5 blocks, 30 minutes, structured.
The default for first conversations and most cold-outreach replies. Five minutes of intro absorbs role/team color; the structured blocks fit in 25 minutes with C1–C7 still anchored. Block 2 (the trigger event) stays load-bearing — don't trade time out of it.
Present mode opens a one-question-at-a-time slide deck for screenshare — questions only, none of the internal probes / claim anchors / don'ts.
Timing
Total 30 minutes: 5 for unstructured intros and 25 for the structured blocks. The intro absorbs greetings, the ask restatement, and role/team color — the structured blocks start from calibration on. Spend the time where it's allocated; don't trade out of Block 2.
Greeting, thanks, restate the ask, confirm note-taking / recording. Let role and team color come out naturally; do not re-ask them in Block 1.
Surface the consequential systems they rely on. Their own language for 'agent' typically falls out of how they describe what's touching what — capture it verbatim as it appears. Role and team came out of intros; don't re-ask.
Surface where the org actually is on agents-acting-on-consequential-systems: shipped, tried-but-stalled, proposed-and-rejected, wanted-but-never-proposed, or not on the table. The branch matters as much as the answer. A blocked proposal is data; so is wanted-but-never-proposed. The only branch that kills C1 is 'no one's thought about it and there's no demand.' This is the load-bearing block; spend the time.
Two open-ended questions: what systems they touch, and whether they run customer-operated. Both wide enough that the rejection list (C4), credential flow (C1 probe), and their own connector layer (C6) typically fall out in passing — capture all of it as it surfaces. The formal probes for those claims live in the full script if you have the time.
One shot at the pitch. Read the line, watch the reaction shape, capture which framing lands. This is the only block where you describe Aileron.
Get a named buyer and a proposed next step. Skip category sizing and procurement shape — both fit in a follow-up if the next-step answer is concrete.
Surface the consequential systems they rely on. Their own language for 'agent' typically falls out of how they describe what's touching what — capture it verbatim as it appears. Role and team came out of intros; don't re-ask.
- 1.
Which of the systems you rely on do you think of as consequential — where taking an action is either irreversible or could have real business impact?
- Probe: Customer-facing systems? Billing, payments, financial systems? Production infra? Internal data stores?
- Probe: Where would a wrong action mean an incident, a refund, an outage — the kind of Slack thread you don't want to be on?
Why: Two reads. (a) Calibrates stakes for Block 2 — what counts as 'consequential' varies wildly. Some teams call a Slackbot consequential; others mean rolling deploys. (b) Surfaces the named consequential systems Aileron needs to connect to safely — roadmap intelligence that compounds with the integration list in Block 3. Their definition of 'agent' usually falls out of how they describe these systems; capture their phrasing exactly.
- × Don't describe Aileron.
- × Don't define 'agent' for them — if they use the word, mirror; if they don't, don't introduce it.
- × Don't re-ask role/team — you got it in intros.
- × Don't introduce 'Skills', 'Actions', or 'Connectors' as Aileron terms. If they use those words, follow.
Surface where the org actually is on agents-acting-on-consequential-systems: shipped, tried-but-stalled, proposed-and-rejected, wanted-but-never-proposed, or not on the table. The branch matters as much as the answer. A blocked proposal is data; so is wanted-but-never-proposed. The only branch that kills C1 is 'no one's thought about it and there's no demand.' This is the load-bearing block; spend the time.
- 1.
Has anyone on your team actually put an agent — or a script that acts like one — in front of one of those consequential systems? If yes, walk me through the most recent time. If no, has anyone tried, wanted to, or proposed it?
- Probe: Shipped: when was this, and what went sideways or almost did?
- Probe: Not shipped: where did it stall, get rejected, or never get proposed — and why?
- Probe: Wanted to but didn't: what were they trying to achieve, and what's blocking it?
Why: C1 lives here, and the branch matters as much as the answer. SHIPPED: incident details = direct C1 evidence. TRIED-BUT-BLOCKED or WANTED-BUT-NEVER-PROPOSED: what got in the way = C1 evidence (the gap Aileron fills). NEVER WANTED: C1 is dead for this org. - 2.
Who in your org owns the question of what an agent is allowed to do — and has that owner had to make a call yet? What surfaced the conversation, and what did they decide?
- Probe: Watch for two owners — sec/compliance vs. platform / enablement / AI rollout. Capture both if present.
- Probe: What surfaced it: a near-miss, an incident elsewhere, a vendor pitch, a policy update from above?
Why: C2 + C3 in one ask. The named owner — by name, not just by title — is C2 evidence; two owners (sec/compliance + AI rollout) means two procurement shapes. What surfaced the conversation + what they decided is C3 evidence: a real decision (even a preemptive policy made before anyone shipped anything) separates 'we should think about this' from 'we did something about this.'
