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How I Chose a Project Management Tool

Project management software logos

Project management software is everywhere, but finding the right tool for your use case can be tricky. In this post, I'm going to explain the requirements I had when performing my analysis, narrow it down to the few options that came close to matching my criteria, and explain how each stacked up.

The criteria I'm using to judge these tools is very specific to my use case. I have a very small team that works with a variety of clients. Your needs may be VERY different.

Table of Contents

This post is rather long, so feel free to use this to jump to the part that interests you.

Personal Requirements
Tools that Might Work
Asana Review
ClickUp Review
Monday.com Review
Teamwork Review
Analysis

tldr; Jump straight to the conclusion

Personal Requirements

I have a small team that does ongoing work with 20+ clients.

My goal is to consolidate communication to one place so that everyone can see what is happening and I'm not a bottleneck for my team.

Here's what I'm looking for:

Organization

Each project management tool has their own naming convention, so I've just tried to use the most common names.

  • Workspaces: Each client has their own workspace
  • Lists: Each workspace can have multiple lists (in my case, one for each website we're working on with that client).
  • Tasks: Each list contains the tasks that we're working on for that project.

Fields

For each task, I want to be able to keep track of these things:

  • Assigned user (who should be working on this)
  • Status (how is this task coming along)
  • Priority
  • Due date
  • Bonus: Start date

Features

  • Subtasks
  • Reply by email. I don't want to require my clients to log into my project management system to stay in the loop. I want the to get status updates via email. I want their email replies to feed back into the system.
  • Marker.io integration. I use Marker to give my clients a visual way to provide feedback and request changes. I also use it to create tasks for my team.
  • Bonus: Assign tasks to clients/guests directly from Marker.io.

Speed

  • I want to load tasks quickly.
  • I don't want it to slow my browser down with heavy memory usage.

Mobile Support

  • Do they have a mobile app, and does it provide the same features as the website?
  • Is the website accessible from a mobile browser?

Views

The data in a project management tool can be viewed in many different ways. In addition to the default workspace/list/task views, I also want to be able to:

  • View all my tasks across all workspaces in one place
  • View all the tasks of a specific team member in one place
  • View all unassigned tasks across all workspaces
  • View all tasks across all workspaces
  • Bonus: Could easily use the same views but limited to a single workspace

Guest/Client Views

Because we're working with 20+ clients (and some clients have multiple people involved), some tools are excluded right away based on price/user.

I'm looking for a tool with either a fixed monthly price or a generous allowance of guest accounts.

  • Clients can see all lists in their workspace
  • Clients can see their tasks across all lists in one glance
  • Bonus: Clients can see all tasks grouped by project, not just by date

How many clicks to…

Lastly, I want to know how many clicks it takes to due the tasks I'll be repeating most often:

  • Create a task
  • Set/change assignee
  • Set/change status
  • Set/change priority
  • Mark task as done
  • Switch lists within workspace
  • Switch workspaces
  • View all my tasks (across all workspaces)
  • View single users tasks (across all workspaces)

 

Tools that Might Work

I believe the most limiting factors in my requirements will be guest/client support, custom views, and Marker.io support.

Those three things ruled out a large number of tools.  Here's what I had left (in alphabetical order):

  • Asana - It's been around forever and has a clean design.
  • ClickUp - It has a quick development pace and is highly configurable.
  • Monday.com - I've talked with multiple agencies using Monday, and they generally seem to be happy with it.
  • Teamwork - It's part of a suite of tools that might be useful down the road.
Asana logo

Asana

Asana was created in 2008 by Facebook co-founder Dustin Moskovitz and engineer Justin Rosenstein.

asana.com

Organization (2.5/3)

As far as I can tell, each workspace is its own Asana subscription, making it prohibitively expensive to have a workspace for each client. I think a better method for handling this in Asana is with the use of "Teams."

Requirement Passed?
Workspaces: Each client has their own workspace Partial
Lists: Each workspace can have multiple lists Yes
Tasks: Each list contains the tasks for project. Yes

Fields (4.5/5)

Asana doesn't have a native implementation of task statuses. Task statuses can be implemented using tags or custom fields. However, this will not impact the native "Project Progress" tools.

Requirement Passed?
Assignee Yes
Status Partial
Priority Yes
Due date Yes
Bonus: Start date Yes

Features (3/4)

Despite being the most requested feature by a large margin, Asana has chosen not to support tasks with multiple owners/assignees. I prefer to be able to assign something to multiple people when I don't know who's feedback I need.

