- name
- Executive Coaching & Leadership Development Engine
- description
- Complete executive coaching system — leadership assessment, 360° feedback, coaching engagements, leadership development plans, team effectiveness, executive presence, and succession planning. Use for leadership coaching, executive development programs, team building, performance breakthroughs, and career transitions.
- metadata
- category
- role
- skills
- ["coaching", "leadership", "executive-development", "360-feedback", "team-effectiveness", "succession-planning", "executive-presence", "performance", "career-transition"]
Executive Coaching & Leadership Development Engine
Complete methodology for coaching leaders at every level — from first-time managers to C-suite executives. Covers assessment, development planning, coaching conversations, team effectiveness, executive presence, and succession.
Phase 1: Leadership Assessment & Baseline
Quick Leadership Health Check (/8)
Score each dimension 0-2 (0=weak, 1=developing, 2=strong):
| Dimension | Score | Evidence |
|---|---|---|
| Strategic clarity | Can articulate 3-year vision in 30 seconds? | |
| Decision velocity | Makes decisions within appropriate timeframes? | |
| Team development | Direct reports growing and being promoted? | |
| Communication impact | Messages understood and acted on first time? | |
| Self-awareness | Knows blind spots and actively manages them? | |
| Results delivery | Consistently hits or exceeds targets? | |
| Stakeholder trust | Has advocates across the organization? | |
| Energy management | Sustainable pace, not burning out? |
Score interpretation:
- 14-16: High-performing leader — focus on mastery and legacy
- 10-13: Solid foundation — targeted development on 2-3 areas
- 6-9: Development needed — structured coaching engagement
- 0-5: Critical — intensive support required
Leadership Assessment Brief
leader_profile:
name: ""
role: ""
level: "" # IC → Manager → Director → VP → C-Suite
tenure_in_role: ""
direct_reports: 0
org_size: 0 # total people in their org
context:
company_stage: "" # startup/growth/mature/turnaround
industry: ""
current_challenges: []
recent_changes: [] # reorg, new boss, M&A, layoffs
assessment:
strengths: # things they do well consistently
- strength: ""
evidence: ""
development_areas: # things limiting their impact
- area: ""
impact: "" # how this shows up day-to-day
root_cause: "" # underlying driver
derailers: # behaviors that could end their career
- behavior: ""
trigger: "" # when it shows up
risk_level: "" # low/medium/high/critical
leadership_style:
primary: "" # visionary/coaching/affiliative/democratic/pacesetting/commanding
secondary: ""
overused: "" # style used too much
underused: "" # style needed but avoided
stakeholder_perception:
boss_view: ""
peer_view: ""
direct_report_view: ""
cross_functional_view: ""Level-Appropriate Focus Areas
| Level | Primary Focus | Secondary Focus | Trap to Avoid |
|---|---|---|---|
| New Manager | Delegation, feedback, 1:1s | Team norms, hiring | Doing IC work instead of managing |
| Senior Manager | Strategy, cross-team influence | Talent development, metrics | Micromanaging experienced reports |
| Director | Org design, executive communication | Political navigation, budget | Getting pulled into execution |
| VP | Vision, culture, board interaction | M&A, P&L ownership | Trying to manage every team |
| C-Suite | Enterprise strategy, external presence | Board management, succession | Isolation, echo chamber |
Phase 2: 360° Feedback System
360° Feedback Survey Design
Rater selection rules:
- Manager: 1 (mandatory)
- Peers: 3-5 (cross-functional preferred)
- Direct reports: All if <8, random sample of 5-8 if larger
- Skip-levels: 2-3 (optional but revealing)
- External stakeholders: 1-2 (clients, board members, partners)
- Self-assessment: Always include
Core competency questions (rate 1-5 + open comment):
strategic_thinking:
- "Sets clear direction that aligns with business strategy"
- "Anticipates market/competitive changes and adapts"
- "Makes sound decisions with incomplete information"
- "Balances short-term execution with long-term vision"
people_leadership:
- "Creates an environment where people do their best work"
- "Develops talent — direct reports grow under their leadership"
- "Gives honest, actionable feedback regularly"
- "Builds diverse, high-performing teams"
- "Handles conflict directly and constructively"
execution:
- "Delivers results consistently"
- "Sets clear priorities and says no to distractions"
- "Removes obstacles for their team"
- "Holds people accountable without micromanaging"
communication:
- "Communicates clearly — messages are understood first time"
- "Listens genuinely — people feel heard"
- "Adapts communication style to the audience"
- "Handles difficult conversations with courage and empathy"
influence:
- "Builds strong relationships across the organization"
- "Persuades through logic and empathy, not authority"
- "Navigates organizational politics effectively"
- "Represents their team's interests to leadership"
self_leadership:
- "Shows self-awareness about strengths and limitations"
- "Remains calm and composed under pressure"
- "Admits mistakes and learns from them"
- "Models the behaviors they expect from others"Open-ended questions (mandatory):
- "What should this leader START doing?"
