it_The_First_100_Days_As_CIO_Storyboard_V3.pptx

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The First 100 Days As CIO
Partner with Info-Tech for success in this crucial period of transition.

The original concept of ‘the first 100 days’ was popularized by Franklin
Delano Roosevelt, who passed a battery of new legislation after taking
office as US president during the Great Depression. Now commonly
extended to the business world, the first 100 days of any executive role is
a critically important period for both the executive and the organization.
But not every new leader should follow FDR’s example of an action-first
approach. Instead, finding the right balance of listening and taking
action is the key to success during this transitional period. The type of the
organization and the mode that it’s in serves as the fulcrum that
determines where the point of perfect balance lies. An executive facing a
turnaround situation will want to focus on more action more quickly.
One facing a sustaining success situation or a realignment situation will
want to spend more time listening before taking action.
Brian Jackson,
Research Director, CIO
Info-Tech Research Group
The first 100 days refers to the 10 days before you start and the first
three months on the job.
ANALYST PERSPECTIVE

Resolution
Situation
Complication
Executive summary
• You’ve been promoted from within to the role of CIO.
• You’ve been hired externally to take on the role of CIO.
Studies show that two years after a new executive transition, as many as
half are regarded as failures or disappointments (McKinsey). First
impressions are hard to overcome, and a CIO’s first 100 days are heavily
weighted in terms of how others will assess their overall success. The best
way to approach this period is determined by both the size and the mode of
an organization.
• Work with Info-Tech to prepare a 100-day plan that will position you for success.
• Collaborate to collect the details needed to identify the right mode for your organization and determine how it will influence
your plan.
• Use Info-Tech’s diagnostic tools to align your vision with that of business executives and form a baseline for future
reference.
1. Foundational understanding must be
achieved before you start.
Hit the ground running before day one by
using company documents and initial
discussions to pin down the company’s type
and mode.
2. Listen before you act (usually).
In most situations, executives benefit from
listening to peers and staff before taking
action.
3. Identify quick wins early and often.
Fix problems as soon as you recognize them
to set the tone for your tenure.

The First 100 Days: Roadmap
C
0 30 60 90
-10
A. FOUNDATIONAL
PREPARATION
B. MANAGEMENT’S
EXPECTATIONS
C. ASSESSING THE IT TEAM
D. ASSESSING THE KEY STAKEHOLDERS
E. DELIVER
FIRST-
YEAR
PLAN
THE 100-DAY PLAN
CIO-CEO Alignment
CIO Business Vision Survey
IT M&G Diagnostic IT Staffing Assessment
INFO-TECH DIAGNOSTICS

Concierge service overview
Organize a call with your executive advisor every two weeks during your first 100 days. Info-Tech recommends completing our
diagnostics during this period. If you’re not able to do so, instead complete the alternative activities marked with (a).
Call 1 Call 2 Call 3 Call 4 Call 5 Call 6 Call 7
Activities
Before you start:
Day -10 to Day 1
1.1 Interview your
predecessor.
1.2 Learn the
corporate
structure.
1.3 Determine
STARS
mode.
1.4 Create a one-
page intro
sheet.
1.5 Update your
boss.
Day 0 to 15
2.1 Introduce
yourself to
your team.
2.2 Document
your sphere
of influence.
2.3 Complete a
competitor
array.
2.4 Complete the
CEO-CIO
Alignment
Program.
2.4(a) Agree on
what success
looks like with
the boss.
2.5 Inform team
of IT M&G
Framework.
Day 16 to 30
3.1 Determine the
team’s
cultural
archetype.
3.2 Create a
cultural
adjustment
plan.
3.3 Initiate IT
M&G
Diagnostic.
3.4 Conduct a
high-level
analysis of
current IT
capabilities.
3.4 Update your
boss.
Day 31 to 45
4.1 Inform
stakeholders
about CIO
Business
Vision survey.
4.2 Get feedback
on initial
assessments
from your
team.
4.3 Initiate CIO
Business
Vision survey.
4.3(a) Meet
stakeholders
and catalog
details.
Day 46 to 60
5.1 Inform the
team that you
plan to
conduct an IT
staffing
assessment.
5.2 Initiate the IT
Staffing
Assessment.
5.3 Quick wins:
Make
recommend-
ations based
on CIO
Business
Vision
Diagnostic/IT
M&G
Framework.
5.4 Update your
boss.
Day 61 to 75
6.1 Run a start,
stop, continue
exercise with
IT staff.
6.2 Make a
categorized
vendor list.
6.3 Determine the
alignment of
IT
commitments
with business
objectives.
Day 76 to 90
7.1 Finalize your
vision –
mission –
values
statement.
7.2 Quick Wins:
Make
recommend-
ations based
on IT Staffing
Assessment.
7.3 Create and
communicate
a post-100-
day plan.
7.4 Update your
boss.
Deliverables
Presentation
Deck Section A:
Foundational
Preparation
Presentation
Deck slides 9, 11-
13, 19-20, 29
Presentation
Deck slides 16,
17, 21
Presentation
Deck slides 30,
34
Presentation
Deck slides 24,
25, 26
Presentation
Deck slides 27,
42

CALL
Before you start: Day -10 to Day 1
1
First 100 Days As CIO

Interview your predecessor
Interviewing your predecessor can help identify the
organization’s mode and type.
Before reaching out to your predecessor, get a sense of
whether they were viewed as successful or not. Ask your
manager. If the predecessor remains within the organization
in a different role, understand your relationship with them
and how you'll be working together.
During the interview, make notes about follow-up questions
you'll ask others at the organization.
• Tell me about the team.
• Tell me about your challenges.
• Tell me about a major project your team worked on.
How did it go?
• Who/what has been helpful during your tenure?
• Who/what created barriers for you?
• What do your engagement surveys reveal?
• Tell me about your performance management
programs and issues.
• What mistakes would you avoid if you could lead
again?
• Why are you leaving?
• Could I reach out to you again in the future?
Ask these open-ended questions
in the interview:

