7 Reasons Why the City of Los Angeles’ Move to Gmail Scares Me

In October 2009, The City of Los Angeles made a monumental business decision to switch its email (Outlook) and basic productivity products (Word, Excel, PowerPoint) to Gmail and Google Apps by June 2010. They cited cost savings as the main driver and I applaud them for such a gutsy move.

Despite unanimous approval from City Council, this move wasn’t without critics. Moving to Google means moving its emails out of City managed data centers and into a private cloud under Google’s surveillance. Issues concerning security and privacy naturally ensued, and both Google and the City published articles and webinars addressing these fears and articulating the additional benefits.

I have no qualms about moving to the cloud. My fear is around IMPLEMENTATION because we’re not just talking about going from chocolate to vanilla…

…we’re talking about ripping away a system that the majority of 30,000 employees have been using for many years, and forcing them to embrace a completely redesigned system that’s been turned on its ear.

I know training is stressed in their plan, but teaching what might be a large number of new users to learn Gmail is no small feat. Below are 7 aspects of Gmail that I hope gets extra attention in their training sessions.

1. There are only two places: “inbox” and “not-inbox”

This is probably the most difficult aspect to grasp for new users. When you want to move something out of the inbox, you don’t drag it into a folder, you tag it with however many labels that apply and then archive it. Gmail never uses the word “folder”. It’s either in your inbox or not. Expect to allow a lot of time for non-gmail regulars to adopt this concept.

2. Speaking of no folders, how do you get any structure?

I have some coworkers who are VERY proud of their well-architected hierarchical folder system. In Gmail, no hierarchy. New users better get used to the Search feature as the main way of retrieving archived mail.

3. Speaking of archived mail… why does it not mean archived mail?

In Outlook, archiving is for transferring the gargantuan weight of antiquated emails that you’ll probably never look at again. You don’t mess with it and just wait for it to automagically do its thing every few months. In Gmail, archive means scooting emails out of your inbox. That’s all. No big deal.

4. What about threaded conversations? That seems pretty intuitive

This is one of the low hanging fruits that make people fall in love with Gmail right away. Especially in government, we enjoy ridiculously long email trails. With threaded conversations, all that back and forth shrinks to one email in your inbox. But it does get tricky when the conversation branches. Sometimes you don’t want to reply all and it could get complicated. Expect a few oops from new users.

5. What about printing my emails?

Something else that government employees love to do… print emails. I don’t know why, but you’ll always find printed emails in the forgotten pile around print areas. With threaded conversations, some folks might not want to bother fishing through threaded conversations and just hit the “print all” button on the side. Or some will forget that if you just want to print one message, you’ll have to select from the drop down menu. Either way…printing could get tricky.

And two features that Google is touting that scares me

6. I can chat from my inbox? How awesome!

Many agencies already have instant messaging, but the reason it’s not ubiquitous is because agencies don’t want to deal with the policies. Now that it’s in Gmail, you’re instant message is automatically saved and searchable. Imagine what this does for e-discovery. Now when someone demands all records related a project, you can include all the chat conversations with it. And you know how professional people sound when they’re instant messaging… (that was sarcastic).

7. Google is proud of its storage space blowing away the competition

I’m not sure this is a good thing. Yes, it’s annoying to get the “Your mailbox is over capacity” email, but that forces employees to archive and delete deadweight. Now without that restriction, watch email management of attachments go even more crazily out of control.

Overall, I’ll be cheering the City of Los Angeles onwards in their endeavor, because I believe Gmail is superior to Outlook. But it’s so tremendously different that it will take a long time for the majority of new users to figure it out. Hopefully, with their extensive training plan, they can emerge as a pattern for other agencies to follow.

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Scott Horvath

Interesting view points. First, I’ll saw that I’m completely speaking on my own opinion and not that of who I work for (and “no” they don’t use GMail). Personally, while I think the move is a definite cost savings in terms of hardware and software management, C&Aing systems, etc, I’m not comfortable with the idea of having government email (and the amount of things that go through it) in a third-party system which has had outages and hacking issues itself in the past. That’s not to say that government systems can’t be hacked, but one is in the public cloud and the other is on internally secured networks. Just the way I see it.

