Free · about 5 minutes · no sales call first
Audit My AI is a free assessment for people making real decisions about AI — founders, college leaders, and small-business owners. Answer a few honest questions about how AI is actually being used around you, hand us your website, and get back a report: what you have, what it is costing you, what to do in the next 30 days, and the questions to ask before anyone sells you anything.
Pick your lane
The assessment is different for each one, because the mistakes are different for each one. Start where you actually sit.
Founders
Questions you are already asking:
Higher Ed
Questions you are already asking:
Small Business
Questions you are already asking:
How it works
Three lanes — founders, higher ed, small business. Sign in with Google or a one-time code. That is the only gate, and it is there to keep bots out, not to start a sales sequence.
Short, specific, and occasionally uncomfortable — the questions a good advisor would ask in the first meeting. Give us your website too; we read it for context so you do not have to explain your business twice.
A score with the reasoning behind it, findings, risks, and moves for the next 30 days, 90 days, and year — each one written as Aim, Release, Impact. It closes with the questions to ask your own team or any AI consultant, including us, and with the work your situation is asking for and who has done it.
The questions take about five minutes. The report takes a minute or two to write while you wait — then it is yours to download, print, or forward.
What you get
Written for the person who has to make the decision, not for the vendor who wants to be in the room when it is made.
One overall number plus the dimensions underneath it, each with a sentence explaining why it landed where it did. A number you can argue with is worth more than a number you cannot.
What your answers and your website say about where AI already sits in your organization — including the parts nobody wrote down.
Data exposure, unreviewed output, spend nobody approved, decisions made on a confident guess. Named, not hedged.
Specific next actions sized to what you actually have — not a transformation program for a team of fifty you do not employ. Each one follows Aim, Release, Impact: what it is meant to move, what ships, and how you will read the result.
A set for your own team, and a set for any AI consultant or vendor pitching you. We include the ones that are inconvenient for us to be asked.
The report closes by naming the product and business-management work your answers point at, and who has done it. No adjectives — the record, with the numbers attached.
Download it as Markdown or print it to PDF. Take it to your board, your co-founder, or your next vendor meeting.
The point of view
AI is useful and oversold, usually in the same sentence. It will not fix an enrollment cliff, a product nobody asked for, or a business whose margins were thin before anyone typed a prompt. Those are structural problems, and structural problems do not care how good the demo was.
What AI does reliably is amplify whatever discipline is already there. Teams with clear priorities get faster. Teams without them get faster at being wrong. The difference is not the model anyone picked.
So this assessment does not start with your tooling. It starts with the lenses Fletching Vane brings to any AI decision: whether the spend is allocated the way a portfolio is allocated, whether each release is tied to an outcome somebody reads afterward, and whether the judgment AI cannot supply is still at the center of the place. They are named below, in plain words, and they run through every finding and every recommendation in your report.
If the honest answer is that you should do less with AI this year, the report will say so.
How we look at it
Each lens is named, and each name comes with what it means. Nothing in your report comes from somewhere else.
Run the roadmap as a portfolio of investments, not a list of requests.
Every product bet goes into one of three accounts: innovation (high risk, high reward — drives new revenue and win rate), retention (known risk, known reward — drives renewals and NPS), and technical debt (no growth, prevents catastrophic failure). Leadership sets the annual allocation across the three, because that split is a strategy call. Inside it, every bet is written up, scored on the same inputs, voted on independently, and stack-ranked. Nothing skips the line.
Tie every release to one measurable outcome, then reinvest on the evidence.
Aim is the outcome the work is supposed to move and how you will know. Release is shipping something real, small enough to measure. Impact is reading the result and deciding, on evidence, where the next dollar and the next week go. It is the difference between a team that ships and a team that learns.
Keep the traits AI cannot replace — integrity, initiative, ingenuity — at the center of how the organization runs.
