Process Map: question bank¶

Everything worth asking, so nothing is forgotten. This is the superset, not the agenda.

The checklist is what you must come away with. This page is what you can draw on, chosen by what the client actually does. Most engagements use perhaps a third of it.

Use it as a prompt, not a script

Reading questions off a list produces short answers. Ask two or three from a section, follow what they say, and come back here between sessions to check what you have not covered.

1. Company context¶

Question	Listening for
Walk me through what the business does	Their words for things, which become the taxonomy
How many people, and in what roles?	Scale, and who the automation affects
How has that changed in the last two years?	Growth pain, or contraction
Busy season and quiet season?	Volumes are seasonal, so a baseline in the quiet month misleads
What has grown fastest?	Where the process is straining
Where do you want the business to be in two years?	Whether automation supports the plan or fights it
Have you tried automating anything before?	What burned them, and what to avoid repeating
What happened with it?	Usually the most honest answer of the day

2. People and roles¶

Question	Listening for
Who touches this process, start to finish?	Handoffs
Who is the bottleneck when they are away?	Single points of failure
Who decides when there is an exception?	Where judgement actually sits
What does each person do first thing in the morning?	The reactive work that nobody counts
What do they do that they think is a waste of time?	The best automation candidates, self-identified
Who would notice first if this went wrong?	Escalation path
Who is sceptical about this?	The real delivery risk
Who has been here longest?	Undocumented knowledge

Ask the person doing the work, not only the owner. The owner describes the process as designed. The person doing it describes the process as run, and the gap between those is where the value is.

3. Inbound communication¶

Question	Listening for
Where does work arrive from?	Channels beyond email: phone, SMS, portal, in person
Which channel is highest volume?	Where to start
Which is most painful?	Not always the same one
Shared inbox or individual?	Shared is a product, individual is a permissions problem
Who monitors it, and when?	Coverage gaps, and out of hours
What happens to it out of hours?	Response-time expectations
Show me the folders and rules you use	Their existing taxonomy, already written down
How do you know something has been dealt with?	Their state model
What falls through the cracks?	The pain, and often the sale
How often does someone chase you because you missed something?	Frequency, and the cost of missing
How many are junk or irrelevant?	The addressable portion shrinks

4. The process itself¶

Ask these per process, not once.

Question	Listening for
What starts it?	The trigger, and where automation attaches
What is the very next thing that happens?	Step one, in reality
Then what? Keep going until it is done	The map
Where does it wait?	Waits are usually the biggest loss and the least visible
Who is waiting on whom?	Handoff friction
What decisions get made, and on what basis?	Candidate structured predicates (ADR-0004)
Is that rule written down anywhere?	Whether it is policy or habit
What are the exceptions?	Exception rate decides viability
How often does an exception happen?	If it is 30%, automation is a poor fit however painful
What happens when it goes wrong?	Recovery work, which is usually uncounted
How would you know it went wrong?	Detection, or the absence of it
Has this process changed recently?	Whether you are mapping something already in flux
What would you change if you could?	Their own improvement ideas, usually good

Chase the exceptions harder than the happy path. Everyone describes the happy path fluently. The exceptions are where the effort actually goes.

5. Systems and data¶

Question	Listening for
What systems are involved? Every one	Connector scope
Which is the source of truth for a customer?	Canonical model mapping
Which for a job? For an invoice?	Often three different answers
Are any of them connected today?	The cross-system join, which is usually the pitch
Where do you type the same thing twice?	Direct automation candidates
What spreadsheets are involved?	Always present, never volunteered
Can I see them?	The real process lives here
Who maintains that spreadsheet?	A single point of failure with a name
What is on paper or in someone's head?	The gap the systems do not cover
Who administers each system?	Whose cooperation the build needs
What plan or tier are you on?	API access and rate limits often depend on it
Can you export data from it?	Backfill route
Has anyone used its API before?	Whether it works in practice, not just on paper

6. Documents and records¶

Question	Listening for
What documents does the business produce?	Quotes, invoices, certificates, reports
Which are templated, and which are written each time?	Generation candidates
Where are they stored?	SharePoint, Drive, a local drive, email attachments
Who asks you for copies, and how often?	High-volume, low-value, highly automatable
How long does it take to find one?	The saving
What is the naming convention?	Whether one exists
Any retention or compliance obligation on them?	Retention floor, residency

"Who asks you for copies" is a high-yield question. Document retrieval is almost always automatable, always underestimated, and easy to demonstrate value on quickly.

Can we actually retrieve them?¶

The questions above establish that document requests are worth automating. These establish whether it is possible at all, and the answer is frequently no.

Question	Listening for
Show me where the last certificate you issued is right now	Watch them find it. This answers more than any description
Is it attached to the job in the system, or filed elsewhere?	The decisive question
If it is in a folder, whose folder?	A local drive means we cannot reach it
Is it also lodged with a regulator or third party?	Their copy may be a manual save, not a system record
Does the job record have a document type field?	Otherwise a job with a dozen attachments is unpickable
What are the files called?	`CoC_J4471.pdf` is workable. `scan001.pdf` is not
Does anything rename or file them, or is it by hand?	Conventions kept by habit break silently
How many attachments does a typical finished job have?	Photos, variations, invoices, certificates, all mixed
Who would notice if the wrong document went to a customer?	The cost of being wrong

Four things must all be true, and any one can kill it

	If not
The document is in a system with an API	We cannot fetch it
We can tell which attachment it is	We cannot pick it
It is reliably linked to the job	We cannot find it
The mail connector can attach files	We cannot send it

The first two fail most often. A certificate saved by hand into \\server\Certificates\2026\ with whatever name the scanner gave it is not retrievable, however good the automation is.

