Welcome to the Post-Email Enterprise: what Skype Teams means in a Slack-Leaning World

Work technology vendors very commonly — for decades — have suggested that their shiny brand-new tools will deliver us from the tyranny of email. Today, we hear it from all sorts of tool vendors:

  • work management tools, like Asana, Wrike, and Trello, built on the bones of task manager with a layer of social communications grafted on top
  • work media tools, like Yammer, Jive, and the as-yet-unreleased Facebook for Work, build on social networking model, to move communications out of email, they say
  • and most prominently, the newest wave of upstarts, the work chat cadre have arrived, led by Atlassian’s Hipchat, but most prominently by the mega-unicorn Slack, a company which has such a strong gravitational field that it seems to have sucked the entire work technology ecosystem into the black hole around its disarmingly simple model of chat rooms and flexible integration.

Has the millennium finally come? Will this newest paradigm for workgroup communications unseat email, the apparently undisruptable but deeply unlovable technology at the foundation of much enterprise and consumer communication?
Well, a new announcement hit my radar screen today, and I think that we may be at a turning point. In the words of Winston Churchill, in November 1942 after the Second Battle of El Alamein, when it seemed clear that the WWII allies would push Germany from North Africa,

Now this is not the end. It is not even the beginning of the end. But it is, perhaps, the end of the beginning.

And what is this news that suggests to me we may be on the downslope in the century-long reign of email?
Microsoft is apparently working on a response to Slack, six months after the widely reported termination of discussions of acquisition. There has been a great deal of speculation about Microsoft’s efforts in this area, especially considering the now-almost-forgotten acquisition of Yammer (see Why Yammer Deal Makes Sense, and it did make sense in 2012). However, after that acquisition, Microsoft — and especially Bill Gates, apparently — believed they would be better off building Slackish capabilities into an existing Microsoft brand. But, since Yammer is an unloved product inside of the company, now, the plan was to build these capabilities into something that the company has doubled down on. So now we see Slack Teams, coming soon.
Microsoft may be criticized for maybe attempting to squish too much into the Skype wrapper with Skype Teams, but we’ll have to see how it all works together. It is clear that integrated video conferencing is a key element of where work chat is headed, so Microsoft would have had to come up with that anyway. And Skype certainly has the rest of what is needed for an enterprise work chat platform, and hundreds of millions of email users currently on Exchange and Office 365.
The rest of the details will have to wait for actual hands on inspection (so far, I have had only a few confidential discussions with Microsofties), but an orderly plan for migration away from email-centric work technologies to a work chat-centric model coming from Microsoft means it’s now mainstream, not a bunch of bi-coastal technoids. This will be rolled out everywhere.
So, we are moving into a new territory, a time where work chat tools will become the super dominant workgroup communications platform of the next few decades. This means that the barriers to widespread adoption will have to be resolved, most notably, work chat interoperability.
Most folks don’t know the history of email well enough to recall that at one time email products did not interconnect: my company email could not send an email to your company email. However, the rise of the internet and creation of international email protocols led to a rapid transition, so that we could stop using Compuserve and AOL to communicate outside the company.
It was that interoperability that led to email’s dominance in work communications, and similarly, it will take interoperability of work chat to displace it.
In this way, in the not-too-distant future, my company could be using Slack while yours might be using Skype Teams. I could invite you and your team to coordinate work in a chat channel I’ve set up, and you would be able to interact with me and mine.
If the world of work technology is to avoid a collapse into a all-encompassing monopoly with Slack at the center of it, we have to imagine interoperability will emerge relatively quickly. Today’s crude integrations — where Zapier or IFTTT copy new posts in Hipchat to a corresponding channel in Slack — will quickly be replaced by protocols that all competitive solutions will offer. And Skype is that irritant that will motivate all these giants to make a small peace around interoperability, in order to be able to play nice with Slack.
We’ll have to see the specifics of Skype Teams, and where Facebook at Work is headed. Likewise, all internet giants — including Apple, Google, and Amazon — seem to be quietly consolidating their market advantages in file sync-and-share, cloud computing, social networks, and mobile devices. Will we see a Twitter for Work, for example, after a Google acquisition? Surely Google Inbox and Google+ aren’t the last work technologies that Alphabet intends for us? How might Slack fit into Amazon’s designs? That might surprise a lot of people.
But no matter the specifics, we are certainly on the downslopes of the supremacy of email. We may have to wait an additional 50 years for its last gasping breath, but we’re now clearly in the chat (and work chat) era of human communications, and there’s no turning back.

