Stages of the upgrade journey, with emphasis on the Technical Readiness stage

This article is part of the Technical Readiness stage of your upgrade journey, an activity you complete in parallel with the User Readiness stage. Before proceeding, confirm that you’ve completed these activities from previous stages:

Evaluate your environment before upgrading to Teams

This article gives an overview of the requirements for properly evaluating your current environment for operating Teams. By evaluating your environment, you identify risks and requirements that will influence your overall deployment. By identifying these items beforehand, you can adjust your planning to drive success.

Introduction to the Discovery Questionnaire

To achieve your objective key results (OKRs), you previously made key service decisions. The next step is to perform environmental discovery to evaluate all aspects relating to your IT infrastructure, networking, and operations to confirm that your organization is ready to implement the solution. Discovery is one of the very first, key steps that you take when planning for your journey to Teams. Environmental discovery must include a network readiness assessment to ensure your network can support upgrading to Teams. You perform a detailed discovery of your environment to better understand its current state and to reveal any difficulties or—even more important—possible blockers to the execution of your Teams rollout.

You identify technical risks as part of an environmental assessment and adoption readiness evaluation, and develop a mitigation plan for each identified risk. You should incorporate this information in the risk register.

All matters related to your existing collaboration infrastructure and Office 365 tenant, networking, endpoints, operations, and adoption and readiness are included as part of the environmental discovery questionnaire. The questionnaire is divided into multiple sections to confirm your organization’s readiness for your Teams deployment in several major areas. Work with your project team to provide the requested information with as much detail as possible to facilitate your planning activities.

Tip

You can start by copying the questionnaire into a Microsoft Word document. Try to answer all questions and capture all details as you move through.

Project team

Ensure that you’ve engaged the right people for your project team. Verify the steps you completed in Enlist your project stakekholders.

Office 365 tenant details

We highly recommend that you have an active Office 365 tenant as you work with this questionnaire. If you haven’t activated or configured an Office 365 tenant yet, see Plan your setup of Office 365 for business.

Use the following table to capture information about the Office 365 tenant.

Question Answer Comments
Note the production Office 365 tenant
name and ID in the Answer column
If you have more than one tenant
associated with your organization,
note all the IDs.
Tenant Name:
Tenant ID:
In what regions are the tenants deployed?
Are these tenants Office 365 Multitenant or
Dedicated?
Multitenant
Dedicated
Which Microsoft Online products are in use today?
Note the number of users enabled for each
service in the Comments column.
Microsoft Teams
Skype for Business
     Online
Exchange Online
SharePoint Online
OneDrive for Business
Yammer
Other
What license level is enabled for Skype for
Business Online users?
E1/G1
E2/G2
E3/G3
E4/G4 E5
Standalone
The number of users
for each SKU:
What is the current Active Directory forest
functional level in the environment?
If there’s more than one forest, note the details
in the Comments column.
Windows Server 2000
Windows Server 2003
Windows Server 2008
Windows Server 2008 R2
Windows Server 2012
Windows Server 2012 R2
Windows Server 2016
What are you using for directory
synchronization today?
No sync (cloud only)
Azure Active Directory
     Connect
Other (Specify in the
     Comments column.)
Is federated identity currently deployed?
(Active Directory Federation Services or
third-party)
Yes
No
If you’re using federated identity, what is the
federation infrastructure?
Windows 2008 R2 AD FS
Windows 2012 AD FS
Windows 2012 R2 AD FS
Windows 2016 AD FS
Third-party federation
     gateway
     (Note the details in the
     Comments column.)
If you currently maintain an active Office 365
tenant, is the SMTP/SIP domain of your
targeted users associated with the tenant?
N/A – No Office 365
     tenant in place
No, users’ SMTP/SIP
     domain isn’t associated
     with any tenants in
     Office 365
Yes, users’ SMTP/SIP
     domain is associated
     with an existing tenant
     in Office 365
Do user UPNs match their primary SMTP address? Yes
No
Inconsistently

Existing collaboration platform summary

Use the following table to capture information about your existing collaboration platform deployment.