However, a few minor things I’ll point out (but not that should change my personal opinion):

“When you want to move something out of the inbox, you don’t drag it into a folder, you tag it with however many labels that apply and then archive it.”
Actually, there is a drag and drop option to move items to your “folders.” There’s a little dotted grabber option to the far left of each email that allows you to grab that item and drag it into your folders…sorry, tags.

While you may not have folders in the normal sense, you can install a greasmonkey script in Firefox called Better GMail which allows you to type tags like “Taxes” and “Taxes\2010” and “Taxes\2011” which then are automagically formatted as nested “folders” in your folder pane.

There’s also some really cool searches that you can save as Quick Links (I think that’s a “Labs” item) which will pull any document type from All Mail. Example: put this into your search box:


As far as chat is concerned, most agencies already have a disclaimer that happens when you log into your computer that says you basically have no right to privacy while using any government system and that everything you do is trackable. You CAN turn off saving your chat history. However, you don’t actually have that option on your internal network because, well, you’re on an internal network and you have no right to privacy. Now, I would imagine that the City would request that the chat history be on all the time and to not have the choice to turn it off. But when you work for the government (city, state, or local) you have to understand that there are some things you have to compromise on…like your right to privacy in a chat window while using it during on-duty hours.

Regarding capacity of the inbox, I can tell you that no matter how much space you provide someone…or how little..it will A) always get filled up some way and B) always have 10,679 emails in the “inbox” which have never been moved or deleted. If you give them space, they will fill it. If you give them less space, they will “archive” it and put that archive in places that you wouldn’t think possible…never to see it again, never to use it again.

The one benefit to having much more space and not having to “archive” items in the traditional sense is that it makes search and discovery through your email MUCH easier than having to import archived files and not knowing which one is the one that has your email in it.

So while there’s a lot of benefits to Google Mail, I would still opt for the in-house systems…simply from a security standpoint and being able control your IT resources yourself and not dependent upon a third-party whose ultimate goal is revenue.

Again…just my personal opinion.

Jon Lee

Wow… thanks Scott for your review. Have you seen Google’s recent announcement that it’s launching a cloud catered to government? It’s supposedly the first private offering that’s FISMA certified http://www.govinfosecurity.com/articles.php?art_id=2785. I don’t know if that solves all security issues but I think it’s success is more determined by large agencies taking the plunge and others following moreso than meeting security requirements.

Regarding your comments:
1) Yes, there are additional ways to move email out of your inbox, such as drag and drop. I didn’t mention that because my point was to differentiate the nature of folders in Outlook vs labels in Gmail. Thanks for mentioning, though.

2) I just discovered that a few months ago, Google labs released a nesting labels feature to get the hierarchy in labels. It’s probably easier and more stable than greasemonkey. I gave up on Better GMail a while back because it crashed too often.

3) I agree with your chat and capacity comments.

Overall, what makes Gmail even more fascinating are all the hacks and easter eggs that people have developed over the years. There certainly are ways to get around or enhance basic features, but I didn’t want to get into them in this post because I’m talking about new users who are trying to understand the basics.

I think my personal position is I would rather go to Gmail for email but definitely Office over Google Apps.

Thanks for posting.

Scott Horvath

Yep, I did see that Google/FISMA announcement which is certainly a boon for them. I think what offers is an excellent option to traditional client-based products. For the majority of users it will be slight transition and learning curve but they’ll pick up on the differences quickly. However, it’s only when you start getting very specialized uses of the tools that some people have done in the past with software products (but they can’t do with the cloud ones…yet) that makes the transition difficult for a few.

But again, outside of the learning curve and differences in functionality…the bottom line is whether you put your full trust of government information, and keeping it secure, to a non-government entity that depends on revenue to keep afloat.

Thanks for the post as well…great thoughts!

Chris Bennett

Great post Jon.

