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.

Busybot: A ‘Parasitic’ Task Management Tool For Slack

Because Busybot and Slack look so much alike and are so tightly connected, I avoid the cognitive costs of switching.

I’ve tried using work management tools like Asana in connection with Slack, and the results have been mixed, principally because — I think — there is a mismatch in the basic orientation of the tools: Slack is messaging centered, while Asana is task centered.

In the case of a tool like Asana, when the Slack connection is used notifications are sent to a Slack channel whenever changes occur in the Asana workspace. For example, whenever a task is created, completed, or commented upon. A slash command (‘/asana’) lists tasks, and arguments to the command can lead to creating tasks, assigning tasks, and commenting on them.

Asana integration in Slack

But I confess that I have found this style of integration difficult. The two models of use — chat-based conversation in Slack and task-based coordination in Asana — don’t align for me, and the mapping from an Asana workspace to a Slack channel doesn’t always line up right. And I don’t necessarily want to have every tweak to a task dumped into the channel in Slack, per se. I don’t want that endless stream of noise, because Slack is noisy enough.

I recently encountered a tool that takes a different tack. Busybot avoids the mismatch problem by operating in a parasitic way. By that I mean it relies totally on Slack’s architecture to the greatest extent possible. For example, there is no independent login: you use Slack’s login. And once logged in, the channels of the team that you sign into are duplicated as contexts for tasks in Busybot.

Here’s the login:

login for Busybot

Here’s the #general channel for workfutures.io in Slack. You can see that I /invited busybot to the channel (I had already created the integration).

Inviting and Creating a Task

I typed a message to busybot, ‘ask Esko for a contribution’. If I had added ‘@stoweboyd’ that would have assigned the task to me, as well.

workfutures.io Slack team

Over in Busybot, everything looks extremely similar:

Task in Busybot

On the left, the design of Slack is emulated, so that for each Slack channel there is an equivalent Busybot channel, where all tasks can be found. I’ve selected the ‘ask Esko’ task, and then the task pane opens. I’ve selected the ‘add checklist’ feature.

Task Checklist

I’ve added a single checklist item, but you can have as many as needed. Also descriptions, comments, deadline, and assignment of the task are available as metadata.

The task list can be sorted, which is moot in this case, since there is only one task:

Also note that the ‘@stoweboyd’ option at the top opens all the tasks assigned to me, and ‘all tasks’ opens all tasks in the team, sorted by channel.

Tasks can be added, edited, and deleted in Busybot, but can only be created and displayed in the Slack side of the integration, at present. I’ve been told by Busybot’s CEO and founder, Damian Bramanis, that various new features are coming, like multi-team functionality, new ways to groups tasks in views, and tags.

Conclusions and Takeaway

Busybot works for me despite the minimal degree of metadata, and I think the reason is the equivalence between the Slack and Busybot information models: I don’t have to switch gears mentally when I move from Slack to Busybot, or vice versa. It feels like I am in the same place, just looking at different attributes of the same system of information. Moving from Slack to Busybot feels like I am just zooming in on task details that are suppressed on the Slack side. Because the two ‘sides’ look so much alike and are so tightly connected, I avoid the cognitive switching costs of moving from Slack to non-parasitic tools, like Asana.

Yes, I’d like to be able to do more with Busybot, though. For example, I’d like to be able to change task attributes on the Slack side, like adding a comment to a task, so that the text of the task comment would appear both in the Slack chat history and in the task comment thread. Damian tells me they are working on ways of accomplishing more sophisticated sorts of integration like that, perhaps with a /busybot command, or clever use of the channel topic (setting the topic to the name of a task, for example, so that commands could refer to that task).

At any rate, I will be watching the developments at Busybot with close attention.

Crossposted 1 May 2016 on workfutures.io.

Update 1 May 2016 4:30pm: Several folks mentioned Swipes for Slack, as another approach to accomplish some or all of what Busybot does. I will review in another post.

Work Management in Theory: Context

This is an excerpt of the upcoming report, Work Management Narrative, in which I will be reviewing around a dozen products, including Asana, Azendoo, Basecamp, Clarizen, Fleep, Flow, Liquid Planner, Mavenlink, Smartsheet, Trello, Work Front, Wrike, Zoho Projects and others.

