OK, just admit that Outlook's lame--and fix it, already

Smart e-mail may be a contradiction in terms, but let's get a show of hands: how many of you believe Microsoft is going to supply the answer?

I didn't think so.

When the company brain trust repairs to the Ballmer Bunker to chew over its next big idea, post-Yahoo, I've got a suggestion: how about doing something to deal with e-mail and its discontents? Something grand--like bringing Microsoft Outlook into the 21st century. I don't mean a tweak here and there; I'm talking about a top-to-bottom overhaul.

The product debuted in 1997 and has improved very little since. Given the absence of real competition for most of the last decade, you shouldn't be surprised at the glacial pace of improvement. We saw the same thing in the browser market after Microsoft disposed of Netscape (though perhaps the nascent rivalry with Google's Gmail is a harbinger of change.)

I was talking earlier with Rafe Needleman, who runs our sister site Webware, about Outlook and its discontents. Rafe noted that while Outlook is the most important application in the business world, the product still remains flawed in any number of ways. At one time, Microsoft had ambitions to build Outlook into a platform. Unfortunately, developers found the APIs difficult to use and nothing much happened.

But it's best to forget about waiting for incremental improvements. Rafe correctly observed that Microsoft can't fix Outlook without a complete rewrite. His conclusion is that you can't patch and make it better. (Listen to our conversation at the tail end of today's News.com daily podcast. For a deeper dive, check out this compendium of "Tech Nightmares" that CNET put together four years ago. The shame is that it remains as relevant today.)

The answers more likely will come from start-ups like Xobni and others investigating ways to add more intelligence to the program. Good luck to any third party that can manage that trick. What with a growing backlog of unread e-mails in my in-box--not to mention the daily dose of spam--users deserve a smarter Outlook that better prioritized and understood the tapestry of shared relationships between people.

Xobni, which came out of beta testing today, has received a bounty of attention because its backers include Vinod Khosla and Niklas Zennstrom. (Getting a freebee compliment from Bill Gates hasn't hurt.)

The challenge for Xobni and the rest is how to build a business that can scale. In the end, Microsoft will wind up spending some of the newly freed $42 billion in its coffers to buy Xobni or some other lucky third-party developers. Then we have to cross our fingers and pray that corporate infighting at the mother ship doesn't make a hash of it all. (I know. That's little help in the near-term. In the meantime, CNET's Josh Lowensohn has a great piece on favorite in-box work-arounds used by some of the folks at Microsoft.)

[sfotoord]

Charlie,
Have you used Outlook recently? IMHO, the 2007 version is excellent. Search works well, the group by date view is a lifesaver and side-by-side calendar views are great. Also, I'm a big fan of displaying two time zones in my calendar. I just don't see it. In my view, Outlook is the second best product that Microsoft makes besides Excel.

[RainCaster]

Even OL2007 has it's problems- like only one Exchange server connection. Fix that and I'd be happy.

[sfotoord]

As an aside, your article didn't actually make a case about Outlook needing a re-write. I just sort of presumed that everyone agreed that the product sucks.

[MadLyb]

Personally, I like Outlook. It could use some improvements, but it is better than any other client available.

[anothdae]

The title of the article suggests that Outlook in its current state is flawed, but no reasons are given. Even following the links in the article, I can't seem to find any writing on outlook's problems at all. Even the link that is four years old just addresses common USER problems that result from outlook not being set up correctly.
So i just don't get it i guess. Whats the problem? I love outlook, I use it daily on two computers and a PDA, both for multiple email accounts and calender / contact use.

If you are going to call for a complete re-write of outlook, AT LEAST write about problems you have with it, or features that you would like to see added. All in all this article is worthless. If you are going to write, at least say something.

[jdedon]

The thing with making email faster and smarter is filtering. And the problem with that is that it has to be managed by the user. Spam is one thing, but telling the difference between the wife's silly cat emails and serious business emails is another. Email is email. We just need to keep up with it or it will bury us all.

