Adam Ochs presented at the March 2018 Sharepoint Fest D.C. on developing an Office 365 roadmap. He discussed that an Office 365 roadmap should communicate an organization's strategy and path for productivity technologies over major steps. The seven steps to building a successful roadmap included: 1) defining goals and strategy, 2) identifying current user issues, 3) grouping issues into problem areas, 4) evaluating Office 365 technologies, 5) creating the roadmap, 6) developing success criteria, and 7) regularly revisiting and updating the roadmap. Developing a comprehensive roadmap is important for strategic planning and communicating an organization's path for Office 365.

1. P r e s e n t e r : A d a m O c h s
D a t e : M a r c h 2 0 1 8
S h a r e p o i n t F e s t D . C .
Developing your own Office
365 Roadmap

2. 2
Introduction
In this session we will be doing the following!
• Discussing what goes into an Office 365 Roadmap
• Going over my recommended steps to be successful
• Discussing tools and options that are available to you
• Looking at real life examples of roadmaps in flight for some of my (anonymous) Enterprise
Customers
• Interaction and Q&A (How this can be applied for your organization)

3. 3
Why is developing a comprehensive roadmap
important?

4. 4
What a good Office 365 roadmap is!
• A high-level plan, defining an overarching strategic objective of the company in
IT and business, while capturing the major steps planned for achieving that
objective.
– A plan with a purpose
• A communication tool that helps communicate the companies path and
strategy in productivity technologies.

5. 5
What an Office 365 Roadmap should not be!!
• It is not a backlog of work!!!
• It is not a list of features!!!!
• It is not a project management tracker!!!!

6. 6
The Seven Steps to building a successful and
comprehensive Roadmap
• 1. Start by thinking about your organizations goals and strategy
• 2. What are your current user issues?
• 3. Put those issues into addressable problem areas
• 4. Evaluate your arsenal of Office 365 technologies against the first three steps
• 5. Create a Roadmap
• 6. Develop Success Criteria
• 7. Plan to regularly revisit points 5 and 6 at least twice a year.

7. 7
Step 1 – Goals and Strategy - The Buzzwords
All the time I have people that come to me and say “My boss said we need to
be/do ……”
• “Collaborative”
• “Agile”
• “Secure”
• “Cloud”
• “Immersive”

8. 8
Step 1 – Goals and Strategy
• These should be Big Picture items, don’t get lost in the details! That is for further down the line
• These should have definition and meaning, not just the buzzwords from the last slide.
• This should be the broad brushstrokes that setup your picture, not the individual details.
• Ex – We need to increase the ease of access for our userbase, allowing them to work on the go and
remotely more often as is more common in the modern workforce.
• Ex – We need to move away from our legacy on-prem servers, and into the cloud, reducing infrastructure
cost and making scaling more easy.
• Ex – We need to ensure our files that are moved into the cloud have classification protection, and do not
compromise our company while accessed on the fly.
• What else!?!?

9. 9
Step 2 – What are your current issues
• Do you have any Business Intelligence (This also can steer you towards power
BI)
• Do you have metrics from your helpdesk?
• INTERVIEW the people on the frontlines. This means both your users, and
your helpdesk staff.
– So often I see VP’s and CTO’s that get lost in the clouds on vision, and maybe miss
their current needs

10. 10
Step 2 – What are your current issues
• These should be the problems facing your users today that you can help to address/solve. *
• Do not worry about IF you have the solution on the tip of your tongue here, this is to help you
roadmap, we try to solve this further down the line!!!
• Ex. My sales staff are on the road, and struggle to always VPN back into work to get the
needed files from on-prem files shares
• Ex. Not all users are on up to date versions of office, the versions date to when their computers
were created.
• Ex. We have no centralized chat program, our only communication is in person or email.
*This will give you quick wins and develop “Champions” both of which can be huge towards your overall
success

11. 11
Step 3 –Put those issues into Addressable Problem
Areas
• Here is where the rubber starts to meet the road, you go from data
gathering/dreaming, to actually starting to find solutions to address your
problems.
• Do not yet worry about specific technologies that solve these problems, that is
the next step, here focus on quantifying the problems you identified in step 2,
and the goals you identified into step 1, into groups together that you can then
work towards.
Problems Goals
Actionable
Items

