blackberry Blackberry is making some very appealing phone/mail devices.

They don’t work the way you think they do. Some of you won’t have any fun with them at all.

Businesspeople have made Blackberries into corporate icons, as omnipresent as iPods on 24-year-olds. Serious users aren’t bothered by jokes about “crackberry addicts” – they just keep on moving their thumbs with their heads down through meetings and in airports and on dates and riding ski lifts and during dental surgery.

The mail comes in, the mail goes out, the phones look stylish. Great, right?

How does the mail get to the Blackberry? Aye, there’s the rub.

Medium to large companies run lots of servers, with lots of IT staff employed to keep them working. These days, one or more of those servers runs enterprise software from Blackberry. Blackberry Enterprise Server integrates with the company’s mail servers to push mail to the company’s Blackberry users. This is more than “software” – it is a dead serious, expensive, enterprise-level platform that requires committed onsite IT staff for setup and support.

You – my loyal small business clients, my friends with home computers – you don’t have a Blackberry Enterprise Server.

But if you buy a Blackberry, it can get your mail! You can send mail! It says so in all the ads!

You get to run Blackberry Desktop Software on your desktop PC. It hooks into your mail program and pushes incoming messages out to your Blackberry. Perfect! Works like a charm, right?

Maybe. Some people use it happily. But consider this.

It only works if you use Outlook. (Or Lotus Notes or Novell Groupwise. I don’t want to leave out Notes and Groupwise users. Why don’t you go off to the corner of the room and chat amongst yourselves?) Using another mail program or web mail? There’s other ways to set up the Blackberry – maybe – but you’ll need help and you have no guarantees.

It only works if Outlook is running on your desktop computer. Your desktop computer has to be turned on, logged in to your desk, with Outlook running, or nothing arrives at your Blackberry, period. The mail to your Blackberry stops if you’re using a notebook, or if your desktop computer goes to sleep, or you forget to leave Outlook running, or the computer restarts after installing an update, or the power blinks, or the Internet connection goes down, or anything else at all interferes.

The Blackberry software is like too many other programs. It works reasonably well for many people but when it goes wrong, it is obnoxious to troubleshoot. I’ve been there. It feels fragile and unfriendly. I had one particularly bitter experience that still makes me shudder, on behalf of a client who has developed a close relationship with Blackberry’s tech support department trying to work out the persistent problems.

blackjack Small businesses and law firms running Microsoft Small Business Server 2003 have a mail system built on Exchange Server, which can be set up to integrate seamlessly with phone/PDAs running Windows Mobile software. Not everyone loves Windows Mobile – a bit cluttered, a bit slow – but I can set it up in minutes to sync e-mail, address books and calendars over the air, with full two-way communication back to the server. Messages sent from the mobile device show up in Outlook’s Sent Items, phone numbers and appointments entered on the fly are immediately displayed back at the office.

Blackberry recently introduced Blackberry Professional, a simplified version of the enterprise platform for small businesses with up to 30 employees. It’s reasonably inexpensive ($499/5 users, $849/10 users) and it can theoretically be installed on a server that is also being used for other tasks. There are stories about successful installations on servers running Small Business Server 2003, although I’ve also seen horror stories about server slowdowns and crashes for the same setup.

I’m discouraging my clients from asking me to take them down that road because I’m old and cynical. If this could be installed and work right away with a minimum of fuss, that would be swell. Except it wouldn’t go that way, because nothing does. Instead, there’d be dozens of hours spent learning the tricks and tweaks and details necessary to keep things running smoothly. The payback just isn’t there.

At some point I’ll set up Blackberry Professional. If the experience is elegant and troublefree, I promise I’ll come back and retract all these negative vibes and try to be less cranky. In the meantime, take a look at Windows Mobile devices – I know what to do with those.

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