• Most common structure.
• Traditional departments such as sales,
marketing, finance, etc.
• Functional managers hold most authority.
Functional
• Most programs are implemented through
projects with focused outcomes.
• Teams are cross-functional.
• Project managers hold the most authority.
Projectized
• Combination of projectized and functional.
• Organization is a dynamic environment.
• Authority of functional manager flows down
through division, while authority of project
manager flows sideways through teams.
Matrix
Learn the corporate structure
Identify the organization’s corporate structure
type based on your initial conversations with
company leadership. The type of structure will
dictate how much control you'll have as a
functional head and help you understand
which stakeholders you'll need to collaborate
with.
To Do:
 Review the organization’s structure list and
identify whether the structure is functional,
prioritized, or a matrix. If it's a matrix
organization, determine if it's a strong
matrix (project manager holds more
authority), weak matrix (functional manager
holds more authority), or balanced matrix
(managers hold equal authority).
Source: Simplilearn
This organization is a ___________________ type.
Presentation
Deck, slide 6

Determine the mode of the organization: STARS
Based on your interview process and discussions with
company leadership, and using Michael Watkins’ STARS
assessment, determine which mode your organization is in:
startup, turnaround, accelerated growth, realignment, or
sustaining success.
Knowing the mode of your organization will determine how
you approach your 100-day plan. Depending on the mode,
you'll rebalance your activities around the three categories
of assess, listen, and deliver.
To Do:
 Review the STARS table on the right.
Source: Watkins, 2013.
Based on your situation,
prioritize activities in this way:
• Startup: assess, listen, deliver
• Turnaround: deliver, listen, assess
• Accelerated Growth: assess, listen, deliver
• Realignment: listen, assess, deliver
• Sustaining success: listen, assess, deliver
This organization is in ___________________ mode.
Presentation
Deck, slide 6

STARS Startup Turnaround Accelerated
Growth
Realignment Sustaining
Success
Definition Assembling
capabilities to
start a project.
Project is
widely seen as
being in
serious
trouble.
Managing a
rapidly
expanding
business.
A previously
successful
organization is
now facing
problems.
A vital
organization
is going to the
next level.
Challenges Must build
strategy,
structures, and
systems from
scratch. Must
recruit and
make do with
limited
resources.
Stakeholders
are
demoralized;
slash and burn
required.
Requires
structure and
systems to
scale; hiring
and
onboarding.
Employees
need to be
convinced
change is
needed;
restructure at
the top
required.
Risk of living
in shadow of
a successful
former leader.
Advantages No rigid
preconceptions.
High-energy
environment
and easy to
pivot.
A little change
goes a long
way when
people
recognize the
need.
Motivated
employee base
willing to
stretch.
Organization
has clear
strengths;
people desire
success.
Likely a
strong team;
foundation for
success likely
in place.
Determine the mode of the organization: STARS

Satya Nadella's listen, lead, and launch approach
When Satya Nadella was promoted to the CEO role at Microsoft in
2014, he received a Glassdoor approval rating of 85% and was
given an "A" grade by industry analysts after his first 100 days.
What did he do right?
• Created a sense of urgency by shaking up the senior leadership
team.
• Already understood the culture as an insider.
• Listened a lot and did many one-on-one meetings.
• Established a vision communicated with a mantra that Microsoft
would be "mobile-first, cloud-first."
• Met his words with actions. He launched Office for iPad and
made many announcements for cloud platform Azure.
CASE STUDY
Industry
Source
Software
Gregg Keizer, Computerworld, 2014
Satya Nadella, CEO, Microsoft Corp. (Image
source: Microsoft)
Listen to 'The First 100 Days' podcast – Alan Fong

Create a one-page introduction sheet to use in
communications
As a new CIO, you'll have to introduce yourself to many people in the organization. To save time on communicating who
you are as a person outside of the office, create a brief one-pager that includes a photo of you, where you were born
and raised, and what your hobbies are. This helps make a connection more quickly so your conversations can focus on
the business at hand rather than personal topics.
For your presentation deck, remove the personal details and just keep it professional. The personal aspects can be used
as a one-pager for other communications.
Source: Personal interview with Denis Gaudreault, Country Lead, Intel.
Presentation
Deck, slide 5

CALL
Day 1 to Day 15
2

Introduce yourself to your team
Prepare a 20-second pitch about yourself that goes beyond your name and title. Touch on your
experience that's relevant to your new role or the industry you're in. Be straightforward about your own
perceived strengths and weaknesses so that people know what to expect from you. Focus on the value
you believe you'll offer the group and use humor and humility where you're comfortable. For example:
“Hi everyone, my name is John Miller. I have 15 years of experience marketing conferences like this one
to vendors, colleges, and HR departments. What I’m good at, and the reason I'm here, is getting the right
people, businesses, and great ideas in a room together. I'm not good on details; that's why I work with
Tim. I promise that I'll get people excited about the conference, and the gifts and talents of everyone else
in this room will take over from there. I'm looking forward to working with all of you.”
• How well is the company performing based on
expectations?
• What must the company do to sustain its financial
performance and market competitiveness?
• How do you foresee the CIO contributing to the team?
• How have past CIOs performed from the perspective
of the team?
• What would successful performance of this role look
like to you? To your peers?
• What challenges and obstacles to success am I likely to
encounter? What were the common challenges of my
predecessor?
• How do you view the culture here and how do
successful projects tend to get approved?
• What are your greatest challenges? How could I help
you?
Have a structured set of questions ready that you can ask everyone.
For example:

