AI Prompts for ChatGPT for Executive Coaching: 360° Synthesis, Leadership Presence, Board-Level Communication

I am running a 360° for my executive coaching client [CLIENT NAME], [ROLE] at [COMPANY]. Here is the raw feedback verbatim from [NUMBER] stakeholders across manager, peers, direct reports, and cross-functional partners: [PASTE RAW FEEDBACK]. Act as a senior executive coach synthesizing this into a working diagnostic. Extract: the three consistent strengths named across quadrants, the two consistent development areas named across quadrants, the strategic blind spot only one quadrant sees (typically direct reports), the theme that shows up in language rather than in explicit ratings, and the one pattern the client will resist most. Give me the internal diagnostic first, then the client-facing summary I present in session two.

For my new executive coaching client [CLIENT NAME], [ROLE] at [COMPANY, INDUSTRY, STAGE], design the eight to twelve stakeholder interview protocol I run alongside the formal 360°. Include: the criteria for selecting the interview set (span of relationship, position in org, exposure to critical moments), the fifteen-minute interview question sequence that surfaces qualitative signal 360° instruments miss, the specific probes for organizational political context, and the confidentiality framing that protects candor without allowing weaponized feedback. Structured so I can run eight interviews in one week without burning out the executive credibility.

For my client [CLIENT NAME], here is the synthesized data: 360° themes [THEMES], stakeholder interview patterns [PATTERNS], client self-description in intake [SELF DESCRIPTION], observable behavior in our first two sessions [OBSERVATIONS]. Diagnose the underlying leadership operating pattern: the leadership archetype they default to under pressure, the specific stress behavior that surfaces under stakes, the compensating behavior that has worked historically but is now capping their scale, and the identity attachment that will make change hardest. Give me the diagnostic memo I hold internally and the specific language pattern for how I surface each element with the client without triggering defense.

For my executive client [CLIENT NAME] at [COMPANY] in [INDUSTRY, STAGE, RECENT INFLECTION POINT], map the organizational context the coaching engagement is embedded in: current board composition and dynamic, CEO or manager expectations of this role, peer executive dynamics, direct report leadership team maturity, current strategic pressure points and inflection horizon, and any recent event (funding round, restructure, product launch, senior departure) that shapes the client bandwidth right now. Coaching that ignores this context produces insight that dies on contact with the calendar.

Draft the executive coaching engagement contract I present to the sponsor (CEO or board) funding the engagement for my client [CLIENT NAME]. Six-month engagement structure with defined outcomes, confidentiality boundary that protects the coaching room while allowing appropriate sponsor visibility on progress themes (never content), the milestone review with sponsor at month three, the exit conditions and success measures agreed at kickoff, and the pricing structure at [FEE STRUCTURE]. Written in language a CFO signing the invoice will respect, not language a self-help book uses.

For my client [CLIENT NAME], synthesize the leadership presence diagnostic from the 360° themes [THEMES] and my direct observation. Presence has four components: physical (body, voice, breath under pressure), gravitas (composure, deliberate silence, refusal to react), warmth (genuine attention, curiosity, permission for others to speak), and clarity (crisp language, no filler, decisive framing). Rate the client one to five on each with the specific evidence, name the one component that most limits their scale, and design the specific behavioral experiments for the next four sessions that upgrade that component.

My client [CLIENT NAME] has [SPECIFIC HIGH-STAKES MOMENT: EARNINGS CALL IN TEN DAYS / BOARD MEETING WHERE THEY MUST DEFEND THE STRATEGY / ONE-ON-ONE WITH THEIR CEO ABOUT THEIR OWN PROMOTION PATH / ALL-HANDS WHERE THEY MUST ANNOUNCE A RESTRUCTURE]. Design the rehearsal I run in tomorrow session. Include: the specific opening they will use (three word-for-word options across registers), the two toughest challenges they will face and the specific frame for each, the pivot they use when they lose the room, the closing that lands the message and invites the response they want. Rehearsal not scripting; they must sound like themselves.

