Operation Email Purge

I’ve been on a crusade against my gmail inbox and am happy to report deleting over 100k unread emails in just a month. 100k unread emails… something is wrong with the state of email marketing when that happens.

Gmail provides a bunch of really good tools for managing email:

  • Unsubscribe link: If the sender has an unsub link in the footer you will likely see a handy link that Gmail inserts in the header. Use it.
  • Filters: Wow, where to start? Is:unread is a favorite.
  • Search Terms: Searching on terms like “casino” and “viagra” yields a massive number of emails I never wanted. Think about terms you never use in conversation and you will be amazed at how prevalent they are in email. Search on names other than your own, in my case Judy, James, John, Jennifer Nolan all resulted in hundreds of unwanted emails. Search on punctuated forms of your email that you don’t use, e.g. j.nolan@gmail.com. Search on phrases like “media briefing” and “embargo” will result in thousands if you are on PR lists. “Webinar” is another solid term to search on.
  • Search on sender. By far the biggest offender in email is notification email. Fortunately, they are easy to identifier based on subject verbage, but also sender. For example, “from:noreply@youtube.com” will yield all notif emails from YouTube.
  • Block. If a sender isn’t behaving well on email, e.g. bestbuy.ca, then block them. Now, nothing gets through.

Now here’s a couple of annoying email behaviors that marketers should be aware of:

  • Unsubscribe takes 10 business days… it takes a company just seconds to subscribe me, it should not take them longer than seconds to unsubscribe me. This is annoying because it reminds me how antiquated your infrastructure is.
  • Long messages. If your email exceeds the display length for Gmail, don’t send it.message too long
  • No unsubscribe. For a reason I cannot explain, PR agencies in Europe and Australia don’t use marketing automation to send emails, while U.S. based agencies do. The result is that U.S. agencies have unsub while the others get blocked.
  • Multi-click unsubscribe. Systems like Mailchimp and Constant Contact have really well constructed unsubscribe features. One click, maybe two and I’m out. If you unsubscribe requires more than 2 clicks, entering your email, or confirming and then sending another message to me after I unsubscribed telling me that I unsubscribed… you blew it.

I used all of the above to pare down my inbox. It didn’t happen quickly but now I’m in a rhythm and just 15 minutes every morning cleans things up. I target deleting a couple hundred email each day, which is more than I get each day so my inbox continues to shrink.

Gmail Tabs: Heartburn for Email Marketers

Like many Gmail users I have adopted the new tabbed interface that started rolling out in June. I like the organization model and find their categorization remarkably accurate, which in light of the ongoing government data privacy scandals only makes me more concerned about the machine processing of communications. However, it is useful and I only wish I could create my own tabs.

Screenshot (21)However, not all is rosy and I have noticed with particular interest that a number of prominent email marketers are sending out “helpful” messages about moving their messages from the Promotions tab to the Primary tab.

There are a couple of outcomes here that are interesting to consider. First and foremost is that a subset of marketers will be successful in moving to the Primary tab, based on the appeal they present to their customers. This will create a two-tier model where preferred marketers are valued disproportionately based on their customer appeal while the blunt force trauma marketers will be forced to change tactics as more email systems, presumably, adopt the Gmail tabbed interface (which for the record is not a new idea, AOL’s Altomail service had this well before Gmail).

The impact on email marketers is being felt and several studies are now coming out that quantify that impact. Email marketing analytics firm Litmus has published some stats showing a significant decline in Gmail open rates. However, their data is more complicated than a single stat would suggest and what they are questioning is how many Gmail web users actually open email in general in the web interface and in alternative apps, such as iPhone’s integrated email app.


ReturnPath has a different study that states that delivery rates are up but open rates are down. My own experience aligns with the ReturnPath data, which is that consolidating marketing email in one tab has increased its visibility to me, and for the merchants I care about I actually read their content more regularly. This aligns with the 2 tier model I suggested in the intro, open rates in my inbox are down overall but for the select vendors that target well and present offers I care about, my open rates are up.

I actually like email marketing but find the vast majority of merchants doing it really poorly. They clearly don’t connect with me on the basis of what I care about and will respond to, it is for the most part dumb marketing. Email marketers will have to deal with the new UX controls that email providers are building in by presenting more utility in their marketing campaigns, which means knowing more about me at an interest level, not just my demographics.

