The Digital Nonprofit – a project of TechSoup Connect Canada

At TechSoup Connect Canada’s April 1 event, we were treated to a deep dive into the practical side of AI and automation with Chaplain Timothy “TIG” Heaslet. Far from a buzzword-laden keynote, this was a grounded, generous session filled with real-world use cases, thoughtful caution, and a whole lot of heart.

TIG, a nonprofit leader and tech educator, brought both wisdom and warmth as he guided participants through how AI-powered automation can help organizations do more with less.

Who Is Chaplain Timothy “TIG” Heaslet?

Chaplain Timothy “TIG” Heaslet isn’t your average tech speaker. His path to nonprofit technology began through a mission to love and empower youth, especially those impacted by the loss of military or first responder parents. His work spans organizations like America’s Children of Fallen Heroes and his latest initiative, MissingPixel.org, which provides underserved youth with tech training, mentorship, and personal development.

Highlights from the Session

Start With Strategy, Not Shiny Tools

Before jumping into AI, TIG emphasized the need to revisit your nonprofit’s goals and workflows. AI can’t fix what isn’t clearly defined. Instead, it’s most powerful when it’s applied to well-understood processes—especially repetitive or data-driven ones.

Understanding Automation: Procedural vs. Agentic

TIG broke down two key automation types:

• Procedural automation: Traditional, rules-based systems (think Zapier or Make.com) that follow predictable steps.
• Agentic automation: Powered by large language models (LLMs) like ChatGPT or Claude, these workflows bring a conversational or decision-making layer into the mix.

While agentic automation opens new doors (like custom chatbots or proposal writers), it’s not without challenges. TIG cautioned about relying too heavily on agentic flows due to inconsistency and potential errors—especially when data accuracy is critical.

Real-World Nonprofit Use Cases

Some practical AI-powered automation examples TIG shared:

• Automatically texting contacts for updated mailing addresses and syncing that info into your CRM
• Building chatbots that escalate complex queries to humans, then learn from the answers
• Using vector databases (like Pinecone or Supabase) to create a searchable knowledge base from internal PDFs or video transcripts
• Testing multiple LLMs via tools like OpenRouter to find the best fit for your content type

Security and Privacy Considerations

For organizations handling sensitive data (like youth programs or legal aid), TIG stressed the importance of self-hosting or choosing tools that meet compliance standards. He recommended open-source options like n8n or Activepieces for building secure, customizable workflows.

The Takeaway: Build Slow and Smart

The nonprofit AI landscape is evolving fast. But TIG’s message was clear: don’t get distracted by hype. Start with simple use cases. Focus on processes you already understand. Build with intention—and always, always test for failure points before scaling.

As TIG put it, “This is the worst this tech is ever going to be. It only gets better from here.”

Want to Learn More?

TIG is open to connecting with other nonprofit folks looking to explore AI and automation. You can find him on LinkedIn or email tig@quietlyworking.org

And stay tuned—TechSoup Connect Canada may just bring TIG back for another session later this year. With the pace of change in AI, three months might as well be a lifetime.

Pacific Legal Education and Outreach Society (PLEO) is pioneering new ways to provide legal education to nonprofits. At the March 11, 2025 TechSoup Connect Canada event Minnie Karanja (Acting Director of Innovation and Engagement), and Kris Elgstrand (Head of Communications) shared insights into their development of an AI-powered chatbot aimed at making legal information more accessible. 

Why Legal Education for Nonprofits Matters

PLEO has been providing legal education to nonprofits for over 20 years. Initially focused on the arts sector, they have since expanded to serve organizations across Canada. Their mission is to make legal guidance more accessible through innovative tools such as LawForNonprofits.ca.

Key legal challenges nonprofits face include:

• Record keeping – Ensuring compliance with regulations
• Privacy laws – Understanding personal information protection
• Employment regulations – Navigating contracts and labor laws

To address these concerns, PLEO developed a range of accessible legal resources, including fact sheets, FAQs, self-assessment tools, and legal guides.

Introducing the AI Chatbot

PLEO’s latest innovation is an AI-powered chatbot, designed to offer nonprofits an intuitive, conversational way to access legal information. This chatbot is built using retrieval-augmented generation (RAG), a model trained primarily on PLEO’s verified legal content to ensure accuracy and reliability.

