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.

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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:

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:

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, CEO of Community IT Innovators


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


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.



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

The Problem with AI-Generated RFPs

Carolyn Woodard: What I was going to ask you about was what you said yesterday about the RFPs being kind of gobbledygook.

Welcome everyone to the Community IT Innovators Technology Topics podcast. I’m Carolyn Woodard, your host. And today I’m really excited to speak to our CEO about a kind of troubling issue that we’re seeing with RFPs that are really hard to respond to. And maybe some advice on how to understand better what you’re looking for in IT support for your nonprofit. So, Johan, would you like to introduce yourself?

Johan Hammerstrom: Hi, I’m Johan Hammerstrom. I’m the CEO of Community IT.

Carolyn Woodard: How do you put in what you need to an AI tool to help it write you a good RFP that actually describes what you need in ways that aren’t contradicting each other but sound good?

Johan Hammerstrom: Well, I think the problem that I’ve observed, and I think this is true not just in IT, I think it’s in lots of areas, is that the problem is you can ask AI to generate something for you, but if you don’t really know what you’re asking for, you have no way of evaluating what it’s generating.

What we’ve seen more of is RFPs being released that sound good, they have a lot of technical language included, but there’s just a sense that the different pieces that are in the RFP don’t all fit together clearly in a way that makes it easy for us to understand. There’s like an essential piece missing, like the heart of the need hasn’t been clearly communicated.

I think actually it would be more effective if when you were putting together an RFP, you just wrote it in your own language from your perspective. Like, “This is what our organization needs.” I’ve long felt that a good IT vendor support provider can bridge the gap between the technology solution and the business need, and that it’s not up to the business owner to articulate their business need in technology terms.

It’s important for the—and I’m using the term business owner, but the business of running a nonprofit, the business of accomplishing the mission of a nonprofit—is something that that organization and everyone in the organization should know really well at the level of responsibility they have within the organization. And so they need to be able to articulate what they need from that business perspective. Then it’s the responsibility of the technology support provider to bridge the gap between the technology solutions and services and the business need.

What AI is doing—AI doesn’t know your business needs as an organization. You can tell it, but one of the things 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’m done figuring out how to talk to these machines and feed them the information they need to give me a useful response, I could just write it myself and then go through the process of thinking about what I’m really looking for and trying to say.

My guess is that a lot of people don’t feed it the knowledge of the business that it needs to craft a good RFP because you have to get very detailed. There’s 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’re looking for information. I think most people aren’t doing that, and so they’re just asking for an RFP. They end up being very generic because they’re not specific to the business needs of the organization.

Instead of trying to focus on the technology solution, AI is now playing the role of the IT consultant or the IT provider because it’s identifying the solutions that are needed. But those solutions aren’t being recommended in response to specific business needs; they’re just the most common or probabilistically identified solutions.

For an IT support provider like Community IT in responding to those RFPs, it becomes very challenging because it’s just asking for technology solutions, but not really explaining what the business need is. In some cases, do you really need to know what the business needs are to recommend an email solution? No. Everybody needs email. Well, some people would argue now that you don’t; you could use a chat solution instead of email. But you don’t need to make a big business case for email.

Chances are if you’re a functioning nonprofit organization, you need email on some level. Even if you don’t communicate internally, you have to communicate externally, you have to get invoices sent to you and contracts, and interact with your financial auditors, your board members, and your constituents.

But the decision to whether to go with Office 365 or Google Workspace for your email could be an important decision that might depend on the business needs of the organization. If those business needs aren’t being clearly articulated or understood, it is going to be hard to make a good decision. If you just go to ChatGPT and ask it, “Should I implement Microsoft 365 or Google Workspace for my new nonprofit organization?” it is going to give you five pages of blah blah blah that aren’t really—it can give you interesting things to think about, but it doesn’t know enough about your situation to really give you advice.

It might give you enough background information and context on those solutions that you can connect the dots yourself. You know your business needs and you could evaluate. But that becomes harder and harder the larger the organization is and the more complex and sophisticated the technology solution is.

Carolyn Woodard: Well, and for the most part, if they’re going to reputable sources, they are going to give you what it says on the website about how great that solution is to some extent. So you could have looked that up yourself.

Interesting that you said if you’re a new organization writing an RFP, because my sense would be that for 90% of the RFPs that are out there, it’s an existing stack. They have some technology that they want to put in the RFP that whoever they hire is going to have to know and be able to work with. And the idea that you just stop there—like you get a very generic RFP, and it gives you the tools you’re using—exactly what you’re talking about, it doesn’t give you what are the issues that need to be addressed for your specific organization and the way you use technology.