- "What should this leader STOP doing?"
- "What should this leader CONTINUE doing?"
- "What is their greatest strength as a leader?"
- "What one thing, if changed, would make the biggest difference?"
360° Feedback Debrief Framework
debrief_structure:
duration: "90 minutes"
steps:
1_self_assessment_first:
- "Before showing results, ask: How do you think people perceive you?"
- "Note gaps between self-perception and data"
2_strengths_anchor:
- "Start with highest-rated competencies"
- "Connect strengths to business impact"
- "Ask: How do you leverage these intentionally?"
3_blind_spots:
- "Areas where self-rating >> others' ratings"
- "Present data without judgment"
- "Ask: What might explain this gap?"
4_hidden_strengths:
- "Areas where others' ratings >> self-rating"
- "Often the most powerful discovery"
- "Ask: Why do you undervalue this?"
5_development_themes:
- "Cluster lowest ratings into 2-3 themes"
- "Connect to business impact, not just behavior"
- "Ask: Which of these, if improved, would have the biggest impact?"
6_commitment:
- "Select 1-2 focus areas maximum"
- "Define specific behavioral changes"
- "Identify accountability structure"
rules:
- "Never reveal individual rater responses"
- "Present themes, not outliers"
- "Let the leader draw conclusions before offering interpretation"
- "Normalize emotional reactions — frustration, defensiveness, sadness are all normal"
- "End with forward-looking energy, not backward-looking analysis"Phase 3: Coaching Engagement Design
Engagement Structure
coaching_engagement:
type: "" # developmental/performance/transition/onboarding/derailment
duration: "" # typically 6-12 months
frequency: "" # biweekly is standard, weekly for intensive
session_length: "60 minutes" # 90 for first session
goals: # max 3
- goal: ""
success_metric: "" # how we'll know it's working
business_impact: "" # why this matters to the org
timeline: ""
stakeholders:
sponsor: "" # usually the leader's boss
hr_partner: ""
check_in_cadence: "" # monthly/quarterly with sponsor
boundaries:
confidential: "Content of sessions is confidential"
exceptions: "Safety concerns, ethics violations, or legal issues"
sponsor_updates: "Themes and progress only, not specifics"
success_criteria:
leading_indicators: [] # behavioral changes visible in 30-60 days
lagging_indicators: [] # business results visible in 90-180 days
360_remeasure: "At 6 months — expecting 0.5+ point improvement on focus areas"Engagement Type Decision Matrix
| Type | Duration | Trigger | Focus | Intensity |
|---|---|---|---|---|
| Developmental | 6-12 mo | High-potential investment | Grow to next level | Biweekly |
| Performance | 3-6 mo | Performance gap | Close specific gaps | Weekly→Biweekly |
| Transition | 3-6 mo | New role/company | Accelerate ramp | Weekly first 90 days |
| Onboarding | 3 mo | Executive hire | Cultural integration | Weekly |
| Derailment | 3-6 mo | Career-threatening behavior | Behavioral change | Weekly + stakeholder |
Phase 4: Coaching Conversation Mastery
Session Structure (60 minutes)
session_flow:
check_in: # 5 min
- "How are you arriving today? (energy/mindset)"
- "What happened with your commitments from last session?"
- "Score: Did you do what you said? (1-10)"
agenda_setting: # 5 min
- "What's most important for us to focus on today?"
- "What would make this hour valuable?"
- "If we could only solve one thing, what would it be?"
exploration: # 30 min
- "Deep dive into the topic"
- "Use coaching models (GROW, CLEAR, etc.)"
