It The First 100 Days As CIO Storyboard V3

The First 100 Days As CIO
Partner with Info-Tech for success in this crucial period of transition.
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© 1997-2019 Info-Tech Research Group Inc. Info-Tech Research Group 1
ANALYST PERSPECTIVE
The first 100 days refers to the 10 days before you start and the first three
months on the job.
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
Info-Tech Research Group 2

Executive summary
Situation
• You’ve been promoted from within to the role of CIO. 1. Foundational understanding must be
achieved before you start.
• You’ve been hired externally to take on the role of CIO. Hit the ground running before day one by
using company documents and initial
discussions to pin down the company’s type
and mode.
Complication 2. Listen before you act (usually).

In most situations, executives benefit from
Studies show that two years after a new executive transition, as many as listening to peers and staff before taking
half are regarded as failures or disappointments (McKinsey). First action.
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 3. Identify quick wins early and often.
way to approach this period is determined by both the size and the mode Fix problems as soon as you recognize them
of an organization. to set the tone for your tenure.
Resolution
• 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.

The First 100 Days: Roadmap
THE 100-DAY PLAN

A. FOUNDATIONAL
PREPARATION
CIO-CEO Alignment
B. MANAGEMENT’S
EXPECTATIONS
IT M&G Diagnostic IT Staffing Assessment
C
C. ASSESSING THE IT TEAM
CIO Business Vision Survey
D. ASSESSING THE KEY STAKEHOLDERS
E. DELIVER
FIRST-
YEAR PLAN
-10 0 30 60 90
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
Before you start: Day 0 to 15 Day 16 to 30 Day 31 to 45 Day 46 to 60 Day 61 to 75 Day 76 to 90
Day -10 to Day 1
2.1 Introduce 3.1 Determine the 4.1 Inform 5.1 Inform the 6.1 Run a start, 7.1 Finalize your
1.1 Interview your yourself to team’s stakeholders team that you stop, continue vision –
predecessor. your team. cultural about CIO plan to exercise with mission –
1.2 Learn the 2.2 Document archetype. Business conduct an IT IT staff. values
corporate your sphere 3.2 Create a Vision survey. staffing 6.2 Make a statement.
structure. of influence. cultural 4.2 Get feedback assessment. categorized 7.2 Quick Wins:
1.3 Determine 2.3 Complete a adjustment on initial 5.2 Initiate the IT vendor list. Make
STARS mode. competitor plan. assessments Staffing 6.3 Determine the recommend-
Activities
1.4 Create a one- array. 3.3 Initiate IT from your Assessment. alignment of ations based
page intro 2.4 Complete the M&G team. 5.3 Quick wins: IT on IT Staffing
sheet. CEO-CIO Diagnostic. 4.3 Initiate CIO Make commitments Assessment.
1.5 Update your Alignment 3.4 Conduct a Business recommend- with business 7.3 Create and
boss. Program. high-level Vision survey. ations based objectives. communicate
2.4(a) Agree on analysis of 4.3(a) Meet on CIO a post-100-
what success current IT stakeholders Business day plan.
looks like with capabilities. and catalog Vision 7.4 Update your
the boss. 3.4 Update your details. Diagnostic/IT boss.
2.5 Inform team boss. M&G
of IT M&G Framework.
Framework. 5.4 Update your
boss.
Presentation Presentation Presentation Presentation Presentation Presentation

Deck Section A: Deck slides 9, 11- Deck slides 16, Deck slides 30, Deck slides 24, Deck slides 27,
Foundational 13, 19-20, 29 17, 21 34 25, 26 42
Deliverables
Preparation

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

Interview your predecessor
Interviewing your predecessor can help identify the

organization’s mode and type.
Ask these open-ended questions
in the interview:
Before reaching out to your predecessor, get a sense of
whether they were viewed as successful or not. Ask your • Tell me about the team.
manager. If the predecessor remains within the • Tell me about your challenges.
organization in a different role, understand your relationship • Tell me about a major project your team worked
with them and how you'll be working together. on. How did it go?
• Who/what has been helpful during your tenure?
During the interview, make notes about follow-up questions • Who/what created barriers for you?
you'll ask others at the organization. • 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?

