<link rel="stylesheet" href="https://53.fs1.hubspotusercontent-na1.net/hubfs/53/hub_generated/template_assets/1/207928094053/1771527327992/template_footer-core-non-critical.min.css">

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.

The Three Critical Prompts

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

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.

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.

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