Google+ Turns 2: How Hangouts Completely Changed My Work Routines

Google+ turned two this week and by all accounts Google has won over critics with a compelling social network experience. I have been a fan from day 1 and perhaps what I admire most about Google is that they ignore the pundits while playing a very long game of their own making… so while my initial reaction that Twitter and Tumblr would be the biggest losers, which obviously was not the case, there are other factors that are worth looking at.

Simply put, Hangouts have been enormously impactful on me and how I work. Here is something they nailed and it is so profound that I didn’t even realize it until just this week, Hangouts are built around the notion that a video experience is YOU first, and then whatever you are sharing second.

Think about how Gotomeeting and Webex handle video, it is something that is added to the act of presenting something and despite a significant push to feature video, I have encountered few instances where someone says “hey share the camera!”. Contrast that to Hangouts where video is a primary experience… Google just figured this out while Webex and Gotomeeting are still locked into their traditional mode, which also limits their ability to have an instant video conference in the absence of a persistent conference room.

We have a very distributed company and on any given day I will have between 3-6 planned video Hangouts and a bunch of ad hoc ones. This has become such a fundamental mode of communication for me that I invested in SteelSeries gamer headsets to provide the best audio quality while also improving the comfort factor.

The integration with Google Calendar is another winner, where adding a video conference to a meeting is as simple as clicking the link. No scheduling service, passwords, dialin numbers. and so on… it just works.

Another experiences I had recently that drove this home was at HP with one of their sophisticated teleconference systems. Yes, it was remarkable but I kept thinking that I could do something a lot easier with Hangouts… instead of getting a bunch of people in dedicated rooms just to talk to each other, we could have each run a separate video in Hangouts and the result would have been the same in terms of what we accomplished… and for free.

The integration of Talk with Hangouts is a mixed bag and I hope that Google restores the ability to place voice calls from the Hangouts add-on in Gmail. Google has an interesting integration challenge that is a result of an embarrassment of riches with a robust chat product that built on XMPP, Google Voice, and Hangouts. A big change they announced last month was the abandonment of XMPP, which has a lot of features as well as a big developer community, and the replacement of Talk with Hangouts. I like the user experience and having my chats pop up in Hangouts in addition to Gmail, but the degradation of features is disappointing, most significantly the inability to place voice phone calls right from Hangouts.

I don’t know where they are going with this but the result for me is that I now use Skype more frequently for voice calls instead of hitting the phone icon in Talk and placing a call.

Lastly, the mobile experience is completely seamless, and that extends to video as well. On my Samsung S4 the mobile video conferencing is surprisingly good and glitch free… how far we have come from commercial video phones that started showing up in the 1980’s that used super expensive hardware and puts POTS through an extreme gymnastics routine.

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Twitter, er Google, Hacked

Twitter makes sure that they throw in the obligatory “this ain’t about Google Apps” disclaimer when actually it pretty much is.

This attack had nothing to do with any vulnerability in Google Apps which we continue to use.

[From Twitter Blog: Twitter, Even More Open Than We Wanted]

If Twitter were using something other than a public cloud for their documents and messaging, well it would have been a hell of a lot more difficult for someone to login with a password retrieved via the recovery feature in Gmail.

I’ll still use Gmail and hope I never have to use Exchange again but let’s not pretend that the ease by which the Twitter document heist was accomplished had nothing to do with the vulnerability of a publicly accessible hosted services. Better passwords, routinely changing them, and not making forgotten password questions easy to defeat would all help… but then again Exchange administrators can force those things on users rather than relying on users to be self-regulating.

Gmail 5 Second Delay

Google’s Gmail team really needs to get a handle on this whole naming thing, as in not naming a new feature something that it really doesn’t do. Zoli sums it up nicely.

First of all, I love Gmail, it’s my one-and-only email system. And I’m certainly glad to see the ever accelerating rate of enhancements, whether “official” or just the Labs variety. But oh, please, can we have some control here and call features what they really are?

[From Gmail’s Undo Send Isn’t Really Undo, Just Like Multiple Inboxes Were Not Really Multiple Inboxes | Zoli’s Blog]

I was so massively disappointed that the much heralded multiple inbox extension actually doesn’t present multiple inboxes but rather multiple panes each with the same inbox content that is tagged with a different label.

Similarly, undo send doesn’t recall a sent message but rather inserts a 5 second delay between the “send” button and actually sending a message so it’s not undoing a send, it’s delaying the send. They would have been more accurate to just call it the “5 second delay” extension.

Gmail to Exchange?

In terms of an email interface, Gmail pretty much delivers the goods. If you have the choice to use Gmail instead of Exchange, well that’s a pretty attractive option for a number of reasons and as good as Outlook is, what a lot of people are discovering is that it’s not the killer app that it was once thought to be.