Microsoft Planner is rolling out on Office 365

Microsoft Planner — the work management complement to Office 365 — was made available as a preview in December 2015, but has entered ‘general availability’, meaning it will become immediately accessible to users of eligible subscription plans. In Office 365, it will appear as another tile in the Office 365 tools (see the leftmost tile in the second row, below).
Screen Shot 2016-03-26 at 3.41.04 PM
Microsoft Planner is a task-centric work management solution, despite the ‘project management’ terminology other reviewers are using. The orientation of the tools is to support teams and team members tracking tasks and coordinating task work through social communications.
Planner is one of several task-oriented solutions that Microsoft is working to integrate, including Wunderlist and Microsoft Project. Conceptually, this means that users will be able to manage personal tasks (in Wunderlist), team work (in Planner), and to manage project planning (in Microsoft Project), and for these to be integrated in sensible ways. So for example, it might be helpful if I could see my work-related tasks, perhaps created and annotated in Planner, in a mobile Wunderlist app. Or to analyze the cost implications for a shift in personnel in a Planner project within the portfolio of company projects managed in Microsoft Project. That’s one part of the company’s long-range vision for Planner and the other tools manipulating task information. But it is going to be a long time before all the kinks and use cases are worked out for that grand vision. And at any rate, ultimately Planner will have to stand on its own, based on how good of a work management tool it is.
And that assessment poses another issue. If Planner requires Office 365 in order to use it — or even experiment with it — many prospective users will simply never jump through the hoops to try it out. I have raised that very issue with Microsoft representatives this year, as I was being briefed on the product. My suggestion is that Microsoft should create a standalone version of planner — at least a web app, if not mobile apps — so that an individual, team, or company could do an apples-to-apples comparison with Asana, Trello, or Wrike, and not the apples-to-oranges comparison with the umpty-ump boxes in that Office image, above. Also, that is the best way for Planner’s functionality to improve — in head-to-head competition — and not as a captive work management ‘capability’ locked into Office 365, relying on its integration with Office email, Outlook, Groups, and other tools.
The following is a condensation of the review of Planner from the in-process 2016 Work Management Narrative (much delayed), that I am authoring.
Planner is based on the well-known kanban-style, ‘board’ architectural model, and three modes of boards are supported at present: user-defined ‘buckets’, task assignment to members, and progress. As shown in the screenshot below, there is a left hand column where I have selected a plan, in this case Work Management Narrative, and I chose to display that plan as Buckets, not by Progress or Assigned to. In the ‘research tools’ bucket there is a single task, ‘research Microsoft Planner’, which shows icons indicating 0 of 2 subtasks have been completed, that there are comments, and the task has been assigned to Stowe Boyd. The half moon icon indicates that the task is in progress, a third state for tasks: unstarted, in progress, and completed.
Screen Shot 2016-03-26 at 5.27.27 PM
Clicking on ‘write method section’ expands that task (or, in the usual terminology, turns over the ‘card’), as we see in the screenshot below. At the foot we see a stream of comments — the one with a white background was entered in an associated discussion, about which more later. There are a variety of other attributes, showing a rich task model, however, lacking support for some common social communications like ‘@mentions’.
Screen Shot 2016-03-26 at 4.03.56 PM
What’s not clear from this zoom into Planner is that the ‘work management narrative’ plan corresponds to a Office 365 group of the same name. Groups support group-oriented communications, but those are not accessed in the Planner section of Office 365.
I believe that Planner users will find the need to return to Outlook to conduct conversations about their projects annoying, as opposed to the more normal model of an in-context — or best, in-project — activity stream. I bet that Microsoft will hear this as a frequent suggestion for additional Planner functionality. However, I often operate in multiple windows on the same project workspace, and so, having a conversation window and a Planner board view open at the same time is really not very different, and may be workable for many. Note also that if Microsoft builds a standalone version of Planner there will be no Outlook to lean upon, so an in-context activity stream or chat model would be best.
Office 365 users are likely using the spectrum of features — Outlook, OneDrive, Office apps, Groups, OneNote, and Planner — and therefore will rapidly habituate to transiting the many loosely integrated components, and will likely adapt to a model of use involving a lot of moving around. 
By itself, Planner would only be considered a team task management tool, not a true work management tool, since it lacks activity streams, @mentions, and other baseline social communications. However, that’s a red herring, since Planner — at present — is never without Groups and Outlook, and can’t be separated from them.

