Skype revolutionised IP-based video calling to such an extent it became a verb, much like Google. This largely consumer technology went pro in 2011 when Microsoft bought the firm for $8.5bn.
Microsoft, of course, already had IP-based video as part of its unified communications platform, first with Office Communicator and then Lync, which combined voice, video, instant messaging and videoconferences in a single client. In 2014, Microsoft killed Lync and applied the Skype branding iron to produce Skype for Business and Skype for Business Server.
Enterprises can migrate this workload to the same umbrella structure as their other Office 365 services. SMBs got the product included with a $5 user/month plan. Considering the deep integration between Skype for Business and Outlook, Sharepoint Online, Yammer and Microsoft Teams, it seems like a no-brainer to embrace this way of communicating.
Six years in, has Microsoft's purchase of Skype revolutionised business communications?
Not quite. Indeed, some of what Microsoft is doing to Skype is actually throwing hurdles in the way of adoption.
It's hard to tell if business customers have been keen. Microsoft doesn't split out monthly active users by product, so we're left with a large Office 365 lump. The current 85 million MAUs include kiosk workers who might only use a mailbox. What is obvious is that Exchange Online is a gateway drug to the cloud, as enterprises replace ageing email infrastructure.
It's rare to find organisations that use all of the Office 365 products that they are licensed for and Microsoft knows it. Redmond is so focused on having you use the full product set that, in addition to the inbuilt Office 365 usage reports, it's released a public preview of the Power BI content pack for Office 365 adoption. Now you're getting serious data, broken down by product, on how much your organisation is using the various online services.
Overall, it's anyone's guess how active Skype for Business Online really is.
A migration to Exchange Online from regular Server presents a similar user experience afterwards, as the majority of email tasks are performed the same way. The same can't be said for a migration from Skype to Skype for Business Online. If your small business started out using Skype, or your users are comfortable with personal Skype accounts at home, everyone's in for a shock.
Microsoft's acquisition of Skype led to the eventual death of the standalone Skype account. Technically, this made sense. Microsoft wouldn't continue to grow a standalone authentication directory when it already had the Microsoft account infrastructure in place. For existing Skype users, it offered to "upgrade" your Skype name to a Microsoft account by simply adding your email address. But not everybody did. Now, new users of the consumer platform must create or use a Microsoft account.
Skype for Business is inconsistent in how it handles non-upgraded, standalone Skype accounts. The PC client does let you add people with only a Skype name, if you choose "Add a contact not in my organization" and search the Skype directory. You can chat with them and see their presence indicator. Access your Skype for Business contacts via Office 365 in your browser (finding the Skype icon above Mail or People) and the directory search will find new contacts by their Microsoft account address, but never by their Skype name. Same limitation with the Skype for Business for Mac client, which has no luck finding old Skype names. The PC client definitely wins here, but it's not ideal in a multi-platform world if people want to be Macbook road warriors.
After Office for Mac and Skype for Business for Mac upgrades, it's surprising to see this capability missing. It might not be an issue for internal communications or for new companies, but it's a roadblock for Mac lovers looking to upgrade from using personal Skype accounts. Decide to stay on the consumer Skype platform for the backwards compatibility and you're left managing personal Microsoft accounts in the background, with no overall admin control.
With any communication platform upgrade, your contacts are sacrosanct. Move from Skype to Skype for Business and there's no way to retain your contact list. It's not possible to export your Skype contacts and import them into Skype for Business. Behind the scenes there could be a bunch of technical challenges preventing this, but that doesn't help users. Be warned – if you've built a history of valuable contacts while using Skype, you'll be sending them new contact requests individually.
A little more conversation
Another change that leaves users scratching their heads is how Skype for Business handles conversations. In a Skype world, double click on a contact to see message history, a la Facebook Messenger. In Skype for Business, you'll be staring at a new blank chat window.
Past conversations are viewed in a separate tab, listed in date and time order, not in Contact Name order. This view retains your most recent conversations, with a link to Outlook to view the rest. Yes, Outlook. At least in the Outlook Conversation History folder you can choose to arrange by From or To, or group by Contact name. The view in Skype for Business has a separate sub tab for calls and missed conversations (with missed conversations also being sent to you via email). This way of displaying information might not be a bad thing, but it's certainly a change to get used to. This is the most likely thing to start users complaining: "It doesn't work like Skype." No. No, it does not.
Last year Skype Broadcast was launched. These town hall meetings (webinars) let you show your face and your PowerPoint presentation to up to 10,000 attendees simultaneously. You've got inbuilt options to make the webinar viewable afterwards and an option to have it generated as a downloadable video file (handy for adding corporate trailers or credits and closed captions). All managed through a web interface, there's one major downside. Natively, Skype Broadcast won't let you share your screen. Nope, we're not kidding – no live demos for you. There are a few third-party tools (including XSplit Broadcaster) that can fool Skype into thinking your desktop is a virtual camera. A nice little trap to fall into for the unaware who have already sent out their meeting invitations.
Before you put Skype for Business in the "too hard" basket, it does have strong points. Skype consumer cannot deal with multiple points of presence. If you have Skype on your PC, your iPad and your phone, you can't get Skype to recognise that when you set one to Busy, you want them all to be Busy. People will see that another device is showing you as online and they won't know the difference. Skype for Business, however, can sync your status across your devices.
Microsoft has worked hard on Skype for Business integration across the Office 365 product set. This strengthens their collaboration story and is most evident inside Microsoft Teams. Even in Outlook, the little integration details add magical touches. Start a Skype conversation by clicking on the colleague who sent you an email, and the email subject appears in the title bar. Reply as a meeting invitation and the Skype Meeting options schedules an online room and sends the participants the joining instructions.
Microsoft kept enterprises happy with Cloud PBX functionality, plugging into your existing phone system or partnering with its own PSTN calling capability. Sadly, PSTN calling isn't available in all countries yet (Australia is still waiting), but Microsoft sings Office 365 E5 loudly, with all these bells and whistles.
Good luck and godspeed
Assuming you haven't ditched the whole idea in favour of Slack's voice and video calls, there are benefits to be had with Skype for Business. You just need to know what you're up for. Microsoft gets that too, increasing its focus on adoption resources. Audit your historical Skype use, pilot the heck out of it and you too can start slashing that corporate travel budget. ®