CTOs can encounter many headaches and district challenges.

CTO headaches: Five complex district challenges

Tech leaders have their plates full--here's how many of them view some of the most stubborn district challenges

CTOs juggle countless district challenges—they have many high-profile systems, implementations, and changes they manage each year. At times, some of the biggest headaches are the low-priority projects that are complex by nature and time-consuming, but that also have a large reach in our districts.

Technology leaders from across the nation shared and discussed some of these district challenges at CoSN’s 2019 conference. While the group shared a number of different solutions, the collective conversation for the session focused on the idea that CTOs have not identified solutions to these district challenges and.

With that said, following are the five main issues CTOs discussed:

Onboarding/existing staff

One of the most complex challenges in any organization is the one that touches the most departments: HR, Technology, Business, Facilities, Curriculum/Instruction, School Leaders, etc. It is the first impression of our district and schools for new employees and a huge risk footprint for existing employees if not managed well. Technology department challenges include ensuring awareness of staffing changes before the start or end date, the timing for system access, transition plans for providing access/files from the outgoing staff member to the new employee, managing family name changes and timing, managing multiple building access levels, first day procedures, etc. Even with a system in place, making sure all departments adhere to the defined processes can be challenging.


  • Streamline onboarding and exiting of staff through automating systems and scripting. (Systems referenced were Laserfiche, Smartsheets, and Powershell scripts.)
  • Leveraging Google forms and Ultradox to automate part of the onboarding process, suggested by Centralia School District (WA)
  • Maintain consistent and open communication/planning with Human Resources and Technology departments throughout the year. Hold standing quarterly meetings to address hot-button items occurring at certain times of the year (i.e. new staff is ready for orientation in August).
  • Use Cloud Migration Systems to simplify user creation and transfer ownership between employees. (Systems referenced were Bettercloud and Syscloud.)

Paper to digital forms

Many districts have too many paper forms that are filled out and then filed into a cabinet. Moving physical paper and multiple signatures is inefficient, costs money and time, does not include any automation, and does not offer search capabilities once papers are in a file cabinet. Challenges include looking at a market that is broken into two segments: digital forms/workflow systems and document management systems. Both are expensive and cumbersome. In addition to the cost concerns, a number of others received mention: workflow solutions with multiple approvers, finding time to implement a solution with fidelity, setting up retention rules, change in practice for accessing digitally rather than print out the forms, and an exit strategy to export all documents if an employee leaves the system are all additional considerations.


  • Systems that manage both digital forms and workflow–Laserfiche to address the workflow and unreliable paper passing process (For PD request forms, contracts, Special Education transportation, field trip request)
  • Manage contracts with Docusign
  • Costs–leverage a subscription model rather than a perpetual/expensive option
  • Leverage the online student/family registration process to include many of the paper-based forms

Application saturation

There is an application for everything. Many districts and organizations are drowning in this challenge. When a new district director takes over a business unit, it is almost a given that they will have an application specific to their part of the organization–HR, Business, Instruction, SPED, etc. When looked at in a vacuum, it may make sense and seem easy to set up and manage. However, new district challenges arise related to the costs when looking at all district applications, end user experience with having to navigate SIS integration, data de-centralization, data privacy, school year rollover processing, and training new staff. These are spinning out of control in many of our districts.


  • Implement a standard application process for new online tools
  • Collaborate with attorneys to have a standard data service and data sharing agreements
  • Partner with Learn Platform to provide transparency in the applications that have been approved, denied and/or in progress in district; in addition; provides a tool to measure impact of ROI (return on investment) and ROV (return on value)
  • Educate leadership–provide a list of applications and costs to create awareness of this issue
  • Single-sign on solutions (such as Classlink, Clever, and Identity Automation)

IT staff training

Training IT staff is critical for development and to make sure district tech leaders are investing in their teams. However, this is easier said than done. Challenges include finding time to provide the training, delivery method for online self-paced or face-to-face, relevant training that can be applied, industry changing to simplification of enterprise technology, staff turnover, and costs.


  • Developing a consistent schedule of professional learning for staff and a test environment for staff to apply learning
  • Bi-weekly IT department hangouts to cover a specific topic
  • Encourage certifications and growth with entry level staff
  • Self-paced solutions such as Pluralsite or curated free videos (i.e. Professor Messer)

Data and data dashboards

Data will continue to become more critical with programs like ESSA, the need to use analytics, and as district tech leaders begin to envision the future with big data and automations. Building a data dashboard is complex. Systems are expensive and can take up to a year to get running. Costs for external systems are usually based on the number of teachers or students to maximize vendor costs (not the true number of users). Other challenges are data cleansing (garbage in, garbage out), de-centralization of data in multiple systems, defining metrics that typically change annually, and data refresh rates all contribute to this headache.


  • Define requirements–district leadership teams should define who will have access, identify goals for the different metrics, and source information
  • Start small–these systems should have a focus with leadership and administrative teams. Many teachers do not have time to navigate data dashboards, so make sure scope and costs are adjusted properly.
  • Ongoing meetings and training with the key groups entering in data–provide data quality reports that emphasize standardizing on fields and entry.
  • External system that has a partnership with the SIS provider or integrates seamlessly

As CTOs start to share and manage the above complex district challenges, they can then move on to additional headaches if they are not already working on the cyber security budget, data breach management, new password management strategies, emergency communications, Artificial Intelligence threats, managing the Internet of Things, etc.

As each district plans for these transitions, we’ve seen one key component for success: the opportunity to network and collaborate with others across the nation doing this work. District tech leaders have an incredible opportunity to learn from their peers in order for future implementations to be successful.

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