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Digital project management toolkit series: Dropbox and Google Drive


When we begin a project here at Fresh Tilled Soil, we fire up an arsenal of digital tools to help us keep the trains running on time. Although our project management process is flexible enough to adapt to the communication style of each of our partners, we’ve landed on a core suite of applications that has streamlined our daily work flow and maximized efficiencies. This is the fifth in a series of posts outlining the Digital Project Management Toolkit.

Dropbox and Google Drive are both cloud-based file management and storage platforms. Functionality of both platforms is fairly straightforward, but with subtle differentiators that become clear based on use cases. I’ll be exploring the pros and cons of each, and – more constructively – debating whether we really need to use both. I’ve collected feedback from Fresh employees to demonstrate how roles (e.g. strategist, designer, developer, project manager) may affect needs and preferences.

Note that YMMV on the Drive/Dropbox advantage in various categories depending on the shape and process of your organization.

Dependability of syncing

Advantage – Drive

“Dropbox syncing can be a data hog. I have to pause it sometimes to get my wireless bandwidth to perform.” (Jenna Bantjes, Sr. Experience Designer)

“Syncing with dropbox can be an absolute pain that requires restarting Finder to work properly.” (Scott O’Hara, Director of Development)

“Has it [Dropbox] synced yet? How about now?” (Geordie Kaytes, Director of Strategy)

Drive gets the nod here, not because its syncing speed and consistency is brilliant, but because syncing with Dropbox is downright painful.


Advantage – Drive

“The collaborative abilities in Drive are unprecedented. It’s essential for activities where group input is needed. It has also been useful for facilitating client input.” (Jenna Bantjes, Sr. Experience Designer)

“Drive is the go-to for things that require collaboration, like docs and spreadsheets.” (Michael Perrone, Sr. Project Manager)

“Drive obviously has better collaboration within Google Docs, can hold any type of file, and is infinitely searchable. Dropbox has no useful collaboration features.” (Geordie Kaytes, Director of Strategy)

“it’s just nice to have all my files in Drive along with all the collaborative documents that already exist in there.” (Scott O’Hara, Director of Development)

This one’s easy. Drive has amazing collaboration features; Dropbox does not.

Folder structure / File organization

Advantage – Dropbox

“I use Drive on the web mostly, probably because the folder structures are so byzantine that I need the web UI search capability to find anything.” (Geordie Kaytes, Director of Strategy)

“So many things just get lost in Drive and never seen again. Folder structuring is like Pan’s labyrinth.” (Jimi Choi, Front-end Developer)

“That things that are shared with me in Drive go into a separate folder from my items is very annoying and causes me to lose things. The fact that I need to go find the item and move it is a waste of time. The division maybe makes sense in Drive’s backend, but I’m curious if any user really thinks of things that way. If they were all actual manila folders with papers in them, I wouldn’t keep the ones I created in one pile and the ones given to me in a separate pile. They’d all go in the same place.” (Michael Perrone, Sr. Project Manager)

“A downfall of Drive is that if you’re using the web UI you can’t see when folders are empty. So when we set up project folders ahead of time and you’re looking for a file, you sometimes have to click through half a dozen empty folders before finding what you’re looking for.” (Jenna Bantjes, Sr. Experience Designer)

“I wish Drive would stop developing features and address its messed up folder structure. I waste more time looking for things in Shared vs My Drive and double checking permissions on things.” (Michael Perrone, Sr. Project Manager)

The deciding factor here is that if a doc is shared with you in Drive, it immediately goes in a separate “shared with me” folder, which is confusing and a time-waster.


Advantage – Draw

“Versioning on both is great – i.e. restoring previous versions. Maybe a bit more intuitive on DB but functionality is similar.” (Jenna Bantjes, Sr. Experience Designer)

A necessary feature – both platforms perform equally well here.

Overall web/desktop experience

Advantage – Draw

“When I use Dropbox within the Finder, I can preview each doc to make sure I’m opening the right one, which saves me a bunch of time. Drive doesn’t currently do this.” (Michael Perrone, Sr. Project Manager)

“Drive is better because I can share ‘edit’ privileges on items at the document level, whereas I need to do that at the parent folder level in Dropbox.” (Michael Perrone, Sr. Project Manager)

“The Dropbox web UI is ridiculous and it’s incredibly hard to find a “download” button, especially when dropbox has ‘synced’ with your machine, but again, you can’t actually find the files without restarting finder.” (Scott O’Hara, Development Director)

“I actually don’t mind the system as it is right now [using both Drive and Dropbox], but that might be because I don’t have Drive synced on desktop, just browser. It’s really helpful for me to have one place for docs, sheets, referring to SOWs or client docs, etc, and then a separate place for all my design work.” (Kat Garcia, Experience Designer)

“I use Drive so infrequently and have such difficulty navigating it that I don’t have it installed on my computer. My guess is the big Drive / Dropbox divide is between design and everyone else.” (Trish Glei, Experience Designer)

The separation here is just as Trish described. Overall, designers like using Dropbox because of ease of use and more intuitive file organization (no “shared with me” going off into the ether like in Drive). But for strategists and PM’s, Drive’s collaboration features make it indispensable.

Mobile experience

Advantage – Dropbox (by a hair)

“I find the Dropbox mobile app to have a much more streamlined interface, so if I’m uploading things from my phone (like whiteboard photos), those always go to Dropbox.” (Michael Perrone, Sr. Project Manager)

drive and dropbox upload screen
Left: Drive mobile upload screen. Right: Dropbox mobile upload screen.

I completely agree with Michael here. As a PM, I find Dropbox to be more efficient for documenting working sessions on the fly and getting photos and screen captures to the team quickly, but for me it has more to do with sync speed than UI. (Drive has improved its UI in the past few months.)

Separation of personal and work files

Advantage – Dropbox

“Better desktop integration and personal/work division. With Drive, You can only sync one desktop account at a time (no equivalent of Dropbox personal/work folders).” (Geordie Kaytes, Director of Strategy)

Although tangential to the workplace-centered conversation, this is a key differentiator, particularly for those of us who use their work machine at home as well.


Because of its collaborative features (obviously key to our process), we definitely can’t work without Drive. The big question is whether the design team can work without Dropbox. The next step in this Drive/Dropbox exploration at Fresh is to redesign our standard project folder structure in Drive to see if that helps keep organization tight and eliminates the need for Dropbox.

Author Jayne Hetherington

Jayne is a lifelong runner and holds a graduate degree in visual and media arts. She believes that a deep understanding of the end user comes from a genuine relationship with each client, built on mutual trust and respect.

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