Email Innovation Lacking, Still a Huge Opportunity, Hard to Exploit

For the last two weeks or so, I was having a ton of Mac problems. It seemed that my OS had gotten corrupted, so I thought that upgrading to OSX Lion would clean up the OS and upgrade me since I was going to do it eventually.

The nightmare that threw me into is probably best told over a beer - somehow I was one of the unlucky few where OSX Lion upgrade over an existing OSX Snow Leopard was just not possible and became unstable over a few days, leading to not being able to boot the Mac at all! I managed to roll back to OSX Snow Leopard (no little trick there!) and think I'm back in action.

But this post is not about my upgrade problems. It's about email. During that small window of time when OSX Lion was working, I opened up the new Mac Mail and saw....a visual makeover and the additions of grouping by conversation. In fact, it defaulted to conversation grouping. What a disappointment. Here was an opportunity to revolutionize email and the most innovative force in technology decided to just do a visual makeover and add what Gmail has had for a few years now?

Like I said, disappointing.

Email has not been innovated in decades. It's still the same old thing. Oh, people have tried, but then most fail miserably as startups. Some of the things people have tried or are doing:

1. Grouping and viewing messages by sender.

2. Turn email into a social network and view messages that way.

3. Adding windows to email to make it into a professional or personal CRM.

4. Graphical views of email that are beyond the rows of messages we see today.

5. Group email by conversation.

Perhaps item 5 is the most dominant innovation in email, and most notably through Google's Gmail. In fact, it is dominant because Google refuses to give you another interface. If you sign up for Gmail (or Google powered business email) and you use their web interfaceYou also see this in Facebook messaging, but I believe Facebook's implementation is subtly better because they always show the conversation that has the latest message in on top. If you use offline Mac mail and pop into Gmail occasionally, Gmail always shows the conversation that came in first on top that you have not read. It takes a few days of working in the Gmail interface before their sorting becomes somewhat effective. This is why I find the web interface to Gmail so annoying; since I go back and forth between Mac Mail and Gmail, Gmail never gets the chance to stay current to what I'm doing and when I do use Gmail in the browser, it's always sorted in the wrong way. And I always lose key messages because the little flags and bolding are the only signals that something new has come in. And it makes me read those messages in the conversation first before I get to the very last, most recent message. Contrast that to Facebook's conversational grouping and they are OK because they sort the recency of messages differently.

Which gets me to what I did next after I rolled back to OSX Snow Leopard. Fearing that my rollback was also corrupted, I ran it for about a week now but storing all changed files on Dropbox and only using the browser for email to minimize changes on the hard drive in case I had to start over again. It was also a rare opportunity for me to really see if I could adapt to the Gmail interface because I was now not switching back and forth between Mac Mail and Gmail.

After 7 days, Gmail (and Yahoo! Mail!) still annoyed the heck out of me. But after 7 days, my Snow Leopard Mac seemed stable, and I got my old Mac Mail back minus their conversation grouping which was the annoying part of Gmail to me anyways and I didn't miss it.

Here, Apple had an opportunity to leap email several levels and didn't take it. They just made the app look a little different and added what Gmail was doing, which I annoys me when I use it. Really disappointing.

Now follows my wish list for what I want or need in email, but hasn't been done yet or needs to be redone:

1. A better search.

Searching on Yahoo Mail is miserable. Searching on Gmail is pretty good which is to be expected from Google BUT is a poor solution for the original reason why I lost the email in the first place due to other UI problems. Searching on Mac Mail is pretty darn good but could use some tweaks.

What's missing in search is the time element. Often I know that an email came yesterday but somehow I can't find it. Can't I filter by only showing results from yesterday? No - I gotta wade through all the other crap that gets returned from the search just to get the one I want.

I believe people naturally use time as a memory aid. Where did I put my keys? I go back in time, retracing my steps through the house, and find that left it on the table by the door and not in my usual place. Or I know he sent me an email right after our meeting....last Tuesday. So I go back to last Tuesday and find the email.

Some searches have advanced filtering but they are all inconsistent. If I search on my boss Elon in Mac Mail, I can only pick 2 choices of where to search (All Mailboxes and my current mailbox) and From, To, Subject, and Entire Message. What if I only want to see messages from Elon that are about one of my companies and not any others? Can't do that. I start typing in the search box all that text and then select Entire Message and then I've got all sorts of random stuff showing up.

2. Taking huge blocks of email headers and using visual techniques to highlight or even remove them completely from view.

If we say that we like the email header view that's been around since the dawn of internet time, then I think this could be optimized further. One of the big problems here is that there is huge information overload. Trying to find something in the clutter is super hard. Spam filters have tried to help somewhat, creative filters which dump certain emails to relevant folders is another.

But one thing I have not seen tried is using some visual technique to highlight or remove completely from view. Well, not completely true. When I search, I remove all the non-relevant results from view. OK one case. Read/unread is now a blue dot in Mac Mail although some mail readers using greying out. So maybe two. I think, though, we need more cases where filtering causes email to either drop back in visual hierarchy or completely disappear from view.

Take my time example. Why can't I select only show me email from Tuesday? Then all other email would disappear and only Tuesday email would be shown? Or show me only email from my boss Elon. I can sort the column, but then I see everyone elses email also cluttering up my view. I can search, but I get every mention of Elon in every field of the email.

