3. ChrisHeaven.com
ENTERPRISE Annual Cycle
ITCq Report
Workshop
IT Infrastructure
Audit Workshop
SWOT Analysis
Workshop
Virtual IT Dep.
Evaluation
Workshop
Business Model
Workshop
Industry
Analysis
Research
Workshop
IT Planning
Session
Operational
Planning
Session
Project Portfolio
Planning
Session
Key Annual Pr.
Visualization
Workshops
Development
Roadmap +
Quarterly plan
Operational IT
Plan creation
Project Portfolio
Plan Creation
Finalize the
Roadmap +
Quarterly Plan
Finalize the
Operational Plan
Finalize the
Project Portfolio
Plan
vCIO
Governance
Plan
Documentation,
Distribution
Annual
Planning
Project
Workshops
Plan
Creation
Finalization
Documentation
and Distribution
Annual
Preparation
Individual service line item
Part of a process
Week 1. Week 2. Week 3. Week 4.
4. ChrisHeaven.com
The annual IT Strategy Planning
Process is the core element of
success with technology. The
process uses special business
opportunity and bottleneck
discovery methods to prepare a
detailed technology plan that
stands as the cornerstone of
execution during the year.
IT Strategy Planning Process
ITCq Report
Workshop
IT Planning
Session
Key Annual Pr.
Visualization
Workshops
Development
Roadmap +
Quarterly plan
Finalize the
Roadmap +
Quarterly Plan
vCIO
Governance
Plan
Documentation,
Distribution
Discovery Draft Plan
2-3 Key Project
Visualization
Detailed Plan Confirmation
Formal Annual and
Quarterly Plan
Formal Annual Plan
Roles, Execution First Quarterly Plan
5. ChrisHeaven.com
During annual planning it is critical to
visualize the initiatives that will shape the
year's development activities. We need to
figure out why we want these activities and
what we expect they’ll accomplish. This is
where great team collaboration can shine -
when the team can express their goal, align
on strategy and get invested.
Key Annual Project Visualization Workshops
ITCq Report
Workshop
IT Planning
Session
Key Annual Pr.
Visualization
Workshops
Development
Roadmap +
Quarterly plan
Finalize the
Roadmap +
Quarterly Plan
vCIO
Governance
Plan
Documentation,
Distribution
Discovery Draft Plan
2-3 Key Project
Visualization
Detailed Plan Confirmation
Formal Annual and
Quarterly Plan
Formal Annual Plan
6. ChrisHeaven.com
SWOT analysis is a classic Business Strategy
creation tool. Using it in an IT context can reveal
many business opportunities that can be
exploited during the IT Planning Process, as well
as bring to light potential threats. This proactive
process makes issues more manageable,
improvements more evident, resulting in
competitive advantages.
SWOT Analysis Workshop
SWOT Analysis
Workshop
IT Planning
Session
Draft PlanWorkshop
7. ChrisHeaven.com
The technical assessment is a crucial
element of the planning, since so much can
change over a year - devices, applications,
even people come and go. Reviews of the
technical infrastructure such as end user
devices, servers, network devices,
documentation, performance, warranties and
all related applications are a preventative
maintenance duty every company should
conduct regularly.
IT Infrastructure Audit Workshop
IT Infrastructure
Audit Workshop
IT Planning
Session
Draft PlanWorkshop
Network
assessment
8. ChrisHeaven.com
The "Virtual IT Department" of the
company can consist of 50 or more
application providers, service providers,
vendors and third party companies. It’s
important to categorize different
participants and evaluate their
performance regularly. With this evaluation
we can decide whom we can dismiss,
change, or negotiate for a better price or
develop a more strategic relationship.
Virtual IT Department Evaluation Workshop
Virtual IT Dep.
Evaluation
Workshop
IT Planning
Session
Draft Plan
Virtual IT Department
Discovery
9. ChrisHeaven.com
The IT Operational Plan is an extension
of the IT Development Roadmap
Process. The roadmap is a generalized
spreadsheet of the goals, projects and
responsibilities regarding the initiatives
needed for the IT strategy. The IT
Operational Plan gives more detail on
the Project level such as description,
benefits and budget.
