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How to Build a Learning Strategy for Your Association

Online learning has been top of mind for associations of all types and sizes over the past few years as they look to find better ways to attract, engage and retain members.  

Yet driving bold, broad change requires decisive, deliberate action. There’s no doubt that having the right technology plays a vital role in enabling digital transformations. There is, however, another piece of the puzzle that can be just as crucial: strategy 

In this guide, we’ll share best practices and frameworks to help you:   

  • set a strong foundation for your learning strategy 
  • develop a vision and purpose to guide it 
  • plan, implement and evaluate the impacts of your learning strategy 

Why a Strategy Matters for Your Digital Transformation

The Canadian Society of Association Executives’ (CSAE’s) 2024 Membership Trends Report revealed that Canadian associations are dealing with an interesting dichotomy. Although 64% of respondents said their value proposition was compelling or very compelling, members not seeing value was also the number two issue when it came to attracting new members and the number one issue when it came to retaining them.

In your opinion, how compelling is your member value proposition? Very Compelling: 26% Compelling: 38% Somewhat Compelling: 29% Not Very Compelling: 6% Not at All Compelling: 1%
What is your biggest challenge recruiting new members? Communication/Outreach: 26% Value/Value Proposition/Benefits of Membership: 20% Overall Membership Recruitment Strategies: 18% Cost/Fees/Price: 18% Confusion/Competition With Other Training Orgs/Other External Factors: 12% Organizational Challenges Within the Association, Including Staff: 9% All Other Challenges: 13% No Challenges or N/A: 8%
Regardless of whether you conduct exit surveys, what, in your estimation, are the primary reasons why members are not renewing their membership? Perceived Lack of Value: 40% Financial Considerations: 34% Career Changes/Transitions: 31% Lack of Participation/Engagement: 15% Competing Associations/External Factors: 15% All Other Reasons: 13% No Reason or N/A: 3% Don't Know/Not Sure: 3%

So what does value look like?

The good news is that, at the core, not a lot has changed about what members want. The top reasons they join an association are still networking, community building, professional development and education.

What is changing is who the members are and how they want to engage with the association. When we look at MGI’s global annual Membership Marketing Benchmarking Report, we see a seismic shift over the past decade. In 2013, millennials made up around 5% of the membership, Gen X around 24% and Boomers around 68%. In 2023, millennials and Gen Z were 30% of the membership, Gen X 31% and Boomers only 32%. On top of that, today’s members want flexibility. According to the CSAE’s research, behind overall engagement, making the best use of members’ limited time is the second biggest challenge associations say they’re up against.

This is what’s pushing a digital transformation past something associations around the world—Canada included—need to consider and into the realm of something they must do to stay relevant and sustain themselves. It’s no longer a nice-to-have extra. It’s table stakes.

In the last 20 years, we’ve seen more change taking place in this space than in the previous two millennia. To meet these new needs, our approach to learning had to evolve too.
Scott Butler executive director, Good Roads

Before You Build Out Your Strategy 

There are three questions you should answer that can help arm you with important information and lay a solid foundation as you go forward. First, you want to understand the resources your organization already has at its disposal that will support you as you launch or enhance your digital learning offerings. Second, you want to determine who your key stakeholders are going to be throughout the process. Third, you want to identify what obstacles you may be up against and where your opportunities may be. 

1. What Existing Resources and Expertise Can You Leverage? 

This will be important, especially when you start to get into the details about your programs that are going to be designed, developed and monitored. Depending on the size of your organization and its experience with online learning, you may already have a lot of what you need in-house. If not, you’ll need to determine whether you want to grow your teams or augment your capabilities by working with partners. Either way, getting a lay of the land upfront will make it easier to quickly fill in the gaps when you spot them. 

Consider tools your organization already uses, such as:  

  • Learning platforms and tools  
  • Enterprise systems, including an association management software (AMS), human resource information system (HRIS) or customer advocacy platform  
  • Mobile applications  
  • Collaboration and web-conferencing tools  

When it comes to expertise, you can break this down into subject-matter expertise and technical expertise

Subject-Matter ExpertiseTechnical Expertise
These are the people you’ll work with to create custom content, if you’re going that route.  There may be people within your organization who are particularly knowledgeable about a topic, product, or service.  There could also be individuals outside the organization who are experts in their industry or in a given area.  You can also think about how you could tap into the knowledge your learners have. Are there members, customers, or employees you may be able to empower as content creators? These are the people who can help you set up, run, and monitor your online learning programs. Do you have experts ready to set up and administer your learning environment, including the learning management system (LMS) and any integrated technologies? Do you have learning and development staff who can work with subject-matter experts to make sure courses are set up as effectively as possible? Do you have an individual or team ready to collect, work with, and interpret learning data? Do you have support and professional development structures in place, especially for your own staff? 

