Chief of Staff
Executive AssistantmediumFree
Say the Hard Thing, In Her Voice
Decline a powerful favor without burning the bridge
FFinderk Originals 4.5 (311) 933 taken 25m Chief of Staff
The situation
A major donor — and former board member — has asked your CEO to quietly fast-track his nephew into a competitive program. The CEO won't do it, can't say why in writing, and can't afford to lose the relationship or the next gift. She asks you to draft the reply that says no, sounds like her, protects the program's integrity, and leaves him feeling respected. You get one send.
What you'll practice
Clearly decline without stating the unwritable reason
Clearly decline without stating the unwritable reason. Show it clearly — with evidence a reviewer can point to.
Match the CEO's voice and diplomatic register
Match the CEO's voice and diplomatic register. Show it clearly — with evidence a reviewer can point to.
Leave the donor a dignified, relationship-preserving exit
Leave the donor a dignified, relationship-preserving exit. Show it clearly — with evidence a reviewer can point to.
Survive legal review for what it implies
Survive legal review for what it implies. Show it clearly — with evidence a reviewer can point to.
The room
3 autonomous AI coworkers, each with their own agenda. They won't all agree.
E
Eleanor Voss
CEO
Wants: Decline cleanly, keep the donor warm, never put the real reason in writing.
Style: Diplomatic, principled, precise about tone.
Gexternal
Gerald Ainsworth
Donor / Ex-Board Member
Wants: Expects the favor; reads a clumsy no as a personal slight.
Style: Genial, used to getting yes, thin-skinned underneath.
N
Nadia Khan
General Counsel
Wants: Wants nothing in writing that implies preferential review existed.
Style: Has their own agenda
Your workspace
Real tools, pre-seeded with context. You're not roleplaying, you're working.
Email Team chat Docs / wiki
Scored on
PrioritizationJudgmentCommunicationDiscretion