Core Conversion
The challenge
Core conversion is more than a technology implementation. It changes the systems, processes, workflows, and behaviors employees rely on to do their jobs.
At Sterling National Bank, the organization was transitioning to core banking systems following the acquisition of Astoria Bank. When I joined Sterling, much of the existing training consisted of job aids and fragmented documentation rather than a cohesive, instructionally sound learning experience.
The initial challenge was to transform that material into structured training for the core systems used by banking-center employees and other business functions.
But there was a larger organizational opportunity.
The instructional design function had traditionally operated more like an order-taking service: a business partner requested a job aid or training product, and L&D produced it.
I saw an opportunity to change that model.
The goal was not simply to produce training.
It was to establish L&D as a strategic partner to the business—one that worked alongside process owners and subject matter experts to understand the business problem, design the right learning solution, and create experiences that supported performance and organizational objectives.
The Webster conversion created a different but related challenge.
Following the merger of Sterling and Webster, the combined organization needed to transition from two sets of core systems to a common technology environment. The organization was significantly larger, and employees came with very different levels of familiarity with the systems.
Legacy Sterling employees had experience with many of the systems.
Legacy Webster employees often did not.
At the same time, the merger created significant organizational change: new colleagues, new managers, new processes, new systems, and the loss of familiar roles and relationships.
The learning challenge was therefore both technical and human.
Core conversion is more than a technology implementation. It changes the systems, processes, workflows, and behaviors employees rely on to do their jobs.
At Sterling National Bank, the organization was transitioning to core banking systems following the acquisition of Astoria Bank. When I joined Sterling, much of the existing training consisted of job aids and fragmented documentation rather than a cohesive, instructionally sound learning experience.
The initial challenge was to transform that material into structured training for the core systems used by banking-center employees and other business functions.
But there was a larger organizational opportunity.
The instructional design function had traditionally operated more like an order-taking service: a business partner requested a job aid or training product, and L&D produced it.
I saw an opportunity to change that model.
The goal was not simply to produce training.
It was to establish L&D as a strategic partner to the business—one that worked alongside process owners and subject matter experts to understand the business problem, design the right learning solution, and create experiences that supported performance and organizational objectives.
The Webster conversion created a different but related challenge.
Following the merger of Sterling and Webster, the combined organization needed to transition from two sets of core systems to a common technology environment. The organization was significantly larger, and employees came with very different levels of familiarity with the systems.
Legacy Sterling employees had experience with many of the systems.
Legacy Webster employees often did not.
At the same time, the merger created significant organizational change: new colleagues, new managers, new processes, new systems, and the loss of familiar roles and relationships.
The learning challenge was therefore both technical and human.
My Role
My role evolved significantly across the two conversions.
Sterling National Bank
I initially joined Sterling as a contractor and supported early core-conversion activities.
After transitioning to a full-time role, I became the lead/senior instructional designer responsible for the instructional design function.
I was responsible for:
Assessing existing training
Establishing learning strategies
Working directly with SMEs and process owners
Designing and developing core-systems training
Establishing instructional standards and structure
Developing facilitator and participant materials
Creating project plans and managing delivery
Bringing structure and consistency to L&D processes
Partnering with business stakeholders
Establishing L&D as a strategic partner rather than an order-taking function
I approached the role not simply as a developer of training, but as an instructional systems designer and business partner.
Webster Bank
Following the merger, I became involved in the larger Webster core conversion and ultimately took on a project leadership role for the learning work.
I brought the strategy, content, documentation, and lessons learned from the Sterling implementation into the new organization.
But this wasn’t simply a lift-and-shift exercise.
I evaluated what could be reused, what needed to change, and where the larger, newly combined organization created opportunities to improve the learning experience.
My role evolved significantly across the two conversions.
Sterling National Bank
I initially joined Sterling as a contractor and supported early core-conversion activities.
After transitioning to a full-time role, I became the lead/senior instructional designer responsible for the instructional design function.