That seemed like a pain, so this week I just started using Gmail as my default. I’ve not looked back. This is anecdotal and maybe I am a market of one, but it is a big deal for me. I have “lived in Outlook” for years. It was the one part of Office that I thought I would never replace. I suspect I am not alone.

[From Breaking Free of Outlook – ReadWriteWeb]

I would actually look forward to a Gmail client app that hooks up to Exchange via MAPI or webDAV, better yet for it to be Gears enabled for offline use (interestingly, with my EVDO card I find that offline requirements simply don’t register with me anymore, I’m always connected).

On my Mac I’ve tried several options to connect to the NewsGator Exchange server, here’s my rundown:

Apple Mail App: My default choice, I use it every day. The integration with Address Book and iCal are super and the general layout and workflows make it a really good email application. Not all is wundabar in Steveland though, if your shop extensively uses Exchange calendaring, forget about looking at other people’s schedules or making your available.

Mail App uses IMAP or POP to connect to Exchange, and they have an “Exchange” account type which I believe is based on WebDAV, but no MAPI support. The Exchange connector is pretty seamless, I’ve never had a problem with it.

Mail app is also very extensible via plugins and add-ons, here’s a list of the best plugins and it has been my experience that these tweaks and addons really do make a big difference.

Zimbra Desktop: I love the idea of Zimbra, I’m less enthusiastic about the actual experience of running Zimbra. Mostly I just don’t like not being able to open a message to a separate window, and yeah that’s pretty specific but with something like email the smallest quirks become annoyances pretty quickly.

The integrated calendaring and address book are adequate but with very little in the way of synchronization, meaning I have to use Zimbra instead of iCal. Plus, you can’t, as far as I could tell, subscribe to additional calendars so using Google Calendar for home, etc. or as a synch hub just isn’t an option. Basically, committing to Zimbra is like using a weak version of Entourage.

Microsoft Entourage: In all respects this is a feature rich app but I still don’t like it. Why? Primarily because it’s a walled garden. I can’t use iCal or Address Book and what that means is that no other apps that use schedule or contact data have access to my data. Sure there is a synch service but I had a horrible experience with it and for the brief period of time I used Entourage I ended up turning Synch off (even then it still kept trying to synch, go figure).

It’s also kinda slow but if you rely on scheduling services, well this is your best bet when going against Exchange. One other note, if you use Time Machine you have to exclude Entourage’s database from backups because it just won’t work.

Synchronization: So I mentioned synch services a couple of times, let me break that out as a separate topic. You can use Microsoft Synch services but I really recommend against it because it’s unpredictable and prone to wiping stuff out that you care about. There are many third party synch services for all or parts of our PIM environment, like Plaxo and SpanningSync. I use both despite the fact that this might be redundant.

First and foremost, SpanningSync kicks ass for synching Gmail to iCal, and even the recently announced calDAV support in Gmail comes up short so I’ll keep paying $15 a year to Charlie for his product. Plaxo is really awesome for address book synching but their calendar sync engine is limited to one google calendar so I’ll use them for address book services but not calendar.

I rely on iCal for a lot more than keeping my work calendar, I also subscribe to my Tripit calendar for travel itineraries, have a family calendar, various subscriptions for other groups I am involved with. In short, calendaring has come a long way from simply managing your daily meeting schedule and Entourage just comes up short on this front.

Also, I should point out that I don’t sync to Google Contacts, just Calendar. No particular reason for this other than Google Contacts has not really proven itself a necessity to me and because I use an Exchange server for work email, it’s not likely to. I love contacts in Gmail but it has yet to cross the threshold to be what I use to manage my address book master data.

Thunderbird: Piece ‘o crap and yeah that is sure to fan the comment flames because there really is a dedicated albeit very small community of people who like this app. It lasted less than a day for me.

Eurdora: Older piece ‘o crap.

Gmail IMAP and Mac Mail: Houston, we have a problem

Glad to hear I’m not alone…. here, here, and here. I’m posting the link in entirety for emphasis and to point out once again that Google has a lot to answer for with the spastic approach to end user support featuring negligible communication, cryptic “maintenance” messages, and most significantly, contact on their terms only.

Ironically, I am using Apple Mail primarily because the fear of my gmail account getting blown away is terrifying (over 15k messages) so my desktop mail client gives me a backup of the message store.

