The origin story is a little circular, so I'll just tell it in order. I wanted to get better at using Claude, and like most people learning a new tool, I went to YouTube first. I found a video walking through a handful of useful projects to build while learning, and one of them was a personal branding website. That felt like a good use of time regardless of whether the tool-learning stuck, so I started building this site.
Building the site meant writing about how I actually think, which turned into the dozen or so field notes now living in the archive. Writing those made it obvious the site needed proof, not just philosophy, so I put together five sanitized case studies pulled from real engagements. And once the site had philosophy and proof sitting side by side, the obvious next question was: what does a visitor actually walk away with? Reading about how I approach alignment is one thing. Experiencing a small piece of it is another.
That question is what became the Alignment Diagnostic. Learning Claude led to a website, the website led to field notes, the field notes led to case studies, and the case studies led to a question I couldn't answer with more writing. The app is the answer.
Underneath, it's a deterministic logic engine, not a model doing inference at answer time. Thirty-four plain-language inputs branch through a fairly involved decision tree and land on a specific, defensible output. No question requires the respondent to know what a domain controller is or what "technical debt" means. The complexity lives in the branching logic, not in the vocabulary asked of the person answering.
I built it for the same reason I built everything else on this site: to give someone outside my existing network a way to gauge what working with me actually looks like. The intended reader is anyone trying to understand how I think about technology alignment: business owners, operators, IT leaders, MSP leaders, and vCIO-style advisors.
On timing: I started the evening of June 26th, 2026, during an extended PTO weekend, and had a working pilot by June 30th. That's the version live today. I still plan to build out a stronger admin panel and look at deeper workflows and expanded question sets, so treat this as the current state, not the finished one.
The rest of this note is the part that matters most, and it's the part that's easiest to skip past in a story this fun to tell. So I'm putting it in its own section rather than burying it in prose.
What this project is, and isn't
Built entirely on my own personal time, using my own personal accounts, subscriptions, and devices. No employer time, systems, resources, or confidential information were used at any point.
No existing client data was used to build or test it. The prototype does not request, store, or process confidential client data. Every question and logic branch was written from scratch. No internal code was copied, no proprietary templates were reused, and no employer-specific language appears in the questions, logic, or output. I am intentionally not using real client environments, employer materials, or confidential operational details in this prototype.
There is no monetization attached to this project and no external sales activity. It is not for sale, and it is not being marketed as a product.
Its purpose today is exactly what the timeline above suggests: a learning prototype and a public example of how I think through technology alignment. If it demonstrates internal value somewhere down the line, that is something to explore carefully and explicitly later, not a plan currently being executed.
It should not be interpreted as a technical audit, security assessment, implementation recommendation, or replacement for professional review.
I'm publishing this note for the same reason I publish the rest of them: I'd rather show my work than describe it after the fact. The app is live, it's a prototype, and this is exactly how it came to exist.
New · Free Tool
Try the prototype: generate a directional technology roadmap in about 15 minutes.
The Alignment Diagnostic asks 34 questions about how your business actually runs, then generates a deterministic technology roadmap: the initiatives worth scoping, in the order that matters. No login required. It's a prototype, so treat the output as directional.
Build Your Roadmap