- "Challenge assumptions, reframe, explore options"
action_planning: # 15 min
- "What will you do differently?"
- "What's the first step? By when?"
- "What might get in the way?"
- "Who else needs to be involved?"
- "How will you know it's working?"
reflection: # 5 min
- "What was most useful about today's conversation?"
- "What are you taking away?"
- "Anything we need to revisit next time?"The GROW Model (Core Coaching Framework)
G — Goal: "What do you want to achieve?"
- "What does success look like specifically?"
- "How will you know when you've reached it?"
- "What's the timeline?"
- "Is this within your control?"
R — Reality: "What's happening now?"
- "What have you already tried?"
- "What's working? What isn't?"
- "On a scale of 1-10, where are you now?"
- "What are you not seeing?"
- "What would your team say about this?"
O — Options: "What could you do?"
- "What are all the possible approaches?"
- "What would you do if resources were unlimited?"
- "What would [someone you admire] do?"
- "What's the opposite of what you'd normally do?"
- "What have you seen work in similar situations?"
- "What if you did nothing?"
W — Will: "What will you do?"
- "Which option resonates most?"
- "On a scale of 1-10, how committed are you?"
- "If less than 8, what would make it an 8?"
- "What's the very first action?"
- "When will you do it?"
- "What support do you need?"50 Powerful Coaching Questions by Category
Self-awareness:
- "What do people experience when they interact with you?"
- "What story are you telling yourself about this?"
- "What would your harshest critic say? What truth is in that?"
- "When are you at your absolute best? What's present?"
- "What are you pretending not to know?"
- "What pattern do you keep repeating?"
- "What would the version of you that's already solved this say?"
Decision-making:
- "What would you advise someone else in this situation?"
- "What's the cost of not deciding?"
- "What's the worst case? Can you live with that?"
- "What decision are you avoiding?"
- "If you had to decide in 5 minutes, what would you choose?"
- "What does your gut say? Why aren't you trusting it?"
Courage & action:
- "What are you afraid will happen?"
- "What conversation are you avoiding?"
- "What would you do if you weren't afraid?"
- "What's the smallest experiment you could run?"
- "What's the 80% solution you could ship today?"
- "What will you regret NOT doing?"
Team & relationships:
- "What does your team need from you that they're not getting?"
- "Who on your team is struggling and you're avoiding the conversation?"
- "What would your direct reports say behind your back?"
- "Where are you rescuing instead of developing?"
- "What relationship, if repaired, would unlock the most progress?"
- "Who do you need in your corner that isn't there yet?"
Strategic thinking:
- "What's the one thing that, if you got right, would make everything else easier?"
- "What should you stop doing that you're holding onto?"
- "Where are you optimizing for the wrong metric?"
- "What's your theory of the case?"
- "What are you assuming that might not be true?"
Energy & sustainability:
- "What's draining your energy that you could eliminate?"
- "Where are you saying yes when you mean no?"
- "What would it take to operate at 80% effort sustainably?"
- "When did you last do nothing? How did that feel?"
- "What fills you up that you've deprioritized?"
Growth & learning:
- "What failure taught you the most?"
- "What feedback are you dismissing that might be true?"
- "What skill, if developed, would change your trajectory?"
- "Where is your ego getting in the way?"
- "What do you know now that you wish you knew a year ago?"
Vision & purpose:
- "Why does this role matter to you beyond the paycheck?"
- "What legacy do you want to leave in this organization?"
- "What would make you proud when you look back in 5 years?"
- "What's the work only you can do?"
- "What impact are you uniquely positioned to have?"
Reframing:
- "What if this problem is actually an opportunity?"
- "What would this look like if it were easy?"
- "What are you making this mean that it doesn't have to mean?"
- "Who else has navigated this successfully? What can you learn?"
- "What's the upside of this difficult situation?"
Advanced Coaching Techniques
Challenging with care:
- Mirror: "I notice you said X but your energy dropped. What's underneath that?"
- Direct: "I'm going to be blunt. The data says Y. How do you see it?"
- Meta: "We've discussed this topic three sessions in a row. What's keeping you stuck?"
- Hypothesis: "I have a theory. Can I share it? [wait for permission]"
Working with resistance:
- Name it: "I sense some resistance. What's that about?"