2. Who Are Your Stakeholders? 

It almost goes without saying that to both initiate a change and drive long-term success, you need to have the support of your organization’s key stakeholders. Depending on your organization’s type and size, these could include representatives from: 

executive leadership Human resources (HR) and talent management 
IT and administration member relations 
Learning and development (L&D) customer advocacy 
communications and marketing end users 

It’s important to make sure you involve the right professionals, both in terms of the total number and the interests they represent. If you involve too many people, you could add confusion and unnecessary hurdles. Too few and you might not get buy-in from the right groups. In one study, going from five stakeholders to six led to a roughly 20% drop in the likelihood of purchase. 

When you’re determining who you want around your decision-making table, it can be helpful to put together profiles for individual or group stakeholders that cover roles, key drivers and needs, the values and expertise they bring to the table, and the questions they’ll need answered:

  • Stakeholder group
  • Role(s)
  • Driver(s)
  • Nature of involvement
  • What needs will they have?
  • What values and expertise will they bring to the table?
  • What questions will they expect to have answered?
  • Additional notes
One of the things that’s different as a regulator compared to an educational institution is that we don’t have semesters or predictable timelines. New standards can be introduced at any time, and we need to respond when there’s new material that RMTs need to learn. The Brightspace platform gives us the ability to develop and launch courses in an agile way when the need arises.
Annette Ruitenbeek director of professional practice, CMTBC

3. Where Could You Encounter Opportunities and Obstacles? 

Getting an early lay of the land can play a crucial role in setting your business up for success. At which points might you face pushback? Where are your biggest knowledge and technology gaps? On the flip sides of those coins, what parts of the project are your stakeholders most excited about, and where are your areas of strength? 


Obstacle Details How can you overcome it? 


Opportunity Details How can you use it? 
Our D2L account team have been great, and we really appreciate the effort that D2L puts into working with its user groups and listening to our feedback. To have that type of interaction with one of our technology partners and be able to work through that feedback with the team is something that I haven’t seen with other LMS vendors.
Nick Crowe vice president, learning solutions, CPSA

Plan, Execute and Evaluate

1. Articulate Your Vision 

Understanding your vision is about getting to the heart of what your organization is aiming to do. For associations and other training providers, it could be something like delivering education programs that equip learners to be leaders in their industries. 

When you’re figuring out your vision, some of the questions you’ll want to ask yourself include:  

  • What does the future of learning, continuing education and training look like?  
  • What are your organization’s mission and values, and how can learning help advance them?  
  • What are some of the challenges or opportunities that lie ahead for you?  
  • Who are the stakeholders you need to engage? What are they expecting?  
  • How does the vision for where you’d like to be compare with where you are right now?  

Ultimately, your aim is to be able to articulate the principles, priorities, challenges, needs and wants that are relevant for your organization—all of which will inform your holistic, long-term vision. 

2. Outline Your Purpose 

While your vision tells people what your organization aspires to do, your purpose tells them why and how you’re going to execute it. This is critical for keeping stakeholders aligned and working together toward a common goal. 

Often, you can divide a purpose statement into two parts: 

To achieve what

This clarifies your desired outcome  


By doing what 

This lays out the steps you’ll take toward it. 

For example, building on the association-specific vision above, the purpose could be to enhance continuing education offerings by implementing a more feature-rich, scalable learning platform. 

Initially, we weren’t sure whether it was even possible for us to offer a program covering the full spectrum of modern marketing—but that’s what we’ve achieved. With help from D2L, we have developed a comprehensive designation program that helps learners become well-rounded, innovative professionals. Today, we believe CM designation will become the gold standard for marketing excellence in Canada and a must-have for aspiring CMOs.
Stephen Ghigliotty associate vice president, curriculum development, CMA

3. Identify Success Criteria 

Once you know what you’re working toward, you can begin breaking it down into concrete steps and pieces. This will give you tangible markers to work toward and will help you establish key metrics and benchmarks. To this end, you want to look closely at your organization’s goals, key performance indicators (KPIs), milestones and actions


The goals are the discrete outcomes you’re looking to achieve. As you’re building them, keep the below in mind: 

  • Priority: What are your priorities? What actions would you say are of high urgency but less challenging? Which are neither challenging nor urgent? For which ones will you need additional information or resources? 
  • Phase: With which phase of your transformation is each goal associated? Will each phase have one overarching goal associated with it or will there be a series of smaller goals? 
  • Relevance: What needs does each goal address? How will individual goals affect your key audiences and stakeholders? Overall, how specific and targeted are your goals? 
  • Realization: What does your organization need to do to achieve its goals? How challenging are they? 


Once you know what your goals are, you need to figure out how you’re going to track your progress. This is where KPIs come in. 

  • What are the key metrics you want to focus on? 
  • Are there any specific benchmarks you need to consider? 

Think too about how technology can help you assess your achievements. 

  • Where will the data be taken from? 
  • What form will it be in? 
  • How often will it be collected? Will it be automated, or does it need to be done manually? 
  • Which stakeholders need to have visibility? 
  • What processes are in place to act on relevant insights? 

Milestones and Actions 

Finally, your organization needs to grapple with what the road ahead will look like by articulating key milestones and the actions you need to take to realize your goals, purpose and vision.  