12. 12
Step 3 – Addressable Problems
• Previous Goal 1 – “We need to move away from our legacy on-prem servers, and into the cloud, reducing
infrastructure cost and making scaling more easy.”
• Previous Goal 2 – “We need to increase the ease of access for our userbase, allowing them to work on
the go and remotely more often as is more common in the modern workforce.”
• Previous Issue 1 – “My sales staff are on the road, and struggle to always VPN back into work to get the
needed files from on-prem files shares”
• Problem that needs addressing – We need to move file share system off of legacy servers, and into a file
system that exists in the cloud.

13. It is helpful to think about what is going to
deliver the most value to your employees
first! Some of the things you might think
about doing right away, might not deliver
immediate visible value.
It may be worth focusing on getting a few
quick wins and return on investment to
build excitement going into the cloud.

14. 14
Step 4 – Evaluate Office 365 Technologies
• This is the first time you really have a barrier of entry that you have not had previously! Every IT and
Business leader can put together the first three steps right now.
– This is why so many of the IT professionals here have jobs!
– You can do this too! Lets setup the basic steps to increase your knowledge
• There are tons of great resources out there for you to consume.
– Y’all here are already ahead of the game, most people I talk to do not attend community events and leverage the
knowledge that exists there.
• Some of the resources I strongly encourage you to use:
– Follow community members on Twitter, blogs, linkedin etc. (Most of the new updates I get are from here)
– Blogs.office.com (atleast once a month)
– Have you looked at the official O365 Product Roadmap - https://products.office.com/en-us/business/office-365-roadmap?filters=
– Take advantage of the free webinars and events Microsoft puts on
– TONS of free material, and tools (more on that later)

15. 15
Step 4 – Evaluate O365 Technologies
• Take the problem areas you created in Step 3, and see if they correlate to O365 technologies.
• Remember you don’t need to have all the details right now!!!!!
– Planning out the specifics of each project is a separate (And very important) step of that
project
– Your companies Office 365 Roadmap is “A plan with a purpose” not a project list.
• Ex. Some will be obvious answers:
– We need a chat client – Hey look at that Skype and Teams fits the bill!
• Ex. Some will be not so obvious:
– A file share migration will include OneDrive and SharePoint…. But what about teams? What about
groups? What goes where?
• These are questions that are flushed out at a project level, for our Roadmap we know we want a File Share
Migration, and know it is going to use some combination of technologies in O365, that is good enough for now.

16. 16
Step 5 –Create your Roadmap
• The hard work is done!!!!! You have done everything you need to have the
content for the roadmap, it is now taking the conclusions from step 1-4, and
organizing them into a plan.
– It will not always be smooth sailing!!!
– It can (and will) change
There are some overall themes I have found to be the
most sticky and successful, we always hit up these
themes when addressing our first road mapping calls.

17. 17
Step 5 – Creating your Roadmap - Themes
• If you are starting off in O365 you WILL need to have training for admins,
helpdesk staff etc. They need to learn the new system, and what to do.
• I strongly recommend some sort of designed end user training, ideally targeted.
• Executive buy-in and sponsorship is a must have. You will be making big
changes that needs to have the goals of the organization aligned.
• Don’t feel like you need the full picture during this roadmap, we are wanting to
put together a basic outline of the next few quarters working towards the big
picture goals.
• As you mature in the product, you will change this roadmap again and again,
that is ok, it should be your “Plan with a Purpose”

18. 18
Step 6 – Develop Success Criteria
• You have your Roadmap now what!?!?!?
• Your success criteria should be measurable objects that you can clearly
quantify, we are no longer up in the sky, we are deliberate and precise!!
• Do these success criteria allow you to confidently say you have both:
– Addressed current issues from step 2
– Addressed overall goals from step 1
– If not, you either need more specific success criteria, or to redo steps 3 & 4!!!!!

