Route A — “Should I pivot, persist or stop?”
- All about pivoting: define reasons and counter-reasons for change. All about pivoting — Y Combinator
- How To Talk To Users: create honest customer evidence rather than relying on opinions from your board network. How To Talk To Users — Y Combinator
- Unforced Errors: reconsider the stage-specific mistake of scaling or committing prematurely. The Startup Podcast: Unforced Errors with Mona Sabet
- When Should You Shut Down the Business?: inspect whether the economic container remains viable. Reboot podcast: When Should You Shut Down the Business?
Reader output: a one-page persist/narrow/pivot/close matrix with an evidence threshold and runway limit.
Route B — “Can I trust my board or coach to challenge me?”
Listen to How To Be a Stable Board Member for the role of stable challenge; pair with Reboot's newer leadership episodes for self-awareness. Then use a three-party confidentiality check rather than assuming investor-paid coaching conversations are privileged. ICF provides professional ethics language on sponsor agreements. Reboot podcast: How To Be a Stable Board Member ICF Code of Ethics, effective 1 April 2025
Reader output: a conflict/information-sharing map and three questions to ask the adviser.
Route C — “Should we hire to solve the problem or redesign the work?”
Pair the YC MVP lecture with the Reboot performance conversation. Ask whether the organisation has actually defined the work and the evidence that the hire would accelerate. How to Plan an MVP — Y Combinator Reboot Podcast, episode catalogue
Reader output: a first-executive-hire challenge sheet with 30/60/90-day evidence and a no-hire alternative.