Johan Hammerstrom: Yeah.

The Value of the Thought Process

Carolyn Woodard: Now I have heard—I have not done it myself yet—but I have heard different people talking about asking your AI to ask you questions. Because I could see a use case where you could have your AI help you walk through what your pain points are. Like, why do you need IT support? What is the thing that’s the biggest problem? Do you have siloed tools that aren’t talking to each other? So your data isn’t valuable. You have to download it, clean it up, re-upload it, make your board report every month. And that takes two staff two days to be able to report on your major donors or something like that. That could be a pain point that you could have your AI pull out of you, and then that would help you put that in your RFP. It could help you clarify.

I think what I’m hearing you say is that if you just ask it a vague prompt, like “Can you help me draft an RFP for my nonprofit for IT support?” you are going to get a really generic answer just based on what else is out there.

Johan Hammerstrom: Yeah, I’m super biased, so I’m putting my biases out there. I think that a lot of people right now—and I think this is going to change because it’s creating issues and problems—but I think a lot of people are using AI to generate documents that they don’t want to have to write themselves. And that applies to RFPs. We’re all now seeing a lot of AI-generated content, whether it’s documents, policies, handbooks, RFPs, or websites, because people didn’t really want to take the time to write them themselves.

And so it raises this interesting question: what’s the value of the document? Is it words on a page? Was it the thought process that went behind writing the document?

There was a fantastic article about Amazon. For decades, they had this practice of a six-page synopsis. When you were proposing something or starting a new initiative, you had to write a six-page synopsis of what you were proposing. You would take your synopsis to the meeting and hand it out, and everybody in silence read it for the first 15 or 20 minutes.

The whole idea was that the process of writing this summary forced you to think through what you were proposing. You don’t really think about your ideas and thoughts until you’re forced to articulate them. It really forced you to be disciplined about what you were proposing.

Conversely, the people reading the document were then required to understand the totality of what was being proposed, because when you’re just explaining the idea in a meeting, people just listen to the first three or four sentences and then they start reacting to that instead of looking at the idea.

The idea was that important concepts, key initiatives in the organization, couldn’t really be expressed in one or two sentences. It required six pages to think through and express and articulate what was being asked for. This article that I read is about this trend that’s happening because of all the buzz and the hype and the pressure to use AI tools. All of these managers at Amazon are now telling their staff, “Use AI tools to write the six-page synopsis for you.”

There are all these longtime Amazon staff who are like, “That’s defeating the purpose of it.” Why even bother writing this six-page summary? Because the whole point of it is to go through the exercise of thinking. But because Amazon needs to be at the forefront of technology and AI, it’s taking over the whole company. That’s an interesting experiment in a massive organizational change. It will be interesting to see the impact that it has on Amazon.

Finding the Right Partner

Carolyn Woodard: Well, along those lines, I wonder if you, having so much experience with reading RFPs or handling assessments and sales calls—someone called it IT therapy, that you just can call someone up and tell them everything that’s wrong, and then they can help you figure out if you need to write an RFP or what you need to respond to those pain points.

Do you have advice for someone who is in that situation where they work at a nonprofit, they’re in leadership or management, and they have IT pain issues? What would you suggest as a way to draw that out into a document or a phone call that is going to be more effective in finding the vendor support and eventually the tools and solutions that will help address those pain points? Because I have this feeling that if you just do a generic RFP, you get a vendor who can respond to that, they give you those generic tools, and it is highly possible that five years from now, none of those tools is actually addressing your business need.

Johan Hammerstrom: Yes. Especially with the line of business that we’re in, managed services, there’s not a lot of differentiation between managed services providers. We’re all installing software on your computers to keep them secure and up to date. We all have help desks that answer calls. We all have, hopefully, IT manager roles that are the point of contact for helping with the big picture and managing initiatives.

So if you just take what your current MSP is doing and put that in an RFP, you are going to get a lot of generic responses from different MSPs who all do the same thing, basically.

Carolyn Woodard: And why would you change? They’re all just going to say they could do the same thing.

Johan Hammerstrom: They are all going to say they could do the same thing. So I would encourage organizations to think about what makes them unique. Maybe it isn’t much more than just a commodity service that you need. But if something is not working well with your current provider or your current situation such that you are looking for someone new to work with, providing the context for what’s not working is the most important thing you can do.

