons when using the search terms "story point estimation" "T-shirt sizing" in a project management context. This can sometimes be good in more hostile environments where workers may be discouraged from giving an estimate in terms of raw hours worked (in case that estimate is wielded against them as if it were a commitment to deliver on a deadline).

e.g. here's a link to a random trello "power up" offering "story points" and "WIP limits" Free Agile Points and WIP limits for Trello

WIP aka work-in-progress limits might be useful for your situation -- tracking that no person has tasks assigned to them and in progress with more then n "story points" of effort or m specific cards, say. WIP tracking encourages people to work on one task at at time and not pick up any new tasks until they have completed their in-progress task and freed up their capacity to take on new work.
posted by are-coral-made at 1:10 PM on March 4, 2022


Whereve you write it down, take the time later to reflect on whether it was accurate and what you can do to keep estimates 'helpfully accurate' but not based on over-specified studies into the detail of the task.
posted by k3ninho at 1:50 PM on March 4, 2022


I'm using Todoist for task/simple project management. You can add labels with time estimates to new or existing tasks. Labels are good for quickly filtering tasks that will take 15 minutes or 15 hours. I've also seen this tool, HourStack, that promises to add time planning and tracking to your Todoist tasks.
posted by gakiko at 11:56 PM on March 14, 2022


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