At present, I think the initial implementation of charts is a better indicator of where Planner is headed. In the screenshot below I’ve pulled an example from the Microsoft website (since my examples aren’t rich enough), and this shows the ease of quickly grasping the status of a Planner ‘document’ through a dashboard view.
charts planner
I also want to give a nod to the designers of Planner for including the three state model for task status: not started, in progress, and completed. The in-progress state is incredibly powerful, and after using it in some tools, I now chafe whenever confronted with a solution that lacks it.
Planner is an obvious choice for those already committed to Office 365 as a baseline for work productivity. However its current level of integration with Office 365 services — like Outlook, OneDrive, and OneNote — falls short of work management nirvana. Still, it’s early days, and when I reviewed it the product was only in a ‘First Use’ release phase.
I can imagine that within a very short time frame the myriad hooks that could make Planner a first-class member of the Office 365 suite will begin to emerge. I wager that creating tasks from email, or in the comments of a Groups or OneDrive comments — as just some of the most obvious examples — will be implemented within the next few releases, or sooner.
 

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.

Wrike is the newest to integrate Dropbox Chooser

Last month, Dropbox released Dropbox Chooser, an API to make integration of Dropbox into other applications much easier. At the time of the announcement Asana, the team task management tool, had already integrated Chooser into their implementation:

The benefits to users are great, since  the integration leverages Dropbox file sync, meaning that I can update a file in a Dropbox folder on my laptop after attaching to an Asana task, and anyone sharing that task will see the most recent version of the doc without me having to do anything.

Wrike, a competing team task manager, today announced that they have integrated Chooser as well:

We are rapidly moving away from the old paradigm of file sharing through web apps, and the confusion caused by users having to upload new versions of documents every time a change is made, and collaborators downloading documents and not knowing if they have the current version or not.

The new paradigm will be the following:

  1. Team members sign up for Dropbox for Teams, or a competitive offering, like Box.
  2. A folder is created for a project or a team, and all the team members share it.
  3. A team task management or work media tool is selected that integrates with the teams file-sync-and-share technology.
  4. Files intended for sharing are dragged into the shared folder, and linked to tasks, updates, messages, or comments in the task manager or work media tool, always staying in sync.

The only unnecessary effort involved is the manual creation and sharing of the project or team shared folder, but that could be simplified so that the task manager or work media tool performed that automatically.

I expect this to be nearly ubiquitous by the end of 2013.

Workers to pollsters: Widespread remote work is imminent

Findings from a new survey that confirm earlier polls showing workers are willing to sacrifice money or vacation time to work remotely may not be shocking, but other revelations about how soon employees expect their offices to go fully virtual may surprise skeptics.

25 Apps for the Virtual Worker’s Toolkit

Working remotely means not having the easy access to the machines and systems you used to when you were cubicle-bound. Here’s a list of five basic categories of tools you should have at the ready, and a variety of options to consider for each category.

Project Management Tool Wrike Gets New Mobile Apps

Looking for a way to keep your team up-to-date with project data when they’re out of the office? Wrike, a well-designed project management tool that we’ve written about previously, has announced the availability of new mobile apps for iPhone, iPad and BlackBerry.

Project Management App Wrike Gets Social

Wrike, an online project management and collaboration tool that we’ve covered previously, today gets a new update that aims to marry its project management functionality, like Gantt charts and reports, with the real-time updates and ease-of-use of social networking tools.

Protect Your Company’s Collaborative Spaces

padlockConsider the following scenario: An employee leaves your company or a virtual team member moves on, and the circumstances have been less than ideal. What do you do to make sure that you keep your company’s (and your clients’) confidential information safe, when someone who is no longer on your team might still have the passwords to the apps you use?
When it comes to collaborative tools such as project management apps, you can usually apply different levels of access to each team member. Still, have you figured out what to do when someone from the team departs? Read More about Protect Your Company’s Collaborative Spaces