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.

Slack moves past slash commands to message buttons

Slack has announced a new mechanism for third party apps to better integrate with its work chat platform. Rather than relying on so-called ‘slash commands’ — like /trello add Taco Drone Delivery — and then sending subsequent messages to assign values to the metadata of that task, third party apps can be configured to present a UI much more like that in a native app, including buttons that can be pressed to assign values.
Here’s a animated gif for the new Trello integration with message buttons:
Note that the buttons can cascade, as when the user selects ‘due date’ and then various options for the due date are presented. Also note that ‘attach conversation’ will attach a link to the Trello card pointing back to the chat context where the task was created.
This is a serious advance for Slack integration, and specifically, the cognitive dissonance problem with a /slash command-style integration like the one with Trello. I wrote about this recently in Slack ‘Spots’, not just Bots, where I suggested that Slack was probably working on something like this. And yes, they were.

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.

4 tips on managing remotely from the founder of Treehouse

Apparently, ProofHQ isn’t the only successful British startup with a remote team across the pond. Ryan Carson, the founder of Treehouse, recently took to his blog to explain how he manages his widely dispersed team of 40 from his home in the UK.