Your ability to learn from others is critical at every stage in your first 100
days. Keep your sphere of influence in the loop as you progress through
this period.
Get to know your sphere of influence: prepare to connect with
a variety of people before you get down to work
Write down the names, or at least the key people, in
each segment of this diagram. This will serve as a quick
reference when you're planning communications with
others and will help you remember everyone as you're
meeting lots of new people in your early days on the job.
• Everyone knows their networks are important.
• However, busy schedules can cause leaders to
overlook their many audiences.
• Plan to meet and learn from all people in your sphere
to gain a full spectrum of insights.
Extended circle
Immediate circle
Presentation
Deck, slide 29

Identify how your competitors are leveraging technology for
competitive advantage
Competitor identification and analysis are critical steps for any new leader to assess the relative
strengths and weaknesses of their organization and develop a sense of strategic opportunity and
environmental awareness.
Today’s CIO is accountable for driving innovation
through technology. A competitive analysis will provide
the foundation for understanding the current industry
structure, rivalry within it, and possible competitive
advantages for the organization.
Surveying your competitive landscape prior to the first
day will allow you to come to the table prepared with
insights on how to support the organization and ensure
that you are not vulnerable to any competitive blind spots
that may exist in the evaluations conducted by the
organization already.
You will not be able to gain a nuanced understanding of
the internal strengths and weaknesses until you are in the
role, so focus on the external opportunities and how
competitors are using technology to their advantage.
Think Like
a Futurist
CIO Trend
Report 2019
For a more in-depth approach to
identifying and understanding relevant
industry trends and turning them into
insights, leverage the following Info-Tech
blueprints:
Presentation
Deck, slide 9

Assess the external competitive environment
• External research
INPUT
OUTPUT
• Competitor array
1. Conduct a broad analysis of the industry as a whole. Seek to answer the following
questions:
a) Are there market developments or new markets?
b) Are there industry or lifestyle trends, e.g. move to mobile?
c) Are there geographic changes in the market?
d) Are there demographic changes that are shaping decision making?
e) Are there changes in market demand?
2. Create a competitor array by identifying and listing key competitors. Try to be as broad as
possible here and consider not only entrenched close competitors but also distant/future
competitors that may disrupt the industry.
3. Identify the strengths, weaknesses, and key brand differentiators that each competitor
brings to the table. For each strength and differentiator, brainstorm ways that IT-based
innovation enables each. These will provide a toolkit for deeper conversations with your
peers and your business stakeholders as you move further into your first 100 days.
Competitor Strengths Weaknesses Key Differentiators IT Enablers
Competitor 1
Competitor 2
Competitor 3

Complete the CEO-CIO Alignment Program
Run the diagnostic program or use the alternative activities to complete your presentation
• CEO-CEO Alignment
Program
(recommended)
INPUT
OUTPUT
• Desired and target
state of IT maturity
• Innovation goals
• Top priorities
• Presentation Deck,
slides 11-13
Materials
• CEO
• CIO
Participants
Introduce the concept of the CEO-CIO Alignment Program using slide 10 of your
presentation deck and the brief email text below.
Talk to your advisory contact at Info-Tech about launching the program. More information is
available on Info-Tech’s website.
Once the report is complete, import the results into your presentation:
• Slide 11, the CEO’s current and desired states
• Slide 12, IT innovation goals
• Slide 13, top projects and top departments from the CEO and the CIO
Include any immediate recommendations you have.
Hello CEO NAME,
I’m excited to get started in my role as CIO, and to hit the ground running, I’d like to make sure that the IT
department is aligned with the business leadership. We will accomplish this using Info-Tech Research Group’s
CEO-CIO Alignment Program. It’s a simple survey of 20 questions to be completed by the CEO and the CIO.
This survey will help me understand your perception and vision as I get my footing as CIO. I’ll be able to identify
and build core IT processes that will automate IT-business alignment going forward and create an effective IT
strategy that helps eliminate impediments to business growth.
Research shows that IT departments that are effectively aligned to business goals achieve more success, and
I’m determined to make our IT department as successful as possible. I look forward to further detailing the
benefits of this program to you and answering any questions you may have the next time we speak.
Regards,
CIO NAME

New KPIs for CEO-CIO Alignment
Info-Tech CEO-CIO Alignment Program
Info-Tech's CEO-CIO Alignment Program is set up to build IT-business alignment in any organization. It helps the CIO
understand CEO perspectives and priorities. The exercise leads to useful IT performance indicators, clarifies IT’s
mandate and which new technologies it should invest in, and maps business goals to IT priorities.
Benefits
Additional materials are available on Info-Tech’s website.
Master the Basics
Cut through the jargon.
Take a comprehensive look
at the CEO perspective.
Target Alignment
Identify how IT can support
top business priorities.
Address CEO-CIO differences.
Start on the Right Path
Get on track with the CIO vision.
Use correct indicators and metrics
to evaluate IT from day one.

The desired maturity level of IT
STRUGGLE
Unable to Provide Reliable Business Services
SUPPORT
Reliable Infrastructure and IT Service Desk
OPTIMIZE
Effective Fulfillment of Work Orders, Functional Business
Applications, and Reliable Service Management
EXPAND
Effective Execution on Business Projects, Strategic
Use of Analytics and Customer Technology
TRANSFORM
Reliable Technology Innovation
Step 1: Where
are we today?
Determine where the
CEO sees the current
overall maturity level
of the IT organization.
Step 2: Where do
we want to be as
an organization?
Determine where the
CEO wants the IT
organization to be in
order to effectively
support the strategic
direction of the
business.
Use only if you can’t complete the CEO-CIO Alignment Program
Presentation
Deck, slide 11

