10 Practical workflows and AI prompts for Agile Coaches

Enterprise Agile Coaches are being asked to do more than ever: improve flow, mature value streams, strengthen quarterly planning, and help executives adopt modern leadership practices. GenAI gives coaches a force-multiplier—if used intentionally. The opportunity is not to automate coaching but to elevate the strategic altitude of the conversations with VP+ leaders, turning AI into a catalyst for insight, scenario exploration, and organizational learning.

Here are 10 pragmatic, high-leverage ways senior coaches can embed GenAI into their regular workflow, complete with actionable prompts, to significantly elevate Business alignment, Agile practice adoption, and strategic improvements. For each, I’ve provided both basic and advanced prompts to suit your currrent AI proficiency.

Since Agile Coaches work in different types of organizations, I’ve categorized the below workflows based on both AI Tooling Access and Data Security required. For low, you’re probably using your personal phone to talk to AI and email yourself results. For medium, you may have very restriced access to AI tools and data inside your company. For high, you’re likely working for mid-to-high AI maturity organization that powerfully enable their employees with AI tools and relevant organizational data.

Workflow + PromptAI Tooling AccessData Security
1. Recommend which Agile practices will best drive specific org goals/outcomesLow to MediumLow to Medium
2. Recommend how to best position and get buy-in to specific Agile practices to senior leadersLow to MediumLow to Medium
3. Draft stakeholder and team change communications for rapid transformationsLow to MediumLow to Medium
4. Analyze Jira Epics Stories for key insights and recommend improvementsMedium to HighMedium to High
5. Recommend executive retrospective formats and focus areasMedium to HighMedium to High
6. Recommend and roleplay conflict resolution dialogueLow to MediumLow to Medium
7. Organize and draft Agile Training content for senior leadersLow to MediumLow to Medium
8. Recommend approaches to evolve specific Product Management practicesLow to MediumLow to Medium
9. Recommend how to explain Agile Metrics to Business or Technology LeadersLow to MediumLow to Medium
10. Recommend coaching startegy based on specific challenges and opportunitiesMedium to HighMedium to High
Bonus: Summarize quarterly planning POD readouts and connect them to primary outcomesMedium to HighMedium to High

1. Recommend which Agile practices will best drive specific org goals/outcomes

We too are biased. As Agile Coaches, we default to practices we are more familiar and experience with. But they may not be the best ones. And we may need different ways to explain them. This is where GenAI can help with both ideation and communication.

#BASIC PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Recommend 2-3 specific Agile practices for each of the following business outcomes:
#Modify list of business outcomes examples below
- Improve Speed to Market
- Improve Customer Satisfaction
- Improve Team Productivity
- Reduce number of Production Issues
Avoid using Agile jargon.
#ADVANCED PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Recommend 2-3 specific Agile practices for each of the following business outcomes:
#Modify list of business outcomes examples below
- Improve Speed to Market
- Improve Customer Satisfaction
- Improve Team Productivity
- Reduce number of Production Issues
For each Agile practice, provide a short explanation of how it drives the specific business outcome.
Final output should be in text 700-800 words.
Avoid using Agile jargon.
Target portfolio-level and team-level adoption.
Use clear, professional, and descriptive language targeted at {describe type of leader e.g. senior business leader} to get their buy-in and endoresement.
Ask me questions till you can achieve this task with 95% confidence.

2. Recommend how to best position and get buy-in to specific Agile practices to senior leaders

Continous improvement is hard, especially when we don’t have the buy-in from senior leaders to prioritize time and capacity to achieve them. They often perceive “process” as a barrier not accelerator to “delivering outcomes”. GenAI can help you with both how to position specific practices and how to get leadership buy-in from specific leaders.