19. 19
Step 6 –Success Criteria
From - https://kartickapur.wordpress.com/

20. 20
Step 6 – Success Criteria
• Ex. We will consider the Chat functionality rolled out, when we have 80% of our
employees deployed onto Skype for Business or Teams.
– We can use metrics from the Office 365 reports to see daily usage
• Ex. We will consider the file share migration complete, when we are able to
successfully decommission our on-prem file shares
– Note that I do not have to say for this to be complete (ALL Issues of use are
resolved), that is an IT support issue, we want to focus on the data move and end
user education

21. 21
Step 7 – Revisit 5 and 6!!!
• In order to do step 5, you really need to be confident in your answers from 1-4.
I would recommend re-doing the entire exercise at least once a year.
• I would recommend doing steps 5 and 6 once a quarter.

22. 22
What is the office 365 Secure Score?
• https://securescore.office.com
• First and foremost this is Brilliant Marketing
• A great idea for roadmap projects
• A way to show improvement and progress
• Account for third party improvements
17

23. 23
Fast Track Program for Office 365
• To Enroll in FastTrack you must be a company of 250+ users
• Available for many products inside of the suite, Exchange Migration,
SharePoint Migration, OneDrive Migration, Intune Deployment, etc
• Even if you are not 250 users, there are WONDERFUL resources built around
adoption for this program that you can get for free!!!!
• https://devfasttrackv4storage.blob.core.windows.net/marketing/en-
us/resources/Office_365_Adoption_Guide.pdf
– ^^^^^^ SAVE THIS LINK!!!! ^^^^^^^

24. 24
IT Roadmap planning tool
• https://techcommunity.microsoft.com/t5/IT-
Resources-Training-Blog/Introducing-the-
IT-Roadmap-planning-tool-preview/ba-
p/114957
• Lightweight tool to help plan for projects
coming up
• Free to use, great to augment your own
work.

25. 0-6 Months
October 2017 – March 2018
•Advanced Threat Protection Purchased and Implementation (December 2017)
•Implement Safe Links for company email
•Implement Safe Attachments for company email.
•Implementation of Transport Rules to ‘stamp’ [External] on external emails sent to HGV employees. (December 2017)
•Optional Outbound Message Encryption based on subject tag
•O365 Secure Score Initial Audit
•MultiFactor Authentication (MFA) enabled for Admin Accounts
•Admin account audit.
•Help Desk Support Training
•High-level troubleshooting, Basic Office 365 and Outlook tips
0-3 Months
Q4 2017
•OneDrive for Business
•Pilot (January 2017)
•Migration
•Implementation of security controls
•Client Sync Roll Out
•Admin Training
•Enduser Training
•Mobile Devices Management
•Purchase
•Scoping
•Pilot
•Security and controls
•Admin Training
•Evaluate suggested objectives for O365 Secure Score.
•Contract Renewal (March)
3-6 Months
Q1 2018
Green Completed | Yellow In Progress | Red Delayed or Cancelled

26. 6-18 Months
April 2018 – June 2018
December 2017
• Mobile Device Management Implementation
• Office Suite Training (ie. OneDrive for business, Outlook, etc.)
• Company Wide Roll Out
• Microsoft Teams Pilot
• Consultation sessions with pilot teams
• Security Controls review
• Exploration of new features and applications in Office 365.
6-9
Months
Q2 2018

27. 0-6 Months
October 2017 – March 2018
February 2018
• Continue Help Desk Support Training
•High-level troubleshooting, Basic Office 365 and Outlook tips
• User Email Address Change (February 28th) .
• OneDrive for Business
•Pilot & Migration (March 2018)
•Implementation of security controls
•Client Sync Roll Out (SCCM)
• Admin & Enduser Trainings
• Security: DLP and Encryption review and implementations
• Mobile Devices Management
•Scoping
• Evaluate suggested objectives for O365 Secure Score.
• Contract Renewal (March)
0-3 Months
Q1 2018
•Mobile Device Management Implementation
•Pilot
•Security and Control
•Admin Training
•Office Suite Training (ie. OneDrive for business, Outlook, etc.)
•Company Wide Roll Out
•Microsoft Teams Pilot
•Consultation sessions with pilot teams
•Security Controls review
3-6 Months
Q2 2018

28. 6-18 Months
April 2018 – June 2018
February 2018
• Azure AD Premium 2 Security Controls and
Auditing.
• Microsoft Teams rollout
6-12 Months
Q3 & Q4
2018