[anothdae]

The title of the article suggests that Outlook in its current state is flawed, but no reasons are given. Even following the links in the article, I can't seem to find any writing on outlook's problems at all. Even the link that is four years old just addresses common USER problems that result from outlook not being set up correctly.
So i just don't get it i guess. Whats the problem? I love outlook, I use it daily on two computers and a PDA, both for multiple email accounts and calender / contact use.

If you are going to call for a complete re-write of outlook, AT LEAST write about problems you have with it, or features that you would like to see added. All in all this article is worthless. If you are going to write, at least say something.

[ktureni]

That's my complaint, too. The writer just takes it for granted that everyone knows or agrees that there's something wrong with Outlook. Works fine with me: mail comes in, mail goes out, etc. If this writer were in my writing class, he would flunk. Who are you? A five-foot tall nerdy thick-lipped lisper in a singles bar trying to impress a couple of overweight chicadoos? Get a life pudgy boy!

[The_Decider]

That is an expensive piece of bloat just to send and receive emails.

[anothdae]

Its not just a program to send / receive email. . . It is a scheduler and contact organizer as well. If you just want to send receive email, use Outlook Express or Vista's Windows Mail. Its not Microsoft's fault if you are using the wrong product for what you want to do.

[The_Decider]

You can easily do all that without the bloat and cost, not too mention the security holes of Outlook.

[ppgreat]

Fix it? Like they fixed Windows XP by cranking out Vista?

Be careful what you wish for.

[MrBritton]

Seriously.

[delf76]

Seriously, what version of Outlook are you using? Outlook 98? Outlook 2003 introduced cached mode, allowing users to work offline and over slow connections more efficiently. The 2007 version improved the 2003 version, with it's built in Search capabilities. It's a great product. My users love it.

I will have to say I think Outlook Web Access (OWA) needs some more improvement, but the Exchange 2007 version is really nice. It would be nice if they could throw all of the Outlook Desktop Features into the Web Client.

[gsekse]

Thunderbird: The spam filter alone is worth trying it. I love watching it the adaptive filter take out nearly 90% of the spam with no actions on my part. I only see the difference when I'm at work and access my personal email there and see all the extra crap I miss at home. I just wish they would upgrade outlook with some of the more modern features since I'm sort of stuck using it at work. (would be nice if my workplace would go all Linux, but... that ain't gonna happen...

[Bill_I]

T-bird is great, takes bit of getting used to. The junk and scam detectors are excellent. Its updated every month or so, compared to the the stale stuf from the Borg of Redmond. Now if I could only find where T-bird saves my Inbox and Sent files so I can archive them....

[Ubuntuboy]

Outlook Express - not bad at all. Outlook - too many features that I can't turn completely off (out-of-sight-out-of-mind), it's not customizable enough. Don't even get me started with Windows Mail on Vista, but that is what to expect if Microsnot "upgrades" Outlook. Bill & his boys have turned into the "gang that can't shoot straight." Since I bought Windows Vista Home Basic, I can't get my "upgrade" back to XP. So I have already rebuilt the 2-month old computer twice. And I am NEVER buying another Microsnot product. Linux, here I come !!

[rapier1]

You bought windows home basic. Someone with the screen name Ubuntuboy bought windows home basic. For some reason I doubt your story. Is this just amateur astroturfing?

[anothdae]

Windows Mail isn't meant to compete with Outlook. . . it is meant to replace Outlook Express. It is really simple to use and "lightweight". It is hands down better than Express for the casual user. I set it up for my mother and she is alot more comfortable with it than her old outlook express under XP. Have you actually tried the new windows mail or are you just jumping on the anti-vista, anti-microsoft bandwagon to fit in?

[JonathanPDX]

It's a matter of capability. Some people are able to handle Windows O/S and apps and some are not.
With a handle like "Unbuntuboy," I'm supposed to take you seriously talking about Windows? Puh-lease.