Learn the corporate structure
Identify the organization’s corporate structure

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

Determine the mode of the organization: STARS
Based on your interview process and discussions with

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

Determine the mode of the organization: STARS
STARS Startup Turnaround Accelerated Realignment Sustaining

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

Satya Nadella's listen, lead, and launch approach
CASE STUDY Industry

Source
Software
Gregg Keizer, Computerworld, 2014
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.
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 2
Day 1 to Day 15

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.”
Have a structured set of questions ready that you can ask everyone.
For example:
• How well is the company performing based on • What challenges and obstacles to success am I likely
expectations? to encounter? What were the common challenges of
• What must the company do to sustain its financial my predecessor?
performance and market competitiveness? • How do you view the culture here and how do
• How do you foresee the CIO contributing to the team? successful projects tend to get approved?
• How have past CIOs performed from the perspective • What are your greatest challenges? How could I help
of the team? you?
• What would successful performance of this role look
like to you? To your peers?

Get to know your sphere of influence: prepare to connect with
a variety of people before you get down to work
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.
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 For a more in-depth approach to
the foundation for understanding the current industry identifying and understanding relevant
structure, rivalry within it, and possible competitive industry trends and turning them into
insights, leverage the following Info-Tech
advantages for the organization. blueprints:
Surveying your competitive landscape prior to the first

day will allow you to come to the table prepared with Think Like
insights on how to support the organization and ensure a Futurist
that you are not vulnerable to any competitive blind spots
that may exist in the evaluations conducted by the
organization already.
CIO Trend
Report 2019
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.
Presentation
Deck, slide 9

Assess the external competitive environment
1. Conduct a broad analysis of the industry as a whole. Seek to answer the following
questions: INPUT
a) Are there market developments or new markets?
• External research
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? OUTPUT
2. Create a competitor array by identifying and listing key competitors. Try to be as broad • Competitor array
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
Introduce the concept of the CEO-CIO Alignment Program using slide 10 of your
presentation deck and the brief email text below. INPUT
Talk to your advisory contact at Info-Tech about launching the program. More information is • CEO-CEO Alignment
available on Info-Tech’s website. Program
Once the report is complete, import the results into your presentation: (recommended)
• Slide 11, the CEO’s current and desired states
• Slide 12, IT innovation goals OUTPUT
• Slide 13, top projects and top departments from the CEO and the CIO
• Desired and target
Include any immediate recommendations you have. state of IT maturity
• Innovation goals
• Top priorities
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 Materials
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. • Presentation Deck,
slides 11-13
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. Participants
Research shows that IT departments that are effectively aligned to business goals achieve more success, and • CEO
I’m determined to make our IT department as successful as possible. I look forward to further detailing the
• CIO
benefits of this program to you and answering any questions you may have the next time we speak.
Regards,
CIO NAME

Re
co
New KPIs for CEO-CIO Alignment mm
en
de
d
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
Master the Basics Target Alignment Start on the Right Path

Cut through the jargon. Identify how IT can support Get on track with the CIO vision.
Take a comprehensive look top business priorities. Use correct indicators and metrics
at the CEO perspective. Address CEO-CIO differences. to evaluate IT from day one.
Additional materials are available on Info-Tech’s website.

Alt
er
The desired maturity level of IT na
tiv
e
Use only if you can’t complete the CEO-CIO Alignment Program
Step 1: Where TRANSFORM

are we today? Reliable Technology Innovation
Determine where the

CEO sees the current
overall maturity level
EXPAND
Effective Execution on Business Projects, Strategic
of the IT organization. Use of Analytics and Customer Technology
Step 2: Where do OPTIMIZE

we want to be as Effective Fulfillment of Work Orders, Functional Business
Applications, and Reliable Service Management
an organization?
Determine where the
CEO wants the IT
organization to be in
SUPPORT
Reliable Infrastructure and IT Service Desk
order to effectively
support the strategic
direction of the STRUGGLE
business. Unable to Provide Reliable Business Services
Presentation
Deck, slide 11
Tim Cook's powerful use of language
CASE STUDY Industry

Source
Consumer technology
Carmine Gallo, Inc., 2019
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.
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
Introduce the IT Management & Governance Diagnostic survey that will help
you form your IT strategy. INPUT
• IT Management & Gover
Explain that you want to understand current IT capabilities and you feel a nance Diagnostic
(recommended)
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 OUTPUT
action on the email when it’s sent to them. • Process to improve first
• Processes important to
Example email: the business
Hello TEAM, Materials

• Presentation Deck,
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 slides 19-20
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
Participants
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. • CIO
• IT staff
Regards,
CIO NAME

CALL 3
Day 16 to Day 30

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
Source: Hope College Blog Network
change about this organization?
• Do the organization's policies and procedures
Note: It is inherently difficult for people to verbalize support your efforts to accomplish work or do
what constitutes a culture – your strategy for they impede your progress?
extracting this information will require you to ask • How effective do you think IT’s interactions are
indirect questions to solicit the highest value with the larger organization?
information. • What would you consider to be IT’s top three
guiding principles?
See Info-Tech’s Cultural Archetype Calculator. • What kinds of people fail in this organization?