Tim Cook's powerful use of language
Apple CEO Tim Cook, an internal hire, had big shoes to fill after
taking over from the late Steve Jobs. Cook's ability to control how
the company is perceived is a big credit to his success. How does
he do it? His favorite five words are “The way I see it..." These
words allow him to take a line of questioning and reframe it into
another perspective that he wants to get across. Similarly, he'll
often say, "Let me tell you the way I look at it” or "To put it in
perspective" or "To put it in context."
In your first two weeks on the job, try using these phrases in your
conversations with peers and direct reports. It demonstrates that
you value their point of view but are independently coming to
conclusions about the situation at hand.
CASE STUDY
Industry
Source
Consumer technology
Carmine Gallo, Inc., 2019
Tim Cook, CEO, Apple Inc. (Image source: Apple)
Listen to 'The First 100 Days' podcast – Denis Gaudreault

Inform your team that you plan to do an IT Management &
Governance Diagnostic survey
• IT Management &
Governance Diagnostic
(recommended)
INPUT
OUTPUT
• Process to improve first
• Processes important to
the business
slides 19-20
Materials
• CIO
• IT staff
Participants
Introduce the IT Management & Governance Diagnostic survey that will help
you form your IT strategy.
Explain that you want to understand current IT capabilities and you feel a
formal approach is best. You’ll also be using this approach as an important
metric to track your department’s success. Tell them that Info-Tech Research
Group will be conducting the survey and it’s important to you that they take
action on the email when it’s sent to them.
Example email:
Hello TEAM,
I appreciate meeting each of you, and so far I’m excited about the talents and energy on the team.
Now I need to understand the processes and capabilities of our department in a deeper way. I’d like to
map our process landscape against an industry-wide standard, then dive deeper into those processes
to understand if our team is aligned. This will help us be accountable to the business and plan the year
ahead. Advisory firm Info-Tech Research Group will be reaching out to you with a simple survey that
shouldn’t take too long to complete. It’s important to me that you pay attention to that message and
complete the survey as soon as possible.
Regards,
CIO NAME

CALL
Day 16 to Day 30
3

Leverage team interviews as a source of determining
organizational culture
Info-Tech recommends that you hold group conversations with your team to uncover their
opinions of the current organizational culture. This not only helps build transparency between you
and your team but also gives you another means of observing behavior and reactions as you listen to
team members’ characterizations of the current culture.
Questions for Discussion:
• What about the current organizational
environment do you think most contributes to
your success?
• What barriers do you experience as you try to
accomplish your work?
• What is your favorite quality that is present in
our organization?
• What is the one thing you would most like to
change about this organization?
• Do the organization's policies and procedures
support your efforts to accomplish work or do
they impede your progress?
• How effective do you think IT’s interactions are
with the larger organization?
• What would you consider to be IT’s top three
guiding principles?
• What kinds of people fail in this organization?
Note: It is inherently difficult for people to verbalize
what constitutes a culture – your strategy for
extracting this information will require you to ask
indirect questions to solicit the highest value
information.
Source: Hope College Blog Network
See Info-Tech’s Cultural Archetype Calculator.

Use the Competing Values Framework to define your
organization’s cultural archetype
THE COMPETING VALUES FRAMEWORK (CVF):
CVF represents the synthesis of
academic study of 39 indicators of
effectiveness for organizations. Using
a statistical analysis, two polarities that
are highly predictive of differences in
organizational effectiveness were
isolated:
1. Internal focus and integration vs.
external focus and differentiation.
2. Stability and control vs. flexibility
and discretion.
By plotting these dimensions on a
matrix of competing values, four main
cultural archetypes are identified with
their own value drivers and theories of
effectiveness.
FLEXIBILITY AND DISCRETION
STABILITY AND CONTROL
INTERNAL
CONTROL
AND
INTEGRATION
EXTERNAL
FOCUS
AND
DIFFERENTIATION
CLAN
ARCHETYPE
ADHOCRACY
ARCHETYPE
HIERARCHY
ARCHETYPE
MARKET
ARCHETYPE
Presentation
Deck, slide 16

Create a cultural adjustment plan
Now that you've assessed the cultural archetype, you can plan an appropriate approach to shape
the culture in a positive way. When new executives want to change culture, there are a few main
options at hand:
Autonomous evolution: Encourage teams to learn from each other. Empower hybrid teams to collaborate and
reward teams that perform well.
Planned and managed change: Create steering committee and project-oriented taskforces to work in parallel.
Appoint employees that have cultural traits you'd like to replicate to hold responsibility for these bodies.
Cultural destruction: When a toxic culture needs to be eliminated, get rid of its carriers. Putting new managers
or directors in place with the right cultural traits can be a swift and effective way to realign.
Each option boils down to creating the right set of incentives and deterrents. What behaviors will you reward and which ones
will you penalize? What do those consequences look like? Sometimes, but not always, some structural changes to the team
will be necessary. If you feel these changes should be made, it's important to do it sooner rather than later.
(Source: “Enlarging Your Sphere of Influence in Your Organization,” MindTools Corporate, 2014.)
As you're thinking about shaping a desired culture, it's helpful to have an easy way to remember the top qualities you want to
espouse. Try creating an acronym that makes it easy for staff to remember. For example: RISE could remind your staff to be
Responsive, Innovative, Sustainable, and Engaging (RISE). Draw upon your business direction from your manager to help
produce desired qualities (Source: Jennifer Schaeffer).
Presentation
Deck, slide 17

