Problems with email integration for work management tools

I’ve been evaluating a long list of work management tools as part of the research for the Work Management Narrative report (see recent post, Work Management in Theory: Context). One issue that comes up a great deal is the integration with email, which is a common trigger for a user to create a task, as well as a means to communicate with other team members who may not be using the same — or any — work management tools.

This post doesn’t look into how work management tools use email as a way to communicate with team member not using the work management tool: that’s a separate use case. I’m focusing on email as a parallel sort of communication, and one from which a great deal of tasks arise.

There are a number of approaches to email integration, which I will categorize like this:

  • Low or no integration: despite the ubiquity of email, and the obvious need to communicate to the wide, wide world through it (and email’s insatiable hunger to communicate with us, too) some vendors offer little or no support for the realities of email. Not good.
  • Loose integration: some vendors have opted for a loose integration, often through bookmarklets or third-party connection services like Zapier and IFTTT. For example, Azendoo supports a Zapier ‘zap’ where gmails that I star become tasks in a specific project. Subsequently, the user can open Azendoo, and perhaps move the task to another project, add notes, fool with metadata (due dates, assignment, etc.). A bookmarklet — like Wrike‘s — accomplishes more or less the same thing. In either case, the connection is one-way, and the work management tool does not try to ‘handle’ email in a general way: the precipitating email is just a starting point for a task. At present, I think loose integration is the best approach.
  • In-inbox integration: Some solutions — like Todoist (a team task management tool) and Sortd (ditto) — provide a Google Chrome extension so that when you are ‘in’ Gmail you can easily convert an email to a task (and add metadata, etc.) in a window while never leaving the Gmail context. This is a lot smoother than loose integration, especially for people who communicate through email a great deal. Also, clicking on a link back to an email makes it more of a two way solution.
  • In-app email: Some tools aspire to replace the email client’s functionality altogether, basically pulling in all emails and implementing the services that emulate — at least in part — capabilities of email services. It is this last case that I want to zoom into in this post.

I’ve tried at least two solutions in recent weeks that seek to bring email integration in-app: Fleep and ScribblePost. I had an exchange with the CEO of ScribblePost, Alon Novy, about his company’s model of email integration. One outcome was the following post, shared with him through the company’s support system. In that post I suggested a more sophisticated version of in-app email integration:

Alon –

I tried and rejected your competitor Fleep’s attempt to act as a email client.

The hybrid failed for some of the same issues I have with your approach:

1. I might have a number of other plugins or features that operate in the Gmail client that I can’t walk away from, like Google Tabs.

2. If I have to undertake email hygiene in both Gmail and in the work management tool, that is an impossible cost.

3. The design of an email client is distinct from that of a work management tool, and intended to meet a wide range of use cases, not just those related to work management.

My bet is that the best approach will be to have a close coupling, but not a full integration of email in the work management tool, like your SP [ScribblePost]. On the work management side, some emails — those that are starred, or labeled in a specific way — would have a handle created, so that the email can be indirectly referenced and annotated: for example, comments can be added to the handle, or a task can be created as a follow-up to the email that would be attached to link to the email handle.

I think that the email handle is a distinct type or object in the work management space, different from tasks, internal messages, and posts. An email handle is a specific example of a general notion: a handle to reference some info object principally or partially managed outside the work management solution. That could also hold for Twitter or Facebook messages, for example, or Salesforce contacts.

At any rate, SP could implement a set of actions for email handles that fall into two groups:

1. those that represent actions on the handle — like creating or deleting the handle, linking it to a task (as a special sort of attachment), sharing it, adding comments, moving a handle from one project to another, etc. — as opposed to

2. actions on the email linked to the handle — like reply, forward, archive, and so on.

I think such a two-faced approach covers the greatest number of use cases, including unforeseen ones.

You might also benefit from a chrome plugin for Gmail, so that some (or perhaps even all) actions that users might want to perform vis-à-vis the intersection of email and SP could happen ‘in’ Gmail. For example, I might read an email and decide to

1. start tracking this thread in SP,

2. associate one or more tags with the handle, and

3.assign a follow-up task to myself referencing the email along with some notes.