IT Operational Planning Process
Operational
Planning
Session
Operational IT
Plan creation
Finalize the
Operational Plan
Documentation,
Distribution
Formal Annual PlanExtended Draft Plan Detailed Plan Confirmation
10. ChrisHeaven.com
The industry technology review
brings input to the planning process
from the competitive perspective.
The team gets together for an
industry review and the CHC
consultant looks for potential
applications and best practices for
solving problems in the current, or
related industries. This helps the
company take advantage of
applications and best practices not
yet well known, which can give
competitive advantage.
Industry Analysis Research Workshop
Industry
Analysis
Research
Workshop
IT Planning
Session
Draft PlanVertical based challenges
and solutions
11. ChrisHeaven.com
Business Model Workshops are an
innovative and very engaging way
to address current complex
business issues easily. Their goal is
to provide a clear picture of the
organization’s main business
model, including how it changes
and evolves, and give some
stability and nurture dynamic
management. It’s also usually the
favourite exercise of our members.
Business Model Workshop
Business Model
Workshop
IT Planning
Session
Draft PlanBusiness Model Discovery
12. ChrisHeaven.com
IT Project Portfolio Planning Process is
an extension of the IT Operational
Process. The Operational Plan is a
detailed project portfolio document
giving more detail on the Project level
such as description, benefits, budget
and so on. The Portfolio plan has more
explanation, details and more precise
budget estimation for the major
initiatives. It goes one step deeper into
the details.
IT Project Portfolio Planning Process
Project Portfolio
Planning
Session
Project Portfolio
Plan Creation
Finalize the
Project Portfolio
Plan
Documentation,
Distribution
Formal Annual PlanExtended Draft Plan Detailed Plan Confirmation
14. ChrisHeaven.com
Quarterly Cycle - Enterprise
Quarterly
Planning
Session
Project Portfolio
Review
Key Stakeholder
Interviews
Project
Specification,
Delegation
Sess.
Key Associates
Surveys
Project Steering
Committee M.
Project
Visualization
Workshops
Solution
Selection
Workshops
Key Project
Review
Workshop
Process
Improvement
Workshop
Productivity
Improvement
Workshop
Way To Go
Award
Business
Opportunity
Workshop
Key Stakeholder
Calls
Department
Reviews
Team
Development
Quarterly
Planning
Project
Workshops
Project
Reviews
Individual service line item
Part of a process
Week 1. Week 2. Week 3. Week 4.
15. ChrisHeaven.com
It is important to regularly review the
project portfolio. We can reenergize
slowed down projects, eliminate
roadblocks quickly and have a better
understanding where our
development initiatives are.
Project Portfolio Review
Progress Report
Session
Project Portfolio
Review
Check Projects Monthly review the progress
of the quarterly plan
16. ChrisHeaven.com
Organizations have many processes
that can determine success or
failure. Regular review of a critical
processes is important to keep them
automated and streamlined. These
team events promote best practices
and tools for the teams to improve
their processes continually.
Process Improvement Workshop
Process
Improvement
Workshop
Quarterly
Planning
Session
Quarterly
Planning
Session
Next QPS
10 point results
WorkshopPrevious QPS
17. ChrisHeaven.com
A critical role of executing is a Quarterly
Execution Plan. Breaking down the annual
and operational plan to specific deliverables
for the next quarter makes the team
accountable and more efficient. Giving
focus to your people will enable them to
execute the strategic initiatives within their
day-to-day operational whirlwind.
Quarterly Planning Process
Quarterly
Planning
Session
Project Portfolio
Review
Project
Specification,
Delegation
Sess.
Process
Improvement
Workshop
Key Stakeholder
Calls
Check Projects
Check Departments
Operational Efficiency
Review, close Previous quarter
and open, plan the next quarter
Help to kickoff projects
Next Quarterly Plan
Previous Quarterly Plan
18. ChrisHeaven.com
In most cases, for smaller projects the
internal team can execute all the
necessary tasks, but they may not have
the time or expertise to plan projects
through to flawless execution. During
the process the necessary information
will be ready and be delegated to the
proper internal resource for execution.
Project Specification and Delegation Session
Quarterly
Planning
Session
Project
Specification,
Delegation
Sess.