Why this matters more than it looks: document_request is the highest-volume, most automatable email category, and it is nearly worthless without the attachment. "Your certificate is ready, log in and find it" saves nobody anything.

So these questions decide whether the best category is a product or a disappointment. Ask them before quoting, not after.

If retrieval is impossible, the honest fallback is a reply that tells the customer the certificate is ready and asks the office to send it, which is a small saving rather than the large one. Price it as the small one.

7. Quoting and money¶

Question	Listening for
How does a quote get produced?	Templating and pricing logic
How long does it take?	The saving
How is the price arrived at?	Rules, or judgement
How many quotes convert?	Whether faster quoting is worth anything
Do you follow up on quotes? How?	Usually the biggest missed revenue
How does a job become an invoice?	The handoff that most often breaks
How long between finishing and invoicing?	Cash-flow impact, and a strong value story
Who chases unpaid invoices, and how?	Automation candidate with a directly measurable return
How often does an invoice get disputed?	Data quality upstream
What is your average days-to-payment?	A number they will already know

8. Scheduling and field work¶

Question	Listening for
How is work scheduled?	The system, or a whiteboard
Who does the scheduling?	Often one person holding it all
How often does the schedule change on the day?	Reschedule volume, which is high-urgency
How are changes communicated?	Where a reschedule request arrives
What do field staff carry, and use?	Mobile constraints
Do they update anything from site?	Data freshness
What comes back after a job?	Photos, notes, certificates, signatures
How long before it is in the system?	The lag, and its downstream cost

9. Customers¶

Question	Listening for
How many active customers?	Backfill scale
Repeat customers or mostly one-off?	Whether history matters
Do you know who is emailing you before you open it?	Whether sender resolution is feasible
Do customers have multiple contacts?	Domain matching, not just address matching
Do the same customers have multiple jobs open at once?	Job resolution ambiguity
How do customers refer to their jobs?	Whether job references appear in text at all
What do customers complain about most?	The pain worth fixing

10. Suppliers and third parties¶

Question	Listening for
Who else emails you regularly?	Suppliers, insurers, regulators
What do they need from you?	A different automation shape
Any portals you have to log into?	Manual work with no API
Who chases you for paperwork?	Compliance automation candidate

11. Compliance and safety¶

Question	Listening for
What certificates or records must you keep?	Retention obligations
For how long?	The retention floor
Who audits you, and how often?	Evidence requirements
Any obligation about where data is stored?	Residency tier
Any contractual constraint on data processing?	Inference residency
What happens if a record cannot be produced?	The cost of the failure

12. Reporting and visibility¶

Question	Listening for
What do you look at to know how the business is going?	Their real metrics
Where do those numbers come from?	Manual assembly, usually
How long does producing that take?	A saving nobody asked for but everyone wants
What do you wish you could see and cannot?	The dashboard scope
What does your current system already report?	Verify the gap rather than asserting it
Who else needs to see it?	Audience, and whether self-serve matters
How current does it need to be? Give me a number	Sync cadence

13. Pain and priorities¶

Question	Listening for
What keeps you up at night about operations?	The real priority
If you could fix one thing tomorrow, what?	Their ranking, not ours
What is stopping you taking on more work?	The constraint, which is what to automate
Where do you lose money without noticing?	Rework, missed follow-ups, late invoicing
What do you say no to because you cannot handle it?	Growth blocked by process

14. Change readiness¶

Question	Listening for
How do people here feel about new systems?	Adoption risk
Who would have to change how they work?	Where resistance lands
How much time can you give to this during the build?	A realistic timeline
Who is the internal owner?	The build fails without one
What would make you stop this halfway?	Kill criteria, which are worth knowing early
What would make this obviously worth it in three months?	Their success measure, in their words

15. Approvals and autonomy¶

Question	Listening for
Who would approve automated output?	Review app users
How quickly could they realistically review it?	Expiry, and the `closed_manual` rate
What if they are on leave?	Fail-closed behaviour
What would you never let a machine do unsupervised?	The autonomy ceiling, more usefully than asking the reverse
What would you be comfortable with after six months of it working?	The autonomy roadmap
Would you rather approve in your inbox, or in a separate app?	Approval surface, one mode only

Things to look at, not ask about¶

The best material comes from watching rather than asking.

Ask to see	Why
Their inbox, over their shoulder	Volume and chaos are visible, and never accurately described
Their folder structure and rules	Their taxonomy, already built
The spreadsheets	Where the real process lives
A recent quote, invoice and job record	The actual data, not the described data
The last twenty emails, categorised together	Highest-value hour of the engagement
Their scheduling board or screen	How work is really sequenced
Their phone, if field staff use one	Mobile reality

High-yield questions¶

If time is short, these five return the most:

"Show me your last twenty emails and let us categorise them together."
"Where do you type the same thing twice?"
"What falls through the cracks?"
"Who asks you for copies of documents, and how often?"
"What would you never let a machine do unsupervised?"

Questions that get poor answers¶

Worth knowing so you can rephrase.

Avoid	Ask instead
"How long does that take?"	"Walk me through the last one you did"
"How often does that happen?"	"When did it last happen? And before that?"
"What would you like automated?"	"What do you do that feels like a waste of time?"
"Is that documented?"	"If someone new started tomorrow, how would they learn it?"
"Do you have any problems with X?"	"Tell me about the last time X went wrong"

Anything asking for a frequency or a duration in the abstract gets a guess. Anchoring on a specific recent instance gets a fact.