Question Answer Comments
Is Microsoft Teams deployed? Yes
No
Is Skype for Business deployed?
For on-premises and hybrid deployments, make sure
you note the version and cumulative update (CU)
details in the Comments column.
Yes, Office 365
Yes, hybrid (with Office 365)
Yes, on-premises
Yes, online, dedicated
     (Microsoft)
Yes, hosted, dedicated
     (third party)
Yes, hosted, shared (third party)
No, other
Is Exchange deployed?
For on-premises and hybrid deployments, make sure
you note the version and CU details in the Comments
column.
Yes, Office 365
Yes, hybrid (with Office 365)
Yes, on-premises
Yes, online, dedicated
     (Microsoft)
Yes, hosted, dedicated
     (third party)
Yes, hosted, shared
     (third party)
No, other
Is SharePoint deployed?
For on-premises and hybrid deployments, make sure
you note the version and CU details in the Comments
column.
Yes, Office 365
Yes, hybrid (with Office 365)
Yes, on-premises
Yes, online, dedicated
     (Microsoft)
Yes, hosted, dedicated
     (third party)
Yes, hosted, shared
     (third party)
No, other
Is Office 365 OneDrive for Business deployed? Yes
No
Do you have any other third-party platforms deployed
and in use today? If so, note the number of users of
these platforms and the usage details in the Comments
column.
Cisco WebEx
Slack
Other (Specify in the Comments
     column.)
Number of users:
Details:
Are you planning to move users from these third-party
platforms to Teams?
Yes
No
What is the current telephony and conferencing solution
of the users who are in scope for this initiative?
Do you have SBCs that support Direct Routing deployed for your offices that are in scope for this initiative?
If Yes, note the details in the Comments column.
Yes
No

Collaboration platform deployment details

Microsoft Teams (if applicable)

If applicable, capture the details of your Teams deployment by using the sample table below. If you haven’t deployed Teams, skip this section.

Question Answer Comments
What types of users are enabled for Teams? All users in the organization
Specific users/user groups
     (Specify in the Comments column)
Which Teams features and modalities are in use? Channel-based conversations
Private chat
Guest access
Channel meetings
Private meetings
Private calling
Ad-hoc channel meetup
Videos in meetings
Screen sharing in meetings
Audio conferencing
Applications (apps)
      Tabs
      Bots
      Connectors
Custom cloud storage integration
      (Box, Dropbox, ShareFile, Google Drive)
Channel email integration
Other (Specify in the Comments column.)
What applications have you deployed to Teams?
Have you specifically blocked any Teams capabilities?
If Yes, note the details in the Comments column.
Yes
No
Which Teams clients are in use? Web
Windows
Mac
iOS
Android
Windows Mobile
Who has permissions to create teams? Everyone in the organization
     (This is the default setting)
Specific people
     (Specify in the Comments column.)
Are you using security and compliance features in Teams? Yes
No

Skype for Business Online (if applicable)

If applicable, capture the details of your Skype for Business Online deployment by using the sample table below. If you haven’t deployed Skype for Business Online deployment, skip this section.

Question Answer Comments
What types of users are enabled for Skype
for Business Online?
All users in the organization
Specific users/user groups
     (Specify in the Comments column)
What modalities and features are currently
in use today?
Instant Messaging and Presence (IM/P)
Meetings
Federation
Meeting Recording
Microsoft Audio Conferencing
Third-party audio conferencing
     (Note the details in the Comments column.)
Calling Plans (formerly PSTN calling)
Organizational Auto Attendants
Call Queues
Have you specifically blocked any Skype for
Business Online capabilities?
If Yes, note the details in the Comments column.
Yes
No
What method are you using or plan to use to
connect Phone System (formerly Cloud PBX) to
the PSTN?
Select all that apply.
Calling Plans (formerly PSTN calling)
On-premises PSTN connectivity (leveraging existing
     Skype for Business 2015 or Lync Server 2013
     deployment)
On-premises PSTN connectivity (using Cloud Connector)
Have you ported any phone numbers to Microsoft?
This is applicable to Calling Plans and Audio
Conferencing features.
Yes
No

Skype for Business on-premises (if applicable)

If applicable, capture the details of your Skype for Business deployment by using the sample table below. If you haven’t deployed Skype for Business on-premises, skip this section.

Question Answer Comments
What versions of Lync or Skype for Business currently
are deployed on-premises?
Office Communications Server 2007 “R1”
Office Communications Server 2007 R2
Lync Server 2010
Lync Server 2013
Skype for Business Server 2015
Skype for Business Server 2019
Skype for Business Cloud Connector Edition
Is hybrid with Skype for Business Online configured? Yes
No
Is this environment hosted and managed by a third party?
If Yes, note the details in the Comments column.
Yes
No
What modalities and features are currently in use
today?
Instant Messaging and Presence (IM/P)
Meetings
Federation
Meeting Recording
Persistent Chat / Group Chat
Microsoft Audio Conferencing
     (formerly Dial in Conferencing) on your
     on-premises Lync Server or
     Skype for Business deployment
Third-party audio conferencing
     (Note the details in the Comments column)
Enterprise Voice using on-premises PSTN
     connectivity
Calling Plans (formerly PSTN calling) via
     Hybrid with Skype for Business Online
Which version(s) of Edge Server do you have deployed? Office Communications Server 2007 “R1”
Office Communications Server 2007 R2
Lync Server 2010
Lync Server 2013
Skype for Business Server 2015
Skype for Business Server 2019
Do you have Lync or Skype for Business Edge deployed
into more than one datacenter?
If Yes, note the details in the Comments column.
Yes
No
Select services that your Edge role provides today. External user access (corporate users)
Remote user access (anonymous external
     meeting participants)
Federation
Media relay
Which of the following voice calling features do you
currently have dependencies on?
Note any additional dependencies in the Comments
column.
Busy options
Call park
Call pickup or group call pickup
Common area phones, or “hot desking”
Response groups or hunt groups
Shared line appearance
Private line
Voicemail
Call via work
Emergency or information numbers
     (911, 811, 411)
Extension dialing
Auto Attendant
Subscriber access
Analog devices
Fax
Caller ID masking or altering
Location-based routing
Least-cost routing
Elevator phones

