CIO

Onboarding
Plan
for the First 100 Days
 Congratulations on your new position!
This e-book walks you through the top critical things to include in your onboarding as the
new Association CIO. It is intended to serve as a guide to the first 100 days of activities
using the framework of People, Process and Technology, which are the three pillars of a
high-functioning IT department.

The onboarding is not just an orientation. Employee orientation usually consists of

paperwork and benefits enrollment, assignment of a workstation or office and a handoff
to the supervisor. This onboarding should be considered a framework for you as the new
CIO to acquire a deep understanding of the organization’s key processes and capabilities
while building relationships with its people.

Who this is for:

This guide is intended for the newly hired CIO, or head of IT, at an association or
non-profit. It contains a comprehensive list of information you’ll need to gather
and comprehend to inform your decision-making, as well as the people you
need to meet and learn from.

This guide contains much information that is also relevant for other senior-level
association professionals. Though certain elements are specific to the role of
the CIO, or the head of IT, in an association or not-for-profit organization, most
information present here is relevant across departments.

This guide can also be useful to Human Resource professionals or supervisors

tasked with creating a robust onboarding plan for the new head of IT.

2 CIO Onboarding Plan for the First 100 Days

 1 People

An important first step in acclimating to the new job is getting to

know your new co-workers. There are the key people and groups that
you will interact with on a regular basis. Use this list as your guide to
plan outreach to these folks and schedule a simple meet-and-greet
conversation. Your Human Resource Officer may be able to provide
insights and help you prioritize this list.

Your Listening Tour

Your first weeks in the position will be well spent on a “listening tour,” where you
meet your colleagues and learn about the organization. As you meet folks and hear
perspectives about how things are working—or not working— you’ll want to begin
tracking a log of things you hear. Make note of things folks mention that you don’t
understand or that you need to research further.

Also be sure to ask, “What are your current pain points with IT?” Part of this initial task is
to just listen and learn. Don’t feel like you need to bring the answers to the table just yet.
Thank them for their feedback and perspective. Promise to investigate and add to a list of
items for further review.

Use this list as your guide to plan outreach to these folks and schedule a simple meet-
and-greet conversation. Your Human Resource Officer may be able to provide insights
and help you prioritize this list.

3 CIO Onboarding Plan for the First 100 Days

 Your Supervisor
Hopefully, Human Resources has scheduled a time for you
to meet with your supervisor on the first day or within the
first week. Be sure to review your job description ahead
of time and be prepared to ask any questions you have. Everyone wants to
Ask about expectations they may have of you. And ask get to know the
what they think are the top priorities for you and the IT
department to focus on. Ask about any opportunities
new boss, so be
for quick wins for IT to accomplish early during sure to spend time
your onboarding.
with everyone
on the team.
Other Key Stakeholders
If your position reports to the Executive Director of the
association, you will have the opportunity to meet with him or her
on a regular basis to learn how they view IT priorities. If you report
to a COO or CFO, you should ask HR to schedule time for you to meet
with folks in other key executive roles, as well. You’ll want to learn their view
of and expectations of IT early in your tenure. To prepare for these conversations, read
the association’s strategic plan and other governance documents. Ask how they view
technology’s role in the organization. Ask what they are hearing from members about the
external facing technology used to engage with the association. Is it working well? Note
which areas need improving.

IT Staff
You will want to meet the folks on the IT team right away. Depending on the size of the
team, some may be direct reports and others may not. First, schedule meetings with
each of your direct reports. Human Resources should be able to provide you with copies
of job descriptions, salary information, the most recent performance review, professional
development plans, and professional goals that may be already established for each
person on the team. These documents should be on your reading list for your first week
on the job.

Use the initial meeting to determine a regular cadence for you to touch base and get
it on the schedule. Within your first few weeks on board, aim to learn what your direct
reports are responsible for and what they are actively working on.