29. 0-6 Months
July 2017- December 2017
August 2017
• PowerBI Content Pack Setup
• FastTrack Analytics Setup
• Exchange Decommission (Carlstadt)
• Retention Policy Enabled (August 2017)
• PST re-ingestion Executing
• Rackspace Contract Renewal
• Rackspace On-site (October)
• Office 365 Groups End-User Trainings and Rollout to IT Department
• Microsoft Teams End-User Trainings and Rollout to IT Department
• File Storage Migration Initiating
• MDM (Intune) Exploration and Planning
0-3 Months
Q3 2017
• PST Re-ingestions Cleanup
• Exchange Decommission (Denver)
• File Storage Migration Planning (OneDrive/Sharepoint)
• Pilot U-Drive Replacement (OneDrive for Business)
• OneDrive for Business End-user Training
• MDM (Intune) Exploration and Planning
• OneNote End-user Training
• Microsoft Forms End-user Training Rollout
• Microsoft Stream Evaluation
• Office 365 Groups Evaluate Fit for company By Department
• Microsoft Teams Evaluate Fit for company By Department
• Azure Transformation
• Skype for Business Calling
• Airwatch Contract due?
3-6 Months
Q4 2017

30. 6-18 Months
August 2017
• File Storage Migration Executing
• MDM (Intune) Implementation Testing Phase
• U-Drive Replacement (OneDrive for Business) Conti.
• Azure Transformation
6-9 Months
Q1 2018
• File Storage Migration Clean Up
• Review of PowerBI Content Pack
• Review of FastTrack Analytics and findings
• MDM (Intune) Implementation Company Wide
• Azure Transformation
• Microsoft License Renewal (Augustish?)
9-12 Months
Q2 2018
• File Storage Migration Clean Up Pt. 2
• Office 2016 Suite Review, Planning, and Rollout
• Azure Transformation
12-18 Months
Q3 & Q4 2018

31. Timeline Overview
August 2017
0-3 3-6 6-9 9-12 12-18
Retention Policy
August 20117
Carlstadt Decom
September 2017
Contract End
October 2017
Denver Decom
PST Ingestion
End-User
Trainings
File Store
Migration
Content Pack &
Analytics Review
MDM (Intune)
Company wide
Deployment
2016 Office
Suite
Deployment
Content Pack &
Analytics Setup
September 2017
Rackspace Onsite
October 25th- 26th
Office 365 Groups &
Teams Exploration
Azure Transformation
MDM (Intune)
Pilot
File Storage
Migration
Planning

32. August 2017
Descriptions
• A full rollout of the Office ProPlus suite to all users still using legacy applications. With Pro Plus you
will be able to roll out this software in tandem to the software currently running on the users
computers. This will allow you to test out, and revert when necessary any applications or add-ins
that are not yet fully compatible with the Pro Plus suite. Microsoft offers the Office Deployment Tool
to facilitate this rollout. (Owner, Rough Dates, Specific Due dates)
Office Professional Plus
• Finalize the decommission of the Carlstadt exchange servers. Most of this work has been done,
we just wanted to ensure the item was captured in your roadmap as it relates to the project as a
whole.
Exchange Decommission Carlstadt
• Finalize the move of all users still left on Denver to O365, or removal. Once all users are removed,
analyze any remaining traffic still traveling through Denver and address accordingly. Once that has
been done we can begin the process of removing all remaining mailboxes, and formalizing the
decommission, leaving just the 2016 hybrid server in the on-premises forest.
Exchange Decommission Denver

33. August 2017
Descriptions
• company Has been exploring the idea of utilizing SharePoint online for collaboration and file storage. We
primarily see this coming into play when we are tackling the file storage problem, as group/shared
storage will end up being encased in SharePoint document libraries. The potential for growth in this
product is huge however. Several of our customers have very robust fully deployed SPO systems to
handle collaboration both internally and externally. That scope has not yet been decided inside of
company, but we see this as the first step towards utilization.
SharePoint
• A PowerBI Content Pack extension to be applied to the company Tenant. This will give increased insight
into adoption and usage across the O365 platform.
O365 Content Pack
• Recently the Microsoft FastTrack program has gotten a facelift that makes it useable and rewarding for
company. Rather than an initial sales tool, the FastTrack program now is designed around enhancing
O365 through product adoption of resources not fully utilized. We see the FastTrack team as a good
resource for us to leverage during the migration of legacy content from your file stores into OneDrive and
SharePoint.
Microsoft FastTrack Integration

