Episode 9 of All About 365 with Jay and Steve – Migrating from CUCM to Office 365

Jason and SteveIn today’s show Jason and I discuss how you approach migrating from Cisco Unified Communications Manager to either Skype for Business Online or Microsoft Teams.

Although we’ve only got just over half an hour we delve into the key areas you must consider.. notes below are courtesy of Jay!

First step: what’s the objective?

Understand the technical and business objectives – why are we moving?

  • Understand what requirements are needed and can they be met from the cloud? Not all functionality can be met by O365 all the time.
  • Understand the limitations of the technology as it will impact what the business decisions are.

Discovery – Knowing what you don’t know and find out what it is.

  • Always start with the myadvisor.fasttrack.microsoft.com – its an amazing first step in how to do a voice migration.
  • Understand what the geographies are impacted.
  • What technology is in place currently, are we displacing video as well as voice?
  • What functionality/ features is being used within those technologies
  • What does the network look like? Can the wan take QoS?  Get a proper assessment done and have the end goal in place, do we want to use an Express Route or we going pure Internet play?
  • Is there PoE in place, what’s the end goal do you need to have handsets or are headsets going to be the end game?
  • What’s the end game for meetings and PSTN Conferencing?
  • Any of your numbers have a DSL attached?
  • What analogue telephones are required to remain? Elevators, Alarms, fax machines…

Decision making:

Once you know what is required and what the Cisco infrastructure is in place and how they work then you can start to do design of how things are going to work in the new world.

  • Not all locations can handle Skype for Business Calling plans, Only Belgium, France, Germany, Ireland, Netherlands, Puerto Rico, Spain, United States, United Kingdom – For Skype for Business you need a different geography it will need local break out through a on-premises Cloud Connector Edition or Skype for Business if it wasn’t a green field. Teams, you can us a direct route and connect to Teams via a 3rd party gateway natively. GA Soon for the Direct Route.
  • Not all porting is the same, different geographies have different rules, always engage early and make sure to get the letter of authorisation signed off at the beginning of the project, you can always move the date back.
  • Document what is possible in Office 365, Skype currently has more functionality than Teams but we know that Microsoft is putting all its weight behind Teams.
  • Know what the limitations – how many hunt groups are there in CUCM and how does that translate to Call Queues in SfBO?
  • Decide whether or not the functionality is right for you currently. Migrate the numbers for sites that don’t have a strenuous requirements.


Always pilot, make sure you have a good mix of people, locations, responsibilities and functional traits.

  • Agree the success criteria ahead of time.
  • Make sure the pilot is timebound
  • Ensure that the metrics are measurable from Office 365 or from a third party solution such as Nectar or IR

Migration planning:

Know that what we call a losing provider can be as awkward as they would like to be.  They cant say no but they can demand that you take all DDI in a single move, and probably will.

  • Use forwarding from a Microsoft Number if moves have to occur before the port forward occurs, but be aware the forward will endure a charge so keep the time limited.
  • Utilise the fast track and Microsoft Partners where you need them.
  • Know your licenses and what is required, E3 or Skype for Business v2, Microsoft Phone System or E5, Calling Plans or consumption billing?
  • Be aware that if you migrate to Skype for Business you’ll need to migrate again in an undisclosed period of time to Teams.


The users need to know what is going on and how to use the technology. It can’t be assumed that the users will understand that a desk phone leaves on a Friday and a Headset is plugged into the PC on a Monday and life will not have changed.

  • Dial tone is not something measured in the same as any other Office 365 technology, milliseconds matter.
  • Have a sensible and complete communications plan
  • Train the users on how the solution works.


You will find Episode nine below, at our our podcast site, on iTunes, SpotifyStitcher and you can subscribe with your favourite podcast app using the feed.

We’ll be back next week, but until then enjoy the latest episode. If you’ve got any suggestions for what you’d like to hear on the next show, reach out to us.