[Jack K1]

The author made it clear that from a developer's point of view, Outlook stinks on ice. It is so. I worked with both Lotus Notes and Outlook in a development environment, and Notes runs circles around Outlook. There's so much more that can be done with a messaging interface, but Outlook ties developers' hands in ridiculous ways. It's simple to customize Notes and integrate it into any number of workflows both structured and ad-hoc. All you can do with Outlook is use it for e-mail and as a PIM. Outlook was introduced over ten years as a Lotus Notes buster. What a bust. What a joke!

[mayadanteamihan]

Those who love Outlook apparently haven't tried anything else.

[anothdae]

Care to offer any suggestions and reasons why people should switch?

[catch23]

Actually, I have.
Always come back to Outlook.
Next moronic statement?

[Sin Jeong-hun]

I have tested many e-mail clients, but as far as I am concerned, Outlook 2007 is the best one (though it has too many unncessary features). Thunderbird's spam filter is tempting but, it has some serious problems with multilingual environment and sort of unstable. Once I had to use Thunderbird because of Outlook 2007's lack of specifying specific encoding for the message, I had a very hard time to edit e-mails on Thunderbird because mails sent with it rendered differenlty on the web mail site. Using GMail with Outlook, most of spams (almost 99%) get blocked by GMail's filter, so I only receive one or two spams a day (and tens of spams at the GMail's Spams folder)

I can not say Outlook 2007 is perfect but still, in my oppinion, is the best out there.

[Leria]

Unstable? Problems with Multi-lingual environments? What are you talking about?!
I've NEVER had Thunderbird crash, though I am using the 3.0prealpha1 version right now, that is loads better than the 2.0 version.
As to the multi-lingual problems...... that is a problem with Windows PERIOD. Some programs I run that were made in Japan and China.... the language and text in them doesn't display correctly in non-Japanese mode, and when I switch to Japanese mode..... a lot of programs have problems because they are locked to the non-Unicode settings.
I don't know whether to blame Microsoft for that, or blame the makers of those programs for that problem.

[skiguy330]

As the first few commentors have said, I personally love Outlook 2007. It would have been nice if the author could give at least one reason why Outlook is broken instead of simply assuming everyone thinks as he does.

As far as Jack's comment is concerned, I'm not a developer but Outlook's functionality is integrated entirely throughout our organization. Reserving an InFocus or a laptop on our intranet adds the event to your calendar. Opening a trouble ticket sends an Outlook task to a technician, and when the task is marked as completed an email survey is automatically sent back to the user. Scheduling a meeting puts your phone in "Meeting" mode when the meeting begins and takes it out of meeting mode when it ends. I'm not sure what you're expecting Outlook to do for you but it's more than adequate for our organization. Just my two cents...

[Mr_Technical_Dude]

Online web email will lead the way. Outlook and Outlook Express have had critically uncontrollable duplicate issues unless of course you buy the fix from Microsoft or a third party made up of MVP's. Microsoft did the same thing with DRM pretending to corral all music buyers while denying the existence of the analog hole and relying on many people not knowing about it.

Microsoft wants to bludgeon its loyal customers and former allies like Yahoo instead of fixing products like Outlook and Outlook express to attract a willing partner instead.

[anothdae]

what are you talking about? Am I alone here in just not understanding anything that this person is saying? What are "critically uncontrollable duplicate issues"? On a serious note, are you really saying that web based email is going to replace mail clients? . . . really?

[krosavcheg]

Outlook is good in some ways and is irritating in others. Search does tak way too long. It feels like you are searching the National Archives instead of just your e-mail inbox.

What worries me about this product is that the privacy policy doesn't make it clear if they collect information from the body of your e-mail and if not, if they plan to do so in the future. I have confidential communications with my clients that I don't want some cubicle jockey reading over as they sell it to some ads database like Google.

