Which Processes Should You Automate First?
Eighteen questions turn a vague "we should use AI" goal into a sequenced shortlist of the processes worth automating first.
- A scored profile across 5 dimensions — see exactly where you're strong and where the gaps are.
- Your biggest opportunities, mapped to specific next moves.
- A personalized video walkthrough from Shawn (optional) — a real read on your results.
Most companies don't struggle with whether to use AI — they struggle with where to start. Faced with a long list of processes that could be automated, the temptation is to pick the loudest complaint or the newest tool and build. That's how automation budgets get spent on the wrong thing. Deciding which processes to automate first is a ranking problem, and the inputs to that ranking are knowable: how often the process runs, whether its data is accessible, how much errors cost, how feasible it is to build, and whether it moves a metric that matters.
This free AI automation assessment scores a process across those five dimensions and returns a clear automation-readiness profile in about six minutes. It's built from 27 years of technology leadership across Fortune 500 and growth-stage companies — the same lens a fractional CTO or fractional CAIO would bring to sequencing your first build.
How to decide which processes to automate first
The best first automation isn't the one that annoys people most — it's the one where high volume, clean data, costly errors, and technical feasibility all line up. This assessment scores five dimensions independently so you can see exactly why a process ranks where it does: Volume & Repetition (does it run often and consistently), Data Availability (are the inputs accessible and clean), Cost of Errors & Rework (what do mistakes actually cost), Technical Feasibility (can it be built reliably), and Strategic Value (does it move a metric leadership tracks). A process that wins on all five is a first build. One that wins on a couple is a fast follow.
Why ranking beats automating at random
Companies that automate the first thing that comes to mind often spend their initial budget proving a hard lesson: a high-effort build on a low-volume process, or one whose data was never accessible, doesn't pay back. The organizations that capture real value treat prioritization as the first deliverable. They rank candidates by ROI, feasibility, and error cost before a single line of code, then sequence the build so the earliest win is also the most defensible. A ranked shortlist turns a vague ambition into a plan — and protects your first budget from a low-odds bet.
What you get at the end
You'll see an overall automation-readiness score for the process you evaluated, a band that tells you how strong a first candidate it is (from Not the First Move through Automate This First), a per-dimension breakdown showing exactly which factors carry or sink it, and a map of the broader areas worth scoping next. From there you can request a personalized video walkthrough — a short, recorded read on your specific results and how I'd sequence the build. No generic sales deck.
Frequently asked questions
How do I decide which processes to automate first?
Rank candidates instead of picking by gut. The strongest first automation scores well on volume and repetition, data availability, the cost of errors and rework, technical feasibility, and strategic value at the same time. This assessment scores a process across all five so you can see why it ranks where it does and whether it belongs at the top of your list or further down it.
What makes a process a good AI automation candidate?
Four things tend to line up in the best candidates: it runs often and the same way each time, the data it needs is already accessible and clean, manual mistakes are expensive, and the logic is clear enough to automate reliably. When all four hold, the build pays back fast. When only one or two do, it's usually worth waiting or scoping a narrow pilot first.
How long does the assessment take?
About six minutes. It's 17 scored questions across five dimensions plus a final opportunity-mapping question. Your progress auto-saves, so you can leave and resume without losing answers.
Is the assessment free?
Yes. The assessment and your scored results are completely free. You can optionally request a personalized video walkthrough of your results, which is also free.
What happens after I get my score?
You'll see a full automation-readiness profile with per-dimension scores and a map of the areas worth scoping next. If you'd like, you can share a few details and receive a personalized video walkthrough explaining your results and how a fractional CTO or CAIO would sequence the build for your specific situation.