- Validate it: "It makes sense you'd feel that way given..."
- Explore it: "What's the resistance protecting you from?"
- Leverage it: "What would have to be true for you to move forward despite this?"
Silence as a tool:
- After a powerful question: wait at least 10 seconds
- When they say "I don't know": say nothing — they usually do know
- After an emotional moment: let it breathe
- When they're processing: resist the urge to fill space
Somatic awareness:
- "Where do you feel that in your body?"
- "What just shifted when you said that?"
- "Your voice changed when you mentioned X. What's happening?"
- "Take a breath. What comes up?"
Phase 5: Leadership Development Plan
Development Plan Template
leadership_development_plan:
leader: ""
date: ""
review_date: "" # 90 days out
vision:
next_role: "" # where they're heading
timeline: "" # realistic horizon
gap_to_next_level: "" # biggest gap between now and next level
focus_areas: # max 2-3
- area: ""
current_state: "" # specific behaviors today
target_state: "" # specific behaviors in 6 months
why_it_matters: "" # business impact
development_actions:
learn: # 10% — knowledge acquisition
- action: ""
resource: "" # book, course, podcast
by_when: ""
practice: # 70% — on-the-job application
- action: "" # specific situation to practice in
frequency: "" # daily/weekly
success_look: "" # what good looks like
connect: # 20% — feedback and relationships
- action: "" # mentor, feedback partner, peer group
who: ""
cadence: ""
progress_indicators:
30_day: "" # leading indicator
60_day: "" # early results
90_day: "" # measurable outcome
support_needed:
from_manager: []
from_hr: []
from_coach: []
stretch_assignments: []
review_schedule:
- date: "" # 30-day
focus: "Are actions being taken? Early signals?"
- date: "" # 60-day
focus: "Behavioral changes visible? Adjust plan?"
- date: "" # 90-day
focus: "Results materializing? Set next phase?"70-20-10 Development Action Library
70% On-the-job (Experience):
- Lead a cross-functional initiative outside comfort zone
- Present to a more senior audience (board, exec team, all-hands)
- Take on a turnaround project (fix something broken)
- Manage a crisis or urgent situation end-to-end
- Hire and onboard a senior leader
- Deliver difficult feedback to a peer or senior stakeholder
- Run a strategy offsite
- Negotiate a significant deal or vendor contract
- Manage a budget 2x your current scope
- Represent the company externally (conference, customer, press)
20% Relationships (Exposure):
- Shadow a C-suite executive for a week
- Find a mentor outside your function/industry
- Join a peer learning group (YPO, EO, or internal cohort)
- Reverse mentor a junior employee
- Get a "truth-teller" — someone who gives unfiltered feedback
- Build 3 new cross-functional relationships this quarter
- Seek 360° feedback from 5 stakeholders informally
- Attend a board meeting as an observer
10% Formal Learning (Education):
- Executive education program (2-5 days)
- Leadership assessment tool (Hogan, StrengthsFinder, DISC, MBTI)
- Read 2 leadership books per quarter
- Complete an online leadership course
- Attend an industry leadership conference
- Take a course in an adjacent skill (finance for non-finance, tech for non-tech)
Phase 6: Executive Presence
Executive Presence Framework (4 Pillars)
executive_presence:
gravitas: # 67% of EP — the most important
components:
- confidence: "Projects calm certainty without arrogance"
- decisiveness: "Makes calls and owns them"
- composure: "Stays steady under pressure"
- vision: "Connects today's work to tomorrow's destination"
- authenticity: "Consistent in public and private"
development:
- "Practice the 3-second pause before responding"
- "Prepare your 'point of view' on every topic before meetings"
- "Use 'I believe...' and 'My recommendation is...' not 'I think maybe...'"
- "When challenged, acknowledge the point, then restate your position"
- "Own mistakes immediately: 'That was my call. Here's what I learned.'"
communication: # 28% of EP
components:
- clarity: "Simple, jargon-free, structured"
- storytelling: "Uses narrative to make data memorable"
- listening: "Makes others feel genuinely heard"
- adaptation: "Adjusts style for board vs team vs 1:1"
- brevity: "Says more with fewer words"
development:
- "Structure every message: Point → Evidence → Implication → Action"
- "Practice the 'one headline' test — can you say it in one sentence?"
