The 38 questions (+ house additions)
Q1–Q38 from The 37signals Guide to Making Decisions. Premise: "A company is essentially two things: a group of people and a collection of decisions." House additions (Q39+) are listed separately at the bottom.
Categorized for triage. The decide skill picks 6–8 per decision based on the situation — never all 38.
Need-to-decide (do we even decide?)
- Q1 — Why are we deciding anything at all? Does a decision actually need to be made here?
- Q4 — Why hasn't this decision been made already? Why didn't we decide before?
- Q5 — What's taking so long to make this decision? Why are we hesitating? What does that reveal?
- Q10 — What would happen if we just didn't make the decision?
- Q22 — When do we have to decide?
- Q31 — Do you even care which way this goes? If not, why are you involved?
Who decides
- Q2 — Is the right person making this decision? Not the right role, but the right person with the right information, context, and insight? Who's merely chiming in?
- Q21 — Could this decision be a good one for someone else to practice making?
- Q27 — Would another opinion help or hinder?
- Q35 — Are we asking multiple people to make a decision that one person should be making?
Reversibility & size
- Q7 — Can we make this decision smaller? Can we take one big decision and turn it into three smaller ones?
- Q8 — How easily can we reverse the decision?
- Q14 — Is there even a wrong decision?
- Q23 — Will this be a one-and-done decision, or will this be a repeating decision?
First instinct
- Q9 — What was our first instinct on this decision? Are we now just walking around in circles trying to justify that gut reaction with data?
- Q28 — If we were forced to make a decision right this second, what would it be?
Cost & payoff
- Q13 — How can we make this decision easier? What parts can we eliminate from consideration?
- Q20 — Will this decision make more work for people that don't have extra time for that work? Or will it eliminate work?
- Q36 — Is the return on effort worth it?
- Q37 — What gets easier if we make this decision? What gets harder? Will easier remain easier in the long term, or is it short-term easy but long-term hard? And vice versa.
- Q38 — In the end, is this about money?
Context & impact
- Q6 — Why would someone else make a different decision? What's the other side — or two or three — look like?
- Q17 — What other decisions will be impacted by this decision?
- Q18 — Will this decision eliminate the need to make other decisions, or will it create the necessity to make even more decisions?
- Q24 — Is anyone outside the company depending on this, or is this a decision of our own making?
- Q25 — How does this decision impact customers vs. impact us?
- Q29 — Where do we think we'd be today if we made this decision 90 days ago?
- Q30 — Is there anything in this decision we'd regret if we didn't take X, Y, or Z into consideration?
Signal & confidence
- Q11 — What happened the last time we made a decision like this?
- Q19 — What missing information would lead to making a different decision?
- Q26 — Is this primarily a data-based decision, or an intuition, gut-based decision?
- Q32 — When and how will we know whether the decision was the right one, or if it even mattered?
- Q33 — When the consequences of our decision appear, are they likely to be visible with the naked eye or do they require a microscope to detect? If the latter, does it even matter?
Principles
- Q34 — What principles are we bending if we make this decision?
Time test
- Q3 — If we remove the immediate impact, how do we think we'll feel about this decision a year from now?
- Q15 — Do we anticipate making a different decision if we wait until tomorrow morning to make it?
- Q16 — Is any decision better than no decision, or is no decision better than any decision?
Emotional check
- Q12 — What are we looking forward to after the decision is made? What are we afraid of?
House additions (not from the 37signals set)
Questions the set was missing in practice. Kept separate so the 38 above stay faithful to the source.
- Q39 — Opportunity cost: if we say yes to this, what are we saying no to? What does this displace — time, money, focus — and is what it displaces worth less than this? (Added after a reader pointed out the original 38 never ask it directly — the nearest are Q36's return-on-effort and Q37's easier/harder.)
Triage cheat-sheet (default selections)
Always: Q1, Q2, Q8, Q9, Q3
Add for irreversible: Q14, Q17, Q34 Add for time-pressure: Q5, Q15, Q22 Add for multi-person: Q21, Q27, Q35 Add for analytical: Q19, Q26 Add for recurring: Q11, Q23 Add for customer-facing: Q24, Q25 Add for money: Q36, Q38, Q39 Add for big time/focus commitments: Q39, Q36, Q20 Add for "I'm stuck": Q4, Q10, Q31