Skype to Teams - which route?

If you're currently using Skype for Business in your organisation, you have almost certainly started to think about how you might start to implement Microsoft Teams, and indeed, eventually, migrate fully to Teams.

The question is, what's the best approach? Inevitably, there is no one answer, as every organisation is different. Microsoft's own guidance is here, and continues to evolve as they work with more and more organisations. Having worked with a customer on this topic recently, I've tried to put down some of the pros and cons of each approach.

Straight-to-Teams

This is my own name for this approach, and it's not covered in the Microsoft guidance, but I've included it for completeness.

Pro

• No messing about with coexistence - users go straight from Skype for Business one day, to using Teams the next.

Cons

• Large change brings the potential for technical risks.
• Users have to get used to a lot of change all at once.

Realistically, you'd only choose this route for a very small organisation, perhaps one not using Skype heavily, where a 'big bang' is feasible both from a technical and business change point of view. Sometimes though, more pain for a short period of time is preferable to a long drawn-out migration, and the parallel running and coexistence challenges that creates. Get it over and done with!

Gradual

This is Microsoft's term for this approach. Initially, Teams is deployed in what is termed 'Skype for Business with Teams Collaboration Only' mode (though that's a bit confusing as you don't actually deploy Skype, it's already there - a better term would be something like 'Teams Collaboration-only mode'). In this mode, Teams has the peer-to-peer chat, calls, meetings and other communications features disabled, only the 'Activity' and 'Teams' buttons work (well, you do get the 'Meetings' button but it just shows your calendar, you can't schedule meetings from it). One important point to make however is that whilst you can't schedule Teams meetings in this mode, you can join meetings too which you've been invited, so in a phased migration, that's a useful feature.

At some point, you then migrate to 'Teams with Collaboration and Meetings' - meaning that users can no longer schedule meetings in Skype (though they can still join Skype meetings they've been invited to), but instead, meetings are scheduled in Teams. Then, as the final stage, you migrate to 'Teams only': chat and calls are enabled in Teams, and Skype is no longer in use (though again, you can still join Skype meetings to which you've been invited).

Pros

• You can deploy Teams without having finalised your network readiness (that is, making sure that your network is ready to carry Teams' real-time media traffic).
• Easy to explain to the users on initial deployment: you don't even have to mention Skype, you just explain you're deploying a new collaboration tool called Teams. Skype carries on working with no change at all.
• Less confusing for end users as chat and calls stay in one product at each stage - they're either in Skype, or in Teams.

Cons

• Users don't get to experience Teams at all as a communication tool until you make the next mode change - and at that stage, it's a sudden change. One day they're scheduling meetings in Skype, the next day, in Teams.
• In a phased migration, you'll have some users already on Teams-only who will need to communicate with others who are in one of the transitional modes - and that means, communicating between Teams-only and Skype. That's not a great experience, for example, desktop sharing doesn't work (you need to setup a meeting). Update: as of August 2019, Microsoft are improving the interop so that screen sharing works directly.

Direct

Again, this is Microsoft's term for this approach (I would call it 'Islands' or 'side-by-side'). Your initial deployment of Teams is in 'Islands' mode - so called because Skype and Teams each work within their own Islands, and don't talk to each other. So you can use Skype to chat/call other users in Skype, or use Teams to chat/call other users in Teams (note that federated communications - even from remote users on Teams - will only come into Skype - though this is changing). The final change is when you switch to 'Teams only' (probably once you've sorted out migrating the telephony aspects).

Pros

• From the start, users get to experience the full functionality of Teams (so, in contrast to the 'Gradual' approach, when they do go 'Teams only', they should already be very familiar with it).
• Anyone in the organisation who has already been moved to Teams only, communicating with someone who has not yet been fully moved over, will communicate via Teams - which is a much better experience than Teams-only/Skype.

Cons

• Can be confusing or at best annoying for users, as messages and calls can (and will) pop up in both Skype and Teams. There's no presence sync either (though you can now get Teams to show when you're in a Skype meeting or sharing your desktop, at least) so you could well get a call on Skype while you're talking to someone on Teams.
• Before you deploy Teams in Islands, you need to make sure that your network is Teams-ready - although you could mitigate this by deploying in Islands but initially disabling meetings and/or P2P calls.
• Another annoyance is that currently, headset controls are 'grabbed' by Skype when you have both Skype and Teams running. So as far as most people are concerned, the controls don't work in Teams (more about that here).

My 2 cents...

Do your own testing, read the Microsoft article and weigh up the pros and cons, but my thoughts are:

• Don't rush into Islands! Once you've deployed Islands in production, there's no going back (you can't really remove functionality once you've deployed something). So, if you're not sure which way to go, and perhaps you're under pressure to deploy Teams as a collaboration tool (and it really is a very good collaboration tool), then play safe and deploy Teams Collaboration only. There's no reason why you can't move from Collaboration only to Islands at a later date.
• The biggest argument, in my view, to going Direct (Islands) is to avoid the sub-optimal experience when communicating between Skype and Teams-only. If you push Teams in Islands out to your entire user base before switching the first users over to Teams-only, you'll get the best experience. Although it's a bit confusing to get messages in both products, if you encourage everyone to use Teams for internal communications, you should reduce those issues.

Update August 2019: that latter bullet point is no longer as true as when it was written way back in June. Now that screen sharing - one of the biggest gaps in the interop - is now available, I think the 'cons' are less clear-cut. There are still some limitations though (for example, not being able to escalate a call between a Teams user and a Skype user into a meeting), but the lack of screen sharing was a significant one.