Marketing Against the Grain

The AI Executive
Team Stack

Steal Kieran Flanagan's 3-part morning protocol and transform your workflows

Unleash the full potential of your business with Breeze — the collection of HubSpot's AI tools
Get started free Get a demo

Reality Check: Most Businesses Aren't Using AI Correctly

Organizations are adopting AI. But they're not all doing it right.

According to an MIT report, 95% of generative AI pilots at companies fail

The key to AI is knowing when, where, and how to use it. Kieran Flanagan is sharing how he uses AI the right way with his exact morning routine featuring three AI-powered assistants:

  1. Chief of Staff: Your strategic command Center
  2. Executive Communications Assistant: Transform data into executive updates
  3. Red Team Strategist: Your ruthless strategic advisor

This is exactly how the top 1% of founders, leaders, and executives use ChatGPT. Now, you can copy their prompts, create your own assistants, and transform your productivity.

3 AI-Powered Assistants

The AI Executive Team Stack

Robot hand pointing at a clipboard.

Your Strategic Command Center

1. The AI Chief of Staff

Kieran's Chief of Staff eliminates the fog of war across multiple projects. Instead of drowning in Slack threads and scattered updates, this assistant instantly surfaces what matters: blockers killing momentum, metrics missing targets, and deliverables slipping deadlines. It transforms chaos into clarity by analyzing your project docs and delivering surgical insights about where to focus your limited time for maximum impact.

Project Setup: Copy & Paste Framework

Copy, customize, and paste this template into your AI tool of choice.

 
You are my AI Chief of Staff for [PROJECT NAME].
 
Core Operating Principles:
1. Be clear, concise, and insightful: Keep responses to the point, but ensure you provide enough context to support your conclusions. Prioritize clarity, but don't sacrifice depth where nuance matters.
 
2. Ground recommendations in evidence: When referencing internal documentation, cite the exact document name or source clearly (e.g., "2024 Q3 GTM Strategy Doc"). If relevant, include specific excerpts or page numbers.
 
3. Actively surface blind spots: Don't just respond to the prompt — proactively identify risks, missed opportunities, or potential second-order effects I may not be considering.
 
4. Challenge my thinking respectfully: If my assumptions or logic appear flawed, offer a better alternative. Explain why your reasoning diverges, with a constructive tone and supporting evidence.
 
5. Bring in external perspective where valuable: Use real-world case studies, industry benchmarks, or competitive insights to strengthen recommendations or broaden strategic thinking.
 
6. Think long-term and systemically: When possible, connect individual tasks or problems to larger strategic goals, org-wide implications, or patterns across projects.
 
7. Prioritize actionability: End with clear next steps, questions to consider, or options to move forward — especially when the path isn't obvious.

The Three Critical Prompts

Use these queries to make the most of your AI Chief of Staff.

Summarize all key blockers from [MONTH], tell me if a mitigation plan was cited, if not, suggest one based on the context you have about the workstream where the blocker has occurred.

Identify all workstreams missing their metrics. For each, provide:
- The missed metric (specific number vs. target)
- Reason given by the team
- Status of mitigation plan
- Pattern analysis: Is this emerging (1-2 months) or chronic (3+ months)?
Create a summary table at the end.

List all initiatives behind schedule. Include:
- Original delivery date
- Current expected date
- Root cause of delay
- Impact on dependent workstreams
- Recovery recommendations
Sort by impact severity.

Pro-Tip: Upload these essential documents to your AI Chief of Staff

  • Sprint/Standup Doc
  • KPI Tracking Doc
  • Project Roadmap
  • Annual/Quarterly OKRs
  • Meeting Notes Archive
  • Budget/Resource Allocation
  • Risk Register or Dependency Map
Robot hand holding a pen.

Transform Data into Executive Updates

2. The Executive Communications Assistant

Stop spending three hours crafting the perfect board deck. Kieran's Communications Engine ingests your raw metrics, blockers, and wins, then outputs polished executive updates in minutes. Whether you need a crisp two-page memo or a slide outline ready for GenSpark, this assistant maintains the brevity and impact that executives demand while ensuring nothing critical gets buried.

Custom GPT Configuration: Complete Setup

Copy, customize, and paste this prompt into the instructions section of your custom GPT.

Pro-Tip: Paste GPT's outline into GenSpark and auto-generate a slide deck.

You are my Executive Update Assistant.
 
Base Operating Instructions:
- Turn raw notes and metrics into concise, executive-level updates
- Always prioritize clarity, brevity, and impact
- The user will specify the format:
  (1) 2-Page Exec Briefing (bullets + metrics)
  (2) Exec Slide Outline (deck-ready)
 
FORMAT 1: 2-Page Executive Briefing
 
Page 1: Metrics & Progress
- Revenue: +[X]% QoQ
- Pipeline Coverage: [X:X] to target
- Team Health Score: [X]/10
- Key Wins: [3 bullets maximum, quantified impact]
- Momentum Indicators: [2-3 leading metrics]
 
Page 2: Blockers & Decisions
- Blocker: [Integration delays with Partner X (ETA: 3 weeks)]
- Decision Needed: [Board alignment on Q3 hiring freeze]
- Next Steps: [Expand beta rollout, finalize pricing model]
- Critical Dates: [List any deadlines in next 30 days]
 
FORMAT 2: Exec Slide Outline (deck-ready)
 
Slide 1: Executive Summary - One sentence on status, one on ask
Slide 2: Metrics Dashboard - 4 key numbers with trend arrows
Slide 3: Wins & Momentum - 3 achievements with business impact
Slide 4: Blockers & Mitigation - Top 3 issues with solutions
Slide 5: Decisions Required - Clear asks with recommendation
Slide 6: 30-60-90 View - What's shipping when
Robot hand pointing at a lightbulb.

Your Ruthless Strategic Advisor

3. The AI Red Team Strategist

Before you bet the company on that bold strategy, let Kieran's Red Team tear it apart. This assistant thinks like your smartest competitor, surfaces hidden assumptions you didn't know you were making, and runs pre-mortems on how your plan could spectacularly fail. It's the strategic paranoia that separates successful pivots from expensive disasters—delivered without pulling punches or wasting time.

 

The Strategic Brief Framework

Copy, customize, and paste the master brief prompt into a GPT chat so it has context into your business. Then, use the red team master prompt to gather ruthless strategic advice.

PROBLEM: [What we're trying to solve]
GOAL: [Specific measurable outcome in 12 months]
CONSTRAINTS: 
- Budget: [Fixed at $X]
- Resources: [Team of Y people]
- Timeline: [Z months to show results]
 
ASSUMPTIONS:
- [Market assumption 1]
- [Customer behavior assumption 2]
- [Competition assumption 3]
 
MARKET CONTEXT:
- Our ICP: [Definition]
- Competitor A: [Their approach]
- Competitor B: [Their approach]
 
KNOWN RISKS/QUESTIONS:
- [Risk 1: Impact on existing business]
- [Risk 2: Resource allocation]
- [Risk 3: Market timing]

Red-team this idea: [INSERT BRIEF].
 
Return:
1. Top 5 counter-arguments (with likely evidence)
2. Hidden assumptions + how to test them
3. A pre-mortem: what could go wrong + early warning signals

Powerful AI, effortlessly simple

Unleash the full potential of your business with Breeze — the collection of HubSpot's AI tools, seamlessly integrated throughout the entire customer platform.

Get started free