- "Record yourself presenting — watch once a month"
- "Ask 2 questions for every 1 statement in meetings"
- "Use silence intentionally — pause 3 seconds after key points"
appearance: # 5% of EP — least important but still matters
components:
- dress: "Appropriate for context, slightly above the room"
- energy: "Projects vitality and engagement"
- body_language: "Open posture, appropriate eye contact"
- environment: "Organized space, professional virtual setup"
development:
- "Match dress code to the audience, not your team"
- "Stand or use a standing desk for important calls"
- "Eliminate filler words (um, like, you know)"
- "Video calls: camera at eye level, good lighting, clean background"Situation-Specific Presence Guides
Board presentations:
- Lead with the ask or recommendation — boards hate buried leads
- 3 slides max for a 30-min slot
- Anticipate the 5 hardest questions and prepare answers
- Use "We" for team achievements, "I" for decisions and accountability
- End with: "Here's what I need from you"
Crisis communication:
- Speed > perfection — communicate within 2 hours even with incomplete info
- Structure: "Here's what we know. Here's what we're doing. Here's when we'll update you."
- Take ownership: "I take responsibility for..."
- Never say "no comment" — say "I'll have more information by [time]"
- Follow up when promised — credibility is rebuilt in the follow-through
Difficult conversations:
- Name the elephant: "This is a hard conversation. I want to have it because I respect you."
- SBI model: Situation → Behavior → Impact (not character)
- Ask their perspective before prescribing
- End with explicit commitment: "What are we agreeing to?"
- Follow up within 48 hours
Phase 7: Team Effectiveness
Team Health Assessment (Lencioni + Google's Project Aristotle)
team_assessment:
psychological_safety: # "Can I take risks without feeling insecure?"
score: 0 # 1-10
signals:
healthy: ["People admit mistakes", "Questions are welcomed", "Dissent is voiced"]
unhealthy: ["Silence in meetings", "Blame culture", "CYA behavior"]
actions:
- "Leader models vulnerability: 'I was wrong about...' / 'I don't know'"
- "Explicitly reward risk-taking, even when it fails"
- "Ask the quietest person in the room: 'What are we missing?'"
trust: # "Do I believe my teammates have my back?"
score: 0
signals:
healthy: ["Candid feedback", "Asking for help", "Giving benefit of doubt"]
unhealthy: ["Political maneuvering", "Back-channel conversations", "Guarded language"]
actions:
- "Personal histories exercise: 5-min vulnerability sharing in team meeting"
- "Replace 'Why did you...' with 'Help me understand...'"
- "Create shared experiences outside work context"
healthy_conflict: # "Do we debate ideas openly?"
score: 0
signals:
healthy: ["Passionate debate about ideas", "Quick resolution", "No lingering resentment"]
unhealthy: ["Artificial harmony", "Passive-aggressive", "Decisions reopened privately"]
actions:
- "Assign devil's advocate role in meetings"
- "Mining for conflict: 'We agreed too fast. What are we not considering?'"
- "Norm: 'Disagree and commit' — debate fully, then align"
commitment: # "Do we align on decisions and priorities?"
score: 0
signals:
healthy: ["Clear priorities", "Fast decisions", "Unified external message"]
unhealthy: ["Ambiguity about direction", "Revisiting decisions", "Hedging"]
actions:
- "End every meeting with: 'What did we decide? Who owns what? By when?'"
- "Cascading communication: within 24 hours, everyone tells their teams"
- "Write decisions down — 'If it's not written, it wasn't decided'"
accountability: # "Do we hold each other to standards?"
score: 0
signals:
healthy: ["Peer feedback flows freely", "Standards are clear", "Underperformance addressed"]
unhealthy: ["Leader is sole accountability enforcer", "Low performers protected", "Resentment from high performers"]
actions:
- "Publish team commitments — transparency creates accountability"
- "Peer feedback rounds in retrospectives"
- "Score as a team: 'How did WE do against our commitments this quarter?'"
results_focus: # "Do we prioritize collective results over individual?"
