I have recently started a new job at a company and love it so far, the main reason I enjoy it is because everyone seems switched on and open to suggestions for improvement.

My boss and I moved to the new company together after an acquisition. I am a creative designer and work on many projects across the company. A problem we have is that not everyone has access to the shared/networked drives internally within the company and they don't seem that reliable to me. Having spoken to my boss's boss and my other colleagues we agreed that the best solution for a big project would be to use a service like dropbox or maybe onedrive. However, my boss is opposed to the idea saying that we shouldnt be introducing shadow IT into the company, I also think that she just doesn't understand these services as she has never used them before.

The issue I see here is that most people in the company use their own shadow IT i.e they work on macs and share files using dropbox, practically speaking the shared drives are rarley used and usually only for sensitve projects.

The question I have is how can I convince my boss to adopt dropbox?

Edit: Thanks for all your comments here.

Generally I agree with the points you are making i.e. this may not be the most secure place, but most of the info stored here will be Marketing related these will be editable versions of banners posted on social media and email for translation by other regions.

I agree that dropbox is not the best solution, but I only suggested it because alot of people in the company already seems to be using it. The issue here is that company provides those who request it with macs bu Mac cant access the networked drives as IT usually have their hands full and don't configure the machines properly.

The company already has a cloud solution in place but it is by a very small little-known company and their product is difficult to use thus gets used very little.

Some teams have Office 365, in my opinion this could be something I could request, but my boss seems opposed to the concept on a broader theoretical level.

What I find frustrating is that I already keep getting files shared as dropbox links as people in regions and those on macs simply use their personal dropbox accounts to share these, it would just be easier to have a shared folder.

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    I'm with your boss here, company dropbox is a nightmare with ever-appearing "end of space" and "user limit exceeded" forcing you to pay more and more. That's however not because problem of shadow IT in general, but because such services are mostly oriented at taking your workflow hostage to ask more money. – Agent_L Aug 2 '16 at 12:51
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    Access to networked drives (and every other local infrastructure) is solved with VPN, not outsourcing services to the internet one by one. – Agent_L Aug 2 '16 at 12:54
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    "the issue we have is that not everyone has access to the shared/networked drives internally " - why not? – WorkerDrone Aug 2 '16 at 13:02
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    Why on earth do you think shared drives are not all that reliable? – HLGEM Aug 2 '16 at 13:26
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    I agree with the other posts here. Don't introducing a new IT structure instead of fixing the actual issue, the machines aren't set-up properly. – random_answer_guy Aug 2 '16 at 15:03

Assuming you really want to go down this route (ignoring that many other employers would fire you nearly immediately if you pursued this particular shadow IT project):

Research, research, research

First, you should make sure you fully understand the implications of hosting your company proprietary information on another set of servers (particularly if your company does project work for other companies). In a past job I had, doing so would have violated a large variety of laws/regulations and included the "perk" of jail time.

Once you have spent the time to verify this, or at least be confident enough that hosting your content there is not violating any laws/policies, you should then verify that the Dropbox terms/conditions don't present your company any legal problems. Dropbox (and other cloud sharing utilities) do things with your files/data.

Also ensure you know the proper account creation process. If you create your dropbox using your personal email address, will this present any problems? What about your companies email?

Finally you must understand the implications for what happens if (when?) you leave the company. Most companies won't like someone using their personal dropbox account to contain confidential information, which means you have to be able to separate your personal from your work. This probably means another account specifically for your work Dropbox.

Present to your boss

Focus on the problems that your current solutions have. People don't react to solutions. People react to solutions only after the case for the underlying problem has been made.

they don't seem that reliable to me

For example, you need to make sure your boss knows why. Why are they unreliable? Are your servers crashing regularly? Do you not have any VPN process? What is the problem here?

Your boss 100% has to know the problems that you currently face and have an appreciation for why they are hard/bad. If you can't make this case then your boss rightfully should reject your proposal.