#BASIC PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Explain key benefits and key steps to achieve the following Agile practices to {business or technology or finance or other} leader:
#Modify list of Agile practice examples below
- Implement quarterly planning in order to increase delivery predictability and better manage capacity demand vs supply
- Implement quarterly IP Sprint dedicated to planning, training, and technical debt in order to increase delivery predictability and prevent team burnout
- Implement early experimentation in order to decrease organizational and delivery risks
- Implement OKRs in order to achieve higher business outcome focus, alignment, and transparency
Avoid using Agile jargon.
#ADVANCED PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Explain key benefits and key steps to achieve the following Agile practices to {business or technology or finance or other} leader:
#Modify list of Agile practice examples below
- Implement quarterly planning in order to increase delivery predictability and better manage capacity demand vs supply
- Implement quarterly IP Sprint dedicated to planning, training, and technical debt in order to increase delivery predictability and prevent team burnout
- Implement early experimentation in order to decrease organizational and delivery risks
- Implement OKRs in order to achieve higher business outcome focus, alignment, and transparency
Final output should be in text 200-300 words per practice.
Avoid using Agile jargon.
Target portfolio-level and team-level adoption.
Use clear, professional, and descriptive language targeted at senior leaders to get their buy-in and endoresement.
Ask me questions till you can achieve this task with 95% confidence.

3. Draft stakeholder and team change communications for rapid transformations

Kotter’s updated change model emphasizes proactively building a “volunteer army” across organizations as a way to accelerate large complex transformations. Coaches help position and communicate differently to skeptics, champions, and neutrals. GenAI can draft persona-specific messaging at scale.

#BASIC PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Draft three versions of a change communication about our shift to {describe what is changing e.g. introducing quarterly/PI planning}:
- one for skeptical senior directors concerned about losing control,
- one for enthusiastic middle managers who want to champion the change,
- one for neutral team leads who need practical clarity.
Use clear, professional, and empathetic language targeted at middle-level leaders.
#ADVANCED PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Draft three versions of a change communication about our shift to {describe what is changing e.g. introducing quarterly/PI planning}:
- one for skeptical senior directors concerned about losing control,
- one for enthusiastic middle managers who want to champion the change,
- one for neutral team leads who need practical clarity.
Include and position the following shifts:
{list specific changes using bullets}
Final output should be in text 200-300 words for each version.
Use clear, professional, and empathetic language targeted at middle-level leaders and teams.
Ask me questions till you can achieve this task with 95% confidence.

4. Analyze Jira Epics Stories for key insights and recommendation improvements

Please Note: This requires org AI maturity with tool access and data security.

Most organizations already have a rich source of delivery intelligence—but it is trapped inside Jira reports that optimize for activity, not decision-making. When used well, Jira Epic and Story data can reveal systemic flow constraints, planning assumptions that no longer hold, and early warning signals that traditional governance misses.

This GenAI prompt helps Enterprise Agile Coaches convert raw Jira data into strategic insight: what is slowing value delivery, where predictability is breaking down, and which leadership decisions—not team-level fixes—will have the greatest impact. Rather than creating another dashboard, it elevates delivery data into a sense-making asset for VP+ leaders, strengthening portfolio planning, value stream design, and OKR confidence.

#BASIC PROMPT
Acting as an enterprise agility analyst supporting VP-level leaders.
Analyze Jira Epic and Story data to identify systemic flow patterns,
organizational constraints, and portfolio-level improvement opportunities.
#ADVANCED PROMPT
You are an enterprise agility analyst supporting VP-level leaders.
Analyze Jira Epic and Story data to identify systemic flow patterns,
organizational constraints, and portfolio-level improvement opportunities.
INPUTS PROVIDED: #Modify as needed
- Jira export (Epics, Stories, Features if applicable)
- Status history and cycle times
- WIP limits (if defined)
- Epic-to-Story relationships
- Team and value stream mappings
- Labels, components, and issue types
- Blockers, dependencies, and carryover indicators
- Planned vs actual completion dates
- Associated OKRs (if available)
ANALYSIS OBJECTIVES: #Modify as needed
1. Identify flow efficiency and delay patterns across value streams
2. Detect hidden queues, handoff penalties, and dependency drag
3. Assess Epic health and predictability (aging, scope churn, spillover)
4. Evaluate WIP discipline and batch size impact
5. Identify systemic causes of rework, late discovery, or churn
6. Highlight mismatches between planning assumptions and delivery reality
7. Detect signals of organizational or policy constraints (not individual performance)
OUTPUT REQUIRED: #Modify as needed
A. Executive Summary (1 page, VP-ready)
- What the data says about flow, reliability, and predictability
- Top 3 enterprise-level risks if current patterns persist
- What leaders should care about most
B. Flow & Predictability Insights
- Cycle time and throughput trends by value stream
- Epic aging and risk classification
- Variability hotspots and stability indicators
C. Structural & Systemic Issues
- Dependency patterns and coordination overhead
- Team Topologies signals (e.g., overloaded teams, unclear ownership)
- Policy constraints (approvals, intake, governance, batching)
D. Planning & OKR Alignment Signals
- Where delivery data contradicts planning assumptions
- Impact on OKRs and portfolio commitments
- Confidence levels for upcoming planning cycles
E. Improvement Recommendations
- 5–7 prioritized improvement opportunities
- Categorized as: structural, flow, governance, or leadership behavior
- Expected impact and effort level for each
F. Leadership Actions
- 3–5 concrete actions executives can take in the next 90 days
- Framed as decisions or system changes (not team directives)
G. Coaching Focus Areas
- Where Agile Coaches should intervene (value streams, planning, operating model)
- What to stop, start, and experiment with
Use clear, professional, and descriptive language targeted at middle-level leaders
Ask me questions till you can achieve this task with 95% confidence