Even if this was to visually set back every email that was an advertising email, and bring to the foreground emails from real people - that would be valuable. Now why wouldn't I want to remove them? Because I'm a shopper and I still want to see some deal emails and not just see them completely. This is why I always go through my junk folder. Who knows what my computer decided to mark as spam? It makes a ton of mistakes.

3. Despite my lack of love for conversations, their OSX Lion Mac Mail visual implementation of conversations is pretty good.

I like how you can just scroll and then you can see conversations, each in its own block. This part I love. On Gmail, they are hidden behind each other once you've read them - now I can't scan them! I have to manually open them all up to refresh my memory on the thread.

I also hate sorting by header to see if the subject can generate conversations. That doesn't work. I'd love to see this combined with visual techniques to drop back other emails or remove them entirely from view, so you ONLY see emails from this thread and conversation.

4. Search by attachment media type.

Why can't I view all emails with pictures attached? Or PDFs? Or Excel docs, Word docs, etc.? If it's all pictures, then why not show them in a UX conducive to that media type, like in a slideshow or grid metaphor, or for docs I have a swipe-able (or equivalent) way of going through them quickly, and then also being able to easily return back to the email that it was attached to.

5. View by calendar.

OK back to my comments on time. Time can also be expressed as a calendar, as a grid with days of the week for any month or similar. If it's a monthly grid, then I can just pick on it and see only emails that came for that day. It could even have a cool graphical representation that abstracts the number of emails that came in on that day, or some other summary information like 3000 emails, 30 attachments, 12 pictures, etc. If it's zoomed in to a weekly via with 7 days, maybe the graphical view abstracts in more detail, like showing me a bar graph of emails that came in at each block of time. I could click on one of those blocks, and then it would show me all the emails that came in within, say, that hour. There would also be easy nav to jump to the next hour.

6. Better personal information tool integration.

My Mac Mail is always open. I have often written notes, keep key information like lists of designers I've worked with, and even written whole blog posts in draft emails. On the Mac, I don't really have a good place to take notes. I'd have to start using Evernote to really get some power but that is a separate thing. And Word just blows for that. Every time MSFT releases a new Word version, it takes that much longer to launch. Sucks!

Maybe notes can be treated like Mail that you never send - you just can file them away, you can search on them, attach them to calendar events, or associate them with emails.

Scheduling often comes with an attached invite.ics which, upon clicking, opens up my calendar and presents the opportunity to reply to the invite. At least on the iPhone, Mail has some nice features where you can auto-create calendar events and the iPhone is smart enough to link some text that seem like dates. But I want more than that. When I create a calendar event, I want it linked back to the email that created it, and I want that email accessible so that when the day of the meeting comes, I can quickly go back and review the purpose of the meeting before the meeting starts.

And I want to only see that as a self contained context; don't show me all the other crap around it. Just show me the emails associated with that calendar event and that's it.

7. Better view by person, and info about that person.

Again, email UIs fail here. You sort in the sender column and then try to find the send there. Man that sucks. Try doing that in Yahoo Mail when your inbox is huge. Their paging eventually stopped working for me.

I should have a way of searching by person, and then having all the time and visual filtering that I have, only I'm acting only on one person's emails with me.

It would be nice to be able to pull up additional info about someone, especially those I don't know. I think this is potentially a more advanced business CRM function than for personal use.

8. Better integration with address book.

Mac Mail's integration with Address Book is pretty good. But it could be better. When I find a contact, I want to be able to easily get to all meetings and emails with this person, perhaps even getting back to the first email or email introduction I had with this person. Right now, when I meet someone new, I always type it in the notes. This is because later, I often forget the person, but I remember I met that person through another person. I search on my friend's name and pull him up because I put that in the notes field.

9. Search the SPAM folder.

This is so simple but ignored. Why can't I search my Spam folder too? At least once a week I always open up my Spam folder because I don't trust the filter to grab and hide stuff I wanted to see. I have to remind myself to do it regularly because there are always emails that get stuffed in there that I want. And it seems that even if I say this is not spam, eventually they get caught again. What's up with that? Woe be to the guy who has a new domain; he'll get tossed in there for sure. Or woe to me for starting a new business with a new name; I have to prove to the spam filters out there that I'm not spam.

10. Better Spam filtering.

No matter what we do, Spam manages to always get through. And non-Spam seems to get caught also. Somebody needs to do this better.

11. Local and location integration.

Everyone else is doing location based services, so why not email? If I knew where an email was sent, that would enhance searching a great deal. Sometimes I remember where I sent an email, as a way to find an old email. Perhaps I was on a business trip in NYC, or at a conference. Speaking of conferences, if I was emailed from someone I didn't recognize and I looked up from where and saw it was at a conference that I was at, it could help jog my memory of who this person was and why he was contacting me.

What other innovations on email are out there? Here are two I recently encountered:

LookAcross - magically, they are able to determine when someone is most likely to respond to various communication modes, like email!

Tout App - templated emails, email management and analytics, plus connection with CRMs.

There is a plethora of email clients on Wikipedia but seems like the dominant ones are the ones we all know and love according to this report from Campaign Monitor.

Anything else interesting out there?

In any case, history has shown that email is hard to create to a successful separate business out of. This is why my disappointment with Apple was so acute; they had the chance to release something really innovative with Mail and didn't do it, AND didn't need to worry about survival as a startup.

In the meantime, I will have my decades old, time sorted, header interface that I've come to know, love, and hate....

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