That will bring out the differentiation in the bidders, hopefully. Because hopefully they’re paying attention to those needs that are being articulated and speaking to how their services, how their firm is a good fit for meeting those specific needs. Providing some context about what’s not working right now and what needs to change is always really helpful in an RFP. If that’s not something that’s included, that’s always a question that we ask, just so that we can have a better understanding of the situation and what they’re really looking for.

Carolyn Woodard: I have worked at for-profits and at nonprofits. One of the big differences that I have come away with is that at a nonprofit, because of the way they work and because people are really dedicated to the mission of the organization in all the different roles, you often find a lot of knowledge in all those different roles. You have a lot of understanding of what the mission is throughout, from the interns to the admin to the managers to the CFO. Everyone knows what the organization does.

People that I’ve interacted with at nonprofits have been very thoughtful. They really think about larger factors, they think about the ecosystem that they’re working in, what the nonprofit is trying to do. I think that that is an advantage.

If there’s some mechanism that you can use, or maybe you can just go on the water cooler conversation or the Zoom chats, but I think a lot of staff at nonprofits know what they wish worked better, where they could save time, where they’re missing opportunities, or where there’s something that’s just a legacy.

Finding some way to gather that feedback as you prepare to identify those pain points that are unique to your organization can really help you craft that RFP or inquiry. However you are going to approach this process of making a short list of vendors that you’re considering for your IT support and what that IT support really needs to be.

Another thing that we run into a lot is I don’t know if I can call it the vibes, the feeling. I have heard that we often have someone who is approaching us who says that their MSP just doesn’t “get” them. They’re either not explaining what they’re doing, they don’t respond quickly, or they kind of feel like they’re the last priority on that MSP’s plate. So being able to identify that we’re looking for a better partner—someone that will partner with us better, communicate better, respond more quickly—whatever it is.

Johan Hammerstrom: I think that’s a great point. There are sort of three areas that we’ve seen pop up over and over again in terms of dissatisfaction with IT support that are specific and unique to nonprofit organizations.

The first area is culture, because nonprofit organizations have a very unique, typically people-centered and people-focused culture. And that is not true of most businesses. Most businesses are all about the bottom line, getting the job done, being efficient and making money. That’s how a lot of MSPs are geared to support their clients. That can be abrasive. It just isn’t consistent with the culture that exists within a nonprofit organization. Nonprofit staff are having one type of interaction with their coworkers all day long, and then they call their vendor for IT support and they’re getting a different type of interaction; it is just dissonant and frustrating.

Carolyn Woodard: It’s jarring.

Johan Hammerstrom: Yeah. So that’s the first.

The second is understanding the need to connect technology solutions to business needs. Most MSPs are used to working with for-profit businesses. They always just assume and their experience is with business needs that have to do with the bottom line. “Buy this technology solution, and you will see your revenue go up.” That is the logic of for-profit business.

But that way of thinking about investment, that way of thinking about planning, and that way of connecting technology solutions to business needs makes no sense in the nonprofit environment. Nonprofits are resource constrained, and getting more efficient at how they do their work isn’t necessarily going to generate more revenue for them. There’s a disconnect between revenue generation and programmatic operations.

If you don’t understand that, if you haven’t been working in that environment for a long time, it’s difficult to understand how priorities are getting made and how budgeting happens. It’s just a very different dynamic. The typical playbook that a lot of IT support providers use just doesn’t seem to work with nonprofits. We’ve talked with a lot of our clients leaving a standard MSP, who are just like, “I just don’t feel like they ever got us. The stuff they were recommending didn’t really make sense to us.”

And then the third kind is that, sadly, for better or for worse, companies prioritize their larger customers and their more financially successful customers. Typically a nonprofit is one of the smaller customers of their IT support firm, and they are probably one of the less lucrative customers. They’re just getting deprioritized relative to the other customers.

No one’s going to admit that; no one is going to tell their client base, “You’re not as important to us,” but they feel it and you hear it. “I just get the sense that our great IT manager got moved to another client account,” or “We always get told to wait when we call the help desk.” The reality comes through.

Carolyn Woodard: We always get the most junior person who has to spend time to understand the problem first before they can even help us work through. That makes sense, or we get a different person every time. It’s not worth it to the MSP to have a consistent support person for us.

I had never thought about it that way, but that is really a helpful way to think about it. I want to just drop a resource on people. 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.

And I just want to thank you, Johan, for sharing all this experience and understanding with us. Hopefully this will help people ask better questions of their AI to get better RFPs and also maybe ask better questions of themselves of what those real pain points are.

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