My client [CLIENT NAME] loses composure under [SPECIFIC TRIGGER: AGGRESSIVE BOARD MEMBER QUESTIONS / PEER EXECUTIVE UNDERCUTTING THEM IN FRONT OF CEO / DIRECT REPORT CRYING IN A HARD CONVERSATION / THEIR OWN CEO TURNING COLD]. Design the composure protocol we build together over the next three sessions. Include: the somatic anchor they use in the first three seconds after trigger, the internal reframe that buys them the pause, the observable behavior that signals to the room they are unshaken, the recovery move if they do react, and the debrief question they ask themselves within an hour of the moment.

My client [CLIENT NAME] communicates in [CURRENT PATTERN: TOO MANY WORDS / TOO MANY CAVEATS / APOLOGETIC FRAME BEFORE SUBSTANCE / EXPERT LANGUAGE THAT ALIENATES CROSS-FUNCTIONAL PEERS / PASSIVE VOICE WHEN THEY SHOULD BE DIRECT]. Design the voice upgrade over the next month: the specific pattern to eliminate, the specific pattern to install, the ten example transformations from their actual language to the upgraded language, the daily practice they run for two weeks, and the specific meeting or moment we test the upgrade in.

For my client [CLIENT NAME] approaching the [MILESTONE: PROMOTION TO C-SUITE / IPO ROADSHOW / BOARD CHAIR TRANSITION / INTERIM CEO ROLE], build the executive presence field guide they carry through the next ninety days. Six sections: the physical presence baseline they hold when tired or under attack, the three signature phrases they own, the three phrases they retire, the meeting-opening behavior they now default to, the meeting-closing behavior they now default to, and the recovery protocol when they slip. Written in their language, not in coach language.

My client [CLIENT NAME] is facing decision [DECISION: HIRE THE INTERNAL CANDIDATE OR RUN EXTERNAL SEARCH / ACCEPT THE ACQUISITION OFFER OR SCALE INDEPENDENTLY / RESTRUCTURE NOW OR WAIT ONE MORE QUARTER / TAKE THE CEO ROLE AT A SMALLER COMPANY OR WAIT FOR THE CEO ROLE AT THE CURRENT ONE]. Run the two-way door framework with them in tomorrow session. Include: the explicit test of reversibility (can this be undone within twelve months without lasting damage), the second-order consequences beyond the obvious first-order ones, the party they are optimizing for that they have not named, the counterfactual (what does not doing this look like in twelve months), and the identity-level question underneath the strategic one.

My client [CLIENT NAME] must recommend a strategic pivot to [AUDIENCE: BOARD / CEO / PEER EXECUTIVES] regarding [PIVOT: KILLING A PRODUCT LINE / RESTRUCTURING THE ORG / CHANGING THE GO-TO-MARKET MODEL / REPRICING]. Design the rehearsal. Include: the opening framing that positions the pivot as strategic clarity rather than as failure to admit, the data narrative in three slides worth of language, the two questions the audience will ask that the client is currently unprepared for, the response frame for each, and the specific ask the client leaves the room with.

My client [CLIENT NAME] needs to build alignment across [STAKEHOLDERS: BOARD MEMBERS / PEER C-SUITE / TWO SKEPTICAL VPS / A CRITICAL CUSTOMER ADVISORY GROUP] for [DECISION OR STRATEGY]. Design the ninety-day alignment plan: the specific pre-work conversation with each stakeholder in the sequence that matters, the objection each will raise (I know these stakeholders by role and by pattern, help me anticipate them), the alignment artifact they see and sign off on, and the moment of formal alignment (board vote, offsite, memo) that closes the plan.

