Executive Brief

What Your Records Don’t Say

A practical brief for executives deciding where AI should go first

By
Scott Jennings
Reading time
About 11 minutes
In two parts
The knowledge · Putting it to work

The person who quotes your work knows which customers never pay the standard price. The person who schedules it knows which promises you can keep. The person who answers complaints knows when following the policy will cost you the customer.

Your records hold what happened: the price, the date, the customer. The reasons sit with the people who made the call.

Measuring what AI returns tells you whether your current spending earns its place. Choosing the next investment starts somewhere else: with how your business actually produces the result you want to improve.

An AI product can arrive ready to run while that knowledge is nowhere near ready to use. Fin, Intercom’s customer service agent, advertises setup in less than an hour. It also needs to learn your goals, policies, rules, and operating procedures. Both things can be true. Easy installation does not make the business decisions underneath it disappear.

It also changes where your advantage sits. Your competitors can buy the same product, the same afternoon. What they can’t buy is what your people know, and how well you’ve put it to work.

Before you buy another tool, identify a decision that matters to your results and find out what your people know about making it. That gives you a better starting point than whatever a vendor has packaged this week.

You can buy the tools. The knowledge of your work has to come from your business.

Part one

What your people know

1

Find the decision that matters

An equipment dealer’s rep has a customer on the phone asking for a quote.

The rep needs to understand the request, choose the right equipment, set a price, and keep the conversation moving. The business needs something else from the same call: a complete, structured quote it can follow up on, report on, and learn from.

Those two needs pull against each other. Every field the rep stops to fill in is a moment they aren’t listening to the customer. So reps serve the customer first and fill in what they can afterward, and the company’s records come out thin.

One decision, three parties. In a quoting tool I’m rebuilding for a dealer, that tension is the real design problem. A smarter form wouldn’t fix it. It’s one decision with three parties: what the rep needs to know, what the customer needs to hear, and what the company needs to keep. Choosing an AI feature comes after you see all three.
The quote Repneeds to know Customerneeds to hear Companyneeds to keep

Map the decisions that carry your own business from first contact to a customer who comes back. For a landscaping company, part of the map might look like this:

  • DecisionWhich jobs to bid, and at what price
    Who makes itOwner
    Where the knowledge livesExperience, old quotes
    What slow or wrong costsThin margins, lost bids
  • DecisionWhich crew goes where on Tuesday
    Who makes itOperations lead
    Where the knowledge livesScheduling system, whiteboard, phone
    What slow or wrong costsDrive time, missed windows
  • DecisionWhat happens when it rains
    Who makes itOperations lead
    Where the knowledge livesExperience, weather forecast
    What slow or wrong costsIdle crews, broken promises
  • DecisionWhich customers need a call first
    Who makes itOffice manager
    Where the knowledge livesCustomer records, memory
    What slow or wrong costsComplaints, lost renewals
  • DecisionWhen to reorder materials
    Who makes itForeman
    Where the knowledge livesInventory records, experience
    What slow or wrong costsStalled jobs

Ask of each row: if we made this decision better or faster, what business result would change?

Pick a consequential one. The quote that takes three days and loses the sale. The schedule that creates idle time every Monday. The pricing decision that quietly erodes margin.

Write down how it performs today: turnaround time, rework, margin, missed commitments, or another measure close to the outcome. You will need that baseline to know whether anything improves. BCG’s 2026 survey of more than 1,300 senior leaders found that companies tracking AI’s value directly in their profit and loss realize three times the value of companies that don’t formally measure it.

An AI support product may be exactly the right purchase. So may a faster month-end close. The question is whether improving that work changes a result the company needs.

Time saved inside a task isn’t a business result until it has somewhere to go.

2

Get the knowledge out of people’s heads

Start with the person who makes the decision. Ask them to explain it out loud, the way they would train a new hire.

Use a recent case so the explanation stays close to actual work. For the dealer, that means sitting with a rep and walking through last week’s quotes: what they asked first, what they already knew about the customer, which combinations of equipment they rule out without thinking, and when a price needs someone else’s sign-off.

Record the conversation, and give the transcript to an AI tool your company has approved for that information. Ask it to describe:

  • What starts the decision.
  • What information the person uses, and which sources they trust.
  • Which rules and exceptions apply.
  • When they ask someone else.
  • How they know the result was good.

Ask the AI to flag gaps and uncertainty rather than fill them in. Then have the decision-maker read what it wrote and work through another case.

The useful part is what it misses or gets wrong. Not every mistake means missing knowledge; sometimes the AI simply misread what it was given. The rest are the sticky notes: facts and exceptions people have learned to carry because the systems don’t. Which customer has a special agreement. Which supplier is late every spring. Which field holds the current price and which one nobody uses anymore. Everybody knows them. Nobody wrote them down.

An hour can produce a useful first draft. A consequential decision may take several conversations, especially when exceptions are the hard part.

When two people disagree

Do this with two people who make the same decision and you’ll find something more important than missing facts: they don’t make it the same way. One rep discounts to keep the customer. Another protects the margin. One treats a delivery date as a promise. Another treats it as an estimate.