34. August 2017
Descriptions
• Take all legacy PST files as well as Enterprise Vault archives and re-inject them into the existing O365
services. To do old PST files, Al will continue to leverage the Azure PST ingestion service. For Enterprise
vault, company is currently engaged with the vendor to figure out the best solution, which most likely will
result in additional PST files to re-ingest into O365. Based on the feedback from the vendor we may
advise looking towards the hard drive re-ingestion rather than the online Azure service.
Archives and PST Ingestion
• One major project that company wants to undertake is the migration of legacy file storage solutions into
the cloud. This is a large project that will have a broad scope. Old file storage solutions need to be
investigated and determined what needs to be migrated. This can be owned by IT, or project managed
down to various business owners. Once the scope has been defined, we plan on working with the
FastTrack team to migrate the content up into the cloud.
File Storage Migration
• Many of the products and options listed in this roadmap will require trainings of end users, admins, or
both. Rackspace plans to fully support these efforts with trainings where needed, and will make not of
them on the roadmap. Additionally on-site trainings are an option and possibility should the need arise.
Trainings

35. August 2017
Descriptions
• company has started in small scope leveraging groups and teams. Over the next several quarters we
would like to expand this scope to more areas of the business. At the time of the creation of this timeline,
Teams are yet to expand to external users, but that should be coming soon. Groups already have the
capability to work with external users. We recommend starting with individual business units or teams,
training and educating them on the functionality of groups/teams, and expanding from there.
O365 Groups/Teams
• Forms has reached public preview as of the writing of this timeline. It will soon pass into General
Availability. We see Forms as filling a specific need for company, and something that can be rolled out
with little investment of resources.
Office 365 Forms
• Intune and the EMS suite as a whole is something that company would like to explore and potentially
deploy. We will scope out this timeline to include dates/best guesses for a deployment, but a proper
scoping and investigation needs to occur before Intune is fully committed to. The Intune suite itself is a
full on mobile and application management platform which can reach across PC’s, Cell Phones, Macs (in
preview) to allow full management across the company.
Microsoft Intune

36. August 2017
Descriptions
• Continued rollout and adoption of OneDrive for Business (ODfB) to the business units. Primarily this can be
achived by making sure the OneDrive Next Generation Sync Client has been rolled out to all of the users.
Trainings will need to accompany this rollout to ensure end users know the preferred/proper way to consume/use
the client.
OneDrive for Business
• Microsoft will over time migrate all content that has been generated in O365 Video into stream for company.
There is no set timetable to accomplish this, but it is something that is going to happen over the next several
quarters. We will work with company to determine if we want to wait on Stream rollout for the migration, or start
the integration before-hand. Like Teams, Stream is built on the fundamental unit of O365 Groups, with the added
option of creating separate channels outside of groups for user consumption.
Microsoft Stream
• company will continue their deployment and rollout of servers into the Microsoft Azure environment. While this
does not directly fall into support with our team, it is in the same space and therefore we felt needed to be
included in the scoping and planning of services. We will likely introduce company to some of our colleagues
who do Managed Services of Azure in the same way our team supports O365 as the company project scope
grows and matures.
Microsoft Azure

37. August 2017
Descriptions
• Having now rolled out the new MRM policy to users, we look towards
the actions needed to enforce it. Post 8-31, we will remove the
retention hold sitting on all users mailboxes, and re-start the Managed
Folder Assistant. This will remove all data that has not been flagged
from the users mailboxes that is older than 3 years. Initial restoration in
the 30 days after the removal can be done through the recover deleted
items inside of outlook, simplifying this request for the helpdesk staff. If
the data is restored, it will go back until the mailbox until the next time
the Managed Folder Assistant runs (approximately once a week). After
the 30 days, we still have litigation hold enabled for all users, thus
capturing all data for discovery in the search in compliance center.
Once we are confident everything is good, we will remove the Litigation
hold on the user accounts that did not have it set previously.
Message Retention Policy

38. August 201738

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