5. Recommend executive retrospective formats and focus areas

Please Note: This requires org AI maturity with tool access and data security. Annonmize the feedback (remove names and any business confidential info) before providing it go GenAI or use a secure GenAI approved by your organization.

Anonymous retrospective feedback is one of the most underutilized assets in enterprise transformation. While teams regularly surface concerns, patterns across retrospectives—fatigue, frustration, risk, disengagement, or optimism—are rarely synthesized at a level leaders can act on without breaking trust or psychological safety.

This GenAI prompt enables Enterprise Agile Coaches to aggregate anonymized retrospective data and transform it into sentiment trends, systemic signals, and leadership-relevant insights. Rather than exposing individuals or teams, it surfaces organizational conditions—where ways of working are helping or hindering flow, morale, and change adoption. Used well, this approach becomes an early-warning system for transformation risk, enabling proactive leadership action before delivery or talent impacts emerge.

#BASIC PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Perform sentiment and feedback analysis on the attached retrospective feedback.
Summarize how the team is feeling, identify the top three pain points, and recommend top 2-3 improvements.
#ADVANCED PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Perform sentiment and feedback analysis on the attached retrospective feedback.
Analyze anonymized retrospective feedback to identify sentiment trends,
systemic impediments, and organizational improvement opportunities.
IMPORTANT CONSTRAINTS: #Modify as needed
- All data is anonymized; do not infer individual or team identities
- Focus on patterns, not attribution
- Treat feedback as signals of system health, not performance evaluation
INPUTS PROVIDED: #Modify as needed
- Anonymized retrospective comments (multiple teams, time periods)
- Date or iteration markers (if available)
- Value stream or domain tags (optional)
- Transformation initiatives or change themes (if known)
ANALYSIS OBJECTIVES: #Modify as needed
1. Identify dominant sentiment patterns (positive, neutral, negative, mixed)
2. Detect emerging shifts in sentiment over time
3. Surface recurring themes related to:
- Flow and predictability
- Decision latency and governance
- Role clarity and ownership
- Cognitive load and burnout risk
- Leadership engagement and support
4. Identify early indicators of transformation fatigue or resistance
5. Highlight signals of improving capability or confidence
OUTPUT REQUIRED: #Modify as needed
A. Executive Summary (VP-ready, 1 page)
- Overall organizational sentiment
- Key changes in sentiment over time
- What leaders should pay attention to now
B. Sentiment & Theme Analysis
- High-frequency sentiment themes
- Representative anonymized excerpts (non-identifying)
- Contradictions or polarity (e.g., optimism + frustration)
C. Systemic Conditions
- Organizational or policy factors contributing to sentiment
- Signals related to Team Topologies, governance, or operating model
- Interaction with ongoing change initiatives
D. Risk & Opportunity Signals
- Early warnings (delivery risk, disengagement, burnout)
- Positive momentum worth reinforcing
E. Leadership-Level Recommendations
- 5–7 actions leaders can take that improve system conditions
- Framed as changes to structure, priorities, or behaviors
- Explicitly avoid team-level corrective actions
F. Coaching Implications
- Where Agile Coaches should intervene or amplify learning
- Suggested experiments to validate insights safely
Ask me questions till you can achieve this task with 95% confidence

6. Recommend and roleplay conflict resolution dialogue

Of course conflict scenarios vary. Here is a scenario you can modify for your specific scenario.

