Moving to a Microsoft Teams world (and my journey getting there)


I love Microsoft Teams. There I said it, bias fully disclosed. I’ve always loved playing with new toys, and when Microsoft Teams came along I was excited! This article is about my own history working with Skype for Business, where Microsoft Teams fit into the future and my advice to those confused about which road they should take.

The glorious past

I’d been hanging out with Skype for Business and its previous incarnations for the last 10+ years, and was getting bored! (only a little). Don’t get me wrong, I still love Skype for Business, and have had, and will continue to have, a great time helping customers get the most out of a great Unified Communications solution. Skype for Busines still has a tonne of mileage left in it, but at the same time, I am excited about a future with Microsoft Teams.

I like to think of things like this: Microsoft Teams is to Skype for Business, what Skype for Business was to the PABX…

Skype for Business was the beginning of a new era in the way we would communicate. When Skype for Business was released with Enterprise Voice functionality way back in 2007 (a.k.a Office Communications Server), it was some serious blending edge stuff. There was little to no documentation on how to make Enterprise Voice work, SIP Trunking was in its very early days (at least here in New Zealand), and generally speaking, nobody thought a software solution would ever replace the good old trusty PABX. At the time I was fortunate enough to have an I.T Manager who loved bleeding edge on a budget. This was great news for me because I love to solve problems; the harder the better! And so my love for Skype for Business began. Thankfully for me, I picked the right horse; turns out Microsoft did a great job building a software solution that could outsmart the PABX.

Over the next 10 years, Skype for Business chipped away at the PABX market at an ever-increasing rate.

The next new era

Now here we are at another turning point. Skype for Business is now set to be outsmarted by the Cloud, and in particular, by Microsoft Teams which leverages its technology. That doesn’t mean it’s going to disappear overnight or that you shouldn’t invest in it; its still an excellent Unified Communication solution, and remember PABX’s still exist today, and likewise, Skype for Business will continue to serve you for the foreseeable future. Case and point Skype for Business 2019 is due for release soon, and that comes with a renewed supportable lifespan of 5 years, and I believe we will see another server version before that expiry.

But one day, just like that PABX, Skype for Business may disappear. On-premises solutions are becoming less and less of a priority for Microsoft. Not so long ago Microsoft tried to retire SharePoint Server; long story short the decision was reversed, however, it does show their intent, and in my option, they are doing the right thing; simply put, Microsoft cannot compete with “born in the cloud” solution providers such as Google and Amazon. On-premises solutions with 3-year release cycles do not work these days! Cloud providers can deliver fixes, features, and enhancements too fast, and it’s not practical to deliver the same to on-premises.

Enter the Cloud and Microsofts Office 365. Microsoft was a little slow off the mark with Cloud but has been going at it full guns blazing for a good few years now. Microsoft are catching up, if not overtaking competitors at least in some areas. Microsoft’s core products which were previously available only on-premises, are largely now more feature rich in the cloud than they are on-premises. Millions of people (Microsoft report 120 million) now use Office 365, and with that brings a lot of data. This “big data” brings with it the opportunity to for insights and AI technology that just wouldn’t be possible on-premises. This stuff is supposedly the next big thing, and Microsoft is now in a good position to deliver. Another thing the Cloud has allowed Microsoft to do is to build a client user experience that ties many Microsoft and 3rd party Cloud microservices together in a single pane of glass…

  • Imagine being able to make and receive video calls, join online meetings and share content powered by Skype;
  • record your meetings and have them translated, transcribed and actions points documented powered by Stream;
  • share and collaborate on documents in real time powered by SharePoint and OneDrive for Business;
  • view create and manage Online Meetings powered by Exchange;

all in a single interface? Now you can, introducing Microsoft Teams 😉

Microsoft Teams is not a replacement for Skype for Business specifically, its the beginning of a new era, and a different way of working. As I mentioned Skype for Business Server is sticking around for the foreseeable future. Skype for Business Online is in the same boat, however, Microsoft has signaled that at some point all online users will need to move to Teams. Microsoft Teams is pretty close to at feature parity with Skype for Business Online already, even so, Microsoft won’t be forcing you to move any time soon. What they are doing, however, is working on providing interoperability and migration paths that will allow your Skype for Business users (Online or On-premises) to communicate with your Microsoft Teams users and vice versa, and give you a simple way to “upgrade” or migrate from Skype for Business to Microsoft Teams when you are ready; that might be now, 2 years from now or sometime further in the future. Microsoft Teams is only going to improve, and at some point, the benefits of moving will be a no-brainer.