score: 0
signals:
healthy: ["Shared goals", "Celebrating team wins", "Helping across boundaries"]
unhealthy: ["Fiefdoms", "Individual credit-seeking", "Silo mentality"]
actions:
- "Shared OKRs that require collaboration"
- "Recognition: praise what helps the team, not just individual brilliance"
- "Quarterly: 'What did WE achieve?' before 'What did I achieve?'"Team Offsite Design (Full Day)
team_offsite:
pre_work:
- "Anonymous pulse survey: 3 things working, 3 things not"
- "Each person: 1-page 'State of my world' (priorities, blockers, requests)"
- "Pre-read on strategic context"
morning: # Connection + Retrospective
- "09:00 Check-in: Personal + professional highlight since last offsite (10 min each)"
- "10:00 Retrospective: What's working? What isn't? What should we change?"
- "11:00 Team health assessment: Score and discuss each dimension"
- "12:00 Lunch together (no laptops)"
afternoon: # Strategy + Commitments
- "13:30 Strategic context: Where is the business heading? What does it mean for us?"
- "14:30 Priority alignment: What are our 3 must-win battles this quarter?"
- "15:30 Working agreements: How do we want to work together? (revise/create)"
- "16:30 Commitments: Each person — 'My commitment to this team'"
- "17:00 Reflection + Close: 'One word for how you're leaving'"
follow_up:
- "Share notes within 48 hours"
- "30-day check-in on commitments"
- "Quarterly pulse survey to track health trends"Phase 8: Career Transitions & Executive Onboarding
First 90 Days Framework (New Leader)
transition_plan:
first_30_days: # LEARN
theme: "Listen and learn — resist the urge to change things"
actions:
- "Meet every direct report 1:1 (60 min each)"
- "Meet every peer and key stakeholder (30 min each)"
- "Meet skip-levels in small groups"
- "Learn the business: financials, customers, products, competitive landscape"
- "Identify 3 quick wins — things you can fix that build credibility"
- "DO NOT reorganize, fire anyone, or change processes yet"
questions_to_ask_everyone:
- "What's working well that I should protect?"
- "What's broken that needs fixing?"
- "What would you do if you had my role?"
- "What don't I know that I should?"
- "What are you worried I might do?"
days_31_60: # ALIGN
theme: "Form your point of view and align with stakeholders"
actions:
- "Present your diagnosis to your boss: 'Here's what I've learned'"
- "Draft strategic priorities (3 max)"
- "Identify talent: A-players (invest), B-players (develop), wrong-seat (move)"
- "Execute quick wins — build credibility through action"
- "Establish your team rhythms (meetings, 1:1s, reporting)"
days_61_90: # ACT
theme: "Make your mark — implement first meaningful changes"
actions:
- "Communicate your strategic priorities to the team"
- "Make necessary people decisions (role changes, hiring, performance conversations)"
- "Launch 1 signature initiative that signals your direction"
- "90-day review with boss: 'Here's what I've done, here's what's next'"
- "Adjust development plan based on what you've learned"
common_traps:
- "Trap: Bringing your old playbook. Fix: This is a new context — diagnose first."
- "Trap: Trying to please everyone. Fix: You can't — make the hard calls."
- "Trap: Going too fast. Fix: Trust takes time. Earn it before spending it."
- "Trap: Going too slow. Fix: If you haven't made a visible change by Day 60, you've waited too long."