This is at least my third mention of a problem between Gmail IMAP and Mac Mail, but I’m raising it again because many others have the same issue and I believe resolution is near. Switching from my hosted Exchange server to Gmail’s IMAP service has worked well in general, but for no apparent reason it just tanked for me about three weeks ago. There were no changes in my environment, nor to Mac Mail and I suspected something changed on the server side.

I spent the next several days doing my own testing and isolated the issue occurrence only when Mac Mail was running. No other client caused the delivery delays and constant message caching I was witnessing. My next step was to share my information directly with the Gmail support folks and over the past three weeks, I’ve written well over 1,000 words to them presenting the evidence in detail. It probably shouldn’t have taken that much effort, but I really don’t mind because I believe I finally got their attention on the right information. Here’s what they said:

“We are aware of this problem, and our engineers are working diligently to implement a solution for all users. We apologize for any inconvenience this issue may have caused.

In the meantime, during the course of our investigation, we’ve identified specific technical circumstances that would allow us to implement a fix for your particular account by placing it under maintenance for up to an hour. You’ll be unable to access your account during this time. Please respond to this message if you’d like us to implement the fix, and also please provide general timeframes and dates during which the maintenance of your account would be least inconvenient.”

I provided them with the OK to take my account down and then proceeded to have no e-mail access for appproximately 18 hours… not the 1 hour I was told. I actually didn’t mind because that tells me all the more that there’s an issue between Gmail IMAP and Mac Mail. Unfortunately, I saw no change in the mail behavior after the maintenance, which was reinforced by the next message from the Gmail support team:

“We regret that your account will require additional maintenace in order to resolve this issue.

Please note that your account will be placed under maintenance again starting at 5:00 pm Pacific Time. We’ll make every effort to complete the maintenance as soon as possible, but please note you won’t be able to access your account for several hours while it is under maintenance.”

I set up a time for that maintenance (yesterday), but didn’t see the account go down. It was just under maintenance a short while ago for a brief time, so I’m hoping that the issue is now resolved. If so, I anticipate a note from the support team indicating it is. If I’m correct in my premise that there’s an issue that’s more global than just my account, I expect it will get quietly fixed on the back end although I’d hope for some public information to come from Google. Needless to say, I’ll be happy when it is resolved. I can avoid the problem by keeping Mac Mail closed and using the web or other clients, but I like to have choices about what clients I want to use.

[From Gmail IMAP and Mac Mail: Houston, we have a problem]

Fixed Gmail

On my own… no thanks to Google. I was unable to get to the gmail login screen even after blowing out the cache, deleting the cookie, doing a dance and sacrificing a baby goat. The gmail community forum was useless and absent of any apparent contact mechanism I put out a call for help here and on Twitter.

Thanks to Zoli, Jake, and Steve for stepping up to help with Google contacts.

As I was writing an email to Jeff Huber I had a thought… what if I went into another Google app and tried to backdoor into gmail? So into google docs I went, clicked on the gmail link and whatdayaknow, it loaded. It is still a mystery why the app thought it was undergoing maintenance and would not reset.

To be really objective, this isn’t a big inconvenience, the sun still rose this morning, but what this does suggest is that Google’s apps are starting to show some cracks. Indeed, I received several emails from people saying that they have noticed unexplained behaviors in Google apps and suspect performance in recent months.

Google’s greater ambitions of gaining significant application market share will surely be frustrated if the company doesn’t rethink their approach to customer support. Simply put, it is awful. Being free shouldn’t mean fend for yourself… they are getting paid for these apps, just not by users.

Google’s Customer Support (ROFL)

My Gmail account has been inaccessible most of the day, something vague about my account being under maintenance. I emailed the provided email address tonight to see what was the status and when I’d get my account back. Here’s their response, I’ve highlighted the part that had me picking my jaw up off the floor… seriously, they can’t possibly believe that putting a “beta” label on a service for 3 years gets them off the hook for actually providing something that could be called support?


Your Gmail account is currently under maintenance, and our engineers are
working to allow access to your account as quickly as possible.

We apologize for any inconvenience this may cause, and we thank you for
your patience during our limited test of Gmail.


The Google Team

Gmail is Seriously Borked

For the second time in as many months, I am having serious Gmail problems.

  1. People are telling me that gmail is replying to them that “your message may not have been delivered”. I know for fact that not all messages are being delivered because I sent one to myself that never got there.
  2. Performance is shitty.
  3. I managed to catch an error code #102 during one hiccup.

As is the case with free services, help is limited to what the community is capable of providing… no one to call at Google for help.

Update: Told ya…