Discovery questionnaire - Evaluate your environment
The following set of tables list questions that will help you evaluate your environment before upgrading to Teams:
- Microsoft 365 or Office 365 organization details
- Existing collaboration platform summary
- Collaboration platform deployment details
- Networking and access to Microsoft 365 or Office 365 services
- Endpoints
- Operations
- Adoption and readiness
Microsoft 365 or Office 365 organization details
We highly recommend that you have an active Microsoft 365 or Office 365 organization as you work with the questionnaire. If you haven't activated or configured a Microsoft 365 or Office 365 organization yet, see Plan your setup of Microsoft 365 for business.
Use the following table to capture information about the Microsoft 365 or Office 365 organization.
Question Answer Comments Note the production Microsoft 365 or Office 365 organization
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 Microsoft 365 or Office 365 Multitenant or
Dedicated?Multitenant
DedicatedWhich 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
OtherWhat license level is enabled for Skype for
Business Online users?E1/G1
E2/G2
E3/G3
E4/G4 E5
StandaloneThe 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 2016What 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
NoIf 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 Microsoft 365 or Office 365
tenant, is the SMTP/SIP domain of your
targeted users associated with the tenant?N/A – No Microsoft 365 or Office 365
tenant in place
No, users' SMTP/SIP
domain isn't associated
with any tenants in
Microsoft 365 or Office 365
Yes, users' SMTP/SIP
domain is associated
with an existing tenant
in Microsoft 365 or Office 365Do 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
NoIs 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, Microsoft 365 or Office 365
Yes, hybrid (with Microsoft 365 or Office 365)
Yes, on-premises
Yes, online, dedicated
(Microsoft)
Yes, hosted, dedicated
(third party)
Yes, hosted, shared (third party)
No, otherIs Exchange deployed?
For on-premises and hybrid deployments, make sure
you note the version and CU details in the Comments
column.Yes, Microsoft 365 or Office 365
Yes, hybrid (with Microsoft 365 or Office 365)
Yes, on-premises
Yes, online, dedicated
(Microsoft)
Yes, hosted, dedicated
(third party)
Yes, hosted, shared
(third party)
No, otherIs SharePoint deployed?
For on-premises and hybrid deployments, make sure
you note the version and CU details in the Comments
column.Yes, Microsoft 365 or Office 365
Yes, hybrid (with Microsoft 365 or Office 365)
Yes, on-premises
Yes, online, dedicated
(Microsoft)
Yes, hosted, dedicated
(third party)
Yes, hosted, shared
(third party)
No, otherIs Microsoft 365 or Office 365 OneDrive for Business deployed? Yes
NoDo 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
NoWhat 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
Dropbox, Box, ShareFile, Google Drive, Egnyte
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
NoWhich Teams clients are in use? Web
Windows
Mac
iOS
Android
Windows MobileWho 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 QueuesHave you specifically blocked any Skype for
Business Online capabilities?
If Yes, note the details in the Comments column.Yes
NoWhat 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 EditionIs hybrid with Skype for Business Online configured? Yes
NoIs this environment hosted and managed by a third party?
If Yes, note the details in the Comments column.Yes
NoWhat 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 OnlineWhich 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 2019Do you have Lync or Skype for Business Edge deployed
into more than one datacenter?
If Yes, note the details in the Comments column.Yes
NoSelect services that your Edge role provides today. External user access (corporate users)
Remote user access (anonymous external
meeting participants)
Federation
Media relayWhich 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 Microsoft 365 or Office 365 services
Use the following table to capture your organization's networking details and how your users are (or will be) connected to Microsoft 365 or 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 Microsoft 365 or Office 365 is through a proxy server, is there
any way to bypass the proxy?Yes
NoIs ExpressRoute being used today? Yes
No
No, but it's being plannedHave you performed a Network Readiness Assessment? Yes
NoAre users required to use a VPN when connecting to
corporate resources remotely?Yes
NoIf a VPN is used, can Teams traffic be excluded from
the VPN to access Microsoft 365 or Office 365 Services directly?Yes
NoDoes your network support QoS? Yes
NoCan you prioritize Teams audio and video traffic
to drive a high-quality experience?Yes
NoDo 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
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.)
Linux (Specify the distribution 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-RunWhat 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 deviceWhat 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, Microsoft 365, or Office 365 deployment
today?Can you outline the current support arrangement for
Lync Server, Skype for Business Server, Microsoft 365, 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 supportAre you following the Call Quality Methodology? Yes
NoHave you assigned an individual or team to the
Quality Champion role for the collaboration platform
in use?Yes
NoHow do you monitor your Lync Server, Skype for
Business Server, Microsoft 365, or Office 365 deployment?Do you experience call quality issues? Yes
NoHow 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
CallingDoes your organization have a User Adoption
and Change Management team?Yes
NoHow 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
BadWhich 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.)
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