I could then get back to other email, some of which never crosses over into SP.

Best,

Stowe

Note that the info handle concept lines up fairly directly with a platform play, obviously.

I applaud Alon and his team for the innovative ideas they are developing in ScribblePost, and likewise the brilliant design of Fleep, both products which I will be reviewing in the upcoming Narrative. I’m sharing this to stimulate discussion around these ideas, and also (shameless plug) to demonstrate the sort of thinking that animates the report.

Gmail for iOS just got easier to use with this software update

Apple iPhone and iPad owners opting to use the official Gmail application have a compelling upgrade waiting for them notes The Verge. The newest version of Gmail for iOS takes advantage of Apple’s willingness to let third-party apps share information and have actionable notifications. Gmail for iOS now lets you reply to incoming mail through notifications, for example, meaning you never have to leave the app you’re in when replying. Messages showing on the lock screen can now be archived or deleted as well, making it quicker to manage email. Gmail can be added to the “share” menu in iOS 8 as well, so you can send images or documents outside of the Gmail app.

Autocomplete fail: Gmail is suggesting the wrong email addresses

Better check twice before firing off that email today: You could be sending it to the wrong person, thanks to a Gmail bug that is suggesting email addresses you rarely communicate with, instead of the people you correspond with most often.

The bug has been widely spotted by media outlets, venture capitalists, and normal Gmail users. Instead of sending your email to your coworkers or family, pressing send without double-checking could result in your email being delivered to someone you haven’t talked to in years. Although I am lucky enough not to have misfired one of my messages today, others haven’t been so fortunate:

The problem seems to be widespread — just this morning, Gigaom’s tips email address ([email protected], send us stories) was inexplicably CC’d on a email thread on which editors of another site were discussing the most embarrassing moments from last night’s Oscars.

Google has provided the following statement:

“We’re aware of an issue with Gmail and auto-complete and currently investigating. Apologies for any inconvenience.”

Until it gets fixed, you might want to consider turning on the undo send feature in Gmail labs.

Google’s Inbox lands on tablets, works in Firefox and Safari too

That radical redesign of email that Google introduced in October can now be used in more places. You’ll still need an invite to use Inbox, but once you have it, you use it to smartly manage your Gmail and to-dos on tablets and in browsers other than Chrome.

Google announced the expansion of Inbox on Thursday via a brief post on its Gmail blog. Previously, Inbox was limited to phones. Now [company]Google[/company] Android tablets and the [company]Apple[/company] iPad support Inbox. You can also access Inbox in a computer browser, with Mozilla Firefox and Apple’s Safari joining Google’s own Chrome on the supported browser list.

google inbox tablets

Google says Inbox is a new take on email management and I’d agree. It’s more of a blend between Gmail and Google Now based on my own look at the app when it debuted. That’s not a bad thing: Google Now insights make for a smarter Inbox with contextual reminders and emails bundled together in groups such as Purchased, Finance, Social, Low Priority and Updates.

As much as I like the concept of Inbox and welcome the device and browser support expansion, I still don’t use it as my primary email management method. There’s too much wasted space and too little information provided for me when looking at Inbox; it has low “information density,” in my view. It’s also limited to personal Gmail accounts and still requires an invite — two things I hope Google addresses in the near future.

Regardless of those qualms, now that there’s a tablet edition, I’ll give Inbox a second chance. Maybe there’s a larger amount of info on the bigger screen of a tablet compared to a phone or the browser, although Google’s own images don’t suggest that’s the case.

For those wanting an invite, Google says you can request one with an email to [email protected].

Do you use Gmail and Dropbox? Get this free, new extension

Even though I’m a Chromebook user with 1 TB of free Google Drive storage, I have multiple cloud storage accounts. That’s mainly for redundancy, but of course it can add complexity: Sometimes I’m not sure which cloud provider has what files or I have to open multiple tabs to get at a file I want to attach to an email.

Enter Dropbox for Gmail: A Chrome extension that adds a Dropbox button to the Gmail Compose screen. As long as you use Chrome for your browsing needs, the extension should work, so it’s handy regardless of your operating system, whether it’s [company]Microsoft[/company] Windows, [company]Apple[/company] Mac OS X, or [company]Google[/company]’s own Chrome OS.

