Walkthrough of a Human Agent’s Workflow – with an eye toward Digital Agents

I am having too much fun fleeing my WordPress instance for Eleventy. I am impressed with how quickly I have already managed to put together some classic Mac OS-inspired pages. I’m working on getting the blog mechanism to work with the templates next, but that will take a while. So in the meantime, I will Sally Forth with my existing blogging rig and continue the themes I touched on in my previous post.

Setting the Scenario: Renewing Social Benefits for an Elderly Relative

My last post was freshly inspired by the frustration I am having renewing Medicaid coverage for an elderly relative. For those who have not had the pleasure of renewing Medicaid, for themselves or for someone else, there is an inherent amount of friction baked into the process that can often lead to unnecessary denials for those who qualify. For those with the time and resources necessary to navigate the system, it’s an exhausting endeavor. For those without the time or resources necesssary to navigate the system, it is often completely prohibitive.

I want to introduce you to the agents and workflows typically involved in this kind of Medicaid scenario.

Defining the Agents and Agencies in our Scenario

Visual diagram categorizing the agents and agencies involved in the Medicaid Renewal Scenario: Principal, Agent, State, Medical and Financial Agencies.
Visual diagram categorizing the agents and agencies involved in the Medicaid Renewal Scenario: Principal, Agent, State, Medical and Financial Agencies.

Principal – I’m borrowing this legal term to define the person on whose behalf the agent is working for. In the context of workflows we’ll discuss, they are typically a relative who is unable to manage their own affairs.

Agent – The agent is the person authorized to act on behalf of the principal. Authorization is provided in the form of a letter granting Power of Attorney (POA). There are typically two types of POA: Medical and Financial. Medical POAs (mPOAs) are given the authorization to make medical decisions on behalf of the principal. Financial POAs(fPOAs) are given the authorization to make financial decisions on behalf of the principal. I’m focusing the scope primarily based on my experience as a Financial POA (fPOA).

State Agency – States are typically given the jurisdiction of running their State’s Medicaid program. When initially applying for Medicaid, another agency such as an Assisted Living Facility, may reach out the State agency to put the State Agency in touch with the fPOA. (Experiences differ from State to State – your mileage may vary).

An AI-generated image of a generic state seal. It shows a seal with an image in the center showing a river, with a forest on one side and grain on the other. The ring around the image reads 'State Seal of the State of.'
I asked ChatGPT to generate a generic state seal. I normally don’t enjoy AI slop, but, in this case, I love it.

Medical Agencies – These are the medical agencies relating to the Principal. I have a main agency I work with, the Assisted Living Facility, but I also have to work with other medical providers as well. Your experience coordinating medical agencies may vary as well.

Financial Agencies – The financial agencies relating to the Principal. These are your typical financial retail products and services: banks, annuities, but you will also have to research and establish direct relationships with retirement benefits or other stocks and dividends. You also have to take into consideration other assets such as pre-paid burial plots.

Now that we know the agents, how do they interact? How do they even meet?

Simplified Agent Workflow

A diagram outlining the relationships between agents and agencies. It shows a two-way arrow between the State and the fPOA. The fPOA has one-way arrows pointing to three financial agencies (bank, securities, and annuities).
A diagram outlining the relationships between agents and agencies. It shows a two-way arrow between the State and the fPOA. The fPOA has one-way arrows pointing to three financial agencies (bank, securities, and annuities).

When the Principal’s Medicaid application is up for renewal, the fPOA is typically contacted by the State Medicaid agency. The State agency provides the fPOA a checklist of updated financial documents necessary for the Medicaid renewal. This checklist is usually a list of specific financial documents, such as updated statements, from various agencies.

As such, the fPOA must often reach out directly to each of the Principal’s financial institutions for updated documents. Each of these agencies has differing processes for authorizing and working with fPOAs, but rarely is the workflow online. And when it is online, it is often problematic for agents – I will explore this topic later. I will put a pin in it for now.

