Are you struggling to articulate what your nonprofit actually needs from an IT provider? In this episode, host Carolyn Woodard and Community IT CEO Johan Hammerstrom discuss the rise of the generic, AI-generated Request for Proposal (RFP). While it is tempting to use AI to handle the heavy lifting of technical writing, doing so often results in a document that lacks the heart of your organization’s mission.

Johan explains why a successful RFP is less about technical jargon and more about your unique business needs. When you rely on a generic template, you end up with a generic partner. This conversation offers a roadmap for moving beyond checklists to find a support model that actually fits your culture and budget.

Johan and Carolyn explore the essential process of defining your requirements, including:

• The AI Pitfall: Why using AI to write an RFP without deep organizational context leads technical jargon. If you can't understand exactly what your rfp is asking for, neither will the vendors.
• The Thinking Process: A look at why the act of writing—rather than just the final document—is a vital exercise in disciplined thinking and clarity for your leadership team.
• Staff Feedback: How to gather input from your team to identify where legacy systems or siloed tools are creating daily friction and missed opportunities.
• Finding a Partner: Practical advice on how to draw out the unique requirements of your nonprofit to ensure your next IT provider is a true partner, not just a vendor.

A key part of this search is recognizing why many nonprofits feel dissatisfied with their current support. Johan identifies three specific pitfalls that occur when working with a regular, for-profit focused Managed Service Provider (MSP):

1. The Culture Gap: Most MSPs are geared toward a bottom-line, efficiency-first mindset that can feel brusque, abrasive or dissonant when it comes up against a people-centered nonprofit culture.
2. Misaligned Logic: Standard providers often recommend solutions based on revenue generation, failing to understand the resource-constrained and programmatic realities of the nonprofit sector when making IT investments or dealing with legacy IT.
3. The Priority Problem: In a large, general-market firm, smaller nonprofit accounts are often deprioritized in favor of more lucrative corporate clients, leading to inconsistent support, junior-level staffing, and frustration.

If you feel your current provider doesn’t quite get you, or if you are preparing to search for new support, this episode will help you ask the right questions of your AI tools, your staff, and your potential partners.

Resources Mentioned in this Episode:

Link: How to Vet an MSP for Your Nonprofit

Link: How do I Know if an MSP is Right for my Organization?

_______________________________
Start a conversation :)

• Register to attend a webinar in real time, and find all past transcripts at https://communityit.com/webinars/
• email Carolyn at cwoodard@communityit.com
• on LinkedIn

Thanks for listening.

In this Nonprofit AI Podcast midweek check-in, Carolyn explores what it means to have agency in the age of AI. With so much pressure to adopt new tools, it can feel like nonprofits have no choice — but Carolyn makes the case that you and your organization have more power than you think, both in the tools you choose and the advocacy you pursue.

The conversation covers the environmental and community impacts of AI infrastructure, and what nonprofits can actually do about it. Carolyn discusses:

• Why individual AI use matter less than local and collective advocacy around data center regulation.
• Advocacy looks different in different locations where data centers are going in at a furious pace. Water issues? Electricity costs? Sites? Your advocacy should be local too.
• The community impacts of data center siting are complex — Carolyn gave just one example of institutional racism and the displacement over time of historic Black landowners in Northern Virginia.
• Creative policy models from Europe that nonprofits can advocate for in their own communities.
• You can align your AI tool choices with your organization's values — and why that matters.
• An update on Anthropic's lawsuit against the Department of Defense over its supply chain risk designation.

As AI infrastructure expands so quickly, Carolyn encourages nonprofits to stay engaged — using AI intentionally while advocating for the communities and values they serve.

Resources Mentioned:

• Webinar: AI Reluctance for Nonprofits, Josh Peskay and Kim Snyder, Meet the Moment: https://www.roundtabletechnology.com/news-and-events/webinar-library/thank-you/ai-resistance-for-nonprofits
• TechSoup AI Training: https://techsoup.course.tc/catalog/exploring-ai-with-microsoft-tools
• Anthropic vs the Pentagon to date: https://techcrunch.com/2026/03/09/anthropic-sues-defense-department-over-supply-chain-risk-designation/
• https://www.npr.org/2026/03/09/nx-s1-5742548/anthropic-pentagon-lawsuit-amodai-hegseth

_______________________________
Start a conversation :)

• Register to attend a webinar in real time, and find all past transcripts at https://communityit.com/webinars/
• email Carolyn at cwoodard@communityit.com
• on LinkedIn

Thanks for listening.

If you have wondered about the real difference between using a free tool like ChatGPT and an enterprise-level solution like Microsoft Copilot or Google Gemini, this episode will provide much-needed clarity. While the potential for efficiency is high, many nonprofit leaders are rightfully concerned about data security and how to ensure they are using these models safely.

In part one from their recent webinar, Community IT Outreach Director Carolyn Woodard is joined by Chief Technology Officer Matt Eshleman to demystify the current AI tool landscape, particularly for data security.

In part two, Matt and Carolyn go over ways to tell you are logged in to your official account or not, the importance of continuous and iterative staff education, and how (and why) to get started creating AI policies to share with staff.

They were only able to answer a few questions from registration and the audience during this webinar; you can find more questions answered on our reddit community page: https://www.reddit.com/r/NonprofitITManagement/ or in the transcript on our website here: https://communityit.com/webinar-how-to-use-ai-tools-safely-at-nonprofits/

Whether you are already using AI daily or are just beginning to explore its possibilities, this discussion offers a professional and grounded look at how to navigate these tools securely.

_______________________________
Start a conversation :)

• Register to attend a webinar in real time, and find all past transcripts at https://communityit.com/webinars/
• email Carolyn at cwoodard@communityit.com
• on LinkedIn

Thanks for listening.