Discovery questionnaire - Evaluate your environment

1/12/2021
11 minutes to read
Applies to:

Microsoft Teams

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
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 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 365

Do user UPNs match their primary SMTP address? Yes
No
Inconsistently

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 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 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 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, 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, other

Is 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, other

Is 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, other

Is Microsoft 365 or 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

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, 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, other
Is 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, other
Is 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, other
Is Microsoft 365 or 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
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
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

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 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

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

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 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
No

Is ExpressRoute being used today? Yes
No
No, but it's being planned

Have you performed a 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 Microsoft 365 or 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

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 No
Is ExpressRoute being used today?	Yes No No, but it's being planned
Have you performed a 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 Microsoft 365 or 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

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-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)?

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-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, 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 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, Microsoft 365, 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?

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 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, Microsoft 365, 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.)

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.)