Decision library
The hard calls,
broken down before you make yours.
Pivots, pricing, hires, raises, vendors, the big personal ones — each taken apart by what pulls each way. Read how a call breaks down, then bring your own to a board of named experts who disagree on purpose.
60 calls
Pick the call
closest to yours.
A playbook is a call you can run: the three things a board asks first, one real run, and a start with your own situation.
Pricing and billing
13 callsWhat to charge, how to bill, and when to change it.
Should I raise prices on my existing customers?
For anyone who sells something people already pay for, a shop, a studio, a service or an app, and whose costs went up while the price stayed put.
With a real runThe playbookCharge enterprise customers 10x SMB pricing
“Should we charge enterprise customers 10x our SMB SaaS pricing?”
The trade-offsKill annual billing in favor of monthly-only
“Should SaaS companies kill annual billing and switch to monthly only?”
The trade-offsMove from per-seat to per-workspace pricing
“Should we switch from per-seat to per-workspace pricing in SaaS?”
The trade-offsDouble prices when hitting a usage limit
“Should we double SaaS prices when customers hit usage limits?”
The trade-offsKill the cheapest paid plan
“Should we kill our cheapest SaaS plan?”
The trade-offsUsage-based vs seat-based pricing
“Usage-based vs seat-based pricing in SaaS: which model fits our business?”
The trade-offsAdd a freemium tier to SaaS pricing
“Should we add a freemium tier to our SaaS pricing?”
The trade-offsOffer a money-back guarantee
“Should our SaaS business offer a money-back guarantee?”
The trade-offsSaaS pricing — $29 vs $49
“Should I price my SaaS at $29 or $49 per month?”
The trade-offsWhen to raise SaaS prices
“When should we raise SaaS prices?”
The trade-offsAnnual vs monthly billing
“Annual vs monthly billing in SaaS: which model aligns with our growth strategy?”
The trade-offsFreemium vs free trial
“Freemium vs free trial SaaS: which model fits our growth and revenue goals?”
The trade-offsPeople
13 callsHires, co-founders, equity, and the customers you keep or let go.
Should I hire my first employee, or a contractor?
For someone running a business alone who has more work than hours, and has to choose between a person on payroll and help by the job.
With a real runThe playbook PlaybookShould I let go of a difficult client?
For a freelancer, agency or small firm with one client who pays but costs more in time and stress than they bring in.
With a real runThe playbookFire the first hire who isn’t keeping up
“Should I fire my first hire who isn’t keeping up?”
The trade-offsOffer equity to early beta users
“Should I give equity to beta users?”
The trade-offsLet employees own their tooling choices
“Should startups let employees own their tooling choices?”
The trade-offsLet a co-founder take a six-month sabbatical
“Is a six-month sabbatical for our co-founder the right move for our startup?”
The trade-offsWhen to convert contractors to full-time
“When is the right time to convert a contractor to full-time?”
The trade-offsWhen to hire the first marketer
“When should our startup hire its first marketer?”
The trade-offsWhen to hire the first salesperson
“When should a startup hire its first salesperson?”
The trade-offsBuild enterprise SSO before having enterprise customers
“Should we build enterprise SSO before landing enterprise customers?”
The trade-offsDrop a customer who is not the ideal fit
“Should we fire a customer who isn’t the ideal fit?”
The trade-offsWhen to hire the first engineer
“When should we hire our first engineer?”
The trade-offsHire a cofounder vs stay solo
“Should I hire a cofounder or stay solo?”
The trade-offsCapital and deals
7 callsRaising, bootstrapping, investors, and offers on the table.
Should I take the offer to buy my company, or keep building?
For an owner with a real offer on the table who has to weigh money now against what the business could become.
With a real runThe playbook PlaybookShould I quit my job for my side business?
For someone with a side business that earns something, a salary that pays the bills, and not enough hours for both.
With a real runThe playbookAccept a strategic investor at a lower valuation
“Should we accept a strategic investor at a lower valuation?”
The trade-offsApply to Y Combinator vs bootstrap
“Should we apply to Y Combinator or bootstrap our startup?”
The trade-offsAcquire your biggest competitor’s smallest competitor
“Should we acquire our biggest competitor’s smallest competitor?”
The trade-offsAccept an acqui-hire offer at 10x annual salary
“Should I accept an acqui-hire offer at 10x my annual salary?”
The trade-offsRaise a seed round vs bootstrap
“Raise a seed round or bootstrap our startup: what’s the right move?”
The trade-offsProduct and company
15 callsWhat to build, what to kill, where to be, and what to call it.
Should I open a second location?
For the owner of a shop, café, clinic or studio that runs well in one place and is thinking about a second.
With a real runThe playbook PlaybookShould I launch now, or wait until it’s better?