Use the Competing Values Framework to define your
organization’s cultural archetype
THE COMPETING VALUES FRAMEWORK (CVF):
CVF represents the synthesis of
FLEXIBILITY AND DISCRETION
academic study of 39 indicators of
EXTERNAL FOCUS AND DIFFERENTIATION

INTERNAL CONTROL AND INTEGRATION
effectiveness for organizations. Using
a statistical analysis, two polarities that
are highly predictive of differences in CLAN ADHOCRACY
organizational effectiveness were ARCHETYPE ARCHETYPE
isolated:
1. Internal focus and integration vs.

external focus and differentiation.
2. Stability and control vs. flexibility
and discretion. HIERARCHY MARKET
ARCHETYPE ARCHETYPE
By plotting these dimensions on a
matrix of competing values, four main
cultural archetypes are identified with
their own value drivers and theories of STABILITY AND CONTROL
effectiveness.
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
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
Listen to 'The First 100 Days' podcast – a 25% reduction target.
David Penny & Andrew Wertkin (Image source: Ryerson University)

Re
c om
me
Initiate IT Management & Governance Diagnostic nd
ed
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
Explore IT Processes Align IT Team Ownership &

Dive deeper into performance. Build consensus by Accountability
Highlight problem areas. identifying opposing views.
Identify process owners and hold
team members accountable.
Additional materials available on Info-Tech’s website.

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

Use the following set of IT capabilities for your assessment

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.
If you are And want to Drive

Innovate around…
here… be here... toward…
• Emerging technologies
Leading • Analytical capabilities
Business
Innovator business • Risk management
Partner
transformation • Customer-facing tech
• Enterprise architecture
Optimizing
• IT strategy and governance
business
• Business architecture
Trusted Business process and
• Projects
Operator Partner supporting
• Resource management
business
• Data quality
transformation
• Business applications
Optimize IT
Trusted • Service management
Firefighter processes and
Operator • Stakeholder management
services
• Work orders
Reduce use
• Network and infrastructure
disruption and
• Service desk
Unstable Firefighter adequately
• Security
support the
• User devices
business

CALL 4
Day 31 to Day 45

Inform your peers that you plan to do a CIO Business Vision
survey to gauge your stakeholders’ satisfaction
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 INPUT
end of your introduction and after listening to what your colleague has to say, • CIO Business Vision
introduce the CIO Business Vision Diagnostic. survey (recommended)
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 OUTPUT
important metric to track your department's success. Tell them that Info-Tech • True measure of
Research Group will be conducting the survey and it’s important to you that business satisfaction
they take the survey when the email is sent to them. with IT
Example email: Materials

• Presentation Deck,
Hello PEER NAMES, slide 30
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
Participants
use the results to plan initiatives for the future that will improve your satisfaction with IT.
• CIO
• IT staff
Regards,
CIO NAME

Gain feedback on your initial assessments from your IT team
There are two strategies for gaining feedback on your initial

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

Susan Bowen's talent maximization
CASE STUDY Industry

Source
Infrastructure services
Interview with Susan Bowen
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 Susan Bowen, CEO, Aptum
roles at the firm and put an emphasis on client-facing services. (Image source: Aptum)
Listen to 'The First 100 Days' podcast – Susan Bowe

n
Re
Initiate CIO Business Vision survey – new KPIs com
me
for stakeholder management nd
ed
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 Credibility Improve Focus

Clarify the needs of the business. Create transparency. Measure IT’s progress. Find what’s important.

Create a catalog of key stakeholder details to Alt
er na
reference prior to future conversations tive
Only conduct this activity if you’re not able to run the CIO Business Vision diagnostic.
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.
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.

