Should you automate this?

Pick the answer that's nearest the truth.

Step 1 of 7 The pain

Name the recurring task — in a sentence.

Every question after this is scored against the single pain you describe here. The sharper your sentence, the sharper the result. One task only — not a list.

The recurring pain you most want solved

A sentence is enough — but please give us more than a few words. characters left

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Step 2 of 7 Frequency & Spread

Frequency & Spread

How often does this pain show up — and how widely does it spread?

Scoring this task

How often does this pain happen?

Daily A few times a week Weekly Monthly Less than monthly

How many people, departments, clients, or suppliers feel it when it happens?

Many — cross-functional, or client-facing Several — multiple teams A few — within one team A small handful — a couple of people One person — mostly mine

Does the same shape of pain show up with different people, or is it isolated to one person?

A pattern that recurs with different people is system information — not a personality flaw.

Same shape, different people — clearly a pattern. Mostly a pattern — one or two people are usually involved. Mixed — sometimes a pattern, sometimes person-specific. Mostly tied to one person or one role. It's a one-off, not a pattern.

Step 3 of 7 Cost & Consequence

Cost & Consequence

What does it cost in time, money, trust — and what would solving it be worth?

Scoring this task

Roughly how much team time does this pain consume each month?

40+ hours 16–40 hours 5–15 hours 1–4 hours Less than an hour

When this pain goes wrong, how serious are the consequences?

Material — hits revenue, delivery, or compliance Significant — visible to clients or leadership Moderate — internal frustration, weekend hours Mild — annoying, but absorbed Minor — easily absorbed, no real downstream cost

If this pain were solved properly, what would it be worth to your business in a year?

A rough sense is fine — time saved, errors avoided, retention preserved, weekends returned. The book's test is economic: a fix is justified when its cost is less than the drift it replaces.

Substantial — five figures or more, or a strategic edge Significant — measurable revenue, margin, or retention impact Worthwhile — meaningful time and frustration saved Modest — quality-of-life rather than commercial Marginal — wouldn't move the needle

Step 4 of 7 Detection & Lead Time

Detection & Lead Time

Do you find out in time to act — or does it usually surface as a surprise?

Scoring this task

When this pain happens, how do you usually find out?

It surfaces as a surprise — at a deadline, in front of a client, or after the damage. Late — by the time we know, the room to act is small. Mid — we usually catch it, but it's tighter than we'd like. Reasonably early — we usually have options. Early and reliably — it shows up as a clear signal in time to act.

When you do find out, do you still have meaningful options — or are you mostly choosing between bad ones?

Mostly bad options — recovery, apology, compromise. Limited options — a small window, often costly. Some real options — depends on the case. Usually we have time and choices. We have plenty of room to act — early signal, multiple options.

Right now, would the pain show up by itself — or only because someone bothered to chase, ask, or check?

A signal that depends on someone remembering to look is not really a signal.

Only if someone chases or remembers to check. Mostly chased — the alert is human, not the system. Mixed — partial automation, partial vigilance. Mostly automatic — chasing is a backstop. Fully automatic — the system tells us before we ask.

Step 5 of 7 Process Shape

Process Shape

Is this informational and repeatable — or judgement-, relationship-, and standard-shaped?

Scoring this task

Is the work involved broadly the same each time — or does it change significantly case by case?

Very repeatable — same steps each time. Mostly repeatable, with minor variation. Some variation, but a clear core. Highly variable — judgement-heavy each time. Different every time — mostly bespoke human work.

Where does the weakness sit — in the information layer (handoffs, lookups, repeated rework, scattered data) or in human judgement, relationship, or a missing standard?

The book's test for "software-shaped pain": when the weakness sits in the information layer itself, a tool can clear it. When it sits in judgement, relationship, or a standard, software won't fix it.

Mostly informational — handoffs, lookups, scattered data, repeated rework. Largely informational, with some judgement involved. A mix of both — partly informational, partly judgement. Mostly judgement, relationship, or a missing standard. Almost entirely human judgement or trust-based work.

Is the data needed to manage this pain already captured somewhere usable — or does it live in heads, threads, and inboxes?

Yes — structured, accessible, in known places. Mostly — some gaps, but the bones are there. Partial — scattered across tools and spreadsheets. Mostly in inboxes, threads, or shared folders nobody curates. It lives in people's heads.

Step 6 of 7 What You've Tried

What You've Tried

Lighter moves first — clarifying ownership, a checklist, a scheduled review, an escalation trigger. Software is rarely the first answer.

Scoring this task

Have you already tried the lighter moves — clarifying ownership, adding a checklist, scheduling a review, defining an escalation trigger, changing what the system rewards?

The book is direct: most of the time, lighter moves do the job at a fraction of the commitment. Software is justified mainly when those have been tried and the pain still recurs.

Yes — multiple of those, properly. The pain still recurs. Some — one or two real attempts; partial improvement. A bit — informally; nothing stuck. Not really — we've mostly just absorbed the pain. Honestly, we've never tried any of them.

When you have tried fixes, do they stick — or do they decay quietly because no one watches whether they're being used?

They decay — within a quarter, we're back to the same pain. Mostly decay — we keep relaunching the same fix. Mixed — some stick, some don't. Mostly stick — we've made real ground. They stick — fixes are owned and inspected.

If a fix existed today — software, process, or a clearer standard — could you act on it, or does it need buy-in from others?

Honest signal, not a trick: if the fix needs three other people, the right next step might be a short conversation before anything else.

I could decide and act on it this week. I'd need a quick sign-off, but the path is clear. I'd need to bring one or two others on board. I'd need a wider conversation — multiple stakeholders. It would need a formal business case and budget cycle.

Final step Where to send your report

One last thing.

Your full report will be on the next screen and emailed to you.

First name

Last name

Company

Your role

Team size

Optional. Helps us tailor the recommendations.

Which best describes the shape of the pain? (pick any that fit)

Optional — helps us point you at the right kind of fix on the next screen.

Manual chasing Stakeholder drift Commercial drift Data fragmentation Bus factor risk Repeated status meetings Quality variance Client visibility gap

Email me my report and product updates (unsubscribe anytime)

Tap-only — no typing until the end. About 3 minutes total.

6 steps

✓ 1 Name the drift
✓ 2 Frequency & Spread
✓ 3 Cost & Consequence
✓ 4 Detection & Lead Time
✓ 5 Process Shape
✓ 6 What You've Tried

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