How to use AI to better understand your IT pain points and write a better RFP for IT support, or notes for an exploratory phone call.
Listen to Podcast
Like podcasts? Find our full archive here or anywhere you listen to podcasts: search Community IT Innovators Nonprofit Technology Topics on Apple, Spotify, Google, Stitcher, Pandora, and more. Or ask your smart speaker.
Why Your AI-Generated IT RFP Might Be Missing the Mark
In this episode, host Carolyn Woodard is joined by Community IT CEO Johan Hammerstrom to discuss a troubling trend in the nonprofit sector: the rise of the generic, AI-generated Request for Proposal (RFP).
While AI tools like ChatGPT are excellent for saving time, using them to draft an IT RFP without deep organizational context often leads to a document that lacks the heart of your mission. Johan explains how to use AI as a collaborator rather than a shortcut, ensuring you find an IT partner who aligns with your culture rather than just your hardware.
The Value of the Process
Johan holds that the process of writing is just as important as the final document. When leadership takes the time to articulate their needs in their own language better things happen with the IT RFP:
- Internal Clarity: The act of writing forces you to define what isn’t working and what success looks like.
- Authentic Communication: You provide potential partners with the context they need to offer tailored solutions rather than generic sales pitches.
- Bridging the Gap: an articulate, individualized RFP allows your IT provider to take the lead on technical translation while you focus on the business and mission needs of the organization.
3 Pitfalls of Working with the “Wrong” MSP
A successful RFP helps nonprofits avoid the friction that often occurs when signing with a provider focused solely on for-profit business logic. Johan identifies three common areas of dissatisfaction:
- The Culture Gap: Most MSPs prioritize efficiency and the bottom line, which can feel abrasive in a mission-driven, people-centered nonprofit environment.
- Misaligned Budget Logic: Standard providers often recommend technology based on revenue generation, failing to understand the resource constraints and programmatic priorities of a nonprofit.
- The Priority Problem: In large, general-market firms, smaller nonprofit accounts are often deprioritized in favor of more lucrative corporate clients.
Listen in to learn how to move beyond technical checklists and RFPs that are hard to understand and learn how to write an RFP that will find your organization an IT partner that truly gets your nonprofit.
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?
Presenters

Johan Hammerstrom’s focus and expertise are in nonprofit IT leadership, governance practices, and nonprofit IT strategy. In addition to deep experience supporting hundreds of nonprofit clients for over 20 years, Johan has a technical background as a computer engineer and a strong servant-leadership style as the head of an employee-owned small service business. After advising and strategizing with nonprofit clients over the years, he has gained a wealth of insight into the budget and decision-making culture at nonprofits – a culture that enables creative IT management but can place constraints on strategies and implementation.
As CEO, Johan provides high-level direction and leadership in client partnerships. He also guides Community IT’s relationship to its Board and ESOP employee-owners. Johan is also instrumental in building a Community IT value of giving back to the sector by sharing resources and knowledge through free website materials, monthly webinars, and external speaking engagements. He has assisted hundreds of nonprofits over his decades of experience at Community IT and has been instrumental in assuring that all clients have access to strategic planning – a service that is uncommon at outsourced IT providers but that Community IT feels is an essence of what we can provide to nonprofit clients to help them be successful at their missions. Johan was happy to discuss how to write a better RFP for IT support for your nonprofit.

Carolyn Woodard is currently head of Marketing and Outreach at Community IT Innovators. She has served many roles at Community IT, from client to project manager to marketing. With over twenty years of experience in the nonprofit world, including as a nonprofit technology project manager and Director of IT at both large and small organizations, Carolyn knows the frustrations and delights of working with technology professionals, accidental techies, executives, and staff to deliver your organization’s mission and keep your IT infrastructure operating. She has a master’s degree in Nonprofit Management from Johns Hopkins University and received her undergraduate degree in English Literature from Williams College.
She was happy to have this podcast conversation with Johan about how to write a better RFP for IT support for your nonprofit.
Ready to get strategic about your IT?
Community IT has been serving nonprofits exclusively for twenty-five years. In fact, we celebrate 25 years of Community IT this month and all year. We offer Managed IT support services for nonprofits that want to outsource all or part of their IT support and hosted services. For a fixed monthly fee, we provide unlimited remote and on-site help desk support, proactive network management, and ongoing IT planning from a dedicated team of experts in nonprofit-focused IT. And our clients benefit from our IT Business Managers team who will work with you to plan your IT investments and technology roadmap if you don’t have an in-house IT Director.
Being 100% employee-owned is important to us and our clients. It is an important aspect of our culture as a business serving nonprofits exclusively for 25 years. Your Nonprofit IT Budgeting strategy is important to Community IT. Unlike most MSPs, Community IT considers budgeting and strategic management a major part of our services to our clients.
We constantly research and evaluate new technology to ensure that you get cutting-edge solutions that are tailored to your organization, using standard industry tech tools that don’t lock you into a single vendor or consultant. And we don’t treat any aspect of nonprofit IT as if it is too complicated for you to understand.
We think your IT vendor should be able to explain everything without jargon or lingo. If you can’t understand your IT management strategy to your own satisfaction, keep asking your questions until you find an outsourced IT provider who will partner with you for well-managed IT.
More on our Managed Services here. More resources on Cybersecurity here.
If you’re ready to gain peace of mind about your IT support, let’s talk.
Transcript coming soon
Photo by Land O’Lakes, Inc. on Unsplash