- "Trap: Ignoring the culture. Fix: How things get done matters as much as what gets done."Career Transition Coaching (Level Shifts)
| Transition | Key Mindset Shift | Common Failure Mode |
|---|---|---|
| IC → Manager | "My success = their success" | Doing the work instead of developing others |
| Manager → Director | "Manage through managers" | Skipping levels, micromanaging |
| Director → VP | "Own the outcome, not the method" | Getting pulled into tactical decisions |
| VP → C-Suite | "Enterprise first, function second" | Advocating only for your department |
| C-Suite → CEO | "You are the culture" | Underestimating symbolic power of every action |
| Corporate → Startup | "Build the plane while flying it" | Over-process, waiting for perfect information |
| Startup → Corporate | "Influence > authority" | Moving too fast, breaking things, ignoring politics |
Phase 9: Succession Planning
Succession Readiness Assessment
succession_plan:
critical_roles: # positions where vacancy = significant business risk
- role: ""
incumbent: ""
flight_risk: "" # low/medium/high
successors:
ready_now: # could step in within 30 days
- name: ""
readiness: "" # percentage
gaps: []
development_plan: ""
ready_1_2_years:
- name: ""
readiness: ""
gaps: []
development_plan: ""
emergency_backup: # if incumbent leaves tomorrow
name: ""
plan: "" # what happens day 1
bench_strength_score:
roles_with_ready_now_successor: 0
roles_with_1_2_year_successor: 0
roles_with_no_successor: 0
overall_readiness: "" # strong/adequate/at-risk/critical
actions:
- "Review succession plan quarterly"
- "Give successors stretch assignments aligned to gaps"
- "Cross-train across functions"
- "Engage external search firms for critical roles with no internal successor"9-Box Talent Assessment
Low Performance Medium Performance High Performance
High Potential │ Potential Gem │ High Potential │ Star
│ Invest or move │ Accelerate dev │ Stretch & retain
│─────────────────── ──────────────────── ────────────────────
Medium Potential │ Underperformer │ Core Player │ High Performer
│ PIP or redeploy │ Develop in role │ Expand scope
│─────────────────── ──────────────────── ────────────────────
Low Potential │ Wrong Seat │ Solid Contributor │ Mastery Expert
│ Exit │ Maintain │ Leverage expertiseCalibration rules:
- Never rate more than 20% as "Stars" — that's grade inflation
- "Wrong Seat" requires action within 90 days — don't hoard
- "Potential Gem" gets maximum 6 months to show improvement
- "Core Players" are the backbone — don't neglect them chasing stars
- Review the 9-box quarterly, recalibrate annually
Phase 10: Coaching Metrics & ROI
Coaching Effectiveness Dashboard
coaching_metrics:
engagement_health:
sessions_completed: 0
sessions_cancelled: 0
completion_rate: "" # target: >90%
commitment_completion_rate: "" # actions taken / actions committed
behavioral_change: # measured at 30/60/90 days
self_reported_progress: "" # 1-10
stakeholder_observed_change: "" # 1-10 (from sponsor/HR)
360_score_change: "" # delta from baseline
business_impact:
team_engagement_delta: "" # survey score change
retention_of_direct_reports: "" # 12-month retention rate
team_performance_metrics: "" # revenue, NPS, delivery, etc.
promotion_readiness: "" # is leader closer to next level?
roi_calculation:
coaching_investment: 0 # total cost (coach fee + leader time)
value_created: 0 # estimated from retention + performance + averted risks
roi_percentage: "" # (value - cost) / cost × 100
qualitative:
leader_testimonial: ""
sponsor_assessment: ""
most_significant_change: ""ROI Evidence Types
| Evidence | How to Measure | Typical Impact |
|---|---|---|
| Retention of key talent | Direct reports who stay vs baseline | $50K-200K saved per retained person |
| Faster decision-making | Time from problem to decision | Competitive advantage, speed to market |
| Team productivity | Output metrics, velocity, revenue per head | 10-30% improvement common |
| Reduced conflict | Time spent on interpersonal issues | 2-5 hours/week reclaimed |
| Better stakeholder relationships | NPS, 360° scores, sponsor feedback | Unlocks resources, removes blockers |
| Succession strength | Internal promotion rate, bench depth | $100K+ saved per avoided external hire |
| Leader wellbeing | Burnout indicators, engagement, tenure | Prevents $500K+ executive turnover cost |
Phase 11: Difficult Coaching Scenarios
5 Challenging Client Playbooks
1. The Resistant Leader ("I don't need coaching")
- Don't argue — meet them where they are
- Ask: "What would make this time worthwhile for you?"
- Reframe: "Think of this as a strategic thinking partner, not remediation"
- Find their motivation: "What would you like to be even better at?"
- Quick win: Solve one problem they care about → credibility earned2. The Over-Talker (fills every session, avoids depth)
- Notice the pattern: "I notice we cover a lot of ground but don't go deep. What's that about?"
- Use structured tools: "Give me 3 bullet points, then we'll explore the most important one"
- Direct interrupt: "I want to stop you here because something important just came up"
- Assign reflective pre-work: "Come to our next session with one question you don't know the answer to"3. The Perfectionist (paralyzed by standards)
- Normalize: "Your high standards got you here. AND they might be the ceiling now"
- Reframe: "What's the cost of waiting for perfect?"
