BoSMark

Conversational laddering diagnostic that takes anything someone says they want — a request, a problem, a feature, a hire, a decision — and asks 'why' repeatedly until it surfaces what they're actually trying to achieve: the root cause, the real want underneath the stated one. Produces a WhyOhWhy Brief showing what they said they wanted first, and what was actually learned by asking why. One of the BoS OS onboarding diagnostics, alongside Your Next Hire and the Founder Alignment Check. Use whenever someone brings a specific ask and there's a deeper driver worth surfacing before acting on the surface request — 'I need X', 'we should build X', 'I want to hire for Y', 'can you just fix this'. MANDATORY TRIGGERS: run WhyOhWhy, why oh why, whyohwhy, what do I actually want, get to the root of this, ladder this up, five whys, 5 whys, root cause, what am I really trying to do.

Pre-bootstrap diagnostic for founders and senior leaders. Surfaces AI anxiety, maps opportunity to their specific business, and funnels toward the BoS OS. Triggers: run AI readiness check, AI readiness, AI check.

A founder wants to know whether their business could run without them — and if not, what it would take to get there. This 5–10 minute conversation surfaces where the founder is the single point of failure, names the pattern, and points to the next step. Use this skill whenever a founder asks about stepping back, making themselves replaceable, building a business that doesn't depend on them, exit readiness, delegation, indispensability, or what would happen if they disappeared for 60 days. Triggers: founder replaceability, company without me, replaceable, step back, not indispensable, run without me, outlast me, business without me, can't switch off, can't take a holiday, everything routes through me.

As a founder, I want a quick check on whether my personal goals are aligned with our companies activities and if they aren't what can I do about it? This 5–10 minute conversation surfaces the gap (if there is one) and points you to the next step. Triggers: check alignment, founder alignment, run founder alignment, skill start founder alignment.

Conversational diagnostic for founders who want to identify the most important gap in their business. Interviews the founder about what they're doing, what's falling through the cracks, and arrives at the central question: money is no object — who's your next hire? Produces a Next Hire Brief and infers what the answer reveals about the founder's thinking and company stage. Use this skill whenever a founder mentions hiring, team gaps, capacity problems, doing too much themselves, what role to hire next, or who they need. MANDATORY TRIGGERS: next hire, who should I hire, team gap, hiring decision, I'm doing everything, I need to bring someone in, what role do I need.

Build the BoS OS for a company, a structured operating system that helps a CEO or founder make better decisions and helps their team understand what they are trying to do. Researches the company from public information, creates the folder structure, populates strategy documents with company-specific content, maps people and their roles, and generates a CLAUDE.md. Triggers: "run the BoS OS", "BoS OS", "Company OS", "bootstrap my company OS", "create an operating system for [company]", "help me organise my AI strategy", "build an agent framework", "I want to do what that talk described", "operating model", "folder structure for agents", "bootstrap my company". MANDATORY TRIGGERS: BoS OS, Company OS, bootstrap, company setup, agent framework, AI strategy, operating model, folder structure.

Operate your BoS OS day to day. The coordination layer that runs after Bootstrap and Workshop: it shapes a rough idea into a measurable Mission Brief, staffs the mission by casting and speccing the agent team, then drives delivery from goal to running system. Three bounded agents — Mission Shaper, Agent Planner, Delivery Manager — plus mission state templates. Use when someone wants to run a mission, shape a goal into a brief, staff or plan a mission, manage delivery, run the backlog, or operate their agent team. Triggers: "run a mission", "run the BoS OS", "run agent run skill", "shape a mission", "mission brief", "staff this mission", "plan the mission", "delivery manager", "run my backlog", "operate my agents", "stand-up", "what's next on the mission". MANDATORY TRIGGERS: BoS OS, agent OS run, run a mission, run agent run skill, mission shaper, agent planner, delivery manager, mission brief, backlog, stand-up.

Guide an executive through refining their BoS OS, deepening strategy documents, mapping the roles and responsibilities of people in the organisation, and defining their first mission with phased validation. Runs as an interactive workshop with a challenger-advisor tone. Use when someone wants to improve agent specs, refine strategy documents, create a mission, define decision boundaries, or build an evaluation framework. Triggers: "help me refine my strategy", "my agent spec needs work", "what should my agent's first mission be", "how do I test my agent", "walk me through the workshop", "I've bootstrapped my BoS OS, now what", "executive workshop", "strategy deep-dive", "agent refinement", "mission planning", "ground truth", "calibration". MANDATORY TRIGGERS: BoS OS, workshop, refine, strategy, agent spec, mission, evaluation framework, ground truth, calibrate, decision boundary.

Interview-driven agent spec builder. Takes ONE named agent and conducts a structured interview to produce a finished, runnable spec — covering role, type, decision boundary, escalation triggers, and evaluation criteria. Use when someone wants to spec an agent, define an agent's decision boundary, write an agent spec, build an agent specification, or turn a vague agent idea into a precise runnable document. Triggers: "spec this agent", "help me define my agent", "write an agent spec", "what should my agent be allowed to do", "decision boundary", "escalation triggers", "agent specification". MANDATORY TRIGGERS: agent spec, agent specification, decision boundary, spec builder, spec an agent.