Every association has seasonal tasks, so be sure to ask about things they do daily, weekly
monthly, quarterly, and annually. Make note of these items to help you build a process
map for your department. These topics can also become agenda items for your regular
meetings with that employee going forward. You can work with them to think ahead to
next month’s project before it is past due. And you can remember to ask if that monthly
task was completed on time or if they need assistance.

4 CIO Onboarding Plan for the First 100 Days

 When you met with direct reports, determine the best way to meet the folks that report
to them. You might attend one of their regularly scheduled team meetings. Everyone
wants to get to know the new boss, so be sure to spend time with everyone on the team.

Plan a social or informal gathering for folks to get to know you, too. With in-person teams,
consider taking the team out to lunch. With virtual teams, try scheduling an informal
meetup online with an icebreaker activity.

Senior Leadership
As the head of IT, you have two teams that you are part of: you are leading your
department and you participate on the senior leadership team. You need to get to know
your peers across the organization.

IT tends to interact with certain departments more than others. Marketing and
Communications, Membership, Events, and Finance come to mind right away. Reach out
to these department heads first to set up initial conversations but be sure to make the
rounds to all the departments in the organization.

At this meeting, you’ll want to learn about what their department has responsibility
for and who are their key team members. You’ll also want to ask about their team’s
involvement with any IT initiatives or projects. Also be sure to ask, “What are your current
pain points with IT?” Part of this initial meet and greet is that you are on a listening
tour. Don’t feel like you need to bring the answers to the table just yet. Thank them for
their feedback and perspective. Promise to investigate and add it to a list of items for
further review.

Vendors and Consultants

Next, determine who you will work with that are outside of your organization. Association
IT departments tend to be small and heavily dependent on relationships with key vendors
and consultants. You might identify those inside the organization acting as key contacts
with these vendors. In that case, you can ask them to send an email introduction. Other
times, you may need to reach out directly and introduce yourself as the new head of IT.

Start with your key vendors first. Identify a contact at your Managed Service Provider or
key hosting/support vendor. Two other key contacts are your account representatives
at your Association Management Software company and your Content Management
software or website vendor.

Most vendors do an annual review with their clients. Ask to see the most recent report
from that meeting. If that meeting is overdue with the organization, invite them to the
office for a visit or schedule a virtual meeting, if they are not located nearby.

Your intent at these vendor meetings is to learn about the current state of the relationship
with the vendor or consultant. Prepare by reviewing the current contract and talking to
team members about the vendor relationship. Aim to leave the meeting with a thorough

5 CIO Onboarding Plan for the First 100 Days

 understanding of the contracted services provided and the terms of the contract. In most
cases, they will look at this first meeting as an opportunity to begin a healthy vendor
relationship with you, especially if the relationship with the association or with your
predecessor was rocky.

Board, Volunteers, and Members

Lastly, don’t forget about the members and volunteer leaders.

Some associations have a volunteer leader or committee that plays a role in IT

governance for the association. Be sure to ask the CEO or COO if there is such a group.
And if so, ask them to make the introductions.

In your first year, you will likely have the opportunity to meet committee members and
board members. When invited, attend Board meetings, officer orientation sessions, and
chapter leader meetings. Take advantage of those opportunities to meet members and
listen to their concerns.

If you are unfamiliar with the industry the association represents, ask HR about
scheduling an onsite visit for you to shadow a member in their workplace. See
what they do in a typical workday. Get a tour of their workplace, especially if it is a
lab, manufacturing site, or a field office. The insights gleaned can be valuable in
understanding how members would want to interact with the association’s technology.

6 CIO Onboarding Plan for the First 100 Days

 2 Process

As the next step in your listening tour after meeting the people who
do the work of the association, aim to learn how work gets done. All
the internal processes are intended to help, yet sometimes hinder,
the people doing the things. Sometimes policies dictate procedures.
Sometimes the employee culture influences the process and how
things get done. You may find that the process is ripe for improvement.
With a fresh set of eyes and a scope of authority to impact change, you
are in a position to identify areas for improvement.

