If you can’t collaborate well then you’re going to have significant problems in your business, regardless of what size it is. The rise of file-sharing software has made collaboration infinitely easier in recent years, driving up the capabilities of remote workers and freelancers.

With a few clicks of a button and drags of a mouse, we can maneuver documents from person to person or simultaneously work on them without the use of a fax machine or the most extensive email chain the world has ever seen. These nifty apps also give us the chance to involve business partners or clients in the process as well as keep them at arm’s length when we’re just looking for approval and not giving them the chance to edit our documents.

Choosing a logical, intuitive file-sharing software can send your business skyrocketing to success or plummeting back to the ground. If it’s easy to use and people can dive right in without having to go through a three-hour training session, you’ve got a hit on your hands. If it has a steep learning curve, your employees – particularly older ones – are likely to push it aside for their more tried and true methods.

This aversion can stall productivity like nothing you’ve ever seen before. When different factions of your office are committed to different software for the same task, you’ve got trouble on your hands.

This conflict becomes an issue when you consider how many different connected devices businesses are using these days – laptops, desktops, smartphones, tablets, etc. If the same software isn’t connecting all of those devices for every employee, one problem will rapidly turn into many.

So, which file-sharing programs top the charts? Which are most comfortable to learn? Which are scalable as your business grows and more people come on board? Which have blind spots in them that can ruin everything? Here’s a look at some of the best options out there for file-sharing platforms.


Slack is more of a communication center than a file-sharing program, but since it is popular and does fit the criteria, we thought to include it here. Slack lets you set up multiple channels inside your own business as well as direct 1-to-1 conversations between you and another user.

File-sharing is as simple as dragging the item into the channel you want to share it. This feature can be a bit cantankerous if you’re trying to share it with a few people, but not everyone on a channel, because if you have access to that channel, you can see all files on it, regardless of whether they’re meant for you. It’s also wise to configure Slack’s settings, so you’re only getting messages when you are specifically mentioned by someone else; otherwise, your computer will ping the day away with all kinds of alerts.

Slack is free to try for small teams, but that trial is very limited: you only get to keep 10k of stored messages and 5GB of shared files. If you jump up to the Standard package of $6.67/user/month, you get unlimited searchable messages along with endless channels, voice and video call up to 15 participants, and 10GB of file storage per user.

Google Drive

Sure, Google might be absorbing data from everything you do online, but you can’t be mad about how great Drive is. Anyone with a Gmail account gets up to 15GB storage for free. Sharing content is a snap – there are options to let people view a page or edit it to keep things in order. If you’re using a Google-connected app like Docs or Sheets, you can work on documents in real time simultaneously with anyone else who has permission on the document.

You can even see who the person is working on the document at the same time and strike up a chat with them. If you need more space, it’s $1.99/month for 100 GB or $9.99/month for 1 TB. Drive’s downside is that if your Internet connection slips even a little bit, you’ll get the notice that Drive is working or reconnecting during which time you won’t be able to edit your document.

Make sure to enable the “working offline” feature for when this happens, or if you’re going to be edit something while not connected. When Drive finds an active Internet link, it will take what you’ve been working on and automatically update it.


Taking the idea of teams working together to the next sports’ metaphor, Huddle is for small businesses that have grown out of their early stages. It promotes its ability to perform a secure collaboration with external parties, which is often a sticking point on other file-sharing software.

It also stands out for its ability to synchronize with both Google for Work apps and Microsoft Office. Its free trial is a lightweight version of the platform that doesn’t let you look at most of the cool features. The price is a big step up from some of its contemporaries, costing $20/user/month up to 25 users.


Nope, this isn’t Dropbox’s younger brother. Box is a custom platform made for people who want to write in Word but don’t want to write in Word online. In essence, Box’s design is for collaboration on a much stricter level. When you use Box, you can download a free extension for Word that opens when you download a file.

When you start working on the said document, you can lock it so nobody else can make changes until you’re done, and you have uploaded the file back to Box. This method is a great way to keep files the way you want them and pass them along a structured chain without confusion. The starter plan offers a whopping 100GB of storage for just $5/month. The business plan is $15/month, but the rewards are even better: unlimited storage.


Dropbox is probably the most recognizable file-sharing program by name. Its premise is as simple as its name: Drop your stuff in the box. However, the interface doesn’t always follow as. Common mishaps occur with permissions, and it’s not all that intuitive when it comes to sending links to share files. More than a time or two you’ve probably gotten a link to the user’s sign-in screen instead of the actual data.

The most irritating downside of Dropbox is that anyone you send a file to must either have a Dropbox account or sign up for one. Clients are not going to be interested in that to see one file one time. On the flip side, the storage for the price factor is phenomenal. Service starts at $8.25/month for up to 1TB of space. The space doubles for $12.50/month.

The best part of these services is that most have free trials or their initial user level is free of charge. That’s essential for small businesses that want to kick the tires and take a test drive before committing their cash flow.


About the Author

James is an avid investor in real estate and the stock market. He has found an edge in his real estate investing with digital marketing.