Somehow I've become the IT Director... Lord help us
February 3, 2010 1:21 PM   Subscribe

I am woefully deficient at anything IT related, yet as a small business owner I need to get my ass in gear. Can you help me figure out how 2 computers in my office can access each others' Outlook? We aren't on a Microsoft exchange server (and I don't think I really understand what that is, if that helps to give you a better picture of how clueless I truly am).

We are using gmail for our office email addresses, and we're running Windows 7 for small business on our computers. The reason we had to go the PC route is that Outlook is critical for our business (Entourage didn't come close to what we needed). We really need to be able to share out contacts and calendars.

A few days ago I had the brilliant notion that if I hooked up my Blackberry to her computer all of our contacts would be populated and all would be well. Oh, the horror. Instead I almost wiped out over 200 clients from the system. (RELATED: how can I make sure we never ever delete any contacts no matter what?)

It also dawned on me that maybe if we used 2 hotmail accounts we could somehow get our systems to talk to each other. Ha.

Ahem. So here I am. Is there a simple way of making this work? And is there any chance you could walk me through the steps I need to take as though you were talking to your grandmother?
posted by ohyouknow to Technology (23 answers total) 2 users marked this as a favorite
in Outlook, you can share your calendar and your contacts.

Go to your calendar and select "share my calendar". In the email that pops up, type in your coworker's email address. Click Send.

Do the exact same thing for sharing contacts: go to contacts -> "share my contacts" -> email your coworker.
posted by royalsong at 1:40 PM on February 3, 2010

Since you're using gmail for your email, you should consider looking at Google Apps Sync for Office. Since you aren't on an Exchange server I'm not sure how it would work. But syncing between your local contacts list and what is on the Google cloud should work. I think you have to buy the Premier Edition of google apps for $50/seat/year for that to work. That's cheaper than using Exchange but more expensive than free. But what you would get is shared calendars and contact lists and you can use Outlook rather than the Gmail interface.

(Weird that you mention Entourage doesn't come close to what you need since it does calendars, email, contact just like Outlook but it isn't that great in Microsoft Exchange environments.)
posted by birdherder at 1:45 PM on February 3, 2010 [1 favorite]

T-H-E number one first thing to learn, then, is how to backup and restore your entire system or an individual critical file(s). Don't start reconfiguring your system - or let anyone else do it, either - if it contains your only copy of anything important. You will make mistakes. Hardware will fail sometime. Make sure your business can keep going or resume quickly in either event.
posted by TruncatedTiller at 1:46 PM on February 3, 2010

royalsong: That "share my calendar" function does not exist on either of our computers. I was told that this was because we don't have an exchange server.

birdherder: Alas, Entourage didn't offer us the same level of functionality with contacts (I really really really prefer MACs, so this was a difficult call). I am right now investigating the Google Apps thing. Thanks!

TruncatedTiller: I have no idea how to back up my contacts. But I do back up my system fairly regularly (without understanding what I'm doing). So I suppose this must mean that my contacts are backed up too, although in a form that I don't know how to access?
posted by ohyouknow at 1:58 PM on February 3, 2010

ohyouknow-- how much money are you guys willing to spend on this? Outlook and Exchange are a huge bitch. You can pay a company (like Apptix/Mi8, etc.) to host an Exchange server for you, and they'll set everything up, including calendar sharing, etc. When you have a problem, you email them and they fix it.

I know a pretty reasonable amount about computer nonsense, and I don't think if I needed to use Outlook and Exchange for a small group of people (meaning, no fulltime admin on staff), I'd do it myself. I'd pay a third party who _only_ did that.
posted by jeb at 2:02 PM on February 3, 2010

You can set up basic Google Apps for your business for free (Standard Edition), and then share calendars in there, but even if you don't do that, you can still share Google Calendars and sync between your Outlook calendar and you Google Calender using the sync tool already referenced.
posted by idb at 2:16 PM on February 3, 2010 [1 favorite]

Don't take this the wrong way, but you really need to hire someone who knows what they're doing. There are a number of problems with the expectations you have and your understanding of the systems involved. There are also probably plenty of better ways to go about things.

Do you have any business relationships that would be willing to share their IT contacts with you? Find someone you can trust to give you a consultation on the way you should proceed.

