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Operations · Strategy · AI

I design operating systems for organizations, the kind that put people at the centre and make process and technology serve them.

Good people and good intentions aren't enough on their own. The organizations I work with know this. They bring me in to build the systems, structures, and clarity that make everything else possible.

New: AI Adoption Readiness Diagnostic and Brief Generator are live. Try them →
About
Hilary Mason, headshot.

I've spent my career walking into organizations where the infrastructure for planning, reporting, and coordination either didn't exist or needed significant repair. Across media, SaaS, and technology companies, I've built reporting systems from scratch, recovered high-visibility programs, and led cross-functional work spanning product, design, engineering, and executive teams.

What I've learned is that the hardest part is rarely the tooling. It's getting people to trust what the data is telling them and actually shift how they work day to day. I do that by bringing people along: hands-on, honest, and always starting with the why before the how.

These days I'm building a portfolio of AI-assisted operational tools, exploring what becomes possible when human judgment and good technology work together.

Work

Frameworks and tools, built from real operational work.

Each framework is open and reusable. The tools below extend each framework into something you can run on your own organization.

01
Live

AI Adoption Readiness

A six-dimension framework for assessing where AI initiatives are most likely to succeed or stall. Includes deep-dive documentation for each dimension.

View the framework
02
In development

Operating Cadence

A framework for diagnosing whether an organization's operating rhythms match how the work actually flows. The framework documentation is in active development. The diagnostic tool below operationalizes the working version.

View the framework
03
In development

Meeting Design

A framework for diagnosing and redesigning meetings that aren't working. Most meetings don't need to be cancelled, they need to be redesigned. Framework documentation is in active development. The reset tool below operationalizes the working version.

View the framework
04
In development

Change Cadence

A framework for diagnosing whether an organization's change capacity matches its strategic ambitions, and what to do when it doesn't. In active development. Tools to operationalize this framework will be added as it matures.

View the framework
AI Readiness

The six dimensions of AI adoption readiness.

Most AI initiatives don't fail because of the technology. They fail because of the operational conditions underneath. This is the framework I use to assess where organizations are set up to succeed, and where they aren't.

Strategic ClarityData & InfrastructureOperating Model FitEducation & EnablementChange CapacityGovernance & Accountability

Illustrative example. Run the diagnostic to see your organization's profile.

Try It

Want a quick read on your own organization?

Answer one question to get an instant signal on where to focus first.

Which of these is most true about your organization right now?

AI Process Log

How I actually work with AI.

A running, honest log of where AI accelerates the work, and where human judgment still does the deciding.

  1. System Design

    Restructuring the site information architecture and completing the AI Adoption Readiness framework

    Overhauled the site information architecture into clear Frameworks and Tools sections, added the Operating Cadence Diagnostic tool, and completed the first iteration of all six dimensions of the AI Adoption Readiness framework. Learned to watch for drift in connective elements like the site index when individual updates land cleanly.

  2. System Design

    Building a portfolio site with Claude and Lovable as a connected workflow

    Spent the day designing and building a full portfolio system: a GitHub repo for canonical content, a Lovable site for the public-facing experience, and a process log to capture the thinking behind both. Claude held the strategy and scaffolding. Lovable executed the build.

  3. Sensemaking

    Designing the AI Adoption Readiness framework

    Used Claude to research the current state of AI adoption. The data was bleak: 48% of orgs call AI adoption a disappointment, 60% of projects expected to be abandoned by end of 2026. Worked backward from the failure patterns to identify what dimensions actually determine readiness. Landed on six.

Contact

If any of this resonates, I'd love to hear from you.

hilary@hilarymason.me