A. “We have six months of runway — should we pivot?”
- [ ] Establish current cash, debt, accounts payable and unavoidable monthly outflows.
- [ ] Identify the smallest revenue/usage hypothesis to test before cash reaches a safety floor.
- [ ] Compare persist, narrow the target, pivot, and managed wind-down.
- [ ] Seek customers with adverse experiences, not only advocates.
- [ ] Hold a blinded pre-mortem; list disconfirming evidence and the next decision date.
Specialist threshold: if the runway reconciliation is contested, bring in a finance modeller; if the team is heavily invested in a narrative and the decision cannot wait, procure bounded independent challenge. Burkland's public offer illustrates available strategic-finance service types. Burkland: Strategic Finance for Startups
B. “We have two investor offers — which should we take?”
- [ ] Normalise cash raised, timing, instrument, conversion, side letters and governance rights.
- [ ] Compare an actual cap-table and dilution scenario for each offer, including earlier SAFEs.
- [ ] List each adviser's investment/referral/closing interests; separate buyer, payer and beneficiary.
- [ ] Get startup securities counsel to review legal terms and required approvals.
- [ ] Do not compensate unregistered parties for investor placement without regulatory review.
Specialist threshold: counsel is appropriate before signing legal instruments or agreeing to regulated introduction activities, not only after a dispute. YC explains SAFE mechanics; SEC flags broker-dealer risk factors. The SAFE — Y Combinator Broker-Dealers — US SEC
C. “Our sales are stalling — should we hire a VP?”
- [ ] Verify buyer definition and founder-led sales evidence; identify the bottleneck.
- [ ] Estimate all-in cash and time to first productive result for a full-time hire.
- [ ] Compare internal enablement, a player-coach, fractional help and no hire.
- [ ] Set 30/60/90-day outcomes that measure reality, not presentations.
- [ ] Review employment and equity terms with qualified professionals where necessary.
Specialist threshold: if unclear whether the problem is market demand, onboarding or leadership, buy a bounded role-and-decision review before the long-term hire.
D. “My board wants one thing, I want another”
- [ ] Put each party's assumptions and evidence in separate columns.
- [ ] Identify relevant investor exposures, governance rights and authority.
- [ ] Invite a neutral challenger; avoid an adviser paid for a particular outcome.
- [ ] Record dissent, options, decision owner and reconsideration trigger.
Specialist threshold: corporate counsel if board powers, fiduciary duties or shareholder rights are disputed; a facilitator alone cannot decide legal authority. Reboot's board episode is a discussion prompt, not a legal template. Reboot podcast: How To Be a Stable Board Member
E. “My investor offers to pay for an executive coach”
- [ ] Define whether the founder or sponsor is the client and who can terminate.
- [ ] Agree exact reporting, access, recordings, retention and exception clauses.
- [ ] Require written conflict and compensation disclosures.
- [ ] Assess coach method against the actual leadership issue; do not assume coaching is a strategy review.
Specialist threshold: use appropriate contract/legal review when sponsor reporting conflicts with founder confidentiality; ICF's 2025 code is a practical ethics reference. ICF Code of Ethics, effective 1 April 2025