Together, each of these elements—from the vision all the way down to the actions—becomes the building blocks that help your organization articulate and ultimately deliver on its online learning strategy. 

4. Create Your Communication Plan

A communication plan is a roadmap that clarifies what your messages will be, who will be sending them and who needs to see them. It’s also a key part of successful change management initiatives. According to a Robert Half survey, 65% of managers said the most important thing when leading organizations through a major transformation was clear, frequent communication.  

Students collaborating around a table

Get the Workbook

Want to plan out how you’ll communicate about and use D2L Brightspace? Download the Communication Planning Workbook, put together by D2L’s Learning Strategy Consulting team.

Assemble the Team 

Before moving onto the finer details that go into your communication plan, you need to understand who in your organization is going to be responsible for which parts of the strategy. Research from Prosci shows that for updates about the personal impacts of change, 70% of employees wanted to hear from their manager. By comparison, for messages about the business reasons for change, 75% of employees wanted communication to come from senior leaders. 

Name  Title  Role  Specialization  

Understand the Audience 

In addition to having a clear picture of who’s going to be creating and sending the messages, you also need to know who will be receiving them. What does an average day look like for them? What methods of communication are they most comfortable using? What pains can you solve? 

Persona Characteristics Pains Gains 
We have instructors and students who live a long way from Calgary, and even the local ones are often away, working at events or training camps in other countries. If we can’t make the learning experience easy to fit in with their busy professional lives, we’re going to lose a lot of good coaches from the program—so flexibility is key.
Jason Sjostrom director of coaching, CSI

Develop the Communications 

As you’re developing each communication or communication sequence, consider the questions below:  

  • What persona are you targeting? How do you expect they’ll respond to the communication? 
  • What’s the aim of your communication? What’s the main message you want to convey? 
  • Who from your team needs to be involved? What are their responsibilities and roles? 
  • What channel(s) will you use? What day(s) and time(s) will your messages be sent? 

Implement and Evaluate 

As with the other components of your online learning strategy, hitting send doesn’t mean your work is done. You need to monitor your communications to make sure messages are hitting the mark. 

5. Execute the Strategy 

Here, it’s all about bringing your best-laid plans to life. Depending on the nature and type of initiatives you have planned, you could further break this down into pilot and scale.  

During the piloting phase, your organization can test and refine proposed changes on a lower, smaller-stakes scale. This can give you information you need to more effectively grow programs. Some of the questions you’ll want to answer include:  

  • What challenges, expected or unexpected, did your organization run into?  
  • What helped you achieve the successes you did?  
  • What adjustments did you have to make? Was there anything you had to sacrifice?  
  • What resources did you use? Were there any additional resources or supports that would have been helpful to have?  

Be ready to document lessons learned and make alterations to the process. You may only need to do a pilot once if it goes smoothly, but be prepared to go through it again in case bigger concerns emerge or you need to reassess the impact of any modifications.  

Once you understand what works and what you can expect to see, it’s time to scale the program to your intended audiences or across the organization. 

6. Evaluate the Impact  

You want the data you pull to showcase the success of your learning programs to align with the needs and challenges of your organization. That’s why it’s so important to clearly articulate your goals early on. If you know what you’re aiming toward throughout, you’ll be better able to pull the right proof points that will help you paint a more complete picture at the end.  

Data could come from a variety of sources, including:  

  • the LMS itself, which can give you valuable insights into trends with adoption, engagement, performance, and more  
  • enterprise-level systems like your HRIS, AMS or customer advocacy platform  
  • your stakeholders and learners, through surveys and interviews conducted before, during and after their experiences with the programs  
  • external tools, including relevant third-party content platforms or apps 

Ultimately, you want to make sure that the online learning strategy you have in place will help you drive growth, that you have the tools to bring it to life, and that you can access data to show it’s working. 

Work With the Experts to Define and Deliver Your Online Learning Strategy

As your partner in learning, we’re here to support you in improving learning outcomes and achieving your strategic goals. Our learning strategists and consultants have the expertise to help guide your vision, plan your approach and execute your learning strategy. 

Learn More


Our work extends far beyond basic LMS consulting. We’ll share extensive knowledge and proven best practices that fit with your specific goals.


From the first steps to the finish line, continuity is key. We’ll support every interrelated part of the strategic change process to keep you moving in the right direction.


Achieve your goals today and into the future. Our experts will help you evaluate where you are today and define the strategic steps and benchmarks you’ll need for continued success.

We were new to the online learning game and so we needed somebody to work in lockstep with us. D2L came with the expertise and the capacity to refine our thinking, give us a plan of action for implementation, and then allow us to connect with our existing processes and products in a way that would be efficient.
Scott Butler executive director, Good Roads
Table of Contents
  1. Why a Strategy Matters for Your Digital Transformation
  2. Before You Build Out Your Strategy
  3. Plan, Execute and Evaluate
  4. Work With the Experts to Define and Deliver Your Online Learning Strategy
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