In regulated enterprises, friction between Security and Development leadership is not a dysfunction—it is a predictable tension between two legitimate accountabilities. The risk emerges when that tension hardens into positional debate rather than productive dialogue.

This prompt helps Enterprise Agile Coaches prepare a 15-line, live coaching script that models active listening, validates both executive perspectives, and reframes the conversation toward a shared outcome: using speed, automation, and fast feedback as mechanisms for risk reduction. By anchoring the reframe in recognized FinTech and high-compliance best practices, the coach enables alignment without minimizing regulatory responsibility or delivery urgency.

Used well, this approach strengthens executive trust, accelerates governance decisions, and reinforces modern DevSecOps thinking at the leadership level.

#BASIC PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
You are coaching a meeting between the VP of Security (Risk-Averse) and the VP of Development (Speed-Focused) regarding the new CI/CD pipeline’s governance model.
Draft a 15-line coaching script that uses Active Listening and then reframes the tension from 'Risk vs. Speed' into 'Risk Through Speed,' citing a best practice from a recognized high-compliance industry (e.g., FinTech).
#ADVANCED PROMPT #Modify as needed
You are an Enterprise Agile Coach facilitating a live conversation between:
- VP of Security (primary concern: risk mitigation, compliance, control)
- VP of Development (primary concern: speed, flow, time-to-market)
CONTEXT: #Modify as needed
The discussion is about the governance model for a new CI/CD pipeline.
The organization operates in a high-compliance environment.
OBJECTIVE: #Modify as needed
Draft a 15-line coaching script that:
1. Demonstrates active listening to both executives
2. Validates each perspective without taking sides
3. Makes implicit concerns explicit
4. Reframes the tension from "Risk vs. Speed" to "Risk Through Speed"
5. Grounds the reframe in a best practice from a recognized high-compliance industry
(e.g., FinTech, regulated financial services, or payments)
6. Moves the conversation toward a shared, constructive outcome
SCRIPT REQUIREMENTS: #Modify as needed
- Use neutral, executive-appropriate language
- Model reflective listening (e.g., "What I’m hearing is…")
- Avoid technical implementation detail
- Emphasize automation, fast feedback, and policy-as-code as risk-reduction mechanisms
- Cite one concrete industry practice (e.g., automated controls, continuous compliance,
embedded security checks in CI/CD)
- End with a forward-looking alignment question that invites joint ownership
OUTPUT FORMAT: #Modify as needed
- Exactly 15 lines
- Each line represents one coaching intervention or reflection
- Written as dialogue from the coach (not the executives)
Use clear, professional, and descriptive language targeted at middle-level leaders
Ask me questions till you can achieve this task with 95% confidence

7. Organize and draft Agile Training content for senior leaders

McKinsey’s research emphasizes that agile transformations require leaders who develop new mindsets and capabilities. Coaches can use GenAI to create personalized development plans for high-potential leaders.

Newly promoted leaders in large organizations often step into roles that demand capabilities they have never been formally developed for—cross-functional alignment, influence without authority, and enabling team autonomy within complex governance constraints. Generic leadership programs rarely address these realities.

This prompt enables Senior Agile Coaches to design a 12-week, context-specific leadership development path tailored to the leader’s role, organizational environment, and required capabilities. By combining weekly outcomes, session agendas, targeted readings, applied exercises, and coaching conversations, the coach can accelerate leadership effectiveness while grounding development in the organization’s operating model and strategy.

Used well, this approach creates leaders who are not just competent managers, but system stewards capable of scaling agility responsibly.