The fPOA and the State agency may be in direct touch, often via secure email. In that relationship, there is usually a responsive two-way interaction. The fPOA’s relationships to the various financial agencies, however, are often more “analog” and one-directional.

Most financial agencies, for example, require you to authorize – by phone – for each individual document request. Sometimes they ask you to resubmit Power of Attorney documents with each outreach. Often these requests are only fulilled by mail or even fax.

I want to walk through a workflow for obtaining one item on the State’s checklist, a financial letter from an annuity agency. As I describe these workflows, imagine how a generative AI agent would handle the same task. Bear in mind, this is only one item on the checklist provided by the State agency – for now we are not going to consider how a generative AI agent would manage the entire checklist.

A Simplified Workflow – Requesting a Current Financial Letter

A diagram showing enumerated arrows between agent and agencies. Arrows 1-4 alternate between the fPOA and the financial agency. Arrow 5 is from the fPOA to the State agency. 6 is from the financial agency to the fPOA. 7 is an arrow from the fPOA to the State agency.

I’ve outlined a typical set of steps involved for an fPOA to contact a financial agency for a checklist item. In this case, we are requesting an updated financial letter from a retirement annuity holdings agency. What is described below is an optimal scenario, where nothing goes wrong. Ideally, most of this would happen over a phone single call but, depending on the agency, these steps might stretch out over days.

  1. Agent calls financial agency and declares POA status tand follows authorization process
  2. Financial agency confirms fPOA authorization
  3. Agent requests updated financial letter
  4. Financial agency confirms financial letter is being sent in the mail
  5. Agent notifies State agency that checklist item will arrive within 3-5 business days
  6. Financial letter arrives in the mail
  7. Agent scans and sends financial letter to State agency

This is just one workflow for one item on the checklist provided by the State agency. For this one workflow alone, you can see a number of barriers for a potential generative AI agent:

  • How does the generative AI agent work out the steps involved for each item on the checklist (phone, online)?
  • Assuming the agent is able to navigate a phone conversation, what mechanisms exist that allow the financial agency to authorize the generative AI agent?
  • Can generative AI agents check the mail? Or at least, can generative AI agents follow up with a human after several days?
  • Assuming the generative AI agent can handle the entire checklist from the State agency, can it keep track of the details for each task, how they relate to each other, and communicate only the pertient information to each of the parties in a secure manner?

My goal is not to denegrate the concept of digital agents. I do not think generative AI models are the best foundation for building digital agents. I believe generative AI models will play a part in enabling digital agents, namely as a natural language interfaces and specialized models, but the bulk of the foundational work for trustworthy digital agents will be in building robust, deterministic systems and web infrastructure. I also contend that this infrastructure can enable many of features we want from digital agents at a fraction of the cost of building with a generative AI-model first approach.

What I am proposing is not a new idea so much as a return to the original vision for digital agents. Sir Tim Berners-Lee proposed in 2001 public Semantic Web infrastructure as being the technology that would enable digital agents to work autonomously. The reason I suggest we revisit this original vision of the Semantic Web is that, nearly 25 years on, with AI hallucinations and misinformation rampant, this original vision is more prescient than ever. Lastly, I propose that, as we build out Semantic Web infrastructure for digital agents, it can make the web more easily navigable for humans in the process.

Automatic Door with Crash Bars. Scott Brody. Wikmedia Commons. CC BY-SA 4.0

The analogy I want to use for this Semantic web infrastructure are the visible effects of the American with Disabilities Act of 1990 on the design of public spaces in America. The design sensibilities that enabled greater accessibility for the disabled in public spaces (such as ramps and automatic doors) proved to have beneficial impacts for the greater society at large. I believe that Semantic Web infrastructure that we build to enable Trustworthy AI can reap dividends for the wider population beyond its initial stated scope. In short, I believe building Semantic Web infrastructure can be other example of universal design, with broad public benefit.