One of the first things you need to learn is the meeting cadence within the organization.
Learn when the all-staff meetings occur, also the senior staff meetings, the Board
meetings, and the association’s major events. Take time to get these all set up on
your calendar. Then layer in standing meetings for your department and any 1:1s with
direct reports.

Before that initial meeting with the Executive Director, learn about the governance
process for the association. Seek out the staff contact who works with the board. S/he
will be able to help you find key documents such as the association bylaws, policies and
procedures that exist. Take a day and read them all.

Similarly, seek out the strategic plan. Include it on your reading list and ask your peers for
their interpretations of it. It may be helpful to get insights from key executives who were
involved in the development process.

There are quite a few financial things to learn about during onboarding.

7 CIO Onboarding Plan for the First 100 Days

 Ask the CFO how to locate a copy of the department budget and any detailed peripheral
documentation, if it exists. A review of these materials can bring to light important details.
Identify all IT department vendors. Learn what new initiatives that have been planned
and resourced before you arrived. Determine how capital items get budgeted and
depreciated.

After you’ve had a chance to review the operating budget and financial reports, be sure
you understand what items are being depreciated on the books. Learn who manages
the fixed asset inventory for the association and if you have the responsibility to prepare
the capital budget annually. Learn the depreciation cycle for IT hardware assets like your
firewall, servers and switches. Compare that information with your purchase records and
warranty status. Learn the minimum threshold for items to be capitalized. Learn if laptops
are depreciated differently. Learn the age of the current equipment and the expected
replacement schedule.

When you meet with the CFO, ask about the annual budget process. Note the timing
in your list of annual association priorities such as dues renewal and major conferences.
Learn the rules and expectations on how bills get submitted and paid. Lastly, learn about
the signature policy for purchasing and signing contracts.

When you meet with HR, ask if there is an annual performance review process. Learn
when it occurs and what’s expected. Learn if salary adjustments occur during this process
or outside it. Learn if performance bonuses outside the annual adjustments are used
within the organization.

Only a few associations have a formal Project Management Office. If yours does, you’ll
need to learn how IT interacts with the PMO team. If you don’t have a formal PMO, then
the IT team may be leading their own initiatives. Ask is there is a process for how staff
vet, prioritize and resource projects. Learn what communication channels can be used to
provide project updates to staff and volunteers. Are outside consultants used as project
managers on certain initiatives such as software selection, etc.? Learn what project
management methodology and norms are used.

Ask your Managed Service Provider for reports on key Helpdesk metrics for the last
reporting period. As you are talking with others across the organization, you want to
understand your average ticket volume, commonly reported issues, the average time to
answer calls, and the average time to ticket resolution. Also, ask who the most frequent
callers are and review recent tickets that were escalated and recent major incidents.

Talk to Human Resources about software end-user training. Learn if and when staff
was given training on the Association Management System and other line-of-business
software applications. Learn if funding is available for the training of new staff who join
the organization. Sometimes software training is provided to new people by a co-worker.
Sometimes using existing documentation and video tutorials, but sometimes not. Ask if
staff have expressed the need for training and in what areas.

8 CIO Onboarding Plan for the First 100 Days

 Also, ask about and check the budget for evidence of a security awareness training
program. The most effective cyber security asset is an educated employee who
recognizes threats and follows communicated policies. Learn the training cadence, topics,
and metrics. What is your click-prone percentage of simulated phishing tests?

Review the IT Policies. Learn of regulatory compliance expectations. Do you need to

maintain PCI compliance? What about GDPR? Make note of the required actions outlined
in the policy. Ask staff for dates and records from the most recent internal audits.

Lastly, read the Employee Handbook to learn all of what’s expected of you as an
employee. Note which end-user IT policies are included in the handbook and which are
stand-alone polices.

With a fresh set of

eyes and a scope
of authority to
impact change, you
are in a position to
identify areas for
improvement.