Requirement Passed?
Subtasks Yes
Task with multiple owners/assignees No
Reply by email Yes
Marker.io integration Yes

Here's what an email notification from Asana looks like:

Views (4/6)

Strangely, I couldn't find a way to view all tasks that weren't assigned to someone.

Requirement Passed?
All tasks Yes
All my tasks Yes
All tasks of specific user Yes
All unassigned tasks No
Bonus: Same views, but limited by workspace/team Partial
Bouns: Same views, but organized by project, not date Partial

Guest/Client Views (1/3)

Requirement Passed?
All lists in their workspace No
All tasks across all their lists Yes
Bonus: All tasks grouped by project, not date No

How many clicks to… (8 tasks, 13.5 clicks  = 1.6875 clicks/task)

It's hard to calculate click numbers accurately, because there are multiple ways to do certain tasks. For example, the first time you view all of a client's tasks across all workspaces, it takes 6 clicks plus keyboard input. After the search has been made though, it can be saved for future use, which will only take a single click. Consequently, I marked it as a two click operation.

Requirement Passed?
Create a task 1
Set/change assignee 2
Set/change status 2
Set/change priority 2
Mark task as done 1
Switch lists within workspace 1
Switch workspaces 1.5
View all my tasks across all workspaces 1
View client's tasks across all workspaces 2

Mobile/App (0.5/2)

The app seems simple enough for lite use, but is missing the saved searches feature that allows tasks from multiple workspaces to viewed simultaneously.

Requirement Passed?
Mobile app Partial
Mobile browser No
ClickUp logo

ClickUp

ClickUp was founded in March 2017 by Alex Yurkowski and Zeb Evans.

clickup.com

Organization (2.5/3)

ClickUp adds another layer to the organizational hierarchy by placing folders between workspaces and lists. In this scenario, each client would have their own folder within a workspace, rather than having their own workspace. Full users can be assigned to a workspace, but not clients/guests.

Requirement Passed?
Workspaces: Each client has their own workspace Partial
Lists: Each workspace can have multiple lists Yes
Tasks: Each list contains the tasks for project. Yes

Fields (5/5)

Requirement Passed?
Assignee Yes
Status Yes
Priority Yes
Due date Yes
Bonus: Start date Yes

Features (4/4)

Requirement Passed?
Subtasks Yes
Task with multiple owners/assignees Yes
Reply by email Yes
Marker.io integration Yes

Here's what an email notification from ClickUp looks like:

Guest/Client Views (3/3)

Requirement Passed?
All lists in their workspace Yes
All tasks across all their lists Yes
Bonus: All tasks grouped by project, not date Yes

How many clicks to… (8 tasks, 16 clicks  = 2 clicks/task)

Viewing all tasks across workspaces is done via dashboards, which aren't configured by default. Accessing a dashboard is a 2 click operation (though switching between dashboards is just one click). Because of the clicks needed to create each dashboard, I've listed the number of clicks for viewing tasks across workspaces as 3 instead of 2.

Requirement Passed?
Create a task 1
Set/change assignee 2
Set/change status 2
Set/change priority 2
Mark task as done 1
Switch lists within workspace 1
Switch workspaces 1
View all my tasks across all workspaces 3
View client's tasks across all workspaces 3

Mobile/App (0.5/2)

The mobile app is nice, though limited compared with the desktop site. Workspaces, lists, and tasks all work as expected.

Sadly, the custom dashboard views which I find so useful aren't included in the app.

Using ClickUp from a mobile browser is completely blocked. Rather than allow access, ClickUp just displays a landing page for their mobile app.

Requirement Passed?
Mobile app Partial
Mobile browser No

ClickUp Summary

I'm not sure if ClickUp is the more configurable than the alternatives, or if it just just works more closely to my desired configuration by default. Either way, setting it up to work as desired was much simpler than any of the other tools.

ClickUp supports custom task statuses yet it also understands what a complete task is, which (strangely) seems to be a rare combination. Most of the other tools either a) don't support custom statuses or b) can't distinguish between a task that is completed and one that still needs work.

The thing that really sets ClickUp apart is the multitude of ways to view data from multiple lists/folders/workspaces. These dashboards can display data from the entire account, or limit it by folder or workspace.