Today that disagreement is invisible, because each person handles their own customers. Build either practice into a system and it becomes company policy, applied to every customer, every time. Recording current practice can’t settle which one is right. That takes leadership.

So decide before anything is automated: which practice should govern, who can make exceptions, and who owns keeping the answer current.

Automation turns a habit into a policy. Choose the policy on purpose.

Part two

Putting it to work

3

Sort the work into three piles

With the decision described, sort its steps by the authority you are prepared to give a system. For the dealer’s quote, it might look like this:

Rules

Explicit conditions with a defined action and an exception route

In the quoteCheck every configuration against the equipment data; route any price outside the approved range to a manager

AI proposes; a person checks

Work where AI can assemble information or recommend an answer for review

In the quoteDraft the structured quote from what the rep says on the call; the rep confirms it before it’s saved

People decide

Work where relationships, consequences, or uncertainty require a person’s judgment

In the quoteThe conversation with the customer, and any commitment beyond the rep’s authority

The middle pile is where the earlier tension resolves. The rep talks to the customer the way they always have. The system turns what they said into the record the company needs, and the rules catch what doesn’t fit.

Some work that feels like judgment will turn out to be a rule nobody had made explicit. Other work will reveal exceptions that an apparently simple rule cannot handle. Neither finding is a reason to rush into automation. Both help you choose the right design.

A clear rule may need ordinary software. A recommendation may benefit from AI. A difficult customer conversation may benefit most from a person who has the right context in front of them.

4

Test it against the work

A convincing description is a starting point. To find out whether it is dependable, test it against recent real decisions, including awkward ones.

Give the proposed process the information available at the time. Check what it recommends, what evidence it uses, and whether it recognizes when to ask for help. Have the people who do the work examine the results.

For the quote, that means replaying recent calls. Give the system what the rep said, compare its draft with the quote the rep actually saved, and check whether it flags what it can’t resolve instead of guessing.

The measure that matters isn’t how much the system typed. It’s whether reps stay with the customer and the record comes out complete.

Then try it on live work with a person reviewing the output before it affects a customer or commitment. Compare the result with the baseline you recorded: did quotes arrive sooner, did rework fall, did the schedule hold?

Before granting more authority, define what the system may do, what it must refer to a person, and who can stop it. Keep checking the business outcome as the work changes.

The aim is to improve the decision without creating more checking, correction, or customer trouble elsewhere.

5

Buy with a clearer brief

You now know what a product has to support: the decision, the required information, the exceptions, the limits on its authority, and the outcome you expect.

If a vendor can meet those requirements, buy the product. There is no prize for rebuilding something that already works. If the missing piece is company knowledge or the way work moves between teams, include that work in the plan.

The case for waiting is reasonable. The tools improve every few months, prices fall, and vendors are packaging AI for every industry. But the work in this brief doesn’t depend on which product you choose. A tested account of how your business makes a decision stays useful when the product changes, and it’s what you’ll judge the next product against. It does go stale as policies, customers, and practices change, so give it an owner.

Wait on the tools if you like. Don’t wait on the knowledge.

6

Where you stand

For the decision that matters most, pick the highest statement you can support with evidence.

You may be at different stages in different parts of the company.

This week

One decision, one hour, three cases

  1. Pick the decision that matters most and the person who makes it most often.
  2. Have them talk it through out loud, using last week’s real cases, the way they’d train a new hire. Record it.
  3. Give the transcript to an AI tool your company has approved, and ask it to describe how the decision gets made and flag what it isn’t sure of.
  4. Have the decision-maker check that description against three recent cases, including an awkward one. Note what it missed.

What it missed is what your records don’t say: the exceptions, the special agreements, the field nobody trusts. If it holds up, you have a clearer brief for choosing a tool. If it doesn’t, you know what needs attention first. Send me what it missed and I’ll tell you what I’d look at first.

Send me what it missed →Send me what it missed: scott@sufficiently-advanced.ai

Everyone can buy the same tools. What they can’t buy is a clear, tested account of how your business makes its decisions.

Sources and example notes. BCG, “The Formula for Agentic AI Value,” 2026 Applied AI Index: more than 1,300 CxOs and senior leaders across more than 20 sectors. Companies tracking AI’s value directly in the P&L get three times the value (3.6% vs 1.2%; BCG doesn’t define the unit, so the body uses the ratio only). This supports measuring a baseline; it doesn’t prove that undocumented knowledge causes the gap.

Fin, product overview (checked October 5, 2026). The equipment-dealer example is design work in progress; the pile assignments and the test approach describe the method, not measured results. The landscaping decisions are illustrative.

Scott Jennings

About this brief

Scott Jennings · Claude Certified Architect

I build AI systems for organizations end to end, and I’m a Claude Certified Architect. Much of the work is sitting with the people who run the business, making their knowledge explicit, and building it into tools they can operate and maintain.

That includes deciding where AI belongs, testing it against real work, and training the people who will run it afterward.

Tell me which stage you’re at and I’ll tell you what I’d look at first. Reply to the email that brought you this, or grab 20 minutes.