Key Features of the Chatbot:

• Conversational Interface – Users can ask legal questions naturally, as they would with a lawyer.
• Verified Knowledge Base – The chatbot pulls from PLEO’s repository of vetted legal information.
• Guided Navigation – Helps users refine their legal questions and locate the most relevant information.
• Guardrails for Accuracy – Strict controls prevent misinformation by keeping responses within PLEO’s area of expertise.

The chatbot aims to enhance existing legal resources by providing another avenue for nonprofits to obtain quick and reliable answers.

Challenges in AI Chatbot Development

Developing a chatbot for legal education comes with unique challenges:

• Ensuring accuracy – Unlike general AI assistants, the chatbot must provide legally sound guidance. Early testing revealed that the chatbot sometimes pulled from non-vetted sources, requiring further refinement.
• Balancing accessibility and depth – The chatbot must be detailed enough to offer useful answers while remaining easy to navigate.
• Guardrails and Testing – Implementing restrictions on what topics the chatbot addresses, such as avoiding advice on real estate law or tax-specific charity regulations.
• Continuous testing – PLEO’s team, including legal experts, conducts rigorous testing using real nonprofit legal queries to refine responses.

The Role of Testing in AI Implementation

PLEO’s development team emphasized that testing is the most time-intensive part of the chatbot’s creation. Their process involves:

1. Developing a standardized set of legal questions
2. Evaluating chatbot responses for accuracy and relevance
3. Rating chatbot performance using a structured review system
4. Refining AI behavior through iterative updates

Unlike other AI applications designed for exploratory research, this chatbot must provide precise and actionable legal guidance, making ongoing refinement essential.

Lessons for Nonprofits Exploring AI

For nonprofits considering AI-powered solutions, PLEO’s journey offers valuable takeaways:

• Start with a strong knowledge base – AI is only as good as the data it’s trained on.
• Ensure legal compliance – If your chatbot provides legal or policy guidance, ensure it is built with reliable, vetted sources.
• Focus on accessibility – Provide multiple ways for users to engage with content (e.g., fact sheets, step-by-step guides, and AI-powered assistance).
• Test rigorously – AI responses should be reviewed and refined by experts to maintain trust and accuracy.

For organizations looking for a lightweight way to explore AI, try experimenting with ChatGPT’s custom GPT builder, which allows users to train AI on specific internal documents and workflows.

Conclusion

PLEO’s AI chatbot is a promising step toward democratizing legal information for nonprofits. By combining structured legal resources with conversational AI, they are making complex legal topics more accessible, actionable, and affordable for organizations with limited budgets.

For those interested in learning more, visit:

LawForNonprofits.ca
Pacific Legal Education and Outreach
Watch the full event replay

As AI tools continue to evolve, nonprofits have exciting opportunities to enhance service delivery, streamline operations, and increase accessibility. PLEO’s chatbot development offers a compelling model for organizations looking to integrate AI into their work while maintaining high standards of accuracy and reliability.

Nonprofits are often stretched thin, navigating tight budgets and competing demands for attention. So, why should you make time to experiment with yet another social platform? Because playing with new tech isn’t just about staying relevant—it’s about finding fresh ways to connect with supporters, amplify your mission, and maybe even spark joy along the way.

At the February 25, 2025 Connect Canada event, digital specialist Madeleine Sugden shared insights from the UK charity sector’s experiences with Bluesky, the decentralized social platform that has been gaining traction as an alternative to X (formerly Twitter). Here’s why nonprofits should consider adding Bluesky to their digital mix and how you can get started.

Read the slides

Why Bluesky? A Safe Haven from X

Since Elon Musk took over Twitter in late 2022, the platform’s environment has changed dramatically. Many nonprofits have struggled with declining engagement, increased toxicity, and algorithmic unpredictability.

Some organizations have quietly stopped posting, others have made dramatic exits. Yet, most large charities remain because they feel they have no alternative.

Enter Bluesky. Nonprofits who have tested the platform report:

• A relief from the negativity of X.
• A more engaged and interactive community.
• A chronological feed (no algorithm manipulating visibility).
• Higher engagement rates despite smaller followings.

Early Movers Are Seeing Big Wins

Organizations like Coast Funds, an Indigenous-led conservation finance nonprofit in Canada, jumped onto Bluesky early and saw rapid growth after the 2024 U.S. election. They now have half the followers they had on X but with significantly higher engagement and more relevant connections.

