A1CFO-led
Cost model
Separates observed operating data from assumptions; shows implementation, usage, maintenance, and sensitivity without manufacturing a return.
- Current-state baseline
- Cost ranges
- Sensitivity cases
- Measurement plan
The Lionwork leadership buying guide
One operating system. A different diligence question for every executive.
A CEO buys authority, a COO buys an owned workflow, a CFO buys a defensible investment case, and a CTO buys an architecture the company can secure and maintain. The decision works only when those views meet around one bounded operating mission.
A buying decision, not a feature tour
Good diligence makes the system smaller before it makes the vision larger.
The first job is to reduce ambiguity: one mission, one signal, one accountable operating path, and explicit boundaries. This lets each executive test the proposal from their responsibility without turning the decision into four disconnected wish lists.
The buying team should leave diligence with four concrete artifacts—a cost model, architecture sample, acceptance plan, and authority model—not only a presentation about what AI could do.
01 / CEO / Owner
Authority
Make the business less dependent on invisible owner intervention.
Which recurring decision should stop routing through the owner—and which decisions must remain visibly theirs?
EXAMINE
- 01The recurring operating question this system must answer
- 02Where work loses momentum, ownership, or context today
- 03Which decisions can move inside policy and which require judgment
- 04The evidence required before the mission earns expansion
02 / COO
Workflow + ownership
Turn operating activity into an owned path from signal to closure.
At which handoff does the work lose a trusted state, a named owner, or a recoverable exception path?
EXAMINE
- 01The real normal path, including the workarounds people actually use
- 02Source-of-truth boundaries and the state each system owns
- 03Queue, assignment, escalation, approval, and closure behavior
- 04The live cases that will prove the first installation works
03 / CFO
Investment + risk
Underwrite the operating case before accepting an automation story.
Which costs and consequences are observed, which are estimates, and what baseline can support measurement?
EXAMINE
- 01Frequency, touches, latency, exception rate, and leadership load
- 02Implementation, usage, maintenance, and change costs
- 03Control points, approvals, audit records, and financial consequences
- 04The acceptance threshold and the condition for further investment
04 / CTO / CIO
Architecture + assurance
Install an accountable architecture, not a hidden chain of prompts.
What owns state, where does data move, how is authority enforced, and who maintains the system when dependencies change?
EXAMINE
- 01Connect-versus-replace decisions and system boundaries
- 02Identity, permissions, secrets, data handling, and retention
- 03Model, API, integration, observability, and fallback design
- 04Deployment ownership, incident response, maintenance, and change control
The decision packet
Four artifacts make the proposal inspectable.
These are representative diligence artifacts. Their contents are fitted to the mission and the evidence available; they are not generic templates filled with invented certainty.
A2CTO-led
Architecture sample
Maps signals, systems of record, data movement, model and tool boundaries, human controls, observability, and failure recovery.
- System boundaries
- Data paths
- Control points
- Operational ownership
A3COO-led
Acceptance plan
Defines the first live cycle, normal and exception paths, test cases, evidence of closure, stabilization, and the expansion decision.
- Live-cycle cases
- Exception tests
- Acceptance evidence
- Stabilization exit
A4CEO-led
Authority model
Makes explicit what AI may retrieve, recommend, draft, or execute—and where people approve, override, escalate, and remain accountable.
- Role boundaries
- Approval matrix
- Override record
- Escalation path
The executive decision room
Six questions the whole coalition should answer together.
Alignment does not mean every executive evaluates the same risk. It means the answers form one coherent operating and technical system.
- 01Mission
- Can every executive describe the same recurring event, operating consequence, and intended change?
- 02Ownership
- Is there an executive sponsor, operating owner, technical owner, and clear owner for every exception?
- 03Authority
- Are automated actions, recommendations, approvals, overrides, and escalations visibly separated?
- 04Evidence
- Can the team distinguish observed facts, repository or system evidence, assumptions, and proposed behavior?
- 05Acceptance
- Will real cases prove the path from signal to closure, including failure and recovery?
- 06Lifecycle
- Who monitors dependencies, maintains the system, manages changes, and makes the expansion decision?
From interest to an investment decision
Move in evidence-producing stages.
The first commitment should improve the quality of the next decision, even when diligence shows that a proposed build should change or stop.
- 01
Name the mission
Choose one consequential recurring loop, its sponsor, its operating owner, and the reason it matters now.
- 02
Underwrite the reality
Map the current path, evidence, systems, constraints, authority, risk, and baseline before prescribing a build.
- 03
Agree on acceptance
Define the live behavior, exception cases, controls, and records that will constitute an installed first cycle.
- 04
Decide from evidence
Stabilize the operating path, inspect what changed, and expand only when the first mission earns it.
Use this in the buying room
Share the guide. Print the checklist. Mark the disagreements.
The checklist is designed for a working session with the sponsor, operating owner, finance lead, and technical owner before scope is fixed.
Start with the operating truth
Give every executive a better decision to make.
The Operating Underwrite collects the mission, workflow, systems, authority, evidence, risk, and investment context for founder review.
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