One installed, you’ll see a Dropbox button in Compose screen when writing a new message in Gmail. Click the button and you’ll see all of your Dropbox files so you can choose to attach one or more of them to your message; there’s also a search function to help you sort through your Dropbox drive.

dropbox for gmail

Dropbox for Gmail inserts links to the files on Dropbox, not the actual attachments. Your message recipients will see a preview of the linked files so they get an idea of what you’ve attached before they even click the link and download the files.

Google Wallet takes its 1st trip overseas into UK Gmail accounts

For the first time, someone outside the U.S. will be able to use a Google Wallet to do something more than buy Android apps and content. Starting on Thursday, Google is bringing Send Money in Gmail money transfer to the UK, allowing users to transfer money to Wallet accounts via email messages, Google revealed in its Commerce Blog.

That’s by no means the full extent of Wallet’s capabilities, but it’s a big step considering the only Google Wallet feature available internationally has been in-store purchases on Google Play. There’s still no word on when the Google Wallet app will be available in the U.K., which would let smartphone users make direct money transfers, store their gift and loyalty cards and make contactless credit and debit card payments on Android phones that sport NFC chips.

But given the runaway success of Apple Pay (which has also driven more use of Wallet), you can bet Google is weighing an international expansion of mobile payments service as well. [company]Apple[/company] has confirmed it aims to bring Pay to U.K. iPhones and merchants in 2015.

For U.K. Gmail users, a £ icon will soon appear in the attachment bar of a Gmail missive (in the same place the $ appears in U.S. Gmail accounts today). You just click on that £ sign to either send money to or request money from the email’s recipient. Google created a video to show how it works:

[youtube https://www.youtube.com/watch?v=FVKwbZOFh3o]

Both parties need to have a Wallet account linked to a debit or bank account for the transaction to process. But as with competing peer-to-peer payment services such as PayPal, Square Cash, Venmo, Google will let you send money to anyone regardless of whether they have Gmail or Wallet accounts. The recipient, however, will be prompted to set up a Wallet account if they don’t already have one.

It’s a smart move by Google to launch with its Gmail money transfer service in the UK because it could lead to more Britons signing up for Wallet accounts. That means Google could have a larger ingrained user base for its financial services when it eventually launches the full-fledged Wallet app overseas.

Peerio is a chat and storage service with big security claims

A Canadian outfit called Peerio has put its eponymous secure messaging and cloud storage app into public beta, promising a much more usable alternative to PGP email and file encryption.

Peerio was released on Wednesday for Windows, Mac and Chrome (which also gives Linux users an option) – apps for Android and iOS are in the works. It’s not quite perfect just yet, but it’s an intriguingly user-friendly take on secure cloud communications and storage.

“Our goal is for Peerio to succeed PGP in the use-cases of mail and file sharing,” co-founder and lead cryptography designer Nadim Kobeissi told me via a Peerio encrypted conversation. “We’ve developed a system built on foundations that are more modern, stronger, and simpler than PGP. Anyone who uses Peerio for a few minutes will quickly see how it’s years ahead of using PGP with Thunderbird, and never go back.”

Open-source and audited

The two-decade-old PGP is certainly a pain to use — at least, if you want to get it right — largely because of the complexity of PGP key management. Rather than requiring users to have their private key file to hand, Peerio requires them to create memorable (and long) passphrases that are then used to locally generate private keys for each session. The passphrase is used to log into Peerio for the first time on each new device. After that, a shorter, easier-to-type password can be created for that device, and two-factor authentication is also available.

Peerio incorporates the encryption technology of Kobeissi’s Minilock file encryption app. Users have usernames rather than email addresses and their client-generated, abstract avatars are used to verify their cryptographic identity (the client can automatically detect changes.)

From a functionality perspective, Peerio is a cross between email (albeit without the universality) and instant messaging. Files can be attached to messages, and conversations are threaded and searchable. There’s no draft functionality at the moment, which can be a pain when jumping between conversations mid-message, but Kobeissi said this will come soon and drafts will be safely encrypted.