Having thought through this, approach your boss and say something like:

  • "Using network drives presents problems X, Y, Z. They cause effects D, E, F. I've spent some time researching Dropbox and it solves them by doing A, B, C. I have also verified that Dropboxes terms of service won't cause any problems and here is how we can create them."*

    • Yes, this should scare you a bit, because by implementing/promoting/convincing your boss to do "shadow IT" you are taking responsibility for it.

Commentary/unsolicited advice

Shared network drives are a fine solution to this problem for nearly all companies.

My strong recommendation is you investigate why they are causing you problems and fix those issues.

Nearly all issues related to network drives can be solved (trust me, I've dealt with them too).

Well implemented network drives provide nearly identical functionality to Dropbox for internal projects.

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    Anywhere I have ever worked using Dropbox for company information would have resulted in an immediate firing. You don't put proprietary data in such places. Shared drives work perfectly, you just need to make sure that the correct people have access. LImiting access is a good thing as well to make sure that people without the need to know don't see the information. Sharepoint is another internal way to share documents that protects your proprietary data. – HLGEM Aug 2 '16 at 13:25
  • @HLGEM yeah, though the fact that the OP's bosses boss seems supportive indicates a more systemic acceptance of the practice. I'll edit in your warning a bit more clearly though as I think that's the case in more companies than not. – enderland Aug 2 '16 at 15:44

The "don't introduce shadow IT" concern is quite genuine. Furthermore, I do not use DropBox because of concerns for information security. If files need to be shared within the company, a shared drive location can be set aside for that purpose. Microsoft SharePoint might be in place and, if so, it does "versioning" extremely well.

In any case, you need to carefully focus your(!) attention on "what needs to be achieved," and not on the one way that you are accustomed to doing it ... or even, the one way (DropBox) that you consider "clearly best." Even as you seek to change your boss's opinion, also be ready to change your own.

  • The OP states "not everyone has access to the shared/networked drives internally within the company and they don't seem that reliable" - so while shared drives would be better if they worked given that they don't work, what is the OP to do? – Kate Gregory Aug 2 '16 at 17:33
  • The OP has no choice but to do what his boss (and IT) tells him to do. If they don't use dropbox, there's a reason. If "not everyone has access to this-or-that network drive, again, there's a reason. A company's information is proprietary, and it is a very foolish company indeed which allows that data to be placed on any public service, whether-or-not the owner of that service promises that the data will be safe. If the OP has made his case once, then it need not be made twice, and should not be made twice. – Mike Robinson Aug 2 '16 at 19:36
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    @KateGregory - if IT allow users to use Macs in the office, but then don't configure them to be able to access shared/network drives, then IT need to be kicked in the backside and told to do a better job supporting users rather than have people work around IT with solutions like DropBox. – HorusKol Aug 2 '16 at 23:56
  • None of you other commenters are strictly wrong. My comment to Mike was that just saying "used shared drive locations" as though that hadn't been considered is not helpful. Your comments about "hey you should be able to make shared drives work" are different from the answer, and I wouldn't have made similar comments if those had been left as answers. – Kate Gregory Aug 3 '16 at 0:07

Your root question is "How do I convince ... ?"

The answer: Do the analysis.

First, "Shadow IT" usually shows up when the existing IT infrastructure isn't enough. You've identified two problems:

  • Unreliable
  • Unavailable to all users

Find out WHY this is happening. Talk to the IT team. What is the issue with reliability? What would it take to fix it? I've worked many places where entire teams of people would grumble about a problem for months, only to find out that no one ever reported the problem to IT. (Yes, it happens. I've been on both sides of it.)

Is the hardware or network infrastructure failing? Have the requests for access been submitted? Have they been turned down? Is there a logistical road-block?

Then, ask IT what can/should be done about it? Maybe they don't have the budget. Maybe they don't have the resources. Maybe they just need management approval to do this. Is VPN a problem, or has no one even asked?