For me, it’s already a no-brainer to move to Microsoft Teams as my single communications and collaboration client. For the past year, I had been drifting between Skype for Business and Microsoft Teams to meet all my needs. I was using Microsoft Teams for the persistent chat and team collaboration space, and Skype for Business for everything else. Over the past year Microsoft Teams has been getting better and better, and with the recent release of Direct Routing, I can now turn on Enterprise Voice and turn off Skype for Business. I now solely use Microsoft Teams, and to give you an idea what is possible, here are some of the things I do on a daily basis:

  • 1:1 chat with internal and external parties
  • Chat and call my colleagues who are still using Skype for Business
  • Group persistent chat and document collaboration with my team
  • Make and receive calls from the PSTN/Telephony network (Enterprise Voice)
  • Simultaneously ring calls to my mobile
  • Invite colleagues and customers to participate in Microsoft Teams Online Meetings with dial-in conferencing option

Sure there are some teething problems, but on the whole, I am very happy with my move to Microsoft Teams, and I am looking forward to helping my customers embrace this new era of “Intelligent Communications”.

Advice and summary

It’s a tricky place to be if you’re a decision maker trying to weigh up Skype for Business vs Teams. Here is my advice today (remember, Cloud moves fast and my comments could be outdated at any moment!):

  • Regardless of where you’re at in your Cloud journey, if you’re a Microsoft shop (or not), you should start trialing Microsoft Teams to see if it fits your business. Becuase its a Teams based collaboration space, choose Teams who work closely together rather than just turning it on for everyone at the outset
  • If you’re looking for a Cloud solution you have the choice for Skype for Business Online or Microsoft Teams. Skype for Business Online will be retired in favor of Microsoft Teams one day in the future, so it makes sense to go straight to Microsoft Teams if you don’t already have any Skype for Business baggage
  • If you’re already using Skype for Business Online/On-premises and are considering moving to Microsoft Teams, ensure you spend time on user adoption. The user experience is quite different and may cause frustration for users without a helping hand
  • The interop between Microsoft Teams and Skype for Business Online/On-premises is not yet perfect. If you plan to have some users in Microsoft Teams and some on Skype for Business Online/On-premises it could cause user frustration; choose your users carefully, run a good pilot and have an adoption strategy. To give you an example of some of my real world frustrations:
    • I have seen large delays in presence updating between the two solutions
    • Chat and calling between solutions occasionally fails
    • Federation from Microsoft Teams is not working very well (it’s only just been released and patience may be required)
  • If you’re looking for a communication and collaboration solution with Enterprise Voice and you have never used Skype for Business Online/On-premises you’re in a good position to consider Microsoft Teams. From an Enterprise Voice perspective its pretty close to at feature parity with Skype for Business Server, and you won’t run into any of the interop problems described above
  • If you are already a Skype for the Business Online/On-premises shop using or wanting to use Enterprise Voice, you’ll need to make sure all the features you require can be delivered by Microsoft Teams and that you can live with some of the interop issues if you plan to migrate users over time
  • Microsoft Teams (or Skype for Business Online for that matter) doesn’t have a rich set of API’s like Skype for Business Server, so if you require 3rd party bolt on’s like Contact Centres, you should stick with Skype for Business Server for now. Likewise, if you require a good set of PowerShell and Management API’s

To summarise this further I would say this:

  • If you’re a small to medium sized company that doesn’t have complex or any calling requirements, Microsoft Teams is ready for you
  • If you are a large company or have complex requirements, continue with Skype for Business Server for now, maybe trial Microsoft Teams where it makes sense and reviews things again in 1-2 years time when Microsoft Teams will be a lot more mature

Hopefully, this has provided you with some food for thought. If you have any questions, comments or want to debate any points in this article please do so in the comments. I love to hear other opinions and I promise you’ll get a response 🙂

Thanks for reading, over and out.




Andrew Morpeth
Andrew Morpeth
Andrew is a Modern Workplace Consultant specialising in Microsoft technologies based in Auckland, New Zealand; Andrew is a Director and Professional Services Manager at Lucidity Cloud Services and a Microsoft MVP.

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  1. Hi Andrew. Is It ok for you to have your team appearing as an option at Outlook for mail sending? If so, How did you deal with It?

  2. Hello Andrew,
    Thanks for writing this article which gives clear understanding of the S4B online and MS Teams.
    Currently my customer is running with Lync 2010 with DID and now they want to move into MS Teams.
    Please can you shed some light like how we can move from Lync 2010 to MS Teams along with DID.
    Any options that we can direct move from Lync 2010 to MS Teams with DID.

    Any help really appreciated.
    Thanks in advance
    Anand Sunka

    • This isn’t an easy question to answer in a few lines. Been a while since I have dealt with Lync 2010, but I think you can manage the migration via PowerShell. Lync 2013 and above have better Cloud integration and so more can be done from the UI. In short, you can certainly get your customer to Teams with DID.


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Andrew Morpeth
Andrew Morpeth
Andrew is a Modern Workplace Consultant specialising in Microsoft technologies based in Auckland, New Zealand; Andrew is a Director and Professional Services Manager at Lucidity Cloud Services and a Microsoft MVP.

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