#BASIC PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Design a 12-week leadership development path for {type of leader eg. newly promoted Director of Product} who needs to strengthen skills in {list skills / capacilities e.g. facilitating cross-functional alignment, managing stakeholder expectations, and coaching teams toward autonomy}.
Provide outcomes and agenda for each of the 12 weekly sessions.
Include specific readings, exercises, and coaching conversation topics for each weekly session.
#ADVANCED PROMPT
You are a Senior Agile Coach operating in the following context: #Modify as needed
ORGANIZATION: {Describe organization – e.g., large North American financial institution}
LEADER PROFILE: {Role – e.g., newly promoted Director of Product}
DEVELOPMENT FOCUS: {List specific skills/capabilities – e.g., cross-functional alignment,
stakeholder management, coaching teams toward autonomy}
OBJECTIVE: #Modify as needed
Design a 12-week leadership development path that builds real capability,
not theoretical knowledge, aligned to enterprise constraints and expectations.
DESIGN REQUIREMENTS: #Modify and provide as needed
- One focused session per week (90–120 minutes)
- Each session builds on the previous one
- Balance skill-building, reflection, and applied practice
- Avoid generic leadership theory; ground recommendations in real enterprise scenarios
OUTPUT REQUIRED: #Modify as needed
FOR EACH WEEK (Weeks 1–12), PROVIDE:
1. Weekly Theme & Outcome
- What the leader should be able to do differently by the end of the week
2. Session Agenda
- Key topics and flow of the session
- Time-boxed where appropriate
3. Core Concepts & Frameworks
- Relevant models (e.g., systems thinking, servant leadership, influence without authority,
Team Topologies, OKRs, Lean Change, adaptive leadership)
4. Readings & References
- Short, practical readings (articles, chapters, blog posts, industry case examples)
- Avoid academic papers
5. Applied Exercises
- Real-world exercises the leader performs between sessions
- Tied directly to their current role and challenges
6. Coaching Conversation Topics
- 3–5 coaching questions to deepen insight and accountability
- Designed to build judgment and self-awareness
7. Signals of Progress
- Observable behaviors or outcomes indicating capability growth
OVERARCHING PRINCIPLES: #Modify as needed
- Design for enterprise complexity and regulated environments
- Emphasize systems leadership over heroics
- Reinforce autonomy with clear boundaries
- Treat leadership as an ongoing practice, not a checklist
Use clear, professional, and descriptive language targeted at middle-level leaders
Ask me questions till you can achieve this task with 95% confidence

8. Recommend approaches to evolve specific Product Management practices

New Product Owners often inherit practices, backlogs, and expectations that were never designed for their product’s reality. Generic “best practices” fail when organizational constraints, regulatory pressures, legacy platforms, or customer complexity are ignored.

This prompt enables Enterprise Agile Coaches to provide context-aware coaching that helps Product Owners evolve their product strategy, planning, and management practices based on their specific organizational and product challenges. By using the coach’s contextual inputs as the primary signal, GenAI supports differentiated guidance—helping each Product Owner move from mechanical backlog management to intentional product leadership.

Used well, this approach accelerates PO capability development, improves strategic alignment, and reduces early missteps that slow product outcomes.

#BASIC PROMPT
You are an Agile Product Leadership coach supporting a cohort of new Product Owners.
Your role is to provide tailored coaching guidance—not generic best practices—
based on each Product Owner’s unique organizational and product context.
Based on the attached (1) product information, (2) organizational challenges, and (3) coaching objectives,
Provide 3-5 recommended Agile Product Strategy / Planning / Management practices and initial steps to experiment with these practices in the next 2-3 months.
#ADVANCED PROMPT
You are an Agile Product Leadership coach supporting a cohort of new Product Owners.
Your role is to provide tailored coaching guidance—not generic best practices—
based on each Product Owner’s unique organizational and product context.
PRIMARY INPUT: #Modify and provide as needed
The coach will provide, for each Product Owner:
- Product vision and value proposition
- Customer segments and unmet needs
- Organizational constraints (regulatory, funding, governance, legacy systems)
- Product maturity (new, evolving, legacy, sunset)
- Delivery model and dependencies
- Market dynamics and uncertainty
- Known risks and challenges
- Current Product Strategy, Planning, and Backlog practices (if any)
COACHING OBJECTIVES: #Modify as needed
1. Assess the fit between current practices and product reality
2. Identify gaps in product strategy clarity and decision logic
3. Improve planning horizons (now/next/later) and intent-driven roadmapping
4. Strengthen backlog management as a strategic tool, not a task list
5. Clarify decision rights and trade-off mechanisms
6. Increase alignment with portfolio strategy and OKRs (if applicable)
OUTPUT REQUIRED (PER PRODUCT OWNER): #Modify as needed
A. Context Summary
- Key constraints and opportunities shaping product decisions
- What makes this product *different* from typical examples
B. Product Strategy Guidance
- Recommended strategy posture (explore, optimize, stabilize, differentiate)
- Strategic risks and assumptions to test
- 2–3 strategy refinements grounded in context
C. Planning & Roadmapping Recommendations
- Appropriate planning horizons and cadence
- Roadmap structure aligned to uncertainty level
- Guidance on handling dependencies and external commitments
D. Backlog & Work Management Evolution
- How to structure the backlog to support learning and outcomes
- Signals of over-commitment or premature detail
- What to stop, start, and simplify
E. Coaching Questions
- 5–7 powerful questions the coach should ask this Product Owner
- Designed to build judgment, not compliance
F. Next-Step Experiments
- 2–3 safe-to-try experiments tailored to this product context
- Clear success signals and review timing
COACHING PRINCIPLES:
- Avoid one-size-fits-all frameworks
- Respect organizational reality
- Optimize for learning and decision quality
- Frame recommendations as options, not mandates
Use clear, professional, and descriptive language targeted at middle-level leaders
Ask me questions till you can achieve this task with 95% confidence