I was responsible for:
Assessing existing training
Establishing learning strategies
Working directly with SMEs and process owners
Designing and developing core-systems training
Establishing instructional standards and structure
Developing facilitator and participant materials
Creating project plans and managing delivery
Bringing structure and consistency to L&D processes
Partnering with business stakeholders
Establishing L&D as a strategic partner rather than an order-taking function
I approached the role not simply as a developer of training, but as an instructional systems designer and business partner.
Webster Bank
Following the merger, I became involved in the larger Webster core conversion and ultimately took on a project leadership role for the learning work.
I brought the strategy, content, documentation, and lessons learned from the Sterling implementation into the new organization.
But this wasn’t simply a lift-and-shift exercise.
I evaluated what could be reused, what needed to change, and where the larger, newly combined organization created opportunities to improve the learning experience.
The Approach
The approach began with a simple instructional design principle: Understand the work before designing the learning.
1. Assess the existing environment
At Sterling, much of the available material consisted of job aids and informal documentation.
I worked with SMEs and process owners to understand what employees actually needed to know and do, then transformed that information into more structured learning experiences.
The initial strategy emphasized strong facilitator materials and participant guides, with opportunities to transition appropriate content to e-learning over time.
2. Build learning around the work
The core systems were not taught as abstract technology. Training focused on how employees would actually use the systems to perform their responsibilities. That meant understanding:
Banking-center workflows
System functionality
Processes and procedures
Employee roles
Customer-facing responsibilities
The relationship between systems and business operations
3. Establish L&D as a strategic partner
One of the most significant changes I helped introduce was a shift in how the instructional design function worked with the business.
Instead of: Business: “We need a job aid.” L&D: “Here is your job aid.”
We moved toward: Business and L&D: “Let’s understand the process, the performance need, the audience, and the desired outcome—and determine the right learning solution together.”
That shift changed the conversations we were invited into.
Rather than being called only when someone needed a deliverable, the team increasingly became part of the upstream business conversation.
4. Use the first conversion to inform the second
By the time the Webster conversion occurred, I had a documented strategy, established processes, structured content, and firsthand knowledge of the systems.
That became an enormous advantage.
Rather than starting from scratch, we could reuse what worked, adapt it to the new organization, and improve the approach based on what we had learned.
The approach began with a simple instructional design principle: Understand the work before designing the learning.
1. Assess the existing environment
At Sterling, much of the available material consisted of job aids and informal documentation.
I worked with SMEs and process owners to understand what employees actually needed to know and do, then transformed that information into more structured learning experiences.
The initial strategy emphasized strong facilitator materials and participant guides, with opportunities to transition appropriate content to e-learning over time.
2. Build learning around the work
The core systems were not taught as abstract technology. Training focused on how employees would actually use the systems to perform their responsibilities. That meant understanding:
Banking-center workflows
System functionality
Processes and procedures
Employee roles
Customer-facing responsibilities
The relationship between systems and business operations
3. Establish L&D as a strategic partner
One of the most significant changes I helped introduce was a shift in how the instructional design function worked with the business.
Instead of: Business: “We need a job aid.” L&D: “Here is your job aid.”
We moved toward: Business and L&D: “Let’s understand the process, the performance need, the audience, and the desired outcome—and determine the right learning solution together.”
That shift changed the conversations we were invited into.
Rather than being called only when someone needed a deliverable, the team increasingly became part of the upstream business conversation.
4. Use the first conversion to inform the second
By the time the Webster conversion occurred, I had a documented strategy, established processes, structured content, and firsthand knowledge of the systems.
That became an enormous advantage.
Rather than starting from scratch, we could reuse what worked, adapt it to the new organization, and improve the approach based on what we had learned.
Leadership & Execution
The leadership challenge extended well beyond instructional design.
At Sterling, I was effectively building greater structure and maturity into the instructional design function itself.
I established project planning practices, clarified processes, created greater consistency, and helped the team move from reactive production toward strategic partnership.