Gary Davenport’s welcome “surprise”
CASE STUDY
Industry
Source
Telecom
Interview with Gary Davenport
Listen to 'The First 100 Days' podcast –
David Penny & Andrew Wertkin
After Gary Davenport was hired on as VP of IT at MTS Allstream, his
first weekend on the job was spent at an all-executive offsite meeting.
There, he learned from the CEO that the IT department had a budget
reduction target of 25%, like other departments in the company. “That
takes your breath away,” Davenport says.
He decided to meet the CEO monthly to communicate his plans to
reduce spending while trying to satisfy business stakeholders. His top
priorities were:
1. Stabilize IT after seven different leaders in a five-year period.
2. Get the IT department to be respected. To act like business
owners instead of like servants.
3. Better manage finances and deliver on projects.
During Davenport’s 7.5-year tenure, the IT department became one of
the top performers at MTS Allstream.
Gary Davenport’s first weekend on the job
at MTS Allstream included learning about
a 25% reduction target.
(Image source: Ryerson University)

Initiate IT Management & Governance Diagnostic
Info-Tech Management & Governance Diagnostic
Talk to your Info-Tech executive advisor about launching the survey shortly after informing your team to expect it. You'll
just have to provide the names and email addresses of the staff you want to be involved. Once the survey is complete,
you'll harvest materials from it for your presentation deck. See slides 19 and 20 of your deck and follow the instructions
on what to include.
Benefits
Additional materials available on Info-Tech’s website.
Explore IT Processes
Dive deeper into performance.
Highlight problem areas.
Align IT Team
Build consensus by
identifying opposing views.
Ownership &
Accountability
Identify process owners and hold
team members accountable.

Conduct a high-level analysis of current
IT capabilities
Run this activity if you're not able to conduct the IT Management & Governance Diagnostic.
Schedule meetings with your IT leadership team. (In smaller organizations, interviewing everyone
may be acceptable.) Provide them a list of the core capabilities that IT delivers upon and ask
them to rate them on an effectiveness scale of 1-5, with a short rationale for their score.
1. Not effective (NE)
2. Somewhat Effective (SE)
3. Effective (E)
4. Very Effective (VE)
5. Extremely Effective (EE)
• Interviews with IT
leadership team
• Capabilities graphic
on next slide
INPUT
OUTPUT
• High-level
understanding of
current IT capabilities
Presentation
Deck, slide 21

Use the following set of IT capabilities for your assessment

If you are
here…
And want to
be here...
Drive
toward…
Innovate around…
Business
Partner
Innovator
Leading
business
transformation
• Emerging technologies
• Analytical capabilities
• Risk management
• Customer-facing tech
• Enterprise architecture
Trusted
Operator
Business
Partner
Optimizing
business
process and
supporting
business
transformation
• IT strategy and governance
• Business architecture
• Projects
• Resource management
• Data quality
Firefighter
Trusted
Operator
Optimize IT
processes and
services
• Business applications
• Service management
• Stakeholder management
• Work orders
Unstable Firefighter
Reduce use
disruption and
adequately
support the
business
• Network and infrastructure
• Service desk
• Security
• User devices
Quick wins: CEO-CIO Alignment Program
Complete this while waiting on the IT M&G survey results. Based on your completed CEO-CIO Alignment Report, identify
the initiatives you can tackle immediately.

CALL
Day 31 to Day 45
4

Inform your peers that you plan to do a CIO Business Vision
survey to gauge your stakeholders’ satisfaction
• CIO Business Vision
survey (recommended)
INPUT
OUTPUT
• True measure of
business satisfaction
with IT
slide 30
Materials
• CIO
• IT staff
Participants
Meet the business leaders at your organization face-to-face if possible. If you
can't meet in person, try a video conference to establish some rapport. At the
end of your introduction and after listening to what your colleague has to say,
introduce the CIO Business Vision Diagnostic.
Explain that you want to understand how to meet their business needs and you
feel a formal approach is best. You'll also be using this approach as an
important metric to track your department's success. Tell them that Info-Tech
Research Group will be conducting the survey and it’s important to you that
they take the survey when the email is sent to them.
Example email:
Hello PEER NAMES,
I'm arranging for Info-Tech Research Group to invite you to take a survey that will be important to me.
The CIO Business Vision survey will help me understand how to meet your business needs. It will only
take about 15 minutes of your time, and the top-line results will be shared with the organization. We will
use the results to plan initiatives for the future that will improve your satisfaction with IT.
Regards,
CIO NAME

Gain feedback on your initial assessments from your IT team
You need your team’s hearts and minds or you risk a short tenure. Overemphasizing business
commitment by neglecting to address your IT team until after you meet your business stakeholders will
result in a disenfranchised group. Show your team their importance.
There are two strategies for gaining feedback on your initial
assessments of the organization from the IT team:
1. Review your personal assessments with the relevant
members of your IT organization as a group. This strategy
can help to build trust and an open channel for communication
between yourself and your team; however, it also runs the risk
of being impacted by groupthink.
2. Ask for your team to complete their own assessments for
you to compare and contrast. This strategy can help extract
more candor from your team, as they are not expected to
communicate what may be nuanced perceptions of
organizational weaknesses or criticisms of the way certain
capabilities function.
Who you involve in this process will be impacted by the size of your
organization. For larger organizations, involve everyone down to the
manager level. In smaller organizations, you may want to involve
everyone on the IT team to get an accurate lay of the land.
Areas for Review:
• Strategic Document Review:
Are there any major themes or
areas of interest that were not
covered in my initial assessment?
• Competitor Array: Are there any
initiatives in flight to leverage new
technologies?
• Current State of IT Maturity:
Does IT’s perception align with
the CEO’s? Where do you believe
IT has been most effective? Least
effective?
• IT’s Key Priorities: Does IT’s
perception align with the CEO’s?
• Key Performance Indicators:
How has IT been measured in the
past?