AI amplifies whatever discipline is already there. Integrity is the person who tells you no and shows the evidence. Initiative is the person who runs the experiment without being told. Ingenuity is the person who finds the simpler path. A plan that quietly assumes the model supplies these will produce faster, more confident versions of the same mistakes.
The four stages an organization moves through to run on decisive data instead of directional data: Fluency, Initiation, Impact, Transformation.
Most organizations collect directional data and make decisions on gut. Getting "data FIT" is a progression. Fluency: understanding what data-native means in your context. Initiation: surfacing where to move first to unlock the most value. Impact: executing with discipline and building the real muscle of using data. Transformation: embedding data thinking into how the organization runs. Each stage has its own work, and skipping one shows up later as a stalled initiative.
Questions worth asking
Product and business management is a specific set of work — allocating a roadmap like a portfolio, pricing a product, owning a P&L, repositioning something customers already bought, hiring the team, operating through an acquisition. The fastest way to find out whether an advisor has done it is to ask. Here are the questions.
Deciding, once a year and on purpose, how much of the team goes to new bets, to keeping customers, and to not breaking — then scoring every request against the same inputs.
Ask Matt
How did you set the annual split between new bets, keeping customers, and not breaking — and what happened the first year the CEO owned that number?
Turning features into something a customer can buy and a finance team can forecast — including what happens when AI capabilities have a different cost shape than the rest of the product.
Ask Matt
How did you price AI features that cost money every time they run, next to a platform customers bought on a flat subscription?
Being the person whose budget, headcount, and roadmap have to add up — and making the cuts and the bets that follow from that.
Ask Matt
What did you cut, and what did you refuse to cut, to get a product organization back to profitable two years running?
Changing what a product is understood to be — in the market and inside the company — without breaking the customers who bought the old thing.
Ask Matt
How did you get customers who bought a texting tool to see a conversation-intelligence platform — and what changed once you saw the retention gap between adopters and everyone else?
Wiring CRM, marketing automation, product analytics, and the website into one loop, so pipeline runs on data instead of on the founder.
Ask Matt
What did pipeline look like before and after CRM, marketing automation, analytics, and the website were one loop — and what did the founder stop having to do?
Deciding who to hire first, what a product person actually does here, and how to keep a team shipping while the org around it changes.
Ask Matt
Who did you hire first when the product team was small, what did you get wrong, and how did you keep a team shipping through executive turnover?
What a buyer, a board, or a private-equity owner will actually look at — and running the product so those numbers hold up.
Ask Matt
What did the buyers and the private-equity owners actually look at, and what would you have cleaned up a year earlier if you had known?
Making decisions that have to be defensible to people who were not in the meeting — trustees, auditors, a cabinet — and building the reporting that lets them trust the answer.
Ask Matt
How do you brief a board that was not in the room so they can trust the decision — and how is that different at a bank, a nonprofit, and a campus?
Choosing the tools, writing the governance, redesigning the workflow, and handling the people side — so adoption shows up in the numbers, not just in the demo.
Ask Matt
Of the seventeen AI capabilities you shipped, which ones did people actually use, how did you know, and what did you do about the rest?
Knowing how a campus actually decides — the stakeholder map, the procurement path, the difference between a data-grounded decision and a political one.
Ask Matt
How does a campus actually decide on a vendor, where does the process turn political, and what did Yale and USC ask you that most schools do not?
Taking a team from directional reports to decisions made on evidence — the instrumentation, the reporting, and the habit of asking what an outcome would prove before building.
Ask Matt
What was the first decision a team you ran made on evidence instead of gut, and how long did it take to get there?
Who is behind it
Fletching Vane is a strategic positioning and advisory practice run by Matt Baker. The name is the feathered vane on an arrow — the part that does not create the shot, only keeps it on trajectory. The practice does that for founders installing product discipline before they scale, and for institutions trying to turn AI spend into something governed and measurable, working from the lenses above. Audit My AI is the free front door: a real assessment, delivered whether or not you ever hire anyone.
Five minutes of honest answers, one report, no obligation. Pick the lane that fits and start.