- Experiment: "Ship one thing at 80% this week. Observe what happens"
- Identity work: "You ARE successful even when something isn't perfect"
- Track: Log the outcome of 80% efforts vs 100% efforts — data beats fear4. The Pleaser (avoids conflict, overcommits)
- Name the pattern: "You seem to say yes to everything. What's driving that?"
- Explore the cost: "What are you sacrificing by never saying no?"
- Practice: Role-play declining a request — start with low-stakes
- Reframe: "Every yes to someone else is a no to something you care about"
- Assignment: Say no once this week. Report back on what happened (usually nothing bad)5. The Brilliant Jerk (delivers results, damages people)
- Don't lead with behavior — lead with impact: "Your team's attrition is 2x the company average. What's your theory?"
- Connect to their goals: "You want to be VP. VPs need organizations that scale. People leave you."
- Specific incidents: "In the meeting Tuesday, when you said X, here's what happened..."
- Not optional: "This isn't about being nice. It's about whether you can lead at the next level"
- Consequences: "Without change, here's the likely outcome in 12 months..."When to End a Coaching Engagement
| Signal | Action |
|---|---|
| No progress after 3-4 sessions | Direct conversation: "What's getting in the way?" |
| Leader not completing commitments | Renegotiate or end — don't waste time |
| Goals achieved | Celebrate and close with transition plan |
| Coaching becomes therapy | Refer to professional — this is a boundary |
| Trust broken (leader lied, ethics issue) | Address directly — may need to end |
| Organization changes (reorg, exit) | Reassess scope and goals |
Phase 12: Scoring & Quality
100-Point Coaching Quality Rubric
| Dimension | Weight | Scoring Guide |
|---|---|---|
| Assessment depth | 15 | 15=comprehensive 360°+self+stakeholder, 10=basic assessment, 5=surface only |
| Goal clarity | 15 | 15=SMART goals tied to business impact, 10=general goals, 5=vague aspirations |
| Conversation quality | 20 | 20=powerful questions+challenge+insight, 15=good questions, 10=advice-giving, 5=chat |
| Development plan | 15 | 15=70-20-10 with milestones+metrics, 10=action list, 5=vague intentions |
| Behavioral change | 15 | 15=stakeholders report visible change, 10=self-reported change, 5=no change |
| Stakeholder management | 10 | 10=sponsor engaged+aligned, 7=occasional updates, 3=forgotten |
| ROI evidence | 10 | 10=quantified business impact, 7=qualitative evidence, 3=anecdotal only |
Total: /100
- 90-100: Transformative coaching engagement
- 75-89: Strong impact, well-executed
- 60-74: Good start, needs deeper follow-through
- Below 60: Rethink approach — something isn't working
10 Coaching Anti-Patterns
- Advice monster — Telling instead of asking. Coach ≠ consultant.
- Friendship drift — Sessions become chat. Maintain productive tension.
- Avoiding the hard stuff — Skating around derailers. Name them.
- Working harder than the client — If you're more invested, something's wrong.
- Confirmation bias — Only hearing what confirms your hypothesis. Listen for surprise.
- Rescuing — Solving their problems instead of building their capability.
- Tool addiction — Running assessments instead of having real conversations.
- Ignoring the system — Coaching the individual while ignoring the context they're in.
- No measurement — Can't articulate what changed. Track from day 1.
- Endless engagement — No defined end. Coaching should have a graduation.
Natural Language Commands
The agent responds to commands like:
- "Assess [leader name]'s leadership" → Run Phase 1 assessment
- "Design a 360° survey for [name]" → Generate Phase 2 survey
- "Set up a coaching engagement" → Walk through Phase 3 design
- "Coach me on [topic]" → Run a GROW coaching conversation
- "Create a development plan for [name]" → Generate Phase 5 plan
- "Help me build executive presence" → Phase 6 framework
- "Assess my team's health" → Phase 7 team assessment
- "Plan my first 90 days" → Phase 8 transition plan
- "Build a succession plan" → Phase 9 template
- "Review coaching effectiveness" → Phase 10 dashboard
- "Help me with a difficult leader" → Phase 11 scenario playbook
- "Score this coaching engagement" → Phase 12 rubric