Leadership guide: Your first 60 days as a CIO

Your first 60 days are divided into two distinct

themes: orientation and reconnaissance, followed
by envision and planning.

Whether you’re a seasoned CIO embarking on a fresh challenge or a recently

promoted executive in a new role, it’s important to get your first few months as a
CIO right. Achieving success at the beginning of your leadership journey is
challenging, but essential.

I’ve spent many years in senior leadership positions, including seven as a CIO, owning
technology strategy, vendor relationships, project management, business processes
and key contract negotiations. I’ll share the lessons I’ve learned in my career and
provide context for those lessons that I wish I had when I started my journey as a
CIO. This guide will be an asset in your leadership toolkit and I encourage you to refer
to it regularly during this decisive time.

A BREAKDOWN OF THE BEGINNING

Your first 60 days are divided into two distinct themes: firstly, orientation and
reconnaissance, followed by envision and planning. I’ll also touch on going beyond
the first 60 days where you’ll leverage the knowledge and strategies of your first two
months and put your plan for change into action.
• 1-30 days – Orientation and reconnaissance
• 30-60 days – Vision and planning
• Beyond 60 days – Execution and change
Note: Apply with context
Although every organization is different, there’s a common set of responsibilities
included in every CIO role. Depending on your organization’s market, maturity and
core business, the emphasis placed on the responsibilities I outline below will vary,
but each will be present to a greater or lesser degree.

0-30 days: Orientation and reconnaissance

So, you’ve arrived at your new assignment and introduced as the new CIO, typically
with a positive and jubilant welcome—things are good. The organization is thrilled to
have filled this important role and you’re becoming familiar with products, culture,
services and organizational design.
The main elements you need to find clarity on within the next 30 days are:
1. Your real boss
2. Purpose and expectations of your role
3. State of technology
4. State of your team
5. Your allies and influence

For an experienced, technically focused leader, some of these may seem obvious.
Are you wondering why we’re even considering them? Welcome to you first lesson:
as CIO – being a CIO is as much about people and relationships as it is about the
technology.
1. Define your real boss
You may think you already know who your boss is, but I urge you to not take your
direct manager at face value. The person you report to on the org chart is probably
not the only one who evaluates your performance.
Your boss could be heavily influenced by others – let’s call these influences “shadow
boss.” A shadow boss could be a shareholder, board member, or a more influential
person than your direct line manager. The shadow boss may not undertake your
performance review, but they’ll be influential to a level that they could enable or
block initiatives you bring forward and affect other’s perception of your success.
Once you’ve identified your shadow boss, you need to identify what type of shadow
boss they are. Are they a puppeteer who likes to control things whilst remaining out
of sight, so that their own objectives are achieved? Or are they a true supporter of
your direct line manager (and, thereby, you) and trust them emphatically?

It’s not unusual that you need to satisfy your direct line manager and one or more
other stakeholders in the organization. Of course, it makes your job easier if you
have established that by satisfying your direct line manager, you’ll be satisfying the
rest of the organization. Establishing your real boss—or bosses—is a fundamental
first step as a CIO.
2. Establish your purpose and the expectations surrounding your role
Again, this may seem obvious, and you may be thinking that your purpose was clear
in the job description or interview; however, organizations can poorly explain why
your role is being filled. Is there a vacancy due to a previous CIO leaving? Is this a
new role where there was no CIO previously in the company? Or is it the result of
splitting responsibilities of a similar role such as a CTO? The reason your role exists
matters.
Sometimes CIOs are hired to “fix a problem.” I recall one organization that struggled
with delivery, and leadership couldn’t achieve reliable delivery times from their
software development teams. The organization wanted someone to take
responsibility for the solution delivery aspect of technology operations and solve
that specific pain. Other, more mature organizations understand the need for
technology services within the organization. They may hire a CIO to ensure that
correct leadership exists for technology to be properly represented.
Understanding the expectation of your role early in your appointment is crucial to
your short and long-term success. Remember: even if you are hired for one specific
issue, your purpose can change over time. You must satisfy your initial hiring purpose
before expanding your responsibilities.
3. Determine the state of technology
Every CIO role involves managing technology, and so you should evaluate the state
of technology you’ve inherited. Some organizations have invested appropriately in
technology, and therefore your job is made easier, but underinvestment or
mismanagement requires a more thorough investigation.
Regarding service delivery and technical operations, track your department against
the ITIL framework (IT Information Library). Although you don’t have to be certified
to ITIL or a similar standard, this baseline will help you define your organization’s
maturity.
Assuming you’re also responsible for the development of and/or support of new
technology products, a great benchmark measurement is Geoffrey Moore’s lifecycle
of technology adoption[1]. Applying Geoffrey’s technology adoption lifecycle bell
chart will help you quickly establish if the organization’s is making progress toward
its product goals.
An early understanding of the state of technology will help you realize the
importance of technology to the organization’s various goals and performance
indicators, and it will also help you determine how critical your role is in the overall
organization.
4. Review the state of your team
In my experience, understanding the state of your teams is commonly overlooked by
CIOs. People management is the most important factor in your career failure or
success, and some CIOs are frustrated that there is no single formula for leadership
that achieves desired results. If you organize technical talent based on skills and
strengths, you’ll create teams that work well together, overcome challenges and
deliver on your behalf.
I’ve built and worked with world-class teams in the past. On these teams, each
member knew their purpose, how they contributed to the department mission, and,
most importantly, recognized their weaknesses and allowed other team members to
demonstrate their strengths. This resulted in strong interdependencies, high trust
and ferocious delivery, but it took several years to arrive at that point.
One tip here: watch out for heroics. You may think you have an excellent team based
on feedback that a small number of staff has worked multiple times through the
night to save a server or a customer database. If you hear a lot of these stories, they
may be suffering from the “Nut Island Effect”[2], and could be displaying symptoms
of poor support for technology within the organization.