Even smaller organizations are seeing real impact. One nonprofit shared that their first donation via Bluesky came from an unexpected supporter—a legal services firm that resonated with their mission. They had never received donations via X, yet Bluesky delivered nearly $1,000 from a single post.

Should Your Nonprofit Join Bluesky? Ask Yourself:

• Is your audience (or potential audience) on Bluesky?
• Do you have time to experiment and build a new community?
• Are you struggling with engagement on X or other platforms?
• Do you want to be part of shaping a new, positive online space?

If the answer to any of these is yes, then it’s time to dip your toes in.

Getting Started: Your First Steps on Bluesky

1. Claim Your Account — Prevent impersonation and secure your nonprofit’s presence.
2. Follow Key Accounts — Use “starter packs” to find other charities, journalists, and partners.
3. Make Your First Post Count — Be playful, mission-driven, or inspiring. This sets the tone.
4. Be Social — Comment, repost, and interact. Bluesky rewards engagement, not just broadcasting.
5. Tell Your Audience — Share your Bluesky handle in your newsletters, website, and social channels.

A Note of Caution: Social Media is Borrowed Land

Madeleine reminded us that nonprofits must not rely too heavily on any single social platform. As we’ve seen with X, platforms can change overnight. Bluesky might be thriving now, but diversifying your digital presence remains crucial.

Invest in what you own: your website, email list, and direct supporter relationships.

Decentralization and the AT Protocol

One of the key advantages of Bluesky is its foundation on the AT Protocol (Authenticated Transfer Protocol). Unlike traditional social media platforms that are centralized and controlled by a single entity, Bluesky is built on decentralized infrastructure, allowing users to own their identities and content across different platforms. This means nonprofits can have more control over their digital presence, reduce dependency on proprietary algorithms, and ensure that their communities remain connected regardless of corporate shifts or platform changes. While adoption of decentralized networks is still in its early stages, Bluesky presents a forward-thinking approach to social media that aligns with nonprofit values of openness, accessibility, and community-driven engagement.

Final Thought: Have Fun With It

Nonprofit work is serious, but social media doesn’t have to be. Bluesky offers a chance to reclaim the joy of online engagement. Post a fun fact, share an unexpected story, or (as one UK museum did) lean into viral humor—their “Absolute Unit” sheep meme still makes waves years later.

So, take a cue from the early adopters. Secure your handle, start experimenting, and most importantly—play a little. The future of nonprofit digital engagement might just be waiting in the (blue) sky.

Resources

Explore these helpful guides and insights to navigate Bluesky for nonprofits:

• Charity Bluesky in January 2025
• Charity Comms’ Social Media Platform Checklist
• How to Leave Twitter Gracefully – Strawberry Social
• How to Choose the Right Social Media Channels for Your Charity – Strawberry Social
• Bluesky App

February’s TechSoup Connect Canada event “How to Build AI Tools That Save Time and Money” was EPIC! We had an insightful discussion with experts Angeline Robertson and Matthew Lichty from Stand.earth Research Group, exploring how nonprofits can use AI and machine learning for advocacy research.

Read the slides

Here are the top 10 takeaways from the session, with examples from the event transcript to help you integrate AI into your research workflows:

1. Have an AI Data Policy

• Establish clear guidelines on what data can and cannot be used in AI-assisted research.
• “We have an AI policy at Stand.earth so that we do not use any confidential, personal, or sensitive information. We’re really looking at publicly available information online for most of our data structuring work.” – Angeline Robertson

2. Start with Something You Know Well but Want to Do Faster

• Identify a repetitive, time-consuming task AI can streamline.
• “We weren’t looking for AI tools to reinvent the wheel. We just wanted to integrate AI into our methodologies in ways that let us get more done, faster.” – Angeline Robertson

3. Hire a Data Coach and Focus on Training Your Team

• Instead of outsourcing, train your team to integrate AI into research workflows.
• “Instead of hiring a firm to build a tool, we hired a data science coach to teach us how to do it ourselves. This meant we could keep learning and improving our methods rather than relying on outside consultants.” – Angeline Robertson

4. Start with Data Structuring and Use Information Available Online

• AI excels at organizing and categorizing unstructured data from PDFs, reports, and websites.
• “One of the biggest gains for us has been unlocking unstructured data stuck in PDFs—things we used to have to comb through manually. AI helps us turn that mess into structured data we can actually use.” – Matthew Lichty