Susan Bowen's talent maximization
Susan Bowen was promoted to be the president of Cogeco Peer 1,
an infrastructure services firm, when it was still a part of Cogeco
Communications. Part of her mandate was to help spin out the
business to a new owner, which occurred when it was acquired by
Digital Colony. The firm was renamed Aptum and Bowen was put
in place as CEO, which was not a certainty despite her position as
president at Cogeco Peer 1. She credits her ability to put the right
talent in the right place as part of the reason she succeeded. After
becoming president, she sought a strong commitment from her
directors. She gave them a choice about whether they'd deliver on
a new set of expectations – or not. She also asks her leadership
on a regular basis if they are using their talent in the right way.
While it's tempting for directors to want to hold on to their best
employees, those people might be able to enable many more
people if they can be put in another place.
Bowen fully rounded out her leadership team after Aptum was
formed. She created a chief operating officer and a chief
infrastructure officer. This helped put in place more clarity around
roles at the firm and put an emphasis on client-facing services.
CASE STUDY
Industry
Source
Infrastructure services
Interview with Susan Bowen
Susan Bowen, CEO, Aptum
(Image source: Aptum)
Listen to 'The First 100 Days' podcast – Susan
Bowen

Initiate CIO Business Vision survey – new KPIs
for stakeholder management
Info-Tech CIO Business Vision
Be sure to effectively communicate the context of this survey to your business stakeholders before you launch it. Plan
to talk about your plans to introduce it in your first meetings with stakeholders. When ready, let your executive advisor
know you want to launch the tool and provide the names and email addresses of the stakeholders you want involved.
After you have the results, harvest the materials required for your presentation deck. See slide 30 and follow the
instructions on what to include.
Benefits
Key Stakeholders
Clarify the needs of the business.
Credibility
Create transparency.
Improve
Measure IT’s progress.
Focus
Find what’s important.

Create a catalog of key stakeholder details to
reference prior to future conversations
While profiling your stakeholders is important, do not be afraid to profile yourself as well. Visualizing how your
interests overlap with those of your stakeholders can provide critical information on how to manage your
communications so that those on the receiving end are hearing exactly what they need.
Use the Organizational Catalog as a
personal cheat sheet to document the key
details around each of your stakeholders,
including your CEO when possible.
The catalog will be an invaluable tool to
keep the competing needs of your different
stakeholders in line, while ensuring you are
retaining the information to build the political
capital needed to excel in the C-suite.
Note: It is important to keep this document
private. While you may want to
communicate components of this
information, ensure your catalog remains
under lock and (encryption) key.
Only conduct this activity if you’re not able to run the CIO Business Vision diagnostic.

Activity: Conduct interviews with your key
business stakeholders
Questions for Discussion:
• Be indirect about your personal questions –
share stories that will elicit details about their
interests, kids, etc.
• What are your most critical/important initiatives
for the year?
• What are your key revenue streams, products,
and services?
• What are the most important ways that IT
supports your success? What is your
satisfaction level with those services?
• Are there any current in-flight projects or
initiatives that are a current pain point? How
can IT assist to alleviate challenges?
• How is your success measured? What are your
targets for the year on those metrics?
1. Once you have identified your key stakeholders
through your interviews with your boss and your IT
team, schedule a set of meetings with those
individuals.
2. Use the meetings to get to know your stakeholders,
their key priorities and initiatives, and their
perceptions of the effectiveness of IT.
a) Use the probative questions to the right to
elicit key pieces of information.
b) Refer to the Organizational Catalog tool for
more questions to dig deeper in each
category. Ensure that you are taking notes
separate from the tool and are keeping the
tool itself secure, as it will contain private
information specific to your interests.
3. Following each meeting, record the results of your
conversation and any key insights in the
Organizational Catalog. Refer to the following slide
for more details.
Presentation
Deck, slide 34

CALL
Day 46 to Day 60
5

Inform your team that you plan to do an IT staffing
assessment
• Email template
INPUT
OUTPUT
• Ready to launch
diagnostic
• Email template
• List of staff
• Sample of diagnostic
Materials
• CIO
• IT staff
Participants
Explain that you want to understand how the IT staff is currently spending its
time by function and by activity. You want to take a formal approach to this task
and also assess the team’s feelings about its effectiveness across different
processes. The results of the assessment will serve as the foundation that
helps you improve your team’s effectiveness within the organization.
Example email:
Hello PEER NAMES,
The feedback I've heard from the team since joining the company has been incredibly useful in
beginning to formulate my IT strategy. Now I want to get a clear picture of how everyone is spending
their time, especially across different IT functions and activities. This will be an opportunity for you to
share feedback on what we're doing well, what we need to do more of, and what we're missing. Expect
to receive an email invitation to take this survey from Info-Tech Research Group. It's important to me
that you complete the survey as soon as you're can. Attached you’ll find an example of the report this
will generate. Thank you again for providing your time and feedback.
Regards,
CIO NAME
Introduce the IT Staffing Assessment that will help you get the most out of your team

Wayne Berger's shortcut to solve staffing woes
Wayne Berger was hired to be the International Workplace Group
(IWG) CEO for Canada and Latin America in 2014.
Wayne approached his early days with the office space leasing
firm as a tour of sorts, visiting nearly every one of the 48 office
locations across Canada to host town hall meetings. He heard
from staff at every location that they felt understaffed. But instead
of simply hiring more staff, Berger actually reduced the workforce
by 33%.
He created a more flexible approach to staffing:
• Employees no longer just reported to work at one office;
instead, they were ready to go to wherever they were most
needed in a specific geographic area.
• He centralized all back-office functions for the company so that
not every office had to do its own bookkeeping.
• Finally, he changed the labor profile to consist of full-time staff,
part-time staff, and time-on-demand workers.
CASE STUDY
Industry
Source
Office leasing
Interview with Wayne Berger
Wayne Berger, CEO, IWG Plc (Image source: IWG)
Listen to 'The First 100 Days' podcast – Wayne Berger

Initiate IT Staffing Assessment – new KPIs
to track IT performance
Info-Tech IT Staffing Assessment
Info-Tech’s IT Staffing Assessment provides benchmarking of key metrics against 4,000 other organizations. Dashboard-
style reports provide key metrics at a glance, including a time breakdown by IT function and by activity compared against
business priorities. Run this survey at about the 45-day mark of your first 90 days. Its insights will be used to inform your
long-term IT strategy.
Benefits
Right-Size IT Headcount
Find the right level for stakeholder
satisfaction.
Allocate Staff Correctly
Identify staff misalignments with
priorities.
Maximize Teams
Identify how to drive staff.

