Business collaboration darling Slack has a new partner — Skype.

It appears to be quite the collaborative match, with the fast-growing tool providing easy access to Microsoft’s ubiquitous communications service. The new integration of Skype with Slack is in preview for now, but it’s a telling add-on that could hold promise.

Skype Away After a Few Keystrokes

According to the Skype blog, the integration mirrors much of the way other services work in Slack. All you have to do is type /Skype to begin a conversation with a member of your team. For example, Slack includes several other slash commands like /close, /away, and the always popular /giphy to perform a related commands.

Teams that want to integrate this into their own Slack can do so by adding the Skype button and selecting which channel you want it to work with first. You’ll then be able to launch a Skype conversation, or join an existing one, with any of your Skype contacts in that channel.

Along with the new tool in the Slack desktop apps for Windows and OS X, the Skype integration is also being tested out in the mobile app for iOS and Android.

A Win for Skype?

Microsoft is more than happy to get Skype in front of more eyeballs, as the company pushes a cross-platform strategy. Skype will work with Slack, even though the company has Yammer. And Office files play well with Dropbox, despite Microsoft’s heavy investment in OneDrive. It’s all part of a strategy that pushes Office and its related apps forward, making them available on any of the major platforms.

The Skype integration will be worth watching over time to see if it becomes a key component to Slack. The much-beloved collaboration tool already has become quite popular, which makes it just the place that Microsoft wants it to be. 

As Alan Lepofsky, vice president and principal analyst of Silicon Valley-based Constellation Research, tweeted:

Lepofsky said the integration gets both Microsoft and Slack some good press. "Slack needs 'real enterprise' integrations, and Microsoft needs street cred with the developer crowd," he told CMSWire.

While Slack is used by a growing number of people, it is missing native video integration. It relies on Google Hangouts, Zoom, Room, UberConference, BlueJeans and a few others to fill that gap. So "it’s smart of Microsoft to try and take a piece of that integration business and reduce the use of a competitive offering. It’s also good to see Slack integration with a true enterprise product versus many of their smaller niche integrations," Lepofsky said.

But the timing does seem odd: It comes just a month after Microsoft's acquisition of Talko, a mobile app for business team communications that was integrated with Slack in mid-2015. "Talko provides simple team calling across mobile and web. Calls are recorded so that people who weren't there LIVE can find and replay important moments," Slack explains in its app directory.

Talko was founded in September 2014 by Ray Ozzie, who was Microsoft’s Chief Software Architect until 2010.

Talko employees, but not Ozzie, are joining Skype and Talko itself is being shut down — a process that will be complete by the end of March.

Strange Bedfellows

But back to Slack and Skype.

While the integration puts Skype smack in the middle of a popular collaboration platform — and there are obvious advantages to that — it still makes you scratch your head a bit.

"It’s weird but I suppose it’s usable," said Microsoft SharePoint MVP Todd Klindt.

"It doesn’t seem to use the Skype client if it’s installed. It always uses a web client, and it seems to require a plugin for all the main browsers. I will say that the video quality is better. I did a Slack Skype with a coworker, then did a video call with the regular Skype client. The Slack web thingee used a lot more bandwidth but the video was much better. I could see my coworker much better. He said my video was clear, but a little choppy."

Learning Opportunities

Sergei Anikin, a former employee of Skype who currently serves as VP of Engineering at Pipedrive, a sales CRM vendor, said he was a heavy user of Skype for the seven years he worked there. Because Skype teams were very distributed in their nature, Skype itself was the ultimate tool to get things done, he recalled.

A lot of information exchange happened within Skype group chats, which were great for asynchronous communication. But because Skype's main focus were voice and video calls, the chat part of the software was heavily underinvested in terms of development effort, he added.

"It was clear that Skype user management and chat products were not usable for the organizations, but it never became a priority to fix those. There was even a group of people who left Skype in order to create a better chat software, called Fleep," Anikin told CMSWire.

He said he was "kind of frustrated" that Skype did this integration instead of fixing its own chat product. "The only reason I can think of is lack of ambition and willpower," he continued.

In 2011 when Skype joined Microsoft, Anikin said it gained all the resources it needed to focus and fix broken things.

But neither technical nor product leadership focused on the right things — "and as a result, there is still a lot of technical legacy which is preventing the Skype team from innovating. The P2P architecture, which was an advantage 10 years ago, has now became an obstacle. But as it is a very complicated part of the software and the original authors left long time ago. Projects which supposed to replace it are failing one after another," he concluded.

'Not Weird at All'

Tom Petrocelli, research director for enterprise social, mobile and cloud applications at Neuralytix, has a more positive perspective — especially from Slack's point-of-view.

"Like all collaboration platforms, Slack has to branch out and create an ecosystem. Integrating Skype, just as it did with Dropbox, Google Hangouts, GoToMeeting, Trello, Wunderlist, Asana and dozens of other applications, is an attempt to make Slack the center of your work day," he explained.

Petrocelli said this is similar to the strategy Enterprise Social Networks have always used: Make your app the center of the knowledge workers’ universe.

"Does it work? A bit. It’s convenient to have your apps talk to each other and not have to switch application context to perform a task or initiate a different mode of communication. So in this case, I might be chatting away on Slack with someone and want to talk to them face to face (virtually anyway). Being able to initiate that from Slack is useful. I don’t have to load up Skype, find the other person’s Skype address and initiate a call.

"Where I think Slack falls down is in how it is implemented. You have to use those irritating / (slash) commands. The initial market for Slack were developers who are used to typing on a command line. For the average end-user who is not a developer or sysadmin, this seems terribly retro," he said.