My biggest concerns are the pricing model (limited number of guest accounts) and the sluggishness of the site, especially when loading from scratch (which happens every time you click through from an email notification).

Monday.com logo

Monday.com

Monday.com was founded in 2012 by Roy Mann and Eran Zinman.

monday.com

Organization (2/3)

Monday adds another layer to the organizational hierarchy by placing folders between workspaces and lists. However, guests/clients can't be assigned to folders, so they have to be added to each list. The folders are merely organizational, not useful for assigning user access to different projects.

Requirement Passed?
Workspaces: Each client has their own workspace No
Lists: Each workspace can have multiple lists/projects Yes
Tasks: Each list contains the tasks for a project. Yes

Fields (5/5)

Monday.com treats all statuses as relatively equal, including the "Done" status. This means that even after a task is marked as "Done", it stays in the task list. To work around this, I created a new task group, labeled it "Complete" and created an automation so that any time a task was marked as "Done" it would be removed from the current task group and moved to the "Complete" group. Unfortunately, doing it this way made configuring dashboards more difficult because of the additional lists.

Requirement Passed?
Assignee Built in
Status Built in
Priority Supported
Due date Built in
Bonus: Start date Supported

Features (4/4)

Requirement Passed?
Subtasks Yes
Task with multiple owners/assignees Yes
Reply by email Yes
Marker.io integration Yes

Here's what an email notification from Monday.com looks like:

Views (3/6)

After much research and many attempts, I figured out a way to do create views of multiple lists. The downside is that there is no simple way to set a view to "all lists" or "all lists belonging to a single folder". This means that every time I add a new list, I have to go back and modify any views that should include the new list.

Requirement Passed?
All tasks Difficult
All my tasks Only easy sorted by date
All tasks of specific user Difficult
All unassigned tasks Difficult
Bonus: Same views, but limited by workspace Difficult
Bouns: Same views, but organized by project, not date Difficult

Guest/Client Views (1/3)

Requirement Passed?
All lists in their workspace No
All tasks across all their lists Built in
Bonus: All tasks grouped by project, not date No

How many clicks to… (8 tasks, 13 clicks  = 1.625 clicks/task)

Switch workspaces.

Since guests can't be added at the workspace level, I would use folders to group client projects. To reflect this, I replaced the "Switch workspaces" click count with the number of clicks it would take to switch from one folder to another.

View client's tasks across all workspaces

I couldn't consistently get the filters in the "My Work" view to show all of someone else's work.

Requirement Passed?
Create a task 1
Set/change assignee 2
Set/change status 2
Set/change priority 2
Mark task as done 2
Switch lists within workspace 1
Switch workspaces folders 2
View all my tasks across all workspaces 1
View client's tasks across all workspaces Buggy

Mobile/App (0.5/2)

The mobile app looks good and appears to work nicely for working directly with tasks. Unfortunately, I couldn't find a way to access the custom dashboards I created.

Using Monday.com from a mobile browser is completely blocked. Rather than allow access, Monday.com just displays a landing page for their mobile app.

Requirement Passed?
Mobile app Partial
Mobile browser No

Monday.com Summary

From my perspective, it appears that monday.com is built primarily for projects with a fixed scope/timeline. Much of my work is ongoing in nature, so it doesn't fit as nicely into monday.com's workflow. For example, Monday.com treats completed tasks just like any other task. When a project has a limited scope, that's not a problem, but when doing work across a number of years, the completed tasks start to pile up. There are workarounds, as I mentioned earlier, but this is just one example of how their approach doesn't align with my workflow as well as I hoped.

Nevertheless, I loved nearly everything about monday.com until I attempted to view tasks from multiple lists. While it is possible to create custom dashboards combining data from multiple lists, it isn't exactly easy. Worse, these custom/saved views would need to be modified every time a new list is created. This is because each lists must be explicitly included when setting up the dashboard, rather than being able to automatically include all lists in a folder or a workspace.

The difficulty of maintaining custom views is by far the biggest drawback I could find, which is sad because monday.com is such a highly polished and configurable product. The site is snappy, keyboard support is good compared to some of the other products, and the interface is easy to understand.

 

Teamwork logo

Teamwork

Teamwork was founded in October 2007 by Peter Coppinger and Dan Mackey.

teamwork.com

Organization (3/3)

Rather than use "workspaces" as the root of their organization structure, Teamwork uses "Companies" to group projects. This is probably closer to my ideal configuration than even my original personal requirements.