Quick wins: Make recommendations based on IT Management
& Governance Framework
Complete this exercise while waiting on the IT Staffing Assessment results. Based on your completed IT Management &
Governance report, identify the initiatives you can tackle immediately. You can conduct this as a team exercise by following
these steps:
1. Create a shortlist of initiatives based on the processes that were identified as high need but scored low in
effectiveness. Think as broadly as possible during this initial brainstorming.
2. Write each initiative on a sticky note and conduct a high-level analysis of the amount of effort that would be
required to complete it, as well as its alignment with the achievement of business objectives.
3. Draw the matrix below on a whiteboard and place each sticky note onto the matrix based on its potential
impact and difficulty to address.
Quick Wins
High impact on business
objectives with relatively small
effort. Some combination of these
will form your early wins.
Long-Term Initiatives
High impact on business
outcomes but will take more effort
to implement. Schedule these in
your long-term roadmap.
Low Current Value
No immediate attention required,
but may become a priority in the
future if business objectives
change.
Future Reassessment
No immediate attention required,
but may become a priority in the
future if business objectives
change.
Low High
Potential
Impact
High
Fully supports
achievement of
business
objectives
Limited support
of business
objectives

CALL
Day 61 to Day 75
6

Start Stop Continue
Activities you're not currently doing
but should start doing very soon.
Activities you're currently doing but
aren’t working and should cease.
Things you're currently doing and
are working well.
Run a start, stop, continue exercise with your
IT staff
This is an alternative activity to running an IT Staffing Assessment, which contains a start/stop/continue assessment. This
activity can be facilitated with a flip chart or a whiteboard. Create three pages or three columns and label them Start, Stop,
and Continue.
Hand out sticky notes to each team member and then allow time for individual brainstorming. Instruct them to write down
their contributions for each category on the sticky notes. After a few minutes, have everyone stick their notes in the
appropriate category on the board. Discuss as a group and see what themes emerge. Record the results that you want to
share in your presentation deck (GroupMap).
Gather your team and explain the meaning of these categories:
Presentation
Deck, slide 24

Determine the alignment of IT commitments
with business objectives
Run this only as an alternative to the IT Management & Governance Diagnostic.
1. Schedule meetings with IT leadership to understand what commitments have been made to
the business in terms of new products, projects, or enhancements.
2. Determine the following about IT’s current investment mix:
a) What are the current IT investments and assets? How do they align to business goals?
b) What investments in flight are related to which information assets?
c) Are there any immediate risks identified for these key investments?
d) What are the primary business issues that demand attention from IT consistently?
e) What choices remain undecided in terms of strategic direction of the IT organization?
3. Document your key investments and commitments as well as any points of misalignment
between objectives and current commitments as action items to address in your long-term
plans. If they are small fixes, consider them during your quick-win identification.
• Interviews with IT
leadership team
INPUT
OUTPUT
• High-level
understanding of
in-flight commitments
and investments
Presentation
Deck, slide 25

Determine the alignment of IT commitments with business
objectives
Run this only as an alternative to the IT Staffing Assessment diagnostic.
Schedule meetings with IT leadership to understand what commitments have been made to the business in terms of new
products, projects, or enhancements.
Document your key investments and commitments, as well as any points of misalignment between objectives and current
commitments, as action items to address in your long-term plans. If they are small-effort fixes, consider them during your
quick-win identification.
Determine the following about IT’s current investment mix:
• What are the current IT investments and assets?
• How do they align to business goals?
• What in-flight investments are related to which information assets?
• Are there any immediate risks identified for these key investments?
• What are the primary business issues that demand attention from IT consistently?
• What remains undecided in terms of strategic direction of the IT organization?
Presentation
Deck, slide 25

Make a categorized vendor list by IT process
As part of learning the IT team, you should also create a comprehensive list of vendors under contract. Collaborate with the
finance department to get a clear view of how much of the IT budget is spent on specific vendors. Try to match vendors to the
IT processes they serve from the IT M&G framework.
You should also organize your vendors based on their budget allocation. Go beyond just
listing how much money you’re spending with each vendor and categorize them into either
“transactional” relationships or “strategic relationships.” Use the grid below to organize them.
Ideally, you’ll want most relationships to be high spend and strategic (Source: Gary Davenport).
Where to
source
your vendor
list:
• Finance
department
• Infrastructure
managers
• Vendor
manager in IT
Further reading: Manage Your Vendors Before They Manage You
Presentation
Deck, slide 26
Type of relationship
S
p
e
n
d
High Spend
Transactional
High Spend
Strategic
Low Spend
Strategic
Low Spend
Transactional

