Email for Solo & Small Firm Practitioners

When I conduct a technology audit, one of the first items that comes up is email. The attorneys and staff are frustrated due to the lack of syncing between emails, calendars, and contacts. For many years solo and small firm attorneys have not had the organizational advantage available to larger firms that could afford an Exchange server. Those times have changed. Invariably, therefore, one of the first things I suggest to my clients is that they switch their email, contacts and calendars to Office 365.

The Nightmare of Not Syncing

One of the benefits of a smartphone is that it enables you to keep your contacts, calendar, and emails with you and organized. However, without the ability to sync everything throughout all of your devices, access on many different devices can actually cause more problems than it solves.

Those who do not have the benefit of a traditional exchange server often run into this issue, which means emails deleted on one device but not another, emails deleted by mistake, contacts with different information, and calendars that are useless.  There are ways to work around these problems utilizing tools to sync back and forth between Google and Outlook, but generally speaking they do not work very well and can cause their own share of problems, such as duplicate contacts. Using IMAP instead of POP for your email can also provide some assistance in terms of syncing emails, but IMAP has its share of issues as well. Fortunately, there are now cloud-based tools that attorneys who do not have an exchange server can utilize to solve these problems. These services work for iPhone, Android, Blackberry and Windows phones. They also work with tablets, all computers, and provide web-based access to email, contacts, and calendars.

Office 365

Microsoft’s Office 365 enables the user to easily sync contacts, calendars, and emails across all devices.  Directly from Microsoft, the price ranges from $4 to $20 per month per seat with a minimum of 25 gigs of space.

Some hosting companies offer cloud based exchange, but normally those services include a lesser amount of storage for a similar or higher cost. Be certain you get the most for your money by choosing the best provider for you. The 1 to 2 gigs of space the majority of providers offer is not enough for most attorneys. I have also found the reliability of these services to be questionable. When I first switched to cloud based exchange I went with my web-host provider instead of Microsoft itself. I experienced constant outages. I have never had an outage with Microsoft.

Google Apps

Google offers its service for $5 per month per seat or $50 per year per seat. Google also offers 25 gigs of space for email. In addition to providing syncing across all devices for email, contacts and calendars, Google also offers access to Google Docs, and Google Video.

Other Benefits

In addition to syncing your own email, contacts, and calendar, you can share your contacts and calendar with others in your office. This makes setting up appointments and sharing contact information much easier.

Set-up Problems

In my experience, the biggest problems with either service come during set-up as opposed to use. Once the services are set up, they tend to work well.

I have set up Office 365 many more times than Google Apps. I have only had set-up go flawlessly once. Admittedly, I was doing  a lot of this work right as Microsoft was introducing the product, and making adjustments to its set up process. I have actually spoken with Microsoft about my experiences and they genuinely seemed to want to improve the process.

As far as Google, the issues tend to come when you already have a free, non-branded Gmail account, and you want to combine your original account with your new one. Why Google doesn’t just allow the accounts to be combined I don’t know. While you can pull all of your old emails into your new account, it really isn’t a seamless change. I will admit it, I don’t like Gmail very much. I have no problem with it as a personal account, but I don’t like it at all for professional purposes.

In both cases you need to prove to the service that you own your domain. This makes sense, you don’t want someone to be able to steal your email address out from under you. Some domain registrars are more cooperative with this process than others. While I use 1and1 for hosting, I have to say, they make the process much more complicated than it needs to be due to some of their limitations. In this case, GoDaddy (which I hate due to its sexist advertising and for other non-technical concerns) makes life much easier.

I won’t claim that the average person will find the process easy. You can set-up either service yourself, but you might want help. It simply depends on your level of technological comfort.

After Set-Up

The problems I have had with Office 365 are as follows:

1. Rule size limitation for those who have a lot of rules. Most people don’t run into this. If you do, it will drive you crazy.
2. Changing the name of the person on an account
3. Transitioning from the original service (called BPOS) to Office 365  – this won’t be an issue for anyone any more.

The problems I have had with Google Apps

1. Since Gmail puts everything in conversation, if you use the same subject line in unrelated emails, and you forward emails from your old account to your new one, the oddest emails end up in the same conversation. This is because Gmail will believe the emails came from the same person (your old address since you are forwarding from your old account) and will believe they are related (because of the subject line.)

Google does not provide an easy way to split up a conversation. This makes a huge mess. And I mean huge. So don’t use the same subject line in your emails. You shouldn’t do this anyway. You should make sure your subject lines are relevant.

2. If you use Google and its labels (without using filters) you can run into issues using the labels with a third party software such as Outlook. The resolution to this is to use both filters and labels.


In terms of outages, I have never had an outage with Office 365 in the year I have been using it. During that time Gmail had one outage. However, BPOS, the service before Office 365, did have an outage about a month before I joined up.

So, after getting the services set up, the reliability is quite good. That doesn’t mean you won’t want to back everything up. You should still back everything up.

My preference

I prefer Microsoft’s service to Google’s. I have issues, ethically speaking with Google, since it will keep your data on its servers, forever. I also just don’t like Gmail very much in terms of how it arranges everything for its web-service. I hate the conversation set up. Other people like it. This is obviously a personal thing, and you might love the conversation set up. If you do, you can turn it on in Outlook 2010. Of course, you can use Google with Outlook as well. So if you don’t use the web-based version of Google, the services essentially look the same.

The amount of space both services provide is the same, 25 gigs. Google provides a more complete package for less, but most attorneys need to use Office 2007 or 2010, so that complete package may not be very useful. You may just find yourself using the email, calendar, and contacts anyway.


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