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

CALL 5
Day 46 to Day 60

Inform your team that you plan to do an IT staffing
assessment
Introduce the IT Staffing Assessment that will help you get the most out of your team
Explain that you want to understand how the IT staff is currently spending its INPUT
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 • Email template
different processes. The results of the assessment will serve as the foundation
that helps you improve your team’s effectiveness within the organization.
OUTPUT
Example email: • Ready to launch
diagnostic
Hello PEER NAMES,

Materials
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, • Email template
especially across different IT functions and activities. This will be an opportunity for you to share • List of staff
feedback on what we're doing well, what we need to do more of, and what we're missing. Expect to • Sample of diagnostic
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.
Participants
Regards, • CIO
CIO NAME • IT staff

Wayne Berger's shortcut to solve staffing woes
CASE STUDY Industry

Source
Office leasing
Interview with Wayne Berger
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.
Wayne Berger, CEO, IWG Plc (Image source: IWG)
• 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.
Listen to 'The First 100 Days' podcast – Wayne Berger

Re
Initiate IT Staffing Assessment – new KPIs com
me
to track IT performance nd
ed
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 Allocate Staff Correctly Maximize Teams

Find the right level for stakeholder Identify staff misalignments with Identify how to drive staff.
satisfaction. priorities.

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.
High
Fully supports
Quick Wins Long-Term Initiatives
achievement of High impact on business High impact on business
business objectives with relatively small outcomes but will take more effort
Potential Impact
objectives effort. Some combination of these to implement. Schedule these in

will form your early wins. your long-term roadmap.
Low Current Value Future Reassessment

No immediate attention required, No immediate attention required,
but may become a priority in the but may become a priority in the
Limited support future if business objectives future if business objectives
of business change. change.
objectives
Low High

CALL 6
Day 61 to Day 75

Run a start, stop, continue exercise with your Alt
er na
IT staff tive
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:
Start Stop Continue
Activities you're not currently doing Activities you're currently doing but Things you're currently doing and
but should start doing very soon. aren’t working and should cease. are working well.
Presentation
Deck, slide 24

Determine the alignment of IT commitments Alt
er na
with business objectives tive
Run this only as an alternative to the IT Management & Governance Diagnostic.

INPUT
1. Schedule meetings with IT leadership to understand what commitments have been made to • Interviews with IT
the business in terms of new products, projects, or enhancements. leadership team
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? OUTPUT
c) Are there any immediate risks identified for these key investments?
• High-level
d) What are the primary business issues that demand attention from IT consistently? understanding of
e) What choices remain undecided in terms of strategic direction of the IT organization? in-flight commitments
and investments
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.
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.
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?
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.
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
High Spend High Spend list:
Transactional Strategic
S
p • Finance
e department
n • Infrastructure
d Low Spend Low Spend managers
Transactional Strategic • Vendor
manager in IT
Type of relationship
Presentation
Further reading: Manage Your Vendors Before They Manage You
Deck, slide 26

Jennifer Schaeffer’s short-timeline turnaround
CASE STUDY Industry

Source
Education
Interview with Jennifer Schaeffer
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 Jennifer Schaeffer took on the CIO role at Athabasca
flexible and ready to incorporate government changes, such as University in 2017 and was asked to create a five-
offering more accessibility options. year strategic plan in just six weeks.
(Image source: Athabasca University)
Listen to 'The First 100 Days' podcast – Eric Wright

CALL 7
Day 76 to Day 90
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.
Presentation
Further reading: IT Vision and Mission Statements Template 43
Deck, slide 42

John Chen's new strategic vision
CASE STUDY Industry

Source
Mobile Services
Sean Silcoff, The Globe and Mail
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
John Chen, CEO of BlackBerry, presents at
"mobile technology company" that pushes handset sales to "a
BlackBerry Security Summit 2018 in New York
mobile solutions company" that serves the mobile computing
City (Image source: Brian Jackson)
needs of its customers.
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. High
High Visibility, Low Risk High Visibility, High Risk
• Low Visibility, Low Risk: Worth consideration, Multiple stakeholders will benefit Multiple stakeholders will benefit
Organizational Visibility
depending on the level of effort required and from the initiative’s from the initiative’s
the relative importance to the stakeholder. implementation, and it has a low implementation, but it has a
risk of failure. higher risk of failure.
• High Visibility, High Risk: Limit higher-risk
initiatives until you feel you have gained trust Low Visibility, High Risk
from your stakeholders, demonstrating your Low Visibility, Low Risk
ability to deliver. No immediate attention is
Few stakeholders will benefit
required, but it may become a
from the initiative’s
priority in the future if business
• Low Visibility, High Risk: These will be your implementation.
objectives change.
lowest value, quick-win initiatives. Keep them in
a backlog for future consideration in case Low High
business objectives change. Risk of Failure
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.
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
38
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
39
Reflect your CIO Business Vision initiatives from slide 31 here.
Slide
40
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.
Slide
41