My philosophy was deliberate: We were not order takers. We were strategic partners.
That philosophy affected how we engaged stakeholders, how we scoped projects, how we approached requirements, and how we positioned the value of instructional design.
The result was that business leaders began bringing the team into conversations they previously might not have considered instructional design conversations.
Leading Through the Webster Merger
The Webster conversion introduced an entirely different leadership dimension: people were experiencing change while simultaneously being asked to learn new systems and processes.
There were two populations with very different starting points.
Legacy Sterling colleagues
Already familiar with many of the systems, but now expected to learn new functionality, processes, and ways of working.
Legacy Webster colleagues
Often encountering the systems for the first time.
Rather than allowing the difference to create a “we know better than you” dynamic, we intentionally framed the transition as:
We’re all learning something new—some people simply have more prior experience than others.
That allowed the learning experience to acknowledge different levels of familiarity without making either group feel diminished.
I also approached the conversion as a change-management opportunity, not merely a systems-training exercise.
When employees expressed frustration about the merger or resistance to new processes, I learned to recognize that the resistance was often about much more than the training.
People were losing familiar systems, colleagues, managers, routines, and sometimes roles.
My responsibility—and my team’s responsibility—was to acknowledge those realities without becoming anchored in them.
Acknowledge the emotion. Then help people find a way forward.
That became an important leadership principle for me.
The leadership challenge extended well beyond instructional design.
At Sterling, I was effectively building greater structure and maturity into the instructional design function itself.
I established project planning practices, clarified processes, created greater consistency, and helped the team move from reactive production toward strategic partnership.
My philosophy was deliberate: We were not order takers. We were strategic partners.
That philosophy affected how we engaged stakeholders, how we scoped projects, how we approached requirements, and how we positioned the value of instructional design.
The result was that business leaders began bringing the team into conversations they previously might not have considered instructional design conversations.
Leading Through the Webster Merger
The Webster conversion introduced an entirely different leadership dimension: people were experiencing change while simultaneously being asked to learn new systems and processes.
There were two populations with very different starting points.
Legacy Sterling colleagues
Already familiar with many of the systems, but now expected to learn new functionality, processes, and ways of working.
Legacy Webster colleagues
Often encountering the systems for the first time.
Rather than allowing the difference to create a “we know better than you” dynamic, we intentionally framed the transition as:
We’re all learning something new—some people simply have more prior experience than others.
That allowed the learning experience to acknowledge different levels of familiarity without making either group feel diminished.
I also approached the conversion as a change-management opportunity, not merely a systems-training exercise.
When employees expressed frustration about the merger or resistance to new processes, I learned to recognize that the resistance was often about much more than the training.
People were losing familiar systems, colleagues, managers, routines, and sometimes roles.
My responsibility—and my team’s responsibility—was to acknowledge those realities without becoming anchored in them.
Acknowledge the emotion. Then help people find a way forward.
That became an important leadership principle for me.
The Solution
The solution was not one course or one training product.
It was a structured learning ecosystem supporting a major organizational transformation.
At Sterling, we transformed fragmented core-systems documentation into structured learning experiences with facilitator materials, participant materials, and increasingly digital learning opportunities.
At Webster, we expanded and adapted that foundation for a larger, newly merged organization.
The learning experience incorporated:
Instructor-led training
Participant guides
Facilitator materials
E-learning where appropriate
Hands-on learning
System demonstrations
Process and procedure guidance
Practice opportunities
Role-specific learning
Supporting job aids and resources
Most importantly, the learning was designed to support the organization’s desired way of working, not simply teach people where to click.
For example, the conversion required employees to move away from maintaining downloaded or locally stored policies and procedures and toward using the organization’s designated repository and tools. Training therefore became a mechanism for reinforcing the new operating model, not simply explaining software functionality.
The solution was not one course or one training product.
It was a structured learning ecosystem supporting a major organizational transformation.