Counter point to consider: The experience/transition can be guided a number of ways by the city, even to the point where email doesn’t look different at all. For example, with IMAP through Google Apps, employees could continue to use Outlook to manage email and contacts the same way they’ve always been able to. Chat can be disabled for everyone if desired. Blackberries will sync just as well using Google Sync, not changing the mobile experience any.

Now of course they could do none of that and hope everyone like the Gmail interface 🙂 I believe the deal was more about wanting Google to manage it and saving money in the long run than a desire for a richer feature set.

Regarding storage, like it or not it seems the government is being forced to move to cloud solutions to save money. Personally I trust Google, Microsoft and Amazon more with keeping up on server security than I think I would most agency server admins (blatant assumption that those are often small IT teams and not 24×7 managed operations)

Jon Lee

Scott – Do you think current trends of government using third party SaaS like Salesforce and other open data related applications is less risky than using Google’s cloud?

Chris – I don’t know all that much, but from what I’ve gathered, it seems like the City is doing away with basic Microsoft Office products completely, unless your job requires advanced features not available on Google. But as far as email, I think Outlook is going out the door. So, it would be a great work around to IMAP your Gmail into Outlook, but my guess is its not an option. Maybe there’s someone that works for the City that can weigh in?

Stephen Peteritas

I mean I love my gmail so as an experienced user a lot of the above points are easily overlooked by me. BUT point 6 is extremely valid. I know the things I say on IM and if my boss was someone beside Steve I don’t think I would want to hand over those convos.

Jon Lee

Thanks for your comment, Stephen. I had IM at my prior job and some of the stuff people said could probably get them fired so I’m with you.

Scott Horvath

@Jon: Hard to really say. I think there’s a definite need for moving some things to the cloud. But we really need to be picky about what, exactly, is moved. Moving entire agencies, I think, has unforeseen complications. Moving bits and pieces of agencies over time…probably fine.

Jon Lee

It’s definitely tricky, Scott. Security is just one of those things that often gets a bad rep when it inconveniences business operations. People take security for granted until something happens, then the security people can say I told you so, then spend the next 72 hours fixing it.

I’m all for consolidation because theoretically, I believe in the benefits. But so far, we’ve seen some failures with gov running it’s own data centers, so it makes sense from a business perspective to let the private sector handle it. I do like the idea of moving bits and pieces at a time, though this can be inconvenient for the employees that work with the data.

Good discussion, thanks.

Dan Israel

Hi Jon,

Interesting post. Your headline is a bit misleading — it should be 5 things L.A. users need to know when moving to Google, plus 2 things that scare me. : ) (Full disclosure, I work for Google.)

It looks like you’ve now heard about the nested labels in Gmail. And as Scott points out, administrators have control over whether Chat history is saved or not, or saved at the discretion of the employee. In fact, admins can turn of Chat entirely, if an agency really doesn’t want their employees to have it.

So, it sounds like the one remaining thing that scares you is giving employees a 25GB inbox. Think of how much time government employees spend today cleaning out their inboxes — time that could more productively be spent on whatever they’ve been hired to do. Google has tools that allow administrators to create email archives & enforce retention policies to ensure that emails are handled appropriately. As for attachment overload — Google’s shared Docs mitigates that. You no longer need to attach a document — simply point people to the URL where that document lives.

One final thought: we announced this week a new version of Google Apps — called Google Apps for Government — with additional measures to meet the needs of government employees. In addition, we’ve completed FISMA certification & accreditation for Google Apps. I’m participating in a live chat on GovLoop next Thursday to help answer people’s questions about this new edition & how government agencies can put Google Apps to work. Please join in.

Jon Lee

Hi Dan, nice to talk to someone from Google’s side. Yes, there are counterpoints for the ones that I made, and in the end, I’m sure the City of LA will be just fine. To clarify, and sorry I didn’t mention in the post, what scares me is just in the beginning when new users are getting acclimated to the new system. During this time, I believe there will be a good deal of frustration, but in the long run, I think it’s a win for everyone involved.

I’ve been a heavy Gmail and Google Apps user since 2004 and I still remember being frustrated for the first week before it all clicked.

Thanks for mentioning the event next Thursday. Will definitely try to be there.