Microsoft Teams vs Skype for Business — get to know Teams

The comparison of Microsoft Teams vs Skype for Business is an inadequate one.

Both tools have changed the way we communicate.

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Both tools offer excellent user interfaces and a fantastic collaboration experience.

However, they are incredibly different ways of working.

This post walks through key differences in technology, but also in processes and the way your business can work using these technologies.

Let’s jump right in.

Microsoft Teams vs Skype for Business basics

1 – Persistent chat

Microsoft Teams and Skype for Business both enable real-time chat. Dispersed teams had long required an alternative to the unproductive phone call experience.

Whilst calls, audio or video, can be productive, interruptions due to lack of presence often disrupted deep work.

Skype for Business and its previous versions (Lync, Microsoft OCS) transformed the way businesses communicated.

However, in Skype for Business, once a chat was closed or the working day was over, the chat was lost.

Chat logs were kept in Outlook or Exchange, but the conversation ended when the chat was deemed over or timed out.

Microsoft Teams introduces persistent chat.

As you can see in the screenshot above, the chat history is presented in a familiar style to Skype for Business.

However, unlike when you log into Skype for Business the morning, the chat will remain from the previous day, week or month.

For as long as you need to retain the information sent or received in a chat, you can keep it in your chat channel.

This applies for both one to one messaging and team messaging. We’ll come onto team messaging in a second.

Images, files and links are all retained, on top of standard messages, emojis and GIFs.

GIFs also appear in Microsoft Teams, making it easier to express yourself than in Skype for Business.

2 – Team messaging

Like persistent chat from one person to another, teams can be created to produce an ongoing stream of information for a set topic.

Teams can be setup on a per department basis, per project, per customer or any basis desired.

Below is an example of multiple users chatting within a set team. You can see a “conversation” is occuring within the “General” group of the O365 Deployment “team”.

Users can share messages, files, emojis, GIFs and stickers with other members of the specified team.

Within the team, users can also start a team meeting by hitting the Meet Now button.

When you hit Meet Now, the screen will launch a pre-meeting screen like the one below.

This transforms your team messaging interface into a full meeting experience.

Included here is a wealth of Microsoft Teams meeting features. Some of these will be familiar from your Skype for Business experience.

3 – Meetings

Many meeting features will be similar to Skype for Business, making Teams adoption simple and intuitive.

Common features like call recording, screen sharing and file uploads are all retained in Microsoft Teams.

The interface changes from blue to purple and a meeting is now hosted within the pane that contains all your team and one to one chats.

New features to start utilizing include in Microsoft Teams include:

  • Background blur (now made available in Skype)
  • Customized backgrounds
  • Whiteboard masking – this means when someone is physically drawing on a whiteboard, their body won’t be in the way
  • Live captions
  • Live events with access available to users outside of Microsoft Teams

Microsoft Teams vs Skype for Business advanced features

Whether you’re moving from Skype to Teams out of choice or due to a Skype for Business auto upgrade, you should be aware that Microsoft Teams opens the door to a raft of functionality you didn’t have before.

Meetings and messaging have always been part of Skype for Business.

The features outlined next are elements you can introduce to your business to enhance productivity, reduce app switching and make teams more collaborative.

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1 – Microsoft Teams integration

Skype for Business native integration was restricted to predominantly calling from telephony apps and systems.

Third party apps like Zapier provided IFTTT functionality.

Integration between other collaboration apps has been introduced but focus has shifted to Microsoft Teams.

Microsoft even announced the end of life program for the integration of Skype for Business with third-party audio conferencing providers.

When you migrate to Microsoft Teams, the Teams app store is full of your most used and most critical apps that can be added to your Microsoft Teams tenant as a “tab”.

The Teams app store features hundreds of apps that bring your favorite apps into Microsoft Teams.

This reduces the time spent switching between apps and tabs and frees up hours of productivity.

Below you can see the KanBo project management interface being used within a tab of Microsoft Teams.

We’ve put together a list of the 38 best Microsoft Teams integrations here.

2 – Microsoft Teams guest access

If you used the federation capability in Skype for Business, you will already know the benefits of enabling a common chat app between external parties.

For example, sales teams can communicate with their customers and partners if both parties have Skype for Business – and both turn on federation.

For any supplier/buyer relationship or external consultant environment, federation was a great way for external parties to remain connected without resorting to email or a phone call.

Below, you can see the label that shows a user is connected via an external network (federation).

In Microsoft Teams, the experience differs due to the team collaboration environment.