For anyone with something almost ready, a product, a shop, a course or a menu, who keeps finding one more thing to fix.
With a real runThe playbook PlaybookShould I rename my company?
For an owner whose business name no longer fits what they do, is hard to say or search, or clashes with someone else’s.
With a real runThe playbookPublish metrics publicly like Buffer
“Should I publish my startup metrics publicly like Buffer?”
The trade-offsChange the company name post-PMF
“Should we rename our startup after achieving product-market fit?”
The trade-offsKill the most-asked-for feature request
“Should we kill the most asked-for feature request?”
The trade-offsKill an underperforming geographic market
“Should we shut down an underperforming geographic market in SaaS?”
The trade-offsOpen source the SDK or keep it proprietary
“Should we open source our SDK or keep it proprietary?”
The trade-offsRelocate to SF vs stay remote
“Should our startup relocate to San Francisco or stay fully remote?”
The trade-offsSign a one-year office lease or stay flexible
“Should our startup sign a one-year office lease or stay flexible?”
The trade-offsWhite-label the product for distribution
“Should we white label our SaaS product for distribution?”
The trade-offsShut down a product line
“When should we shut down a SaaS product line?”
The trade-offsOpen source vs closed source
“Open source vs closed source startup: which path aligns with our growth and control goals?”
The trade-offsPivot from B2C to B2B (or vice versa)
“Should we pivot from B2C to B2B SaaS (or vice versa)?”
The trade-offsPivot vs keep pushing
“Should I pivot my startup or keep pushing?”
The trade-offsWork and career
6 callsOffers, raises, breaks, moves, and changing field.
Which of my two job offers should I take?
For someone holding two offers who wants more than a gut call on pay, people, and where each job leads.
With a real runThe playbook PlaybookShould I ask for a raise now, and how much?
For someone who feels underpaid and wants to know whether now is the moment, what to ask for, and how to say it.
With a real runThe playbook PlaybookShould I move to another city or country for work?
For someone with a job offer or a reason to move far away, weighing the career against family, friends, money and the life they have now.
With a real runThe playbook PlaybookShould I go back to school at 35?
For someone in their thirties or later thinking about a degree or a long course, and wondering whether the time and money will pay back.
With a real runThe playbook PlaybookShould I take a career break?
For someone worn out, curious or needed at home, thinking about months off work and worried about the money and the way back.
With a real runThe playbook PlaybookShould I change careers into a new field?
For someone who wants out of their field and into a new one, and has to weigh starting over against staying where they know the ropes.
With a real runThe playbookHome and money
2 callsThe house, the car, and the big purchases that outlast the month.
Should we sell the house and buy something smaller?
For people whose house is now bigger, costlier or harder to keep than their life needs, children grown, a move, or retirement in sight.
With a real runThe playbook PlaybookShould I pay for a big purchase from savings or on credit?
For someone about to buy something big, a car, a kitchen, a course, and deciding between using savings and paying over time.
With a real runThe playbookFamily
2 callsSchools, caring for a parent, and the people the decision is for.
How do I care for my parent and keep my job?
For someone whose parent needs more help than before, trying to work out the care, the money, their job and their own life at once.
With a real runThe playbook PlaybookWhich of two schools should we choose for our child?
For parents choosing between two schools who want to weigh what matters for their child, not only the rankings.
With a real runThe playbookDisputes and partings
2 callsComplaints, separations, and ending a partnership well.
Should I make a formal complaint to a public body?
For someone treated unfairly by a company, landlord, school or official, deciding whether to escalate to a regulator, ombudsman or authority.
With a real runThe playbook PlaybookHow do I split a business I share with a friend?
For two friends or partners who own something together and no longer want to, and want to part without losing the money or the friendship.
With a real runThe playbookBefore and after
Already decided?
Or still testing the plan?
Questions
Fair questions
about the library.
Or read how SynthBoard works.
Are these pages real board runs?
The playbooks are: each one shows a real board run on a SynthBoard test account, with the situation it was given, and the call, positions and first step it delivered. The other pages are written breakdowns of one hard call: what pulls each way and a framework to settle it. A board runs on your call only when you bring it, and its memo is yours.
What happens when I bring my own call?
Talking to your Chief of Staff is free within a daily allowance. A consult or a board shows its price on the card before anything runs, and nothing runs until you tap. A board ends in a memo: the call, how sure the board is, what would flip it, who disagreed and why, and one first step with a date.
Who sits on the board for a call like these?
Your Chief of Staff proposes who sits for the call, and every board is built with someone whose job is to argue against the obvious answer. Name an expert and they take a seat. How many seats a board has depends on your plan.
Can the experts be wrong?
Yes. They are AI and can be wrong. That is why a board’s confidence drops with dissent and is never rated above 90, and why the memo says what would change the call.