Review, close Previous quarter
and open, plan the next quarter
Help to kickoff projects
Project Task list
19. ChrisHeaven.com
The Project Steering Committee is a
team inside the organization responsible
for the complete Project Portfolio
success. We set guidelines, organize and
facilitate meetings and follow up on
corrective action items. This ensures that
IT related projects are going to have
more momentum, buy-in and overall
success.
Project Steering Committee Meeting
Progress Report
Session
Project Steering
Committee M.
Project portfolio review
with the Steering Committee
Monthly review the progress
of the quarterly plan
Collect the project
reviews prior the session
20. ChrisHeaven.com
We have to gather information
from the key stakeholders: COO,
CFO, Marketing VP, Sales VPs
etc.. The people leading the
company need a platform with
the CHC consultant to review
their needs, undiscovered
opportunities, and ongoing
projects under their direction.
Key Stakeholder Interviews
Key Stakeholder
Interviews
Quarterly
Planning
Session
21. ChrisHeaven.com
Productivity and operational
excellence are the surest
foundations for maintaining a healthy
bottom line. Reviewing the
productivity of teams and individuals,
the state of communication and
tools used is essential for becoming
leaner, faster and staying ahead of
the competition.
Productivity Improvement Workshop
Productivity
Improvement
Workshop
Quarterly
Planning
Session
Quarterly
Planning
Session
Next QPS
10 point results
WorkshopPrevious QPS
22. ChrisHeaven.com
During the Quarterly planning we propose
a candidate for the “Way to Go Award” for
extraordinary achievement. It can be for
proactive work, valuable research,
leadership or any other value we would
like to highlight.
Way To Go Award
Way To Go
Award
Quarterly
Planning
Session
Nomination Preparation
Communication
23. ChrisHeaven.com
During the quarterly it is critical to visualize
the initiatives that will shape the year's
development activities. We need to figure out
why we want these activities to be and what
we expect they’ll accomplish. These can be
projects already in the plan that need to be
made more actionable or urgent, or brand
new projects with urgent priority. This is
where great team collaboration can shine -
when the team can express their goal, align
on strategy and get invested.
Project Visualization Workshops
Project
Visualization
Workshops
Quarterly
Planning
Session
Review, close Previous quarter
and open, plan the next quarter
Help to kickoff projects
Updated Quarterly Plan
Solution
Selection
Workshops
Solution decision
24. ChrisHeaven.com
There are major projects for the company
that need more attention from the CHC
consultant. A monthly project review meeting
with the project team can increase the
formality, accountability, clarity and the
success factor of all projects. Even in cases
where the CHC consultant isn’t the project
manager it’s good to meet for a review. We
recommend 2-3 project reviews every month.
Key Project Review Workshop
Key Project
Review
Workshop
Project Team
Weekly Huddle
Project Steering
Committee M.
Project Portfolio
Review
Check Projects with
the Committee
Check Projects with
the Project Leaders
Check Projects with the
Project Team
In depth review
with the Team Monthly Key Project
Review Memo
25. ChrisHeaven.com
Gathering information with a
comprehensive scope on the
company is critical to be able to
address bottlenecks, inefficient
processes, missing information and
other hurdles. These regular surveys
collect intelligence from the users
and key vendors that add detail and
perspective to the quarterly plans.
Key Associates Survey + analysis
Key Associates
Surveys
Quarterly
Planning
Session
26. ChrisHeaven.com
Organizations often have way more
business opportunities – "low hanging
fruit" - than they realize. There’s a
wealth of improvements easily
implemented in areas like customer
service, the value proposition and
many competitive factors, such as
client communication, sales, and
marketing related opportunities. Using
this unique method uncovers these
opportunities quickly.
Business Opportunity Workshop
Business
Opportunity
Workshop
Quarterly
Planning
Session
Quarterly
Planning
Session
Next QPS
10 point results
WorkshopPrevious QPS
27. ChrisHeaven.com
Many times we are able to scope
out a project, and we have the
visualization, but we haven’t
chosen a specific
product/solution/service. This is a
research exercise to ensure we
choose the right direction and stay
aligned as a team.
Solution Selection Workshops
Solution
Selection
Workshops
Decision making 10 points
decision making sheet
Project
Visualization
Workshops
Help to kickoff projects
29. ChrisHeaven.com
ENTERPRISE Monthly/Weekly Cycle
Mangement
Coaching
Session
Progress Report
Session
Project Portfolio
Review
Project Steering
Committee M.