As a leader, you must identify and assess the state of your team, and ask yourself
hard questions about their potential. Do these teams deliver the required level of
output? Are they experienced or inexperienced? Can these teams take you and the
organization where it needs to go?
5. Find your allies and influence
Today’s CIO needs to forge strong relationships across the business. And so, you
must establish who throughout the organization has a stake in your success. It’s
important to understand how your peers view IT—some will see it as a cost or a key
enabler and others will be indifferent. Forging strong relationships across the
company increases your ability to create real change in the organization.
You may be wondering why I haven’t focused more on container technology, the
state of core enterprise systems and platforms, and the type of database technology
in use. To succeed as a CIO, you need to first understand the business and its
dynamic—all the technology information will come to you eventually. The CIO must
quickly establish themselves as a business executive and business stakeholder,
otherwise you run the risk of self-isolating to the back room where IT is done. You
want to avoid this outcome from the very first day you start your new role.
30-60 days: Vision and planning
By now you have a thorough understanding of the organization. Some of your
preconceptions may have changed. You may be excited about the organization or
you may have learned a few things you wish you knew during your interview.
Whatever your impression now, it’s time prepare for your next 30 days. In this
period, you need to develop a vision that inspires your teams and make a plan to
reach your goals.
Days 30-60 are spent creating:
6. Department priorities
7. First line management team
8. Mission clarity and adoption

1. Establish your priorities

By now you will know how IT is viewed within the organization and whether you’re
being welcomed to the senior leadership table or kept in the back room. You’ll also
know the key stakeholders determining how successful you’ll be in your role. Now
it’s time to prioritize what’s important to you. These priorities will map directly to
the purpose for your hire and the state of technology you spent reviewing in days 1-
30.
For example, if you were hired to help launch a new product to the market, then you
should not dedicate resources to increasing the company-wide usage of the ERP
system. It’s necessary that you relentlessly set and deliver on your priorities—make
it a fundamental part of your role.
2. Identify your first line management team
In most reasonably sized organizations, you need a team around you to deliver on
goals and objectives. This core team is vital to creating time and bandwidth for you
to engage across the company and embed yourself as a business executive. You
won’t have these abilities if you’re managing every single project, dealing with every
incident and approving every change yourself.
This is where you need a strong team with you. It can be difficult to identify your
strongest technology leadership team after 30 or 60 days, so I recommend you leave
yourself plenty of flexibility when establishing this team. You will need to make
changes in the early years, and hiring may make sense to fill the competency gaps.
 3. Clarify the mission and make sure everyone knows what it is and why it’s
important
As CIO, you need to demonstrate leadership by declaring a department mission. It’s
common for technical teams to be “order takers” who feel disconnected from
business strategy. Your staff may fail to see how day-to-day IT work impacts the
business’ overall success. So, it’s important to have a clear team mission, a mission
that’s connected to day-to-day technical work and also linked to the overall
organization.
The mission for your department needs to be meaningful, easy to understand and
related to daily work. This statement doesn’t have to be perfect or permanent. In
fact, I find a three year tenure for department missions to be effective. After three
years, you can take stock of progress, re-base activities and ensure you keep pace
with changes in the market. Of course, depending on the size and complexity of your
organization, three years may be too long or too short for an effective mission, so
adjust accordingly based on your needs.

BEYOND 60 DAYS: EXECUTE AND CHANGE

Now it’s time to put your mark on the organization. After spending 60 days assessing
and planning, the execution of your priorities begins. You were most likely hired to
effect change in the organization, so it’s important to demonstrate visible changes
that stakeholders view as positive movement. This is going to be a very busy time as
you drive multiple initiatives in parallel.
Start by getting the core team you identified in the previous 30 days engaged and
committed to your plan. Establish a regular check-in cadence with this team, and
ensure they all know their contribution to your role, the team’s responsibilities and
the organization’s goals.
When you arrive at the point where you have a high performing team, are enabling
the business, and contributing to a growing and successful enterprise, you’ll feel a
great sense of achievement and satisfaction. However, this ongoing execution phase
can present numerous and unexpected challenges. This is why it’s important to have
clarity on the items we covered in the first 60 days, so you can utilize critical
knowledge when something goes wrong.
The road to achieving continual success as a CIO isn’t always easy or, at times, clear.
It’s my hope that the steps I’ve outlined provide clear direction, enumerate key
factors that impact your role, and make your first 60 days a positive foundation for
the many more you’ll experience as a technology leader.
ROADMAP SUMMARY