5. Harness Your Domain Knowledge

• AI can process large datasets, but human expertise is essential for quality control.
• “We didn’t just plug in AI and hope for the best. We used years of experience analyzing bank policies to train AI on what actually matters. The human touch makes all the difference.” – Matthew Lichty

6. Use More Than One LLM

• Diversifying models reduces bias and enhances accuracy.
• “We’ve started using Perplexity, which lets us test different AI models side by side. This helps us spot inconsistencies and reduce the risk of relying too much on one tool.” – Matthew Lichty

7. Remember: Good Prompt Engineering Requires Good Writing

• The way you phrase prompts impacts AI output quality.
• “Writing clear, specific prompts is half the battle. If you ask AI a vague question, you’ll get a vague answer. We spend a lot of time refining our prompts to get the best results.” – Angeline Robertson

8. LLMs Have Short Attention Spans—Break It Down for Them

• Complex tasks should be split into smaller sub-tasks for better accuracy.
• “AI models don’t do well with long, complicated tasks. We had to break things into smaller steps, like focusing on one policy classification at a time, to get better results.” – Matthew Lichty

9. Use Coded Approaches to Analyze at Scale

• GUI-based tools (e.g., ChatGPT, Perplexity) are good for small tasks.
• “We started with the ChatGPT interface, but once we needed to analyze hundreds of documents, we wrote Python scripts to automate the process. That shift saved us an enormous amount of time.” – Matthew Lichty

10. Keep the Human in the Loop!

• AI is a tool—not a replacement for human judgment.
• “We’re not trying to replace researchers. AI helps us clear out the grunt work so we can spend more time thinking critically and making decisions.” – Angeline Robertson

Final Thoughts

The session showed that AI isn’t about replacing researchers—it’s about freeing up time for meaningful work. By using AI for structuring, analyzing, and summarizing data, advocacy organizations can dig deeper into their research and push for change more effectively.

I hope to see you at our next event!

The “How to Fundraise with AI Marketing” event, hosted by TechSoup Connect, brought together nonprofit professionals and enthusiasts eager to understand how artificial intelligence can revolutionize their fundraising strategies. Deepa Chaudhary, the founder of Grant Orb and a seasoned nonprofit expert, guided participants through the intricacies of AI and its potential to empower organizations with limited resources. Here’s a recap of this insightful session.

Introduction to AI in Fundraising

Deepa Chaudhary kicked off the session by highlighting her nonprofit background and her journey with AI. She shared how AI, a once complex and distant technology, has now become a practical tool for nonprofits. AI simplifies tasks, allowing organizations to do more with fewer resources by creating, personalizing, and optimizing fundraising efforts.

Understanding Generative AI and Its Impact

Deepa delved into the core of recent advancements in AI, focusing on generative AI powered by large language models. She discussed the transformation from machine learning-driven predictions to real-time interactive AI tools like ChatGPT, which have democratized AI access. This wave of generative AI enables nonprofits to generate content, whether it’s text, images, or even music, in ways previously unimaginable.

AI Tools for Nonprofit Success

Deepa introduced several AI tools that are instrumental for nonprofit fundraising:

• Chatbots and Real-Time Interaction: Tools like ChatGPT, Claude, and Grok provide interactive platforms for nonprofits to engage, learn, and generate insights.
• AI Visual Creations: Platforms such as MidJourney and Grok allow nonprofits to create compelling visuals that resonate with their audiences.
• AI Music and Art Creation: AI technologies enable nonprofits to integrate music into their communication strategies, enhancing their emotional appeal.

Practical Applications of AI in Nonprofits

The session explored practical applications of AI, focusing on creating visuals, generating captions, and optimizing image prompts. Deepa demonstrated how AI could empower organizations to create stunning, impactful content on a minimal budget, allowing small teams to achieve big results.

Ethical Considerations and Data Privacy

Deepa addressed important ethical considerations, particularly around the use of photorealistic AI-generated images of people. She encouraged nonprofits to align AI use with their organizational values and priorities, ensuring ethical practices and data privacy.

Deepa’s Top AI Tools

Deepa shared her personal go-to AI tools: Claude for general use, MidJourney for image creation, Grok for real-time research and image generation, and HeyGen for producing videos. She emphasized the importance of understanding tool capabilities and selecting those that align with organizational needs and goals.