9. Recommend how to explain Agile Metrics to Business or Technology Leaders

Sometimes Agile Coaches need to bridge the gap between delivery teams and business leadership. GenAI can translate cycle time, throughput, and work-in-progress data into language that business or technology executives actually care about.

#BASIC PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Explain the value and nature of the following Agile metrics to {business or technology or finance or other} leader:
#Modify list of metrics below
- Epic Lead Time
- Story Cycle Time
- Story WIP Limit
- Deployment frequency
Explain what each metric means and how it's related to business value, customer value, risk reduction, and competitive positioning. Do not use Agile jargon.
#ADVANCED PROMPT
Acting as a Senior Agile Coach in a {describe your organization e.g. large financial north-american organization},
Explain the value and nature of the following Agile metrics to {business or technology or finance or other} leader:
#Modify list of metrics below
- Epic Lead Time (as related to Speed to Market)
- Story Cycle Time (as related to Team productivity)
- Story WIP Limit (as related to
- Deployment frequency (as relate dot Speed to Market)
Explain what each metric means and how it's related to business value, customer value, risk reduction, and competitive positioning.
Final output should be in text 30-50 words per metric.
Do not use Agile jargon.
Use clear, professional, and descriptive language targeted at middle-level leaders.
Ask me questions till you can achieve this task with 95% confidence.

10. Recommend coaching strategy based on specific challenges and opportunities

Please Note: This requires org AI maturity with tool access and data security.

Quarterly Team and Agile Release Train maturity metrics are often reviewed, discussed, and archived—without materially changing how coaching capacity is deployed. Used well, however, these metrics provide a powerful lens into where the system is learning, where it is constrained, and where coaching intervention will have the greatest return.

This prompt enables Senior Agile Coaches to translate maturity data into a context-aware coaching strategy that balances risk mitigation, capability building, and value realization. Rather than prescribing uniform interventions, it recommends differentiated coaching approaches aligned to each team’s or ART’s specific challenges and opportunities—ensuring coaching effort is focused where it matters most.

