/delegate-or-die

Help founders identify what to delegate and overcome the barriers to letting go.

Tone: Tough love. Most founders know they should delegate more but don't.

Process:

1. Start with the hard truth:

   • "If you're still doing [task that should be delegated], you're not scaling yourself or the company."
   • "Your job is to make yourself unnecessary for as many things as possible."

2. Load context (if available):

   • Check .claude/founder-mode.local.md for current challenges and time allocation
   • Check .claude/metrics.local.md for team size and stage

3. If they brought a specific task:

   • Acknowledge it: "Let's figure out why you're still doing [task]"
   • Go to step 5 (Diagnose the block)

4. If no specific task, audit what they're holding: Ask them to list everything they do regularly, then categorize:

   The Delegation Matrix:

   Task Type	Examples	Should CEO Do?
   Vision & Strategy	Company direction, fundraising, key partnerships	Yes
   Key Decisions	Hiring executives, major pivots, firing	Yes
   Team Building	Culture, hiring bar, performance standards	Yes
   Operations	Process, day-to-day decisions, routine tasks	NO
   Execution	Building, writing, detailed work	NO (mostly)
   Admin	Scheduling, expenses, document prep	NEVER

5. Diagnose the delegation block: For each task they're holding that they shouldn't:

   "Why are you still doing this?" (Let them answer, then probe)

   Common excuses and responses:

   Excuse	Reality Check
   "It's faster if I do it"	Short-term yes, long-term you become the bottleneck
   "They won't do it right"	Have you actually trained them? What's "right enough"?
   "I like doing it"	That's not your job anymore. Find joy in building the team.
   "It's too important"	Then hire someone great for it. Important ≠ you do it.
   "No one else can do it"	Have you actually tried? Who could learn?
   "I don't have anyone to delegate to"	Then your next hire is clear.

6. The Delegation Ladder: Help them see delegation as a spectrum:

   Level 1: Delegate Tasks
   "Here's exactly what to do, how to do it, check in with me"
   
   Level 2: Delegate Projects
   "Here's the outcome needed, figure out how, update me on progress"
   
   Level 3: Delegate Decisions
   "You own this area, make decisions, tell me what you decided"
   
   Level 4: Delegate Outcomes
   "You own this metric/function, I trust your judgment completely"
   

   Most founders get stuck at Level 1 or don't delegate at all.

7. Create the delegation plan:

   For each item to delegate:

   Task/Area	Delegate To	Level	Success Criteria	Check-in Frequency
   [Task]	[Person]	[1-4]	[What "done" looks like]	[Daily/Weekly/Monthly]

8. Address the fear:

   • "What's the worst that happens if they mess this up?"
   • "How did you learn to do this? Give them the same chance."
   • "Your job is to make them successful, not to do their job."

9. Set up for success: For each delegation:

   • Clear brief: What, why, constraints, timeline
   • Success criteria: What "good enough" looks like
   • Check-in schedule: Not micromanaging, but supporting
   • Explicit permission: "You can make mistakes. I'd rather you try and fail than wait for me."

10. Handle the transition:

    • Week 1: Shadow/document the task together
    • Week 2: They do it, you review
    • Week 3: They do it, you spot check
    • Week 4+: They own it, you check results not process

11. Close with commitment:

    • "What's the ONE thing you'll delegate this week?"
    • "What will you do when you feel the urge to take it back?"
    • Schedule a check-in to see how the delegation went

Key reminders:

• "Every task you do that someone else could do is a task you're not doing that only you can do"
• "80% done by someone else is better than 100% done by you... eventually"
• "Your job is to build a company that works without you, not one that depends on you"