Embracing AI for Nonprofit Growth

The session concluded with Deepa encouraging nonprofits to embrace AI technologies. She urged organizations to actively build their “AI muscle” by integrating AI tools into their workflows, fostering innovation, and improving efficiency in their fundraising efforts.

In sum, this event equipped nonprofit professionals with the knowledge and tools needed to harness AI for enhanced fundraising and communication. Deepa’s insights and practical examples showcased the potential of AI to accelerate nonprofit missions and amplify impact.

Stay tuned for more engaging events from TechSoup Connect Western Canada, where innovation meets purpose!

Resources

Here are links for some of the tools mentioned in the webinar:

• AI for Nonprofits newsletter
• LinkedIn Article on AI Music for Causes
• TechSoup Blog on Generative AI Policy

Generative AI and AI Community Resources

• Illuminate AI
• Vancouver AI Community Meetups
• OpenAI for Nonprofits

Google Tools

• Google Workspace Video Products
• Google Notebook LM

Audio and Video Tools

• HeyGen
• Udio
• Suno

In the dynamic landscape of project management, the foundation laid before a project begins can often be the deciding factor between success and failure. On October 15th, 2024, TechSoup Connect Western Canada hosted an insightful event titled “Feasibility Studies 101: Increasing Project Success With Preliminary Evaluation.” The session featured Alida Horsley, a renowned user experience researcher and designer from Tandem Studios, who shared valuable insights into the art and science of feasibility studies and their crucial role in driving successful project outcomes.

Meet the Expert: Alida Horsley

Our guest presenter, Alida Horsley, the research and design lead at Tandem Studios, brought nearly a decade of experience in user experience research and design to the table. She articulated how UX design is instrumental in aligning projects with the needs of end users, operational capabilities, and business objectives. This alignment ensures that projects are not only efficient but also cater to both user satisfaction and business goals.

Understanding Feasibility Studies

Alida defined feasibility studies as comprehensive evaluations that assess a project’s viability and determine whether the expected return on investment justifies the initial costs. She outlined essential components of feasibility studies, including business operations, strategy, stakeholder relationships, user experience, technical and financial resources, market analysis, and brand impact.

The Advantages of Feasibility Studies

Delving deeper into the subject, Alida shared numerous benefits of conducting feasibility studies. These include minimizing risks, reducing biases, enhancing decision-making processes, and boosting operational efficiency. Most importantly, feasibility studies facilitate an early understanding of stakeholder and end-user perspectives, leading to stronger partnerships and more successful project outcomes.

Real-World Examples and Best Practices

Throughout her presentation, Alida provided compelling real-world examples showcasing the significant influence feasibility studies can have on a project’s direction. One striking case involved BC United (formerly the BC Liberal Party) and United Way BC, where a lack of proper preliminary evaluation resulted in brand confusion and public backlash. This example underscored the necessity of thorough planning and foresight in project management.

Engaging Stakeholders: Effective Interviews and Buy-In

A critical aspect of feasibility studies is conducting interviews with stakeholders, staff, and end users. Alida stressed the importance of active listening and capturing unbiased feedback to gain a comprehensive understanding of the project landscape. She also offered strategies for securing buy-in from relevant parties by clearly communicating the purpose, benefits, and expected outcomes of the study.

Crafting the Feasibility Report

A successful feasibility study culminates in a well-structured report that captures key findings. Alida emphasized the importance of creating an impactful executive summary, as it often becomes the primary reference point for stakeholders. This report should clearly outline the study’s main insights and recommendations for moving forward.

Conclusion: Embracing the Future

As the event wrapped up, participants engaged in a lively Q&A session, tackling specific queries and discussing further applications of feasibility studies in their work. Alida reinforced the essential role that feasibility studies play in mitigating project risks and building client trust.

By adopting a systematic, user-centered approach to feasibility studies, organizations can unlock new levels of project success. This methodology fosters an environment where informed decision-making and effective resource allocation lead to sustainable outcomes. The insights shared during “Feasibility Studies 101” remind us all—nonprofits and businesses alike—of the immense value that thoughtful, systematic project evaluation brings.

TechSoup Connect and Alida Horsley inspired attendees to explore how feasibility studies can enhance their projects, emphasizing that early investment in research lays the groundwork for greater achievements and innovations.

Resources

• User Interviews
• Diary Studies
• Survey Best Practices
• Affinity Diagrams