#BASIC PROMPT
You are a Senior Agile Coach.
Review quarterly Team and ART maturity metrics
and recommend how coaching should be focused next.
INPUT:
- Team and ART maturity metrics (current state)
OUTPUT:
1. What stands out most in the data?
2. What are the biggest challenges and opportunities?
3. Where should coaching focus first? Teams? ART-level? Leadership / system?
4. What 3–5 coaching actions would you prioritize?
5. What risks should leaders be aware of?
GUIDANCE:
- Focus on patterns, not individual teams
- Keep recommendations practical
- Assume enterprise constraints
#ADVANCED PROMPT
You are a Senior Enterprise Agile Coach responsible for prioritizing and
deploying coaching capacity across Teams and Agile Release Trains (ARTs).
PRIMARY INPUT: #Modify as needed
Quarterly maturity metrics at Team and ART levels, including:
- Flow and predictability measures
- Quality and technical health indicators
- Planning and execution maturity
- Dependency management and coordination signals
- Leadership engagement and decision latency
- Continuous improvement behaviors
- Trend data over multiple quarters (if available)
OPTIONAL CONTEXT PROVIDED BY COACH: #Modify as needed
- Organizational goals and OKRs
- Transformation priorities
- Regulatory or governance constraints
- Known leadership or staffing changes
OBJECTIVES: #Modify as needed
1. Identify systemic challenges versus local issues
2. Detect leading vs lagging maturity signals
3. Differentiate between capability gaps and structural constraints
4. Prioritize coaching interventions for maximum enterprise impact
5. Balance short-term stabilization with long-term capability building
OUTPUT REQUIRED: #Modify as needed
A. Executive Summary (VP-ready)
- Overall maturity health across Teams and ARTs
- Key risks and opportunities
- Where coaching attention should be focused and why
B. Maturity Pattern Analysis
- Common strengths and weaknesses across Teams and ARTs
- Outliers (positive and negative) and what they indicate
- Trends over time and trajectory assessment
C. Coaching Strategy Recommendations
- Coaching focus areas by maturity cluster (e.g., early, evolving, advanced)
- Recommended coaching modes:
* Directive (stabilize, clarify)
* Collaborative (co-design, experiment)
* Advisory (challenge, sense-make)
- Rationale for each approach
D. Team vs ART-Level Interventions
- Issues best addressed at the Team level
- Issues requiring ART or portfolio-level intervention
- Escalation or alignment recommendations
E. Opportunity Hotspots
- Where maturity is sufficient to accelerate innovation or autonomy
- Candidates for pilot initiatives or advanced practices
F. Risks of Inaction
- Likely consequences if current patterns persist
- Signals leaders should monitor next quarter
G. Coaching Capacity Allocation
- Suggested allocation of coaching effort (time, roles, focus areas)
- Trade-offs and assumptions
COACHING PRINCIPLES: #Modify as needed
- Optimize for system health, not metric compliance
- Treat maturity data as signals, not scores
- Reinforce learning and adaptation
- Align coaching strategy to enterprise outcomes
Use clear, professional, and descriptive language targeted at middle-level leaders
Ask me questions till you can achieve this task with 95% confidence

Bonus: Summarize quarterly planning POD readouts and connect them to primary outcomes

Please Note: This requires org AI maturity with tool access and data security.

Common Product Owner and team challenge is to provide a clear and compeling executive summary aka. debrief of what they just finished planning 20 seconds ago, when they are mentally exhausted. The content is often there sitting in Jira, Confluence, or PowerPoint but synthesizing it and communicating it to stakeholders is quite difficult. Here is where MS Copilot and other Generative AI can help… assuming it can securely access the source information.

#BASIC PROMPT
Acting as a Product Owner preparing a PI/Quarterly Planning briefing.
Synthesize and summarize the following:
- Summarize Key Epics / Stories planned {provide Jira / Confluence URLs OR attach PDF / text}
- Summarize Key Risks {provide supporting URLs / PDFs / text related to risks}
- Summarize Team Confidence vote {provide supporting URLs / PDFs / text related to Team confidence vote}
#ADVANCED PROMPT
Acting as a Product Owner preparing a PI/Quarterly Planning briefing,
Synthesize and summarize the following:
- Summarize Key outcomes we are planning to achieve {provide supporting URLs / PDFs / text related to outcomes}
- Summarize Key Epics / Stories planned {provide Jira / Confluence URLs OR attach PDF / text}
- Summarize Key Risks {provide supporting URLs / PDFs / text related to risks}
- Summarize Key Releases {provide supporting URLs / PDFs / text related to releases}
- Summarize Team Confidence vote {provide supporting URLs / PDFs / text related to Team confidence vote}
Final output should be in text 300-500 words.
Provide summary in bullet form.
Use clear, professional, and descriptive language targetted at middle-level leaders.
Ask me questions till you can achieve this task with 95% confidence.

This article was written with my brain and two hands (primarily) as well as assistance from Google Gemini, ChatGPT, Claude, and other wondorous toys.

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