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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.
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:
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:
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.
Link: How to Vet an MSP for Your Nonprofit
Link: How do I Know if an MSP is Right for my Organization?
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. You can find more in-depth coverage here: How to Write a Nonprofit IT RFP that Works.
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.
Welcome everyone to the Community IT Innovators Technology Topics podcast. I am Carolyn Woodard, your host. Today I am really excited to speak to our CEO about a troubling issue we are seeing with RFPs that are really hard to respond to, and perhaps some advice on how to understand better what you are looking for in IT support for your nonprofit. Johan, would you like to introduce yourself?
Johan Hammerstrom:
Hi, I am Johan Hammerstrom. I am the CEO of Community IT.
Carolyn Woodard:
How do you input what you need into an AI tool to help it write a good RFP that actually describes your needs in ways that are not contradicting each other but still sound good?
Johan Hammerstrom:
I think the problem I have observed, and I think this is true in many areas besides IT, is that you can ask AI to generate something for you, but if you do not really know what you are asking for, you have no way of evaluating what it is generating.
What we have seen more often are RFPs being released that sound good and include a lot of technical language, but there is a sense that the different pieces do not fit together clearly in a way that makes it easy for us to understand. There is like an essential piece missing; the heart of the need has not been clearly communicated.
I think it would be more effective if, when you were putting together an RFP, you just wrote it in your own language from your perspective. You should state clearly what your organization needs. I have long felt that a good IT support provider can bridge the gap between the technology solution and the business need. It is not up to the business owner to articulate their business need in technology terms.
I am using the term “business owner,” but the business of running a nonprofit and accomplishing its mission is something that the organization and everyone in it should know very well at their specific level of responsibility. They need to be able to articulate what they need from that business perspective. Then it is the responsibility of the technology support provider to bridge the gap between the technology solutions and the business need.
What AI is doing—and AI does not know your business needs as an organization—is playing a role it cannot fully fulfill. You can tell it what you need, but one thing that is starting to dawn on me about AI is that you have to feed a lot of information into it to get a useful response. Personally, I feel like by the time I am done figuring out how to talk to these machines and feeding them the information they need, I could just write it myself. That process of writing it myself forces me to think about what I am really looking for.
My guess is that a lot of people do not feed it the specific knowledge of the business that it needs to craft a good RFP. You have to get very detailed, and there is a certain way of framing prompts for AI tools that is almost like a new command-line interface. You need to understand the syntax and how they are looking for information. I think most people are not doing that, so they are just asking for an RFP. The results end up being very generic because they are not specific to the business needs of the organization.
Instead of focusing on the technology solution, AI is now playing the role of the IT consultant because it is identifying the solutions that are needed. But those solutions are not being recommended in response to specific business needs; they are just the most common or probabilistically identified solutions.
For an IT support provider like Community IT, responding to those RFPs becomes very challenging because they are just asking for technology solutions without explaining the business need. In some cases, do you really need to know what the business needs are to recommend an email solution? Everyone needs email. Some might argue you could use a chat solution instead, but you do not need to make a large business case for email. If you are a functioning nonprofit, you need email to communicate externally, receive invoices, handle contracts, and interact with auditors, board members, and constituents.
However, the decision of whether to go with Office 365 or Google Workspace for your email could be an important decision that depends on the business needs of the organization. If those business needs are not being clearly articulated or understood, it is going to be hard to make a good decision. If you go to ChatGPT and ask, “Should I implement Microsoft 365 or Google Workspace for my new nonprofit?” it is going to give you five pages of text that are not really specific. It can give you interesting things to think about, but it does not know enough about your situation to really give you advice. It might give you enough background information and context that you can connect the dots yourself, but that becomes harder as the organization grows larger and the technology solution becomes more complex.
Carolyn Woodard:
For the most part, if the AI is going to reputable sources, you are going to get what the website says about how great that solution is. You could have looked that up yourself.
It is interesting that you mentioned a new organization writing an RFP. My sense is that for 90% of the RFPs out there, they have an existing stack and existing technology that they want to put in the RFP, and whoever they hire is going to have to work with that. The idea that you just stop there and get a very generic RFP—it does not address the issues that need to be solved for your specific organization.
Johan Hammerstrom:
Yes, exactly.
Carolyn Woodard:
I have heard—though I have not done it myself—people talk about asking AI to ask you questions. I could see a use case where you have AI help you walk through what your pain points are. Why do you need IT support? What is the biggest problem? Do you have siloed tools that are not talking to each other, making your data less valuable? If it takes two staff members two days to clean up data to make a board report, that is a pain point that you could have AI help you pull out of yourself to include in the RFP. It could help you clarify your needs.
What I am hearing you say is that if you just use a vague prompt like “Help me draft an RFP for IT support,” you are going to get a really generic answer.
Johan Hammerstrom:
I am biased, so I am putting my biases out there. I think many people right now are using AI to generate documents they do not want to have to write themselves. We are all now seeing a lot of AI-generated content—documents, policies, handbooks, RFPs, and websites—because people did not want to take the time to write them.
This raises an interesting question: what is the value of the document? Is it the words on a page, or was it the thought process that went into writing the document? There was a fantastic article about a practice Amazon had for decades regarding a six-page synopsis. When you were proposing a new initiative, you had to write a six-page summary. You would take it to the meeting, hand it out, and everyone would read it in silence for the first 15 or 20 minutes.
The idea was that the process of writing this summary forced you to think through what you were proposing. You do not really think about your ideas until you are forced to articulate them. It forced you to be disciplined. Conversely, the people reading the document were required to understand the totality of what was being proposed. When you are just explaining an idea in a meeting, people often listen to the first few sentences and then start reacting instead of looking at the whole idea.