Federation does not currently exist natively for one to one messaging. Microsoft’s official stance on federation within Microsoft Teams is highlighted here:

“In order to currently federate within the Microsoft Teams client to an external user outside of your organization who’s not currently a Guest of your AAD/Tenant, you must be correctly setup for hybrid and moved to Skype for Business Online. “

Instead, Microsoft enables guest access so that external parties with Microsoft Teams accounts of their own can act as guests in your Microsoft Teams team.

Here, the user can access files, messages, and meetings of the team they are invited to – even if they are part of another organization.

Guest access doesn’t grant full access to the external party. Admins are able to prescribe what can and cannot be accessed by guests.

Guest access in Microsoft Teams gives access to an individual. Federation in Skype for Business gives access permission to an entire domain.

Adding a guest to a team is simple. Check out this GIF showing you how.

Federation with platforms outside the Microsoft stack

Do you communicate with people outside your organization?

Do they use apps other than Microsoft Teams?

If the answer is yes to both of these questions, according to research, they’ll likely be using Slack or Cisco Webex Teams.

When this is the case, it becomes extremely unproductive moving out of Teams, into your external contact’s choice of app, and starting the conversation again.

Or even worse, end up resorting to email like it’s the 90s. (Okay, email has a purpose but you get the point).

That’s why Mio has created universal channels for Microsoft Teams with Slack or Webex Teams…

You can stay in Teams and send messages to your contractors, suppliers, or clients that use Slack or Webex.

They stay in their platform too and Mio translates the messages across platform.

And it’s not just messages that are supported! GIFs, emojis, channels, DMs, and message edits/deletes are all supported.

If this sounds like something you need, try it for free here.

3 – File storage

When you create a new team in Microsoft Teams, this also creates a new SharePoint site in your Microsoft back end.

Because of this, each document or file that you upload to the team – either in the team messaging area or to the files tab – will be saved in SharePoint.

You will, of course, need the necessary licensing to achieve this. Microsoft Teams Free doesn’t include SharePoint access.

Restriction on usage also applies in the free version.

The limit for file storage is set as 2GB per user in Microsoft Teams Free and 1TB per user in paid versions.

Microsoft Teams vs Skype for Business future

If you have decided to migrate now, or are planning to soon, you’ll want to know what’s coming for both apps.

1 – Skype for Business Online

Skype for Business Online is set to go end of life on 31st July 2021.

Whilst Microsoft Teams is not a direct replacement for Skype for Business Online, it is where Microsoft is moving to – which means customers must too.

2 – Skype for Business Server

Microsoft has commitment to Skype for Business Server for years to come.

SFB server is the software that provides the infrastructure for enterprise messaging, presence, VoIP, ad hoc and structured conferences and PSTN connectivity.

Skype for Business Server 2019 continues to see enhancements on a regular basis. New features added in February include:

  • Cloud Voicemail
  • Call Data Connector
  • Side-by-side migration

However, the below features were announced end of life in Skype for Business Server in November

  • XMPP Gateways for Skype for Business Server
  • Persistent Chat for Skype for Business Server (functionality available in Teams)
  • SQL Mirroring for Skype for Business Server
  • In-place upgrades
  • Mobility Service (Mcx)

3 – Microsoft Teams roadmap

During Enterprise Connect, Microsoft announced some new features aimed to enhance productivity and tie up the meeting and collaboration experience.

  • Secure private channels
  • Information barriers
  • Calendar app
  • Live captions
  • Customized backgrounds
  • Content cameras and intelligent capture
  • Microsoft whiteboard
  • Enhancements to the Chrome browser meeting experience
  • Live events in Microsoft 365
  • Meetings first
  • New meeting devices
  • New supported handsets

The public Office 365 roadmap is available here. At the time of writing, there are 7 in-development items that Microsoft is working on bringing to Teams:

  1. Location-based routing
  2. Calendar app to replace Meetings app
  3. Commercial cloud trial
  4. Org-wide team for 5,000 users
  5. Easily add new members to a team
  6. Broadcast meetings (Skype for Business feature)
  7. Outlook meeting schedule from other platforms (Skype for Business feature)

You can also view items that are currently being rolled out and that have been recently launched.

For an in-depth rundown of the best Microsoft Teams features you could be utilizing, we’ve also put together a Microsoft Teams feature guide.

Microsoft Teams vs anything else?

If you are using your Skype for Business upgrade to shop around or consolidate other messaging apps, you may not need to.

It is often thought that moving to one app means you have to move all users to this app. This is no longer the case.

If you use Skype for Business as your primary chat tool, and are moving to Microsoft Teams, you can keep your internal Slack or Cisco Webex Teams users too.

With Mio’s enterprise tool, you can achieve messaging interoperability so users on each platform are forever in sync.

Teams users can stay in Teams.

Slack users can stay in Slack.

See for yourself in this video.

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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.

Hurdles

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.

The pros

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. ®

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