Key Project
Review
Workshop
Individual service line item
Part of a process
CEO Weekly
Huddle
Project Team
Weekly Huddle
IT Team Weekly
Huddle
CEO Weekly
Huddle
Project Team
Weekly Huddle
IT Team Weekly
Huddle
CEO Weekly
Huddle
Project Team
Weekly Huddle
IT Team Weekly
Huddle
Week 1. Week 2. Week 3. Week 4.
30. ChrisHeaven.com
Weekly huddle is an alignment
session among the CEO and the
vCIO. Mostly the CEO is involved
on the key decision makings
during the project life cycles. He
might not be part of the project
but we have to make sure there
are clear communication lines
with weekly huddles to help the
execution and keep the CEO
informed.
CEO Weekly Huddle
CEO Weekly
Huddle
CEO Weekly
Huddle
CEO Weekly
Huddle
Current Team meetingPrevious meeting Next meeting
31. ChrisHeaven.com
It is important to regularly review the
project portfolio. We can reenergize
slowed down projects, eliminate
roadblocks quickly and have a better
understanding where our
development initiatives are.
Project Portfolio Review
Progress Report
Session
Project Portfolio
Review
Check Projects Monthly review the progress
of the quarterly plan
32. ChrisHeaven.com
Quick progress reports are
great for keeping a high but still
stable pace of execution and
raise the sense of priority for
particular projects. Like driving
in the city, checking for
obstacles and reviewing the
progress of the quarterly plan
execution will always promote
success.
Progress Report Session
Progress Report
Session
Project Portfolio
Review
Check Projects Review the progress
of the quarterly plan Updated Quarterly Plan
33. ChrisHeaven.com
Executives are often need the most
coaching and support with technology.
Disruptive technologies are emerging from
all directions and can influence strategies
or even overall management of the
organization. These events help keep
executives personally ahead of the curve
and more business-technology savvy.
Management Coaching Session
Mangement
Coaching
Session
Mangement
Coaching
Session
Mangement
Coaching
Session
Previous Session Current Session Next Session
34. ChrisHeaven.com
The IT team is responsible for the
day-to-day IT operation,
maintenance, support and for
development projects. The
weekly huddles help them focus
and stay aligned and
accountable. It also gives
management necessary visibility
and control over the IT team.
IT Team Weekly Huddle
IT Team Weekly
Huddle
IT Team Weekly
Huddle
IT Team Weekly
Huddle
Current Team meetingPrevious meeting Next meeting
35. ChrisHeaven.com
The Project Steering Committee is a
team inside the organization responsible
for the complete Project Portfolio
success. We set guidelines, organize and
facilitate meetings and follow up on
corrective action items. This ensures that
IT related projects are going to have
more momentum, buy-in and overall
success.
Project Steering Committee Meeting
Progress Report
Session
Project Steering
Committee M.
Project portfolio review
with the Steering Committee
Monthly review the progress
of the quarterly plan
Collect the project
reviews prior the session
36. ChrisHeaven.com
Weekly Project huddle is a
placeholder meeting we can use
to energize project teams lacking
focus or cadence, or to assist in
critical stages like starting off,
milestones or closing. The quick-
online sessions help to
quarterback the project leaders
and generate some momentum
when needed.
Project Team Weekly Huddle
Project Team
Weekly Huddle
Current Team meetingPrevious meeting Next meeting
Project Team
Weekly Huddle
Project Team
Weekly Huddle
37. ChrisHeaven.com
There are major projects for the company
that need more attention from the CHC
consultant. A monthly project review meeting
with the project team can increase the
formality, accountability, clarity and the
success factor of all projects. Even in cases
where the CHC consultant isn’t the project
manager it’s good to meet for a review. We
recommend 2-3 project reviews every month.
Key Project Review Workshop
Key Project
Review
Workshop
Project Team
Weekly Huddle
Project Steering
Committee M.
Project Portfolio
Review
Check Projects with
the Committee
Check Projects with
the Project Leaders
Check Projects with the
Project Team
In depth review
with the Team Monthly Key Project
Review Memo