Important concepts and key initiatives in the organization could not be expressed in just one or two sentences; it required six pages to think through and articulate. This article was about a trend where managers at Amazon are now telling their staff to use AI tools to write that six-page synopsis. Longtime staff members are arguing that this defeats the purpose. Why even bother writing it if the whole point is the exercise of thinking? Because Amazon needs to be at the forefront of technology, AI is taking over. That is an interesting experiment in massive organizational change.
Carolyn Woodard:
Along those lines, I wonder if you—having so much experience reading RFPs and handling assessments and sales calls—have advice for someone in leadership or management who has IT pain issues. It has been called “IT therapy,” where you call someone up and tell them everything that is wrong so they can help you figure out what you need.
What would you suggest as a way to draw that out into a document or a phone call to find the right vendor and solutions? If you just do a generic RFP, you get a vendor who responds to that, but five years from now, those tools might not actually be addressing your business need.
Johan Hammerstrom:
In the line of business we are in—managed services—there is often not a lot of differentiation between providers on the surface. We are all installing software to keep computers secure and updated, we all have help desks, and we all hopefully have IT manager roles for the big picture. If you just take what your current provider is doing and put that in an RFP, you are going to get a lot of generic responses from different providers who all do the same thing.
Carolyn Woodard:
And why would you change then? They are all just going to say they can do the same thing.
Johan Hammerstrom:
Exactly. I would encourage organizations to think about what makes them unique. Perhaps it really is just a commodity service that you need. But if something is not working well with your current provider or your current situation, providing the context for what is not working is the most important thing you can do. That will bring out the differentiation in the bidders. Hopefully, they are paying attention to those articulated needs and speaking to how their firm is a good fit for meeting them.
Providing context about what is not working right now and what needs to change is always really helpful in an RFP. If that is not included, it is always a question we ask so that we can better understand what they are really looking for.
Carolyn Woodard:
I say this quite frequently, but having worked at for-profits and nonprofits, one of the big differences is that at a nonprofit, people are really dedicated to the mission. You find a lot of knowledge across all roles—from interns to admin to the CFO—about what the organization does. In the for-profits where I worked, it was possible that people on different teams could not really articulate what the company did or just focused on their specific role without seeing the bigger picture.
People I have interacted with at nonprofits are very thoughtful. They think about the ecosystem they are working in and what the nonprofit is trying to accomplish. That is an advantage. If there is a mechanism you can use—Zoom chats or “water cooler” conversations—staff at nonprofits often know what they wish worked better, where they could save time, or where they are missing opportunities. Finding a way to gather that feedback as you prepare to identify those unique pain points can help you craft an RFP or inquiry that allows you to make a better short list of vendors.
Another thing we run into is what I might call the “vibe.” We often have people approach us saying their current provider just does not “get” them. Maybe they are not explaining what they are doing, they do not respond quickly, or the nonprofit feels like the last priority. Identifying that you are looking for a better partner—one that will communicate and respond better—is key.
Johan Hammerstrom:
That is a great point. There are three areas that we see pop up repeatedly regarding dissatisfaction with IT support that are unique to nonprofits.
The first is culture. Nonprofits typically have a unique, people-centered culture. Most businesses are focused on the bottom line, efficiency, and making money, and that is how many MSPs are geared to support their clients. That can be abrasive and dissonant for nonprofit staff who have one type of interaction with coworkers and then get a completely different, jarring interaction from their IT vendor.
The second area is the need to connect technology solutions to business needs. Most MSPs are used to working with for-profit businesses where the logic is: “Invest $100,000 in this technology and you will make $300,000.” That logic makes no sense in a nonprofit environment. Nonprofits are resource-constrained, and getting more efficient does not necessarily generate more revenue. There is a disconnect between revenue generation and programmatic operations. If you have not been working in that environment for a long time, it is difficult to understand how priorities are set or how budgeting happens. The typical playbook just does not work. We have talked with many clients leaving a standard provider who say, “I just do not feel like they ever got us.”
The third area is prioritization. Sadly, companies often prioritize their larger or more lucrative customers. Typically, a nonprofit is one of the smaller customers of an IT support firm. No one is going to admit that they are deprioritizing you, but the clients feel it. They notice when their great IT manager is moved to another account or when they are always told to wait when they call the help desk.
Carolyn Woodard:
Or they always get the most junior person who has to spend time understanding the problem from scratch before they can even help.
Johan Hammerstrom:
Exactly.
Carolyn Woodard:
It is not worth it to the provider to have a consistent support person for a smaller account. That makes sense. I had never thought about it that way, but that is a helpful perspective.
I want to mention that we have a couple of free downloads on our website about how to vet a provider and how to know if an MSP is right for your nonprofit – if a specific solution is a good fit for your nonprofit based on size and complexity.
I want to thank you, Johan, for sharing your experience. Hopefully, this will help people ask better questions of their AI to get better RFPs, and also ask better questions of themselves regarding their real pain points.
Johan Hammerstrom:
Thank you. Thanks, Carolyn.
As advocates for using technology transparently to work smarter, we’re practicing what we recommend. This transcript was edited lightly with the assistance of AI for clarity, and is not a verbatim transcript. The content was reviewed, edited, and finalized by a human editor to ensure accuracy and relevance.
Photo by Land O’Lakes, Inc. on Unsplash
Wednesday March 25th at 3pm Eastern join Hugo Castro and Gozi Egbuonu to learn how to make the transition.
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