Business Decisions
Every business purchase, deconstructed.
Each series pairs long-form articles with a paid workbook. Buy once, use for every future decision in that category.
Decision Frameworks
Criteria: Buying a CRM
Five articles. Narrow first, then one criterion at a time in weight order. Then the Playbook, if you want to run it with your team.
Criteria: Buying an AI Tool
Five articles. Narrow first, then one criterion at a time in weight order. Then the Playbook, if you want to run it with your team.
Criteria: Choosing Payroll Software
Five articles. Narrow first, then one criterion at a time in weight order. Then the Playbook, if you want to run it with your team.
Latest Articles
The deal: what payroll software actually costs at your size, next year, and on the way out
The weight-3 deal criterion for payroll software. Base and per-employee fees, year-end charges, implementation, contract term, price locks, off-cycle runs, contractor seats and float.
The people: what your staff see every two weeks, and what the owner sees on the first
The weight-4 people criterion for choosing payroll software: employee self-service, pay stubs on a phone, onboarding, time off, support on payday, and the owner's labour report.
The filings: what payroll software files for you, and who pays when it is late
The weight-4 filings criterion for payroll software. CRA remittances, ROEs and T4s in Canada; 941, 940, W-2 and state filings in the USA. Plus the penalty clause.
The pay run: the sixteen questions that decide whether payroll software belongs on your list
The weight-5 criterion for choosing payroll software. Sixteen questions on overtime, stat pay, contractors, multi-province or multi-state runs, corrections and approvals.
How to choose payroll software before you sit through a single demo
A six-gate method for narrowing payroll software for a small business in Canada or the USA. Write the shape, run gate 0, pick the rung, then run the gates.
How to Choose a CRM for a Small Business (Before You Look at One)
A method for choosing a CRM for a small business: write the shape, run the spreadsheet test, pick the rung, and use six pass-or-fail gates to get from hundreds of CRMs to five.
AI Tool Pricing: Per Seat vs Usage, and One Annual Number
Normalise every option to one annual all-in number in Canadian dollars. Then ask which pricing model gets expensive if the tool works, what the bundled tool costs, and what the price is at double the seats. Eight questions, weight three.
Can You Trust an AI Tool With Client Data? 12 Questions to Ask First
Trust has two halves. Accuracy on your job and data handling from the terms. Twelve questions, weight four. Read the data processing terms, not the marketing page.
Why Employees Don't Use AI Tools: Score Adoption Before You Buy
The standard failure of an AI tool purchase is not that it does not work. It is that nobody opens it in week three. Score for adoption before buying. Twelve questions, weight four.
Testing an AI Tool on Real Work: 14 Questions Before You Pay
Run the real job with real inputs in the free trial. Time the job by hand first. Then rate fourteen questions from the trial. This is the weight-five criterion. Nothing else matters until it passes.
Choosing an AI Tool for a Small Business: Shape, Gates and the Bundled Test
Before you shop, prove you need a tool at all by running the job through the AI assistant you already pay for. Then write an eight-line shape, pick a rung on the ladder, and run every shortlisted tool through six pass-or-fail gates.
CRM Pricing Hidden Costs: 10 Questions Before You Take the Quote
Ten questions on CRM pricing: the tier you actually need, seat count at eighteen months, add-ons, support, onboarding fees and the written quote. Weighted 3 out of 5.
How to Switch CRM Without Losing Your Data: Check the Exit Before You Buy
Ten questions on CRM exit costs: export format, renewal price caps, contract terms, cancellation and data portability. Weighted 4 out of 5.
Why Sales Teams Stop Using the CRM, and 12 Questions to Ask Before You Buy
Twelve adoption questions to rate before buying a CRM: automatic logging, mobile, inbox plugin, admin time, and the reluctant seller test. Weighted 4 out of 5.
CRM Requirements Checklist: 14 Questions That Test the Job, Not the Features
A 14-question CRM requirements checklist built on the three jobs the tool must do, scored 1 to 5 and weighted 5 out of 5.
The dispatch
One email a month. Just what we're working on.
A short note each month with every new criterion we've added. No promotions, no pitches, just a heads-up on what's in progress.