At Sterling, we transformed fragmented core-systems documentation into structured learning experiences with facilitator materials, participant materials, and increasingly digital learning opportunities.
At Webster, we expanded and adapted that foundation for a larger, newly merged organization.
The learning experience incorporated:
Instructor-led training
Participant guides
Facilitator materials
E-learning where appropriate
Hands-on learning
System demonstrations
Process and procedure guidance
Practice opportunities
Role-specific learning
Supporting job aids and resources
Most importantly, the learning was designed to support the organization’s desired way of working, not simply teach people where to click.
For example, the conversion required employees to move away from maintaining downloaded or locally stored policies and procedures and toward using the organization’s designated repository and tools. Training therefore became a mechanism for reinforcing the new operating model, not simply explaining software functionality.
Impact
The most significant impact of the Sterling work was not a single training metric.
It was the transformation of how the organization perceived and used instructional design.
L&D became increasingly viewed as a strategic partner rather than a production function.
The team was invited into conversations earlier, stakeholders increasingly wanted comprehensive learning solutions rather than individual job aids, and instructional design became more closely connected to business needs.
The Webster conversion extended that impact.
The documented strategy and learning assets from Sterling became reusable organizational knowledge, allowing the team to accelerate development for a significantly larger organization.
At the same time, the learning experience helped employees navigate not only new systems, but the behavioral and cultural changes accompanying the merger.
The most significant impact of the Sterling work was not a single training metric.
It was the transformation of how the organization perceived and used instructional design.
L&D became increasingly viewed as a strategic partner rather than a production function.
The team was invited into conversations earlier, stakeholders increasingly wanted comprehensive learning solutions rather than individual job aids, and instructional design became more closely connected to business needs.
The Webster conversion extended that impact.
The documented strategy and learning assets from Sterling became reusable organizational knowledge, allowing the team to accelerate development for a significantly larger organization.
At the same time, the learning experience helped employees navigate not only new systems, but the behavioral and cultural changes accompanying the merger.
Reflection
The core conversions taught me that instructional design can be a catalyst for organizational change.
I learned that people don’t resist technology simply because they don’t understand how to use it. Sometimes they resist because the technology represents something they are losing.
A merger can mean losing a familiar system, a familiar process, a familiar manager, a colleague, or even a sense of identity within the organization.
Training sits directly in the middle of that experience.
That means instructional designers have an opportunity—and a responsibility—to do more than explain the new system.
We can help people understand where they are, why they are there, and how to move forward.
The Sterling conversion also changed how I thought about the role of an instructional design function.
I didn’t want my team to be an order-taking service.
I wanted us to be strategic partners who were invited to the table because we understood learning, performance, people, and the business.
That philosophy shaped how I led the team, how I worked with stakeholders, and how I approached every project that followed.
And the Webster conversion reinforced another lesson: When you document your thinking, your work can outlive the project that created it.
The strategy developed for one organization became a foundation for another.
What began as a training solution became organizational knowledge that could be reused, adapted, and scaled.
The core conversions taught me that instructional design can be a catalyst for organizational change.
I learned that people don’t resist technology simply because they don’t understand how to use it. Sometimes they resist because the technology represents something they are losing.
A merger can mean losing a familiar system, a familiar process, a familiar manager, a colleague, or even a sense of identity within the organization.
Training sits directly in the middle of that experience.
That means instructional designers have an opportunity—and a responsibility—to do more than explain the new system.
We can help people understand where they are, why they are there, and how to move forward.
The Sterling conversion also changed how I thought about the role of an instructional design function.
I didn’t want my team to be an order-taking service.
I wanted us to be strategic partners who were invited to the table because we understood learning, performance, people, and the business.
That philosophy shaped how I led the team, how I worked with stakeholders, and how I approached every project that followed.
And the Webster conversion reinforced another lesson: When you document your thinking, your work can outlive the project that created it.
The strategy developed for one organization became a foundation for another.
What began as a training solution became organizational knowledge that could be reused, adapted, and scaled.