In the next article I want to call attention to the work that’s already been done to build out this Semantic infrastructure and demonstrate how it can be leveraged by agents, human and digital, to reduce friction.

If you have been reading this far, thank you. Feedback, as always, is welcome.

The Web Doesn’t Work for Human Agents. How Can It Work for Generative AI Agents?

America, like many countries, is an aging population. This is resulting in a growing number of younger people in america taking on the role of unpaid family caregiver. According to a report put out by AARP and the National Alliance for Caregiving, the number of family caregivers has increased by 45% to a record 63 million Americans. The Caregiver Action Network has published statistics on the financial and emotional impact that the work has on caregivers. The numbers going forward aren’t enccouraging, as you might imagine. Within that population of 63 million American caregivers, I want to focus on a growing segment: adult caregivers to adults with dementia. The NIH has published projections that the financial (and emotional) burdens are set to double by 2060.

With this in mind, I want to write about my personal experience of being an administrative caregiver to a non-household aging releative at this early stage of this steep curve. I want to walk through the problems I encounter, the (enormous) hurdles I see for digital agents and solutions that I propose (which is really highlighting other people’s work that I believe needs more visibility).

Unseen Caregivers: Powers of Attorney

Caregiver” by havens.michael34 is licensed under CC BY 2.0

What little attention that is given to the caregiving crisis in America is, rightfully, mostly given to clinical, assisted living, or live-in or hands-on caregivers. That work is valuable and deserves more attention. However, I also want to highlight the unseen work of thousands of administrative caregivers, a term I’m using for those, like myself, who are handling the administrative affairs for those who cannot or can no longer manage their own – often having to do so remotely.

This work is unseen by most people, but other caregivers are aware of this work. Assisted living professionals are often fielding calls from exasperated family members trying to piece together financial information over the phone. In addition to calling and emailing, they are often taking trips so to find information so they can file taxes or renew public services. This work is time intensive and thankless. It is a legitimate burden in America, especially if you already have a full-time job and/or are already a caregiver or a parent.

And it is even harder since there are few legal frameworks to standardize your experpience and expectations. The lack of these legal frameworks often mean there is no single way to authorize yourself as a financial Power of Attorney across different types of organizations across different states. As a result, being a legal power of attorney for someone in America often feels like an extralegal and quasi-criminal process.

I have been doing this work for a relative since 2012. It is now 2025 and in all that time, I have been hoping that legal and technical solutions would emerge and they just haven’t. It’s basically just as bad as when I started doing this.

Photo by Christa Dodoo on Unsplash

It’s this personal experience that I draw from when I personally laugh at the idea that Agentic AI is ready to go out on the open web and do anything substantial on anyone’s behalf. Rather than just criticize, I propose we revisit a previous technology before we talk about building Trustworthy digital agents (Generative AI-based or not). Specifically we should be collectively revisiting Tim Berners-Lee’s original vision of the semantic web to support authoritative information retrieval infrastructure to enable trustworthy decision-making for digital agents.

Thankfully, I’m not the only one who’s had this idea. Projects like the Linked Open Data Cloud and The Proto Open-Knowledge-Network have been working on this issue and have created demonstrable case studies across legal, medical, and academic domains for years and decades. I believe this work, specifically in the context of developing Trustworthy AI, deserves more public attention.

This is a lengthy topic that requires deep exploration to flesh out. I don’t know how many posts there will be total, but the next topics I want to cover include:

  • A walkthrough of how human agents currently navigate the web (and the world) for other people – and what would be required for a digital agent to be able to do so
  • The Semantic Web infrastructure – the afformentioned teams who are already building it, and how this could be useful for agents
  • How Semantic infrastructure should be governed to align with legal frameworks
  • Why we need to revisit the legal frameworks for human agents before we set the framework for digital agents

    I hope other people find my exploration of this topic to be helpful. If so, thank you for reading. Feedback is always appreciated. See you soon.