Next, evaluate the security concerns. DropBox was notoriously insecure, but they've recently overhauled their business product line to address that (although I haven't dug through it, yet). Box.com is a really good, if expensive alternative. OneDrive is good, as is Google Drive. However, you need to understand your license agreement(s). For instance: the "Free" Google Drive gives over some IP rights, whereas the Google Apps for Business model does not. IT may actually be perfectly fine with hosted services, so long as they are able to administrate them.

Add to that any potential risks. Network shares come with file locking, so conflicts don't arise. Cloud sharing services allow for conflicting versions to spawn because of the way they work. How are you going to handle that?

Now that you know what your alternatives are, find out what not implementing them is costing the company. You can't know salaries, but you can know man-hours. How much time is being wasted limping around these problems? This will be a little subjective, but do your best to get it as accurate as possible.

Then, put this in front of your manager, and preferably have the IT team send someone to be with you when you do. If your manager is weak in this area, she may be THRILLED that someone mapped it out for her. If not, then she'll at least know that it's a problem, and (hopefully) start working on her own solutions.

  • Remember also that "not available to all users" is very likely to be intentional. People are given access to what they need, and nothing more. Services like DropBox are an anathema to that. Remember that the company's data belongs to them. It's the most precious thing that they own. They have the sole prerogative to dictate how their data is to be handled, disseminated, and used. You have a duty to comply. And, of course, to offer your suggestions ... "once." If you've said it once, and the answer is presently "No," then ... there's your answer. "So be it." – Mike Robinson Aug 3 '16 at 14:34
  • @MikeRobinson - I'm sure it was intentional on someone's part. It seems like there is a disconnect between this department's management and IT. In any event, the data is getting to the other staff/contractors, but not through "authorized" channels. There's already a "leak." – Wesley Long Aug 3 '16 at 16:17
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    Indeed, so, "don't be a part of it!" – Mike Robinson Aug 3 '16 at 21:55

You convince your boss by presenting a well reasoned argument that:

  1. Shows the advantages of drop box over all other potential solutions
  2. Shows how you can mitigate/eliminate the issues raised by your boss

Now whether Drop box is a worthwhile solution to your problem is a different question and would be better answered on something like the Super User or Server Fault sites


It sounds like everyone in the office sees the value in having a common location to share data. If your boss does not like drop box then find other options to propose.

Do a compare and contrast on Drop Box vs shared network resources vs a portable hard drive vs ....

If Drop Box is really the best option it will show to your boss.

Personally I would go for improving the network resources so that files are stored and shared on a locally managed system pared with VPN for remote access rather than trusting my IT management to some external company, but that is just me.


There are better ways to share files when that's appropriate. There are better ways to back data up. Trendy does not necessarily mean good; it definitely does not necessarily mean better.

If you can't come up with a better argument than that, your manager is right.

So your action should be to find reasons to do this that are important to the business. Show that the security is adequate for the data involved, that the system is reliable, and most importantly that it will save the company money somehow.

If you can't, let it go.

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    While I agree with you 100%, this is not an answer to OP's question ("How do I convince") at all. – Agent_L Aug 2 '16 at 12:58
  • Edited. Happier, @Agent_l? – keshlam Aug 2 '16 at 13:02
  • I'm not the one who downvoted. – Agent_L Aug 2 '16 at 13:05

First you should present your boss more solution that just one.

So he can weight the cost and usefullness of each one before making his choice.

To be honest, they were many incident of document leaking because of using an external tool to stored confidential information. Then people get their login/password stolen or cracked because it was too weak. And since dropbox is available on Internet (instead of having something only available in the intranet) everyone having the login / password can get the documents.

If you want to convince your boss you will have probably to set some guidelines to be followed when using dropbox, like don't share confidential information, save documents to shared storage as archives and delete unactive documents from dropbox, and definitively, don't use it as a back up, use it for active documents only.

If you want a tool that handle documents for you (versioning, collaborative work) check ECM solutions, Sharepoint, Documentum, Alfresco are some products like this.

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