Founder Mode: Where to Go Deep
Decide which 1-2 areas a founder should get hands-on in now, and how to go deep with the owner, not around them, with a time box and exit.
Before & after
Same prompt, same agent — the only difference is the skill.
Those are two major issues that need attention, but they require different expertise. Runway pressure is primarily a financial and operational question - it's about cash flow, burn rate, and prioritization. Retention drop is a product and customer success question - understanding why customers are leaving, what changed, and how to improve. Both are serious but need different solutions. I could help you think through either one separately, but ideally you'd want to get your CFO involved in the runway discussion and your product or customer success lead involved in the retention issue. What would be most urgent to tackle first?
ROUTING ANALYSIS: COMPOUND CRISIS RUNWAY PATH → CFO ADVISOR PRIORITY: IMMEDIATE (week 1) Key questions for financial advisor: 1. Current runway in months (burn rate vs. bank balance) 2. Committed spend (payroll, contracts, obligations) 3. Revenue ramp timeline if retention improves 4. Cost-cutting options if no immediate revenue 5. Fundraising timeline (if pursuing capital) Recommended first action: Monthly cash-flow projection updated daily RETENTION PATH → CCO/PRODUCT ADVISOR PRIORITY: PARALLEL (days 2-3) Key questions for retention advisor: 1. Churn rate by cohort (when did retention drop?) 2. Exit reasons (feature gap, pricing, support, competitor?) 3. Affected customer segment (small/large, new/long-term?) 4. Win-back viability (can churned customers return?) 5. Quick retention lever (discount, feature, support boost?) Recommended first action: Customer exit interviews (top 5 churned accounts) CRISIS CASCADE DYNAMICS • Tight runway limits product investment (retention tool) • Retention drop reduces future revenue (worsens runway math) • This creates a feedback loop SYNCHRONIZATION POINT By day 4: Combine financial constraints + retention data into single scenario: • Scenario A: Cost cuts + retention recovery timeline • Scenario B: Fundraising + retention investment timeline • Choose path based on probability-weighted outcomes
About this skill
Founder mode works when it is targeted and done in the open, and fails when it becomes drive-by micromanagement. This skill tells you where your personal attention is needed right now and how to go deep without breaking trust with your leaders.
What it does
- Tests each worry against concrete signals: unexplained metric moves, leader reports that contradict customers, slipping core craft, one-way decisions
- Caps active deep dives at two and names what you stop doing to make room
- Plans each deep dive with the owner: time box, raw sources to read, skip-level questions, exit criteria
- Keeps decisions flowing through the owner so you do not become the bottleneck
- Switches to a direct-conversation-first plan when the real issue is one leader's performance
What you get
A quick yes or no on getting hands-on, or a one-page founder attention plan: go deep, keep delegated, drop, first conversations, and the bottleneck and trust risks.
Best for
Founders and CEOs of 10 to 300 person companies who feel out of touch with part of the business or worry they are micromanaging.
SKILL.md preview
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name: founder-mode
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