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

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

Bibliography
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Bersohn, Diana. “Go Live on Day One: The Path to Success for a New CIO.” PDF document. Accenture, 2015. Web.
Bradt, George. “Executive Onboarding When Promoted From Within To Follow A Successful Leader.” Forbes, 15 Nov. 2018.
Web.
“CIO Stats: Length of CIO Tenure Varies By Industry.” CIO Journal, The Wall Street Journal. 15 Feb. 2017. Web.
“Enlarging Your Sphere of Influence in Your Organization: Your Learning and Development Guide to Getting
People on Side.” MindTools Corporate, 2014.
“Executive Summary.” The CIO's First 100 Days: A Toolkit. PDF document. Gartner, 2012. Web.
Forbes, Jeff. “Are You Ready for the C-Suite?” KBRS, n.d. Web.
Gallo, Carmine. “Tim Cook Uses These 5 Words to Take Control of Any Conversation.” Inc., 9 Aug. 2019. Web.
Giles, Sunnie. “The Most Important Leadership Competencies, According to Leaders Around the World.” Harvard Business
Review, 15 March 2016. Web.
Godin, Seth. “Ode: How to tell a great story.” Seth's Blog. 27 April 2006. Web.
Green, Charles W. “The horizontal dimension of race: Social culture.” Hope College Blog Network, 19 Oct. 2014. Web.
Hakobyan, Hayk. “On Louis Gerstner And IBM.” Hayk Hakobyan, n.d. Web.

Bibliography
Hargrove, Robert. Your First 100 Days in a New Executive Job, edited by Susan Youngquist. Kindle Edition. Masterful
Coaching Press, 2011.
Heathfield, Susan M. “Why ‘Blink’ Matters: The Power of Your First Impressions." The Balance Careers, 25 June 2019. Web.
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Reddy, Kendra. “It turns out being a VP isn't for everyone.” Financial Post, 17 July 2012. Web.
Silcoff, Sean. “Exclusive: John Chen’s simple plan to save BlackBerry.” The Globe & Mail, 24 Feb. 2014. Web.

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The First 100 Days As CIO

Partner with Info-Tech for success in this crucial period of transition.

Info-Tech Research Group 2

Complication 2. Listen before you act (usually).

Info-Tech Research Group 3

THE 100-DAY PLAN

IT M&G Diagnostic IT Staffing Assessment

CIO Business Vision Survey

D. ASSESSING THE KEY STAKEHOLDERS

Info-Tech Research Group 4

Presentation Presentation Presentation Presentation Presentation Presentation

Info-Tech Research Group 5

First 100 Days As CIO

Interviewing your predecessor can help identify the

Info-Tech Research Group 7

Identify the organization’s corporate structure

This organization is a ___________________ type.

Info-Tech Research Group 8

Based on your interview process and discussions with

This organization is in ___________________ mode.

Info-Tech Research Group 9

STARS Startup Turnaround Accelerated Realignment Sustaining

Info-Tech Research Group 10

CASE STUDY Industry

When Satya Nadella was promoted to the CEO role at Microsoft

Listen to 'The First 100 Days' podcast – Alan Fong

Info-Tech Research Group 11

Source: Personal interview with Denis Gaudreault, Country Lead, Intel.

Info-Tech Research Group 12

First 100 Days As CIO

Info-Tech Research Group 14

• Everyone knows their networks are important.

Info-Tech Research Group 15

Today’s CIO is accountable for driving innovation

Surveying your competitive landscape prior to the first

Info-Tech Research Group 16

Competitor Strengths Weaknesses Key Differentiators IT Enablers

Info-Tech Research Group 17

Info-Tech Research Group 18

Master the Basics Target Alignment Start on the Right Path

Additional materials are available on Info-Tech’s website.

Info-Tech Research Group 19

Step 1: Where TRANSFORM

Determine where the

Step 2: Where do OPTIMIZE

CASE STUDY Industry

Tim Cook, CEO, Apple Inc. (Image source: Apple)

Listen to 'The First 100 Days' podcast – Denis Gaudreault

Info-Tech Research Group 21

Hello TEAM, Materials

Info-Tech Research Group 22

First 100 Days As CIO

Info-Tech Research Group 24

EXTERNAL FOCUS AND DIFFERENTIATION

1. Internal focus and integration vs.

Info-Tech Research Group 25

Info-Tech Research Group 26

CASE STUDY Industry

After Gary Davenport was hired on as VP of IT at MTS Allstream, his

He decided to meet the CEO monthly to communicate his plans to

During Davenport’s 7.5-year tenure, the IT department became one of

Gary Davenport’s first weekend on the job

Info-Tech Research Group 27