I think people are giving up privacy too easily for a few little gizmos. I am willing to go back to a paper calendar and address book if these jerks take this even one step further. It's already getting way out of hand.

I think people should stop using credit and debit cards to buy anything and should avoid surfing the net without using someone else's unlocked WiFi network. The combinations of these marketing databases is just too disturbing. The average marketer will have a more intimate understanding of a person's habits soon than the person himself. A marketer will be able to look back five or ten years and run reports on everything a person has bought during that time, vacations, drinking, prescriptions, what sort of food a person eats, where you drive and when from gas purchases, toll and parking receipts, etc. I don't want anyone to be able to "offer me great products and services targeted specifically to my needs!"

That's a lot of crap. It's targeted to your vulnerabilities and insecurities. Some of them you don't even know about and the marketers already know. The most intimate relationship a person will have pretty soon is with the marketing algorithm that generates call and talk scripts for salespeople to use when talking to you. Reject it before it's too late.

If these folks promised in their privacy policy to never ever data mine your e-mail for search terms, catalog your e-mail lists, contacts lists and other information for marketing purposes, I might consider it, but Courts are so light on privacy policy violations because they've held in the past that the person suing couldn't prove any harm or damages. The court reasoned that a mere violation of one's privacy wasn't a real harm in the post modern world.

We can't rely on the Congress or courts to fix this. The only way is to reject all of it.

[anothdae]

. . . you are writing from a computer. way to "reject all of it"

[rcrusoe]

"I have confidential communications with my clients"

Sorry, but if you aren't encrypting your messages nothing is confidential. The admins of both your server and your clients can easily read your messages as well as anyone on any Internet segment between you and your client.

Email is more public than a postcard so don't let privacy issues influence your thoughts about this software.

[pc_potato]

Ranking within one of the 5 happiest days of my life: The day I dumped Outlook and started using Thunderbird. You couldn't pay me to use Outlook. It's broken, it's been broken, and Microsoft has (obviously) no intentions of fixing it.

[anothdae]

Like the author, you fail to address what is broken about Outlook.

[devahaz]

it's hard to believe people really think Outlook is fine! Search in 2007 definitely is a big advancement, that's true. But performance degradation over time is a huge issue with Outlook and it is a major undertaking to develop really stable add-ins (very few really well-written add-ins are out there). And there are so many innovative feature areas that have yet to be even touched upon. I could go on - and do here: http://www.emaildashboard.com/2008/05/there-are-peopl.html

[anothdae]

Once again people fail to give real reasons why Outlook is bad. Performance degradation? My main outlook data file is over 5gb with tens of thousands of emails from the last decade. Outlook starts and runs just as fast now as ever. Searches literally take seconds. I guess there are advantages to using vista. Given, addon support may be bad. The real point is that no one cares about writing addons for outlook, it does its job all ready. The vast majority of people don't need or want addons. Your article (2 links deep) states 3 areas that outlook needs to improve. 1) Volume. You say that people that receive 100+ emails need support for processing them. Say hello to email rules, tags, color coding and files, all automated. I am sorry, no email client is going to read your email for you. 2) Integration. There are a number of products that integrate with outlook. PDA push contact / calender support for one. Have you ever worked with microsofts business software? It integrates with outlook very closely. and 3) Context. see number 1. If you don't want your facebook messages next to your business emails, create a rule to move them to a folder. Problem solved.

[nickbyfleet]

I love Outlook 2007 with my exchange account- nowhere in this article and nowhere in the comments has anyone come up with a major and valid flaw with it.

[rmva]

"When the company brain trust repairs to the Ballmer Bunker to chew over its next big idea, post-Yahoo, I've got a suggestion: how about doing something to deal with e-mail and its discontents? Something grand--like bringing Microsoft __________ into the 21st century. I don't mean a tweak here and there; I'm talking about a top-to-bottom overhaul."

Just fill in the blank. No documentation necessary. We'll call it Coop's Club. Everyone is welcome to join.