9 CIO Onboarding Plan for the First 100 Days

 3 Technology

Inevitably, there are a whole host of technology-related things to

learn about. Resist the urge to jump into hands-on training on the
Association Management System or dive into the details of the
current IT project. During the onboarding period, focus on learning
the big picture. The items outlined below are not strictly technical in
nature, but they represent the management and governance side of
technology in use.

The easiest technical documentation to begin a review with is the network

infrastructure diagram. Assess if it can be delivered quickly, if it is up to date, contains
the appropriate level of detail, and is easy to follow. If it doesn’t exist, you can add it to the
list of things to create.

Next is the asset inventory and depreciation schedule. Reconcile this data with the
information learned from the CFO about the capital budget and the asset lifecycle.

Investigate if there is an application portfolio inventory or application architecture

diagram. You’ll want to maintain a complete list of software in use across the association,
then review licenses, learn who uses it, which department budgets for it, and who
manages the user access accounts. Learn which are SaaS products and which are
managed by IT. Learn where the applications are hosted and who manages them. If a
diagram doesn’t yet exist, segment your list by applications that have an external-facing
component, those used exclusively by staff, a department or select staff users, then all
the utility apps used by IT. This simple exercise will give you a jump start on a simple
application architecture diagram.

10 CIO Onboarding Plan for the First 100 Days

 Ask your IT staff or your Managed Service Provider for a copy of the current on-boarding
and off-boarding checklists. Reconcile these checklists for consistency with what you
learned about your applications and who is managing the user access accounts. Identify
any gaps where access is not being actively managed and ask when the internal audits
were last conducted for each app.

Next, learn about privileged access management. First, review the administrator
accounts to the network devices such as the firewall, switches, appliances, wireless
access controller, domain administrator, Global Admin for M365, and the SQL
administrator account for database servers. Review internal procedures around security
and the use of these credentials. If these are managed by your Managed Service Provider,
have a conversation about procedures when staff turnover in their organization. Also,
discuss protocols in the case that one of those accounts is compromised.

Review all Standard Operating Procedures (SOPs) that exist. Remember that initial
interview when staff reported that they are responsible for certain tasks on a regular
basis? Look for SOPs on each of those procedures. Make note of those you think may be
lacking documentation and those that are out of date.

Review any software training materials for staff use. Do staff have access to general
end-user software training for core applications like Word and Excel? Does the
association have overview training materials for staff on the Association Management
System? Do association staff have access to training on how to perform tasks critical for
their job function? Is the training up to date using the current version of the software? Is
it easy to use? Note any gaps in training and ask folks about them when you hold your
initial meetings with each department head.

Ask to review data flows and integrations. Many associations maintain a document
with circles and arrows mapping data flows across software programs. Dig deeper to
learn about the types of APIs in use and if documentation exists. Learn which data points
are being stored in each application, which data points are being shared, and in which
direction the data flows.

Review business intelligence metrics in use by the association and any reports that are
being delivered to senior management on a regular basis.

Ask to review the backup schedule for the servers managed onsite and by your
Managed Service Provider. Schedule a test of a restore from a SQL backup and a full
server snapshot restore. Also, ask about configuration backups of all network devices.

Review the disaster recovery plan. Often IT plays a key role to get a business back up
and running in a disaster situation. It is critical for IT to know and understand their role
and expectations of them.

11 CIO Onboarding Plan for the First 100 Days

 Building your Annual
IT Department Process Map
During the onboarding period, build an annual process map for all of the things that
occur regularly that IT is responsible for.

The suggested format is to create a grid with the months of the year across the top, then
list the staff positions down the left side. Fill in the grid with the monthly, quarterly, and
annual tasks and activities.

This tool can be a handy reference guide for you to spot periods where certain staff may
be overloaded and when your team has the bandwidth to assist with ad hoc projects.

Jan Feb Mar Apr May Jun Jul Aug Sept Oct Nov Dec

Director

Manager

Coordinator

Developer

Helpdesk Tech

MSP Tech Admin

12 CIO Onboarding Plan for the First 100 Days

 Building your
First-Year IT Roadmap
With all of the information you learned during the onboarding period, you are in a great
position to map out the priorities for the rest of your first year. Compile the notes from
your interviews with stakeholders, notes from the process reviews, and notes regarding
the technology-related pain points. It’s time to whiteboard an IT roadmap.