Kobeissi, a PhD student in applied cryptography, is best-known as the creator of the Cryptocat chat app, which had a nasty security scare in 2013 (a bug left group chats vulnerable for months). However, this time round his co-creation has been audited by “expert cryptographers and system penetration testers” (Germany’s Cure53, per Wired). What’s more, the client code is open source and available on Github for scrutiny by whoever can offer it.

Metadata issue

Kobeissi seems pretty confident about Peerio’s security. When I asked whether it was tough enough to be a secure channel for leaking information, he replied: “I think people doing something like leaking state secrets should not depend on the internet at all, personally. But I would say that Peerio can protect the content of people’s communications, even if they’re operating from a highly surveilled context.”

However, the service’s end-to-end encryption only protects the contents of communications, not the metadata about who contacted whom and when. Peerio’s Canadian servers still hold users’ contact lists, the number of files and messages sent, and message timestamps. Kobeissi told me access to this metadata is “quite minimal and well-guarded” and he and his colleagues “pledge to fight any overreaching government requests”, but still, the information is there and, unlike the contents of messages, available to Peerio itself. Will Peerio create a way to encrypt this metadata? “One thing at a time,” Kobeissi said.

Peerio’s team includes four permanent staff, but numbers 12 with hired contractors – the outfit has $250,000 in seed funding. The plan is to make money by charging for premium features such as more than a gigabyte of storage, and by targeting the business market at some point.

For a product just entering public beta, Peerio seems admirably clean, functional and user-friendly. As long as people don’t find nasty vulnerabilities – and the firm deals with its metadata-related issues — it could be a viable mass-market encrypted communications and collaboration service. (A minor warning, though: If you import a contacts list, Peerio will send out an invite to everyone on it.)

A top apps list worth a look from Meldium

Tis the season of “top apps of the year” lists. Many are skippable. But this one compiled by password management company Meldium, now part of LogMeIn, caught my eye.

Based on the examination of usage data from “multiple tens of thousands” of users — the exact number wasn’t disclosed — Meldium came up with a list of the most popular applications across six categories — communication, collaboration, retail and service, sales and marketing, and social media.

Some results were hardly surprising: [company]Twitter[/company], for example, was undisputed overall champ and the champ within social media by far.

But a few results were more eyebrow-raising. In the dev tools category for instance, [company]Heroku[/company] got the top slot over perennial dev favorite [company]Github[/company]. No offense to Heroku, which is popular, but it just seems odd that it would have more users than Github, which as far as I know, pretty much every developer uses.

Chris Corde, Meldium’s director of products, agreed that this was surprising on the surface, but given that Meldium is designed to enable workgroups to securely share account credentials, it’s really not a shocker. Github users tend to have individual accounts even if they work in groups, while Heroku is particularly suited for groups of colleagues, Corde noted.

Other tools filling in the top five development tools category were Zapier, an API integration service; [company]Amazon[/company] Web Services Management Console; and Bitbucket’s free source code hosting.

It was also somewhat surprising to Corde that [company]GoDaddy[/company] won the retail and service category, but then again, a ton of accounts use that company’s DNS registration services.

Take a look at the whole post for other interesting tidbits, but the top-line results are below.

 Overall winners:

  1. Twitter
  2. MailChimp
  3. Gmail
  4. Amazon Web Services
  5. Mixpanel

Category winners

  1. Collaboration — MailChimp
  2. Dev tools — Heroku
  3. Retail and service — GoDaddy
  4. Sales and marketing — Salesforce.com
  5. Social media — Twitter
  6. Analytics — Mixpanel

Google’s alpha-stage email encryption plugin lands on GitHub

Google has updated its experimental End-to-End email encryption plugin for Chrome and moved the project to GitHub. The firm said in a Tuesday blog post that it had “always believed strongly that End-To-End must be an open source project.” The alpha-stage, OpenPGP-based extension now includes the first contributions from Yahoo’s chief security officer, Alex Stamos. Google will also make its new crypto library available to several other projects that have expressed interest. However, product manager Stephan Somogyi said the plugin still wasn’t ready for the Chrome Web Store, and won’t be widely released until Google is happy with the usability of its key distribution and management mechanisms.