You should be willing to spend some money on this if you're saying things like "We never, ever want to delete contacts. Ever." Just ask yourself what the impact would be if you did delete every single contact and could not recover them. What would you do? How quickly would you lose business, and how much?
posted by odinsdream at 2:45 PM on February 3, 2010

Uh oh. I just downloaded Google Aps Sync and ran it with my email address, restarted Outlook... and now all of my emails are missing.

Please tell me that my computer is just taking 10 minutes to think about things before it makes everything okay again.
posted by ohyouknow at 2:47 PM on February 3, 2010

odinstream: You are 300% right. I know I absolutely need to outsource this. We've just been in business for 4 months, there are only 2 of us (it was just me for the first 3 months), and we only hit profitability yesterday. So it's been a mad dash to get here, and now it's critical I keep everything organized and kosher. I am the very last person on the planet who should be on the helm on this. I have no delusions about that at all whatsoever.

But for the next week or so, I'm the only one who's going to be able to do anything about this. So far I just keep fucking everything up. Please bear with me.
posted by ohyouknow at 2:55 PM on February 3, 2010

I would ditch Outlook and go 100% with Google Apps. Using just the web interface is so much simpler than having to sync with outlook, and all the inconsistencies this causes. Just play around with all the features of google and you will find that it's so much better than being bound to software living on one machine, that can crash.
posted by parallax7d at 2:57 PM on February 3, 2010

ohyouknow: "I have no idea how to back up my contacts. But I do back up my system fairly regularly (without understanding what I'm doing). So I suppose this must mean that my contacts are backed up too, although in a form that I don't know how to access?"

ohyouknow: "Uh oh. I just downloaded Google Aps Sync and ran it with my email address, restarted Outlook... and now all of my emails are missing."

It sounds like you get to test whether those backups work and backed up the right things. You might check the first gmail app acct and see if it's got the goods? I'm not at all sold on Outlook and use gmail personally, but you know your business requirements better than I do.

If I were you I'd look for a contractor, preferably with recommendations from people you know. Or outsource as much as possible. I know our very large organization is looking for alternatives to locally hosted MS Exchange now.
posted by pwnguin at 3:03 PM on February 3, 2010


I sympathize entirely. In that regard, I heartily second parallax7d's suggestion to ditch Outlook entirely and just use Google Apps directly. Calendar sharing is built in.

Outlook is only reasonable if you're using Exchange. You're not. Ditch it. It's a confusing nightmarish hell even when you use it correctly.
posted by odinsdream at 3:26 PM on February 3, 2010

I'm feeling wedded to Outlook because I have a few thousand contacts and I have pretty substantial (and ongoing) notes that I need to take for each contact. Also, most of my clients use Outlook and it's useful for reminders.

I also need to sort my contacts by various criteria. And I like that I can color code things in Outlook to keep things super visual. I haven't been able to find a way to do that using Google directly yet (of course I haven't been able to figure out how to do any of this yet for fuck's sake).

I took a few deep breaths and read that it can take 24 hours for the new version to sync up all my old emails. So I've decided I'm not allowed to have a full-blown anxiety attack until tomorrow.

I'm just going to putter along at a 75% anxiety attack for the rest of the day, thank you...
posted by ohyouknow at 3:42 PM on February 3, 2010

Phew. I think I figured it out. I had to enable API somewhere in Google land, which I did, and now emails are loading.
posted by ohyouknow at 4:06 PM on February 3, 2010

If Outlook is so important to you that went to use PCs because of it, then I'd look into getting an Exchange server. Google's tools, while they're getting better, aren't nearly as well-suited to Outlook as Exchange is, and they'll always be a little bit hacky.

Happily, it doesn't have to be expensive, or mean you setting up your own server. Just get a hosted exchange account (they start at about $5 a month per user), and make sure it's with a host that do proper backups. I'm afraid I can't recommend anyone in particular, but a google search suggests a fair few.
posted by bonaldi at 4:26 PM on February 3, 2010 [1 favorite]

FWIW, I've supported clients who used 123together for Exchange hosting. I'm not sure they'd be the cheapest option, but they were super helpful with everything. They have packages for including Blackberry Enterprise support as well*, which if you have Blackberries, you'll want sooner or later if you stick with Exchange**.

* Blackberry Enterprise Server, or BES, is a software product from Research in Motion, the blackberry people, that talks to Exchange server and links this information with your Blackberries. In today's world where almost all smartphones link to Exchange with ActiveSync, which requires no extra software, it's a little odd that RIM has this extra non-free software requirement, but that's their core business and it used to be the only game in town.