- × Don't accept abstract worries. If they answer with 'we'd worry about...', steer back: 'has that worry actually shown up in a proposal, a near-miss, or a conversation that mattered?' Speculation isn't data. The wanted-to-but-didn't branch IS fine — that's a real organizational moment with a real blocker. 'We'd worry someday' is not.
- × Don't describe Aileron's approach. The pitch is Block 4.
- × Don't lead toward security framing. If they raise it, follow. If they don't, don't.
Two open-ended questions: what systems they touch, and whether they run customer-operated. Both wide enough that the rejection list (C4), credential flow (C1 probe), and their own connector layer (C6) typically fall out in passing — capture all of it as it surfaces. The formal probes for those claims live in the full script if you have the time.
- 1.
What systems does the agent — or the script — actually touch today? (Or if nothing has shipped: which systems would it need to touch to be useful?) Walk me through the integration list.
- Probe: Anything you needed that didn't have a clean integration story — proprietary, internal-only, no public connector?
Why: Roadmap intelligence (the named services Aileron must support) plus a sharpening read on C6 (rate at which they had to wire up unknown services). Open-ended enough that rejected vendors (C4), credential flow (C1 probe), and their own connector layer (C6) typically surface unprompted — capture all of it verbatim. - 2.
Are you running anything customer-operated — self-hosted in your own VPC, on-prem — for this category? Or is it all SaaS?
Why: C5 lives here. If buyers prefer SaaS only for this category, the v4 customer-operated ordering needs revisiting.
- × Don't mention Clawvisor, Infisical, Anthropic Managed Agents, Devin, Composio, or LangSmith unprompted. Note carefully when they raise these names — that list is your competitive map.
- × Don't say 'connector hub' or 'runtime' — borrow their language back to them.
- × Don't use 'Homebrew', 'substrate', or 'Skills' as Aileron terms — those are wedge hypotheses, not pitch fodder. Borrow only their language.
- × Don't pitch deterministic-execution-as-architecture in this block. Capture only what they've already built.
One shot at the pitch. Read the line, watch the reaction shape, capture which framing lands. This is the only block where you describe Aileron.
- 1.
If there were a substrate that let your teams share the same vetted skills, gated approvals where they mattered, kept the irreversible actions deterministic instead of LLM-decided, and gave you an audit trail per action — would that have helped here?
- Probe: Capture the reaction shape: enthusiasm, skepticism, clarification questions, silence.
- Probe: If they ask a clarifying question: answer it briefly, then return to silence. Do not elaborate unsolicited.
Why: The line is fixed. Variability in your phrasing kills the signal. Read it once, slowly. - 2.
Of those four — shared skills across teams, gated approvals, deterministic execution, action-level audit — which one would have moved the needle most for you?
Why: Positioning signal. Shared skills → D (Homebrew-for-skills / org-rollout wedge). Gated approvals → B (compliance). Deterministic execution → A (runtime / fleet) restated in the buyer's verb. Audit → B (compliance). All four equally → C (vendor-neutral hub). This is the cleanest read on which candidate to lock at the 20-conversation gate. - 3.
If you imagine telling your VP about this in one sentence, what's the sentence?
Why: Their words for the value, not yours. If they can't compose one, the framing isn't sticky yet — useful feedback. If they can, the sentence is gold for the outreach next-iteration.
- × Don't demo. Don't open a tab.
- × Don't elaborate the architecture. Shell mediation, PTY interception, TEE attestation — none of this belongs here.
- × Don't promise features. Every 'we could build that' is debt. The right response is 'tell me more about that need' and then write it down.
- × Don't sell. Read the line, listen.
- × Don't add a fifth dimension on the fly. The four are fixed.
- × Don't explain what 'deterministic' means architecturally. If they ask, the one-sentence answer is: 'the LLM decides what to do, regular code does the doing.' Then return to silence.
Get a named buyer and a proposed next step. Skip category sizing and procurement shape — both fit in a follow-up if the next-step answer is concrete.
- 1.
Who would sign off on something like this in your org?
Why: C2 sharpens. A named buyer is much warmer than a title. Two buyers (sec/compliance vs. platform/enablement) means two procurement shapes and two pitch routes. Capture both if they volunteer them. - 2.
If we kept talking, what would the next step look like for you? A sandbox trial? An LOI? A pilot?
Why: Design-partner ladder. Their answer tells you if this is real or polite. Anyone who proposes a concrete next step is a candidate for #8 (LOI). C7 budget signal often falls out of this answer naturally — capture it if so, don't push for it if not.
- × Don't quote a price.
- × Don't promise a free tier or a discount.
- × Don't pitch the next step. Let them propose it. What they propose is the signal.
- × Don't push for a budget number — if the 30-min slot ran tight here, a follow-up is the right surface for category sizing.