Last week’s thoughts about the past ten years of email have got me thinking about how we collect, maintain, and use our digital contacts. And really, when you think about what and how you use email, it is all about staying in touch with people that we have met, and answering and asking their questions.

To do this right, you need a decent contact manager. And over the years I have used dozens of products, starting with a venerable rolodex card file back in the pre-computer days. There was a great and simple program called Dynodex that ran on Macs that I used for many years: it was fast, it didn’t take up tons of screen or computer real estate, and it didn’t have a lot of fields to mess with. Right now I use Gmail’s contact manager, and while it is cumbersome to have all my contacts online, it isn’t fatal, even when (as what happened earlier this week) when Gmail goes down.

I tell you up front that I am not a big fan of Microsoft Outlook. Outlook standalone, without Exchange, is overkill for me, and besides, it ties me too closely to Windows. But there are some people that swear by it (and sometimes swear at it). My sister’s company uses Outlook in standalone mode, which is probably the worst choice for any enterprise contact system.

Some people love ACT for keeping track of contacts: I think it is also overkill, and the latest versions have suffered from feature bloat. Really, all I need besides a person’s name and email address is a phone number and maybe a short description or job title. I can search through my Gmail archive and see all of my correspondence with that individual, so I don’t need to replicate that in ACT. I realize that many people want a lot more out of their contact managers, and that is why ACT and Outlook are so popular.

There are several things that I look for in a contact manager. One is the ability to put a single contact in multiple groups: for example, I could have a client who is a CIO that also is someone that lives in Boston. This person would be in three different contact groups: clients, CIOs, and Bostonians. I have about 50 different groups in Gmail, and one of the reasons I like the service is because I can have this kind of structure – and also for my emails too. Outlook and other desktop emailers only allow messages to be placed in a single “folder.” Gmail uses labels, and you can have an almost unlimited number of them, but more importantly, each message can have multiple labels attached. Why is this important? You want to be able to sort through similar collections of people, or find out who on your list meets particular criteria, just to name two actions. Once you start using labels and groups, you wonder how you ever got along without them.

Another test is what happens when the contacts aren’t personal, and need to be shared around your enterprise. Then you might want to consider one of several hosted contact management services. I actually wrote something about this for the New York Times last year:

http://www.nytimes.com/2007/11/14/business/smallbusiness/14contact.html

And then there is the issue of what happens when you want to migrate from one contact manager to another, and that is usually hard to do. While most products support some kind of import and export feature, the devil is in the details: for example, Gmail doesn’t allow you to export your group memberships of each contact, so you have to re-create that even if you export from one account and import to another Gmail account. Others don’t fare well with the free-form text fields: if you have commas or other punctuation inside them, they will mess up the particular contact record.

There are other online services that are somewhat useful for managing contacts, such as Plaxo’s Pulse and LinkedIn. Neither works well enough for me to use them exclusively, but are helpful to keep track of when someone has moved to a new job (or in the case of LinkedIn, about to consider such a change). There are also other synchronizing services, such as Glide, but it didn’t like to deal with 9,000 addresses and took a while to catch up.

Stepping into this space are the various social networks that try to enumerate all your “friends” but again they are flawed: not everyone you know is a member of one particular social network, and not everyone wants to use the social network as a means to keep up with their business contacts (seeing people’s sexual or religious preferences for my business contacts comes under the heading of Too Much Information, for example).

Ideally, I would like one system to use for maintaining my contacts that could also be used as a publishing platform for this newsletter, so you could subscribe to various other editorial products of mine for example, or change the way you hear from me. Most of you like these weekly emails, but not everyone – some people want RSS feeds, for example, which is why I cross post the Web Informant on my Strominator blog too. (I know, brand confusion: I probably should fix this sometime soon.)  The social network that understands that will get my immediate attention, for sure.