** You really should consider not doing exchange, especially doing it yourself. Google Apps is fantastic and reasonably priced for a small business. Exchange is really overkill for a small operation, and you're married forever to Outlook. You can never expect proper support on non-Windows platforms, and you're stuck in an upgrade cycle with Windows, Office, and all of the server products. Google will read meeting invitations and reminders that people send out of their Outlook just fine.
posted by odinsdream at 5:46 PM on February 3, 2010 [1 favorite]

To fill you in on what an Exchange Server actually is...

One of the big things in computing these days is to keep as little as possible on a physical PC, and instead keep it all on a server somewhere, or "in the cloud" if you don't have a server to call your own. With MS Exchange, you would have a server that holds all your mail, and acts as the coordinator for all things Mail-related - Calendar, Contacts, etc. Since everyone's accounts are on the same server together, and Exchange is designed to allow it, you can then share information between your accounts on that server.

Google's Apps work the same way, but instead of having your own server, it's generally stored on Google's systems. You still have your account, and such, but it's not YOUR server, it's Google's system, and you're leasing space on it.

The other nice advantage to this is that if something bad happens to your PCs - if they get stolen, break down, etc. - all the data isn't lost. It's still on the server, and you just copy it down again (Your Outlook keeps a copy locally, but never actually removes it from the server). This will NOT prevent someone from deleting it by hand, however!

If Google won't suit your needs (and I will recommend them - they will do email, calendar, documents, and can sync to your Blackberry), you can look at a Hosted Exchange Service. I know several people that use Intermedia, and are pretty happy with them. You get all the benefits of a full Exchange server, but you're only paying a monthly fee instead of paying thousands for hardware, backups, licenses, etc. There's a 3-user plan you can start with, and upgrade as needed. Be warned, it will get pricier the more options you add (like Blackberries).
posted by GJSchaller at 5:57 PM on February 3, 2010 [1 favorite]

You can set up basic Google Apps for your business for free (Standard Edition), and then share calendars in there, but even if you don't do that, you can still share Google Calendars and sync between your Outlook calendar and you Google Calender using the sync tool already referenced.

I get that we can share calendars now, which is cool. What doesn't seem right though is that we still don't seem able to share contacts. And sharing contacts is 90% of what this is all about for us. We could print our calendars everyday for each other and that would be slightly irritating, but nothing compared to not having access to complete personality profiles, interview notes, conversations with each candidate about the types of people they really hate working with, etc. to help us remember who we're supposed to be having a meaningful conversation with, just as 5 emails come streaming in from people who are are each frantic or highly concerned about something. We need to be able to know/remember what that frantic feeling is coming from. This is what makes us great at what we do, and Outlook has really been an unsung hero to us so far.

I know Microsoft gets a lot of crap (from me too) but Outlook is really a thing of beauty when it's working. < --Important caveat.
posted by ohyouknow at 12:00 AM on February 4, 2010

It sounds like what you need is an Exchange Server with a Public Folder for all of your contacts, where you both access a central source. You may also need some sort of CRM software, perhaps in place of Exchange, that lets you centralize them, manage them, and sync them back to your Outlook on both PCs.
posted by GJSchaller at 8:58 AM on February 4, 2010

GJSchaller, what is CRM software?
posted by ohyouknow at 5:33 PM on February 4, 2010

CRM = Customer Relationship Management

Some popular options include SalesForce and SugarCRM.
posted by odinsdream at 8:08 AM on February 5, 2010

With regards to CRM, I have heard good things about Highrise

They do offer a free 30 day trial...
posted by TheAnswer at 12:47 AM on February 27, 2010

UPDATE: I am now running Salesforce and I even have a consultant who's been organizing the interface for us and making it ridiculously user friendly (and more importantly completely fail safe!). This program has been completely molded to our business model and it is such a thing of beauty I'm almost speechless.

You guys were all so massively helpful I wish I could hug you all. Thank you for pointing me in this direction. I didn't even know what CRM was and now I feel like I've just stepped into an alternate universe.

What this means in practical terms is that my chaotic, fly-by-night, just barely profitable company is now totally making it rain in a big way, and I am so enormously grateful to all of you for holding my hand as I had (my not so mini) panic attack that day. You've shown me the light.

The internet is just the raddest thing ever. I love what all you brilliant tech geeks have created. Thank you and HOORAY!!!!
posted by ohyouknow at 3:04 PM on March 24, 2010 [1 favorite]

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