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Workflow legibility

1Pick the workflow that would hurt most if it broke tomorrow. If a new hire had to run it next week, what would they work from?

Scattered notes, an outdated Notion page, a few Slack threads.A documented workflow with named owners, triggers, exceptions and an escalation path.Whatever lives in people’s heads. They’d shadow someone for a month.A written SOP exists and is mostly accurate.

2How does work actually move between your people and tools?

Mostly structured tools. Handoffs are defined but enforced by habit.Forwarded emails, Slack DMs, and someone remembering to chase.Defined handoffs inside systems that show where any piece of work is right now.Real tools, but people copy data between them by hand.

Context readiness

3Your most experienced operator resigns tomorrow. What walks out the door with them?

Very little. Decision criteria, exceptions and edge cases are explicit and maintained.A lot. Some of what they know is written down somewhere.A few painful weeks. Most decision rules are documented.The operating manual. It exists only in their head.

4Could a competent outsider make your routine decisions from written rules alone? Approve or reject, route, prioritise.

No. “It depends”, on things we’ve never put into words.For most decisions, with some effort.Partially, for the simple cases.Largely. Thresholds, routing logic and approval rules exist as explicit criteria.

Data and systems

5Two of your systems disagree about the same customer, order or ticket. Which one is right?

We know the system of record for most things.One defined source of truth per domain. Everything else syncs from it.Depends who you ask. The spreadsheet usually wins.Unclear. We’d ask around.

6Can your tools talk to each other?

Some Zapier-style glue. It breaks quietly.Mostly closed tools. Manual exports, if anything.API access across the core stack. Data moves without a person routing it.Core tools are connected. The gaps are filled by hand.

Human–agent boundaries

7If you deployed an AI agent into one workflow tomorrow, could you state exactly what it may do alone, what it only drafts, and what it must never touch?

Yes. We already define explicit boundaries, including what triggers an escalation.Rough intuitions. Nothing written.We’ve never thought in those terms.We could define it per workflow if pushed.

8Who can access what in your stack, and would an AI agent inherit sane permissions?

Mostly clean. An agent could be scoped, with work.Everyone has access to everything. Shared logins exist.Some role-based access, plenty of exceptions.Role-based, auditable access. Scoping an agent to least privilege would be straightforward.

Production controls

9An automated system in your operations makes a mistake. How do you find out?

Someone might notice, if they happen to be paying attention.Monitoring, logs and failure thresholds surface it before anyone stumbles on it.Spot checks and ad hoc review.A customer or employee complains. Eventually.

10How do you decide whether an automation’s output is good enough to act on?

Test sets and evals with acceptance thresholds, before anything touches production.Gut feel.Defined acceptance criteria, for some workflows.We’d eyeball a few examples.

Adoption and ownership

11How does your team actually use AI today?

Real individual productivity gains, and some shared prompts and templates.A few people paste things into ChatGPT occasionally.Teams own repeatable AI workflows that keep working when one person is on holiday.Most people have subscriptions. Usage is individual and invisible.

12Who owns a workflow end to end, including the authority to improve it?

The founder. By default. For all of them.Named owners who can change the rules without filing an engineering ticket.Nobody. Workflows are everyone’s, which means no one’s.Informal owners exist for the big ones.

Business impact

13What has AI measurably changed in your business so far?

Tracked impact on cost, cycle time or revenue, attributable to specific workflows.People say they save time. We can’t see it in any number.Nothing measurable. Vibes.One or two metrics actually moved, such as response time or cycle time.

14How do you pick what to automate next?

A rough sense of volume and pain.Whatever the last impressive demo was.Scored against frequency, measurable pain, and whether the context exists to do it safely.Loudest pain wins.

In one or two sentences, which workflow hurts most right now?

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