My client [CLIENT NAME] must [HARD PEOPLE DECISION: EXIT A LONG-TENURED EXECUTIVE WHO IS CAPPED / PROMOTE ONE OF TWO PEERS TO A NEW SVP ROLE / HANDLE A DIRECT REPORT PERFORMANCE ISSUE THAT WILL SURPRISE THEM / NAVIGATE A BOARD MEMBER WHO IS UNDERMINING THEM]. Rehearse the specific conversation. Include: the pre-meeting framing they hold themselves in, the opening three sentences, the two hardest turns of the conversation and the language for each, the follow-through communication (email, private note, all-hands), and the recovery ritual after the conversation so the client sleeps that night.

My client [CLIENT NAME] is facing [PERSONAL STRATEGIC DECISION: WHETHER TO STAY AT THE CURRENT COMPANY POST-IPO / WHETHER TO TAKE THE CEO OFFER / WHETHER TO STEP DOWN AND START SOMETHING / WHETHER TO ACCEPT THE BOARD SEAT THAT CONSUMES HALF THEIR WEEK]. Design the two-day personal decision retreat they take alone or with one confidant. Structure: day one is data (write out the honest reality on ten dimensions), day two is future (write the two life stories from each path in specific detail). Include the reflection prompts, the walking questions, and the specific artifact they bring back to our next session so we integrate rather than analyze.

My client [CLIENT NAME] is presenting a board update on [TOPIC: QUARTERLY PERFORMANCE / A STRATEGIC BET / A CRITICAL PEOPLE SITUATION / A RISK THEY ARE MANAGING] in [TIMEFRAME]. Rehearse the update. Include: the opening slide in three sentences (headline, evidence, ask), the middle in five slides worth of narrative language, the closing that lands the ask, the four board questions they should expect and the response frame for each, and the follow-through email that goes to the board within twenty-four hours of the meeting.

My client [CLIENT NAME] must communicate [SITUATION: A MISSED QUARTER / A STRATEGIC PIVOT / A SENIOR DEPARTURE / A MAJOR HIRE] to [AUDIENCE: INSTITUTIONAL INVESTORS / VENTURE BOARD / LIMITED PARTNERS] in [FORMAT: SHAREHOLDER LETTER / ALL-INVESTOR CALL / QUARTERLY UPDATE]. Draft the communication. Include: the opening that acknowledges reality without defensiveness, the reframe that positions this in the larger arc, the specific actions being taken with specific accountability, the ask (if any), and the closing that reinstates confidence honestly. Their voice, not corporate boilerplate.

For my executive client [CLIENT NAME] at month three of a six-month engagement, design the sponsor update meeting with [SPONSOR: CEO / BOARD CHAIR / CHRO]. Sponsor confidentiality boundary: I share themes and progress, never content. Include: the three-theme progress summary I present, the specific behavioral evidence the sponsor can look for in the coming ninety days, the honest naming of any work still open, the sponsor role I ask for (feedback loop, opportunity design, specific stretch), and the closing that reinstates the coaching room boundary.

My client [CLIENT NAME] is positioning for [ROLE EXPANSION: PROMOTION TO C-SUITE / ADDITIONAL SCOPE / INTERIM TO PERMANENT CEO / BOARD SEAT]. Draft the internal memo or conversation opener they use with [DECISION MAKER: THEIR CEO / THE BOARD / THE NOMINATING COMMITTEE]. Include: the opening that names the ask directly without apologizing, the three-sentence case for readiness anchored in specific evidence, the acknowledgement of what they are still growing into, the specific transition plan, and the request for the specific next step in the process.

For my client [CLIENT NAME] completing the six-month engagement, design the closing arc. Final two sessions plus a written closing memo. Include: the review of the initial diagnostic and where the client actually landed, the three identity shifts (not achievements) that will persist, the specific ongoing practices they carry forward, the trigger conditions that would warrant a check-in six months out, and the referral or graduation path (peer coaching, board seat coaching, alumni cadence). Written for the client, cc-usable to sponsor with client permission.