Requirement Passed?
Workspaces: Each client has their own workspace Yes (Companies)
Lists: Each workspace can have multiple lists Yes
Tasks: Each list contains the tasks for project. Yes

Fields (4/5)

The status functionality is extremely limited. By default, the status options are checked (task closed) or unchecked (task still open). I found a blog post from teamwork.com on creative project management that suggesting using the Kanban view with columns for each status so that tasks could be moved through the columns as the status changed. I thought this would be a promising workaround, until I ran into two issues:

  1. I couldn't find a way to surface this info in the list view (though I could add it to the table view).
  2. I couldn't find an automation that could change which column a task was in. This means every time a task is marked as complete using the built-in status feature, it will continue to exist in an incomplete status in the kanban view. This means that it takes two actions instead of one to mark a task as complete (once for the built-in status and another for the kanban columns). It seems to be impossible to mark a task as complete in both ways from the list view.
Requirement Passed?
Assignee Yes
Status No
Priority Yes
Due date Yes
Bonus: Start date Yes

Features (4/4)

Requirement Passed?
Subtasks Yes
Task with multiple owners/assignees Yes
Reply by email Yes
Marker.io integration Yes

Here's what an email notification from Teamwork looks like:

Views (5/6)

Teamwork provides an "Everything" view that that does just that. It shows everything across all projects, all in one place. It offers a range of filters to target just a subset of tasks. It also allows filter settings to be saved, so the filter setup doesn't need to be repeated every time.

Requirement Passed?
All tasks Yes
All my tasks By Filter
All tasks of specific user By Filter
All unassigned tasks By Filter
Bonus: Same views, but limited by workspace Difficult
Bonus: Same views, but organized by project, not date Yes

Guest/Client Views (3/3)

Requirement Passed?
All lists in their workspace Yes
All tasks across all their lists Yes
Bonus: All tasks grouped by project, not date By Filter

How many clicks to… (8 tasks, 16 clicks  = 2 clicks/task)

Setting/changing the assignee is the killer here. That's a feature I use all the time.

Requirement Clicks
Create a task (starting from list view) 1
Set/change assignee 4
Set/change status NA
Set/change priority 1
Mark task as done 1
Switch lists within workspace 1
Switch workspaces 2
View all my tasks across all workspaces 3
View client's tasks across all workspaces 3

Mobile/App (1/2)

The mobile app looks nice and appears to function well but with somewhat limited functionality compared with the full website. The "Everything" section of the website that is so handy for viewing filtered lists of tasks was nowhere to be seen. A lot of the info was still available, just scattered across the app instead of in a central location.

Using Teamwork in a mobile browser is difficult. It isn't responsive in the least. However, it is at least possible. Some of the other tools don't even allow access from mobile browsers.

Requirement Passed?
Mobile app Partial
Mobile browser Partial

Teamwork Summary

There is a lot to love about Teamwork. It does almost everything I'm looking for, and I appreciate the clean and logical interface.

It's target market is definitely larger teams with more complex projects. It includes many communication related features that aren't relevant for me, but I can imagine would be useful to a large team.

The biggest red flags for me are the lack of status management for tasks and the number of clicks it takes to assign a task to someone.

I also couldn't find a way to assign colors to different projects, so the only thing separating projects/lists appears to be the title. This makes it more difficult to differentiate between projects at a glance.

Final Analysis/Conclusion

In the end, I chose to go with ClickUp. Their pricing structure isn't ideal due to their limitation on guest accounts. However, just about everything else about their platform aligns with the way I want to structure my projects. Their custom statuses worked perfectly, common tasks didn't take extra clicks, and their dashbooards could be set to automatically include all lists in a folder.

Asana had some real drawbacks. Tasks can't have custom statuses or be assigned to multiple people. There was also no way that I could find to view all unassigned tasks across all lists.

Monday.com was wonderful, but had a structure that worked better for individual projects with set beginnings and endings. Since my projects often include ongoing maintenance contracts, this wasn't the structure for me. While Monday.com did have highly configurable dashboards, the settings would need to be adjusted every time a new list was added to a folder.

Teamwork seemed to be focused on larger teams and larger projects, with additional communication features such as team member status updates and live chat. It also lacked custom task statuses, and some common tasks took a large number of clicks.