Networking and access to Office 365 services

Use the following table to capture your organization’s networking details and how your users are (or will be) connected to Office 365 services.

Question Answer Comments
How do (or how will) the users in scope for migration
access Teams when they’re in the office?
Select all that apply.
Routed NAT connection
Proxy server
Public Wi-Fi
Managed (not public) Wi-Fi
ExpressRoute (Microsoft peering)
If access to Office 365 is through a proxy server, is there
any way to bypass the proxy?
Yes
No
Is ExpressRoute being used today? Yes
No
No, but it’s being planned
Have you performed a Network Readiness Assessment?
For more information, see Network Readiness Assessment.
Yes
No
Are users required to use a VPN when connecting to
corporate resources remotely?
Yes
No
If a VPN is used, can Teams traffic be excluded from
the VPN to access Office 365 Services directly?
Yes
No
Does your network support QoS? Yes
No
Can you prioritize Teams audio and video traffic
to drive a high-quality experience?
Yes
No
Do all locations within a region have internet egress,
or is internet egress centralized for the entire region?
Regional access to the internet
Centralized access to the internet

Tip

To calculate the amount of bandwidth and other network requirements for your cloud voice deployment, depending your organization’s details and estimated usage, visit Network Planner in MyAdvisor.

Endpoints

Use the following table to capture the details of the clients and endpoints in use.

Question Answer Comments
What desktop OS are the users using? Windows XP
Windows 7
Windows 8
Windows 10
Mac (Specify the version in the Comments column.)
Other (Note the details in the Comments column.)
What version of Microsoft Office is deployed
to these devices?
Office 2003
Office 2007
Office 2010
Office 2013
Office 2016
Office for Mac 2011
Office for Mac 2016
Other (Note the details in the Comments column.)
Which Office deployment technology is in use
in your organization?
MSI
Click-to-Run
What are the allowed and supported mobile
platforms in use?
Select all that apply.
Windows
Mobile
iOS
Android
Other (Note the details in the Comments column.)
How are mobile devices provided?
Select all that apply.
Corporate devices
Bring your own device
What devices do users currently use to access
voice and conferencing services
(handsets, headsets, phones, video)?

Operations

Use the following table to capture the details of the operational aspects of your environment.

Question Answer Comments
What is your operations model for your Lync Server,
Skype for Business Server, or Office 365 deployment
today?
Can you outline the current support arrangement for
Lync Server, Skype for Business Server, or Office 365?
If you’re deploying to multiple countries or regions,
does each country/region have its own IT/telephony
staff to work with, or will this be managed centrally?
Regional operations and support
Centralized operations and support
Are you following the Call Quality Methodology? Yes
No
Have you assigned an individual or team to the
Quality Champion role for the collaboration platform
in use?
Yes
No
How do you monitor your Lync Server, Skype for
Business Server, or Office 365 deployment?
Do you experience call quality issues? Yes
No
How and when do you provide training to your
helpdesk on new services and capabilities?

Adoption and readiness

Use the following table and capture the current adoption and readiness state of your organization.

Question Answer Comments
What is your current active usage of
Skype for Business?
__ % total active users versus enabled users
How is your organization using
Skype for Business?
1:1 conversations
      IM
      Calling
      Sharing
Meetings
      Conferencing
      Sharing
      Calling
Does your organization have a User Adoption
and Change Management team?
Yes
No
How do you currently measure success for technology
rollouts like Skype for Business?
What percentage of your user base would you say has
adopted Skype for Business?
What is user sentiment around Skype for Business? Good
Neutral
Bad
Which of the following best describes the rollout
strategy used for your Skype for Business
deployment?
Broad reach: Email campaign with
     links to training
Expanded: Broad reach plus a variety
     of awareness campaigns (posters,
     events, champions) and training
     (videos, user guides, in-person)
Tailored: Expanded, plus targeted
     messaging and training by persona
Other
     (Note the details in the Comments column.)

Decision point
  • Who will be responsible for completing an environment assessment?

Next step
  • Document the results of the environment assessment.

After you evaluate your environment, proceed to the next step: Prepare your network.