Jennifer Schaeffer’s short-timeline turnaround
Jennifer Schaeffer joined Athabasca University as CIO in
November 2017. She was entering a turnaround situation as the
all-online university lacked an IT strategy and had built up
significant technical debt. Armed with the mandate of a third-party
consultant that was supported by the president, Schaeffer used a
people-first approach to construct her strategy. She met with all
her staff, listening to them carefully regardless of role, and
consulted with the administrative council and faculty members.
She reflected that feedback in her plan or explained to staff why it
wasn’t relevant for the strategy. She implemented a “strategic
calendaring” approach for the organization, making sure that her
team members were participating in meetings where their work
was assessed and valued. Drawing on Spotify as an inspiration,
she designed her teams in a way that everyone was connected to
the customer experience. Given her short timeline to execute, she
put off a deep skills analysis of her team for a later time, as well as
creating a full architectural map of her technology stack. The
outcome is that 2.5 years later, the IT department is unified in
using the same tooling and optimization standards. It’s more
flexible and ready to incorporate government changes, such as
offering more accessibility options.
CASE STUDY
Industry
Source
Education
Interview with Jennifer Schaeffer
Listen to 'The First 100 Days' podcast – Eric Wright
Jennifer Schaeffer took on the CIO role at Athabasca
University in 2017 and was asked to create a five-
year strategic plan in just six weeks.
(Image source: Athabasca University)

CALL
Day 76 to Day 90
7
First 100 Days As CIO Concierge Service

Finalize your vision – mission – values statement
A clear statement for your values, vision, and mission will help crystallize your IT strategy and communicate what
you're trying to accomplish to the entire organization.
Mission: This statement describes the needs that IT
was created to meet and answers the basic question of
why IT exists.
Vision: Write a statement that captures your values. Remember
that the vision statement sets out what the IT organization wants
to be known for now and into the future.
Values: IT core values represent the standard axioms by which
the IT department operates. Similar to the core values of the
organization as a whole, IT’s core values are the set of beliefs or
philosophies that guide its strategic actions.
Further reading: IT Vision and Mission Statements Template
Presentation
Deck, slide 43
Presentation
Deck, slide 42

John Chen's new strategic vision
John Chen, known in the industry as a successful turnaround
executive, was appointed BlackBerry CEO in 2014 following the
unsuccessful launch of the BlackBerry 10 mobile operating system
and a new tablet.
He spent his first three months travelling, talking to customers and
suppliers, and understanding the company's situation. He
assessed that it had a problem generating cash and had made
some strategic errors, but there were many assets that could
benefit from more investment.
He was blunt about the state of BlackBerry, making cutting
observations of the past mistakes of leadership. He also settled a
key questions about whether BlackBerry would focus on
consumer or enterprise customers. He pointed to a base of 80,000
enterprise customers that accounted for 80% of revenue and
chose to focus on that.
His new mission for BlackBerry: to transform it from being a
"mobile technology company" that pushes handset sales to "a
mobile solutions company" that serves the mobile computing
needs of its customers.
CASE STUDY
Industry
Source
Mobile Services
Sean Silcoff, The Globe and Mail
John Chen, CEO of BlackBerry, presents at
BlackBerry Security Summit 2018 in New York
City (Image source: Brian Jackson)
Listen to 'The First 100 Days' podcast – Erin Bury

Quick wins: Make recommendations based on the CIO
Business Vision survey
Based on your completed CIO Business Vision survey, use the IT Satisfaction Scorecard to determine some initiatives.
Focus on areas that are ranked as high importance to the business but low satisfaction. While all of the initiatives may be
achievable given enough time, use the matrix below to identify the quick wins that you can focus on immediately. It’s
important to not fail in your quick-win initiative.
• High Visibility, Low Risk: Best bet for
demonstrating your ability to deliver value.
• Low Visibility, Low Risk: Worth consideration,
depending on the level of effort required and
the relative importance to the stakeholder.
• High Visibility, High Risk: Limit higher-risk
initiatives until you feel you have gained trust
from your stakeholders, demonstrating your
ability to deliver.
• Low Visibility, High Risk: These will be your
lowest value, quick-win initiatives. Keep them in
a backlog for future consideration in case
business objectives change.
High Visibility, Low Risk
Multiple stakeholders will benefit
from the initiative’s
implementation, and it has a low
risk of failure.
High Visibility, High Risk
Multiple stakeholders will benefit
from the initiative’s
implementation, but it has a
higher risk of failure.
Low Visibility, Low Risk
Few stakeholders will benefit from
the initiative’s implementation.
Low Visibility, High Risk
No immediate attention is
required, but it may become a
priority in the future if business
objectives change.
Low High
Risk of Failure
Organizational
Visibility
High
Presentation
Deck, slide 27

Create and communicate a post-100 plan
The last few slides of your presentation deck represent a roundup of all the assessments
you’ve done and communicate your plan for the months ahead.
Slide
38
Based on the information on the previous slide and now knowing which IT capabilities need improvement and
which business priorities are important to support, estimate where you'd like to see IT staff spend their time in
the near future. Will you be looking to shift staff from one area to another? Will you be looking to hire staff?
Slide
39
Take your IT M&G initiatives from slide 19 and list them here. If you've already achieved a quick win, list it and
mark it as completed to show what you've accomplished. Briefly outline the objectives, how you plan to
achieve the result, and what measurement will indicate success.
Slide
40
Reflect your CIO Business Vision initiatives from slide 31 here.
Slide
41
Use this roadmap template to list your initiatives by roughly when they’ll be worked on and completed. Plan
for when you’ll update your diagnostics.

Expert Contributors
Alan Fong, Chief Technology Officer, Dealer-FX
Andrew Wertkin, Chief Strategy Officer, BlueCat Networks
David Penny, Chief Technology Officer, BlueCat Networks
Susan Bowen, CEO, Aptum

Expert Contributors
Wayne Berger, CEO, IWG Plc
Erin Bury, CEO, Willful
Denis Gaudreault, Country Manager, Intel Canada and Latin America

Expert Contributors
Eric Wright, CEO, LexisNexis Canada
Gary Davenport, past president of CIO Association”
of Canada, former VP of IT, Enterprise Solutions
Division, MTS AllStream
Jennifer Schaeffer, VP of IT and CIO, Athabasca University

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