Table of Contents:

• Table of Contents:
• First Off, Who Am I? Why Trust Me and What I Am About to Say?
• White House Chief of Staffs
• Chief of Staff at a New Organization? Do This in the First 90 Days on the Job
• Part 1: 30-60-90 Day Plan — "The Anatomy of Success"
• 🦴 30 Days → The Skeleton (Foundation | Structure)
• 💪 60 Days → The Muscles (Strength | Execution)
• 🧠 90 Days → The Nervous System (Coordination | Scale)
• Part 2: Leadership & Working Style Assessment
• 🏆 Recipe for Success
• 🚀 Ideal Working Relationship
• 🔎 Traits of a Strong CoS
• 🚨 Red Flags

First Off, Who Am I? Why Trust Me and What I Am About to Say?

My name is Anthony and here is a brief part of my story.

Part of the 2016 nationally-ranked and state-championship winning football team and 2015 county-championship winning basketball team at SJR high school.

2017-2021: Dropped out of university to build his Dream BIG & Co media production company, hosted and produced 100+ podcast episodes, created featured films and mini-documentaries, with founders, industry leaders, and top figures across all industries.

2021-Present: Moved to Austin, TX to join an elite team in building a first-of-its-kind restaurant chain called ZIKI. Grew into the role of Chief of Staff to the CEO. From 0 to 10 locations in 7 months. From $0 to $8+ million in annual revenue. Also, tasked to co-lead the setup of international operations and a factory in MX.

I strive to become the greatest chief of staff to ever walk this planet. I’ve become enamored with this position and I’m grateful to have been put in this role by the great Nick Nanakos — my business partner and good friend.

White House Chief of Staffs

The man who is pictured in this guides header is Sherman Adams. He is the first ever Chief of Staff to a U.S President in the White House. He was Chief of Staff to President Dwight Eisenhower.

I learned next-level best practices and the exact tendencies of Chief of Staffs by studying the White House Chief of Staffs to each president since Dwight D. Eisenhower.

All my notes about this can be found here — from the book The Gatekeepers.

Why not learn from those who have the same role as me, but within politics, who are executing at the highest level possible? It’s a great way to learn and apply the best of the best skills and strategies to my specific focus of Chief of Staff in business.

Chief of Staff at a New Organization? Do This in the First 90 Days on the Job

I didn’t just build a plan.

I've mapped it to mirror a human body.

I will show you how I would onboard a Chief of Staff, and for that person to become a top tier role player in the organization, using a structured approach that mirrors how you’d build a peak-performing body

— from the foundation to peak performance.

The sections include:

🦴 30 Days → The Skeleton (Foundation | Structure)

💪 60 Days → The Muscles (Strength | Execution)

🧠 90 Days → The Nervous System (Coordination | Scale)

Part 1: 30-60-90 Day Plan — "The Anatomy of Success"

🦴 30 Days → The Skeleton (Foundation | Structure)

GOAL: Establish structural integrity.

Onboarding → Absorb the mission, vision, and operational structure. → Establish boundaries and standards for CoS. → Observe everything the CEO does.

Relationship Building → Meet with key stakeholders, understand pain points. → Meet with all A players to understand their work style and their relationship with the CEO. → Establish trust and rapport with leadership and the team.

Operational Diagnosis → Conduct a business audit — assess existing processes, priorities, and gaps. → Identify immediate bottlenecks. → Suggest marginal improvements in how the CEO can perform better as a leader and operator.

Quick Wins → Execute 2-3 small but impactful wins to build momentum and credibility. → i.e. Daily or Weekly Memos. → i.e. Avid note taking within every meeting. → i.e. Identify and communicate bottlenecks.

💪 60 Days → The Muscles (Strength | Execution)

GOAL: Strengthen the foundation, drive execution, and improve ops efficiency.

Systems Optimization → Start refining and streamlining key processes. (trim the fat) → Remove friction, areas of energy leakage, and close gaps. → Build SOPs (Standard Operating Procedures) where missing. (i.e. onboarding, project formation) → Start initial build out of The Dashboard for the CEO. → Larger memo briefings: conduct research necessary to upcoming meetings / larger projects.

Strategic Execution → Using specific knowledge, the CoS can attack top priority projects with measurable impact — that are secondary to the CEO

Feedback Loop → Establish weekly huddles with leadership for execution. → Get direct input from the team to improve operational flow and output. (i.e. feedback mechanisms)(i.e. VO2 Max) → Strengthen team's capacity to execute. (increased speed, increased trust, increased empowerment)

🧠 90 Days → The Nervous System (Coordination | Scale)

GOAL: Achieve strategic alignment and operational synchronization.

Cross-Functional Synergy → Ensure seamless communication between teams and leadership. → Remove any remaining friction points.

Data-Driven Adjustments → Measure key performance indicators (KPIs) and adjust strategies.

Strategic Roadmap → Develop a 12-24 month strategic vision based on the CEO's desires and present it to leadership. → Ensure adaptive systems can scale without breaking. → Task CoS with more. CoS is now a sponge that has soaked up everything necessary by day 90.

Part 2: Leadership & Working Style Assessment

🏆 Recipe for Success

1. Trust + Transparency: Open communication and clarity on expectations.
1. DEFINE.
2. MAINTAIN STRUCTURE within the desired parameters of success and the standard.
3. HIRE.
4. EMPOWER - (d1) Connect (d2) Inspire w/ vision (d3) Instill w/ confidence (d4) Share everything (d5) Involve in decisions.
2. Autonomy + Accountability: Empowerment with clear performance metrics.
1. Framework: PLAN, ACT, EXECUTE, VALIDATE.
3. Adaptability: Flexing to match the executive’s work style without compromising results.
1. i.e. Always having my schedule open for all to see.

🚀 Ideal Working Relationship

1. Direct + Honest Feedback: No sugar-coating — clear, real-time input.
2. Strategic Thought Partner: Not just execution — proactive problem-solving and ideation.
1. Hardship = pressurized moments. Intense conversations. Game-time decisions.
2. Always seek understanding first.
3. Mutual Respect + Confidence: Space to own responsibilities and take initiative — this comes with time.

🔎 Traits of a Strong CoS

✅ Highly strategic, operationally sharp, and adaptable.

✅ Exceptional communicator and decision-maker.

✅ Humble but confident — no ego, just execution.

🚨 Red Flags

❌ Inability to handle ambiguity.

❌ Lack of accountability or ownership.

❌ Misalignment with core values or leadership philosophy.

© Anthony Dap III | 2025-2030