With your list of tasks, note those that have dependencies. Note which items are already
resourced with staff, time, and budget and which need resources to be allocated before
they can begin. Note which items directly impact members and which are related to
priorities in the association’s strategic plan.

Also, include the core responsibilities that the staff reported to you with the appropriate
frequency. This recognizes that ongoing maintenance work continues while we layer in
the additional tasks or projects. It will help you map out how much additional workload
each team member can reasonably handle.

Now you are ready to review each task by which skills are needed and which resource has
bandwidth available. It may be helpful to move projects between grids with staff names
on the side and a timeline along the top.

Review your challenges and priorities with your team, your supervisor, and your peers. Be
mindful of other departments’ priorities and adjust your timeline accordingly.

At the end of the day, you will have created an IT roadmap using a well-informed,
thoughtful process. This plan can be layered into your annual performance plan with
goals and expected outcomes.

13 CIO Onboarding Plan for the First 100 Days

 Reading List
Below is the summary list of all of the materials to locate and read during your
onboarding period. Use this checklist to keep track for yourself.

The association’s bylaws

The association’s policies and procedures
The association’s strategic plan
The department operating budget and the capital budget
Job descriptions (yours and your team’s)
Performance reviews and salary history
Vendor License agreements and support contracts
Consultant contracts and Scopes of Work (SOWs)
Helpdesk ticket reports
Employee training reports
Phishing test reports
Network or internal IT audit reports
IT Policies
Employee Handbook
Network Diagram
Asset Inventory
Application Portfolio Inventory
Onboarding and Offboarding Checklists
Standard Operating Procedures
Data Governance Guide
Web Governance Guide
Software Training Materials
Data Integration Maps or process flow diagrams
Disaster Recovery Plan and Backup Schedule
Business Continuity Plan

14 CIO Onboarding Plan for the First 100 Days

 Staff Interview Template
Use this template to interview your direct reports during your
first one-on-one meeting with them.

Name:_______________________________________________________________________________________

Job Title: ____________________________________________________________________________________

Tenure at the Association: ___________________________________________________________________

Tenure in Workforce: ________________________________________________________________________

Daily Tasks Weekly Tasks

Monthly Tasks Quarterly Tasks

Annual Tasks Active Projects

Vendor Relationships (which vendors are you Key Stakeholder Relationships (who do you
the primary point of contact) work closely with across the association)

Meeting Cadence (how often, what format) Work Schedule (typical work hours, when in
office vs home)

Administrator Access in which software apps Server Access to which hosts

Certifications (or area of specialization) Professional Development Goals/Plans

15 CIO Onboarding Plan for the First 100 Days

 About Cimatri
Cimatri provides strategic leadership and
world class IT services to associations and
non-profits looking to make technology an
advantage in delivering on their mission.

Cimatri’s North-America-based, fully remote

team, works tirelessly on behalf of their
clients, ensuring that people, process, and
technology are aligned to mission and
strategy. Cimatri is committed to fostering,
cultivating, and preserving a culture of
diversity, equity, and inclusion.

About René Shonerd

René joined Cimatri in 2017. She is a Certified Association Executive with extensive on-the-
job expertise in IT Strategy and Governance, IT Operations, and Application Management.
She is our resident data wizard extraordinaire having experience as a database
administrator in several major AMS systems. She served as the founding President of the
Association Women Technology Champions and is a Past Chair of the ASAE Technology
Section Council. She earned a Master of Education in Higher Education Administration from
the University of Toledo and a certificate in Data and Business Intelligence from InfoTech
Academy. Outside the office, René can frequently be spotted in a local dance fitness class.
She lives in Alexandria, Virginia with her husband and daughter.

LinkedIn: linkedin.com/in/reneshonerd/

16 CIO Onboarding Plan for the First 100 Days