Work Management in Theory: Context

Work management is a term that has emerged in recent years as task management tools were enhanced with various social communication capabilities, principally derived from design motifs from work media tools. This increase of capabilities — and the resulting overlap of work management capabilities with those of work media tools — means that trying to assess the trends that are prevalent  in work management really require stepping back. Today, there are a wide range of approaches to supporting cooperative work in the workplace, and they have many features in common. So, in many instances, groups or companies evaluating tools for  team cooperation may consider offerings that are very different in their underlying design, and require correspondingly different approaches to their use.

The Lay of the Landscape

Here’s a table that attempts to make sense of a variety of technologies that are used in business to support cooperative work. It is not exhaustive, but I hope it will clarify some of the distinctions between these classes of tools. At the same time, there is a great deal of overlap so some degree of confusion is inevitable.
Screen Shot 2016-03-24 at 2.37.22 PM
Today, there are a wide range of approaches to support cooperative work in the workplace, and they have many features in common. So, in many instances, groups or companies evaluating tools for team cooperation may consider offerings that are very different in their underlying design, and require correspondingly different approaches to their use.The primary distinction here is the degree of emphasis for task-centric versus message-centric tools. Those that we will focus on in this report are task-centric, even though there have to include some fundamental level of social communication to be considered work management tools. So for example, Todoist is a leading team task management tool, widely used in business. However, the tool lacks social communication aside from comments (‘notes’) associated with tasks: Todoist does not support messaging, discussions, activity streams, or ‘call outs’ (also called ‘@mentions’). While tasks can be assigned to others by the task creator, there is no other way that users can reference each other, or ‘talk’. And at the least social level of task management, personal task management tools don’t allow even the most basic level of business-oriented task assignment. As a result, team task management tools are not covered in this report, although Gigaom may develop a report like this one for that market, at some time in the future.
Work management tools share a lot of similarities with various message-centric work technologies. Note that I have divided the message-centric tools into two sorts:

  1. Follow centric — like Yammer, where the primary orientation of messaging is around following of message sources, and messages are primarily displayed in activity streams based on the user choosing who and what to follow.
  2. Chat centric — such as Slack, where the primary orientation of message is around chat rooms, or channels, and messages are principally displayed in those contexts when the user chooses to’ join’ or ‘enter’ them.

Some work media tools provide a degree of  task management, although it may not be the primary focus of the tool. And, as a general case, products like Jive, Yammer, and IBM Connections have little or no native task management, relying instead on integration with third party solutions. Likewise, many leading work chat offerings, like Slack and Hipchat, don’t have native task management, also relying instead on integration with task management tools, like Asana and Jira.
Lastly, the class of tools I refer to as workforce communications (like Lua, Avaamo, Fieldwire, and Sitrion One) have characteristics that are like those of work media and work chat tools, but are principally oriented toward communications management with an increasingly mobile contingent of the out-of-office ‘hard’ workforce, such as construction, retail and restaurant workers, field sales, security, and others.
At the bottom tier of the table in figure 1 are tools that are not principally oriented toward business use, like personal task management (Todoist, and Google Tasks), social media (Facebook, and Twitter), and consumer chat apps (Facebook M, and WhatsApp). This are widely used in business contexts, although they aren’t geared for it. Note however that this doesn’t mean that they couldn’t be recast as team or work oriented tools, like the trajectory of Facebook for Work.
There are other less-closely related work technologies that are also not investigated here, like curation tools, conferencing tools, and so called ‘productivity’ tools (like Microsoft Office 365, Dropbox Paper, and Google Docs/Sheets/Slides). These, again, are candidates for inclusion in another report.

Next week, I will be posting another excerpt from the report. 

Revealed: the finalists for the 2012 Crunchies

Five finalists have been chosen in 20 different categories for the 2012 Crunchies awards, and we’re proud to release the worthy nominees today. Voting for the winners starts today, and the winners will be announced January 31st.

Coming from Salesforce.com: A Dropbox for the enterprise

The tension between scrappy young startups and legacy companies in the enterprise world was on display Tuesday, with Salesforce CEO Marc Benioff noting his company’s challenges to some enterprise products from Box.net, Asana, and

Asana raises $28M to ease workplace collaboration

Getting workers to better collaborate together is becoming a hot opportunity. Asana, started by former Facebook co-founder Dustin Moskowitz, just raised $28 million led by Peter Thiel’s Founders Fund. The company helps workers communicate around projects and helps them act quickly.

Asana tries to end email frustration with Inbox

Asana, the startup that wants to help workgroups collaborate easily, is adding a new feature to its SaaS to attack what it calls a huge productivity suck: email. And it’s doing so with a new feature ironically called Inbox.