🏴☠️ ⚡️Why and How to Hire a Chief of Staff: The Exec Force Multiplier
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TABLE OF CONTENTS:
THE OPERATIONAL LEVERAGE A CHIEF OF STAFF (CoS) PROVIDES
POSITION OVERVIEW, KEY RESPONSIBILITIES & SUCCESS METRICS
SIMULATION OVERVIEW, EVALUATION CRITERIA & SCENARIOS
SIMULATION SYNTHETIC REFERENCE MATERIAL (SAMPLE)
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As an organization grows, so do the demands on the CEO’s time and the complexity of keeping the team aligned and focused on the 20% of activities that yield 80% of results. As we say, ‘focus creates the space for performance’, and distractions / misalignment only increase with scale.
Enter the Chief of Staff, the CEO’s secret weapon, and the unsung hero who transforms chaos into clarity. Like an orchestra conductor, the Chief of Staff ensures every section—strategy, operations, and people—plays in harmony, empowering the CEO to focus on the most critical moves for growth.
Whether untangling operational bottlenecks, diffusing a high-stakes customer issue, or synthesizing data to make a tough decision, the Chief of Staff is the linchpin who bridges vision and execution.
In this post, we’ll explore why the Chief of Staff is among the most impactful hires a leader can make. We’ll uncover the unique leverage they bring, break down what makes an exceptional CoS, and provide a toolkit—including a job description and vetting simulation—for finding the right person to fill this critical role.
Note: LLMs are a GAMECHANGER for creating synthetic reference material to accompany respective scenarios.
Let’s get to it!
// THE OPERATIONAL LEVERAGE A CHIEF OF STAFF PROVIDES
1. Maximizing CEO Capacity
Time is a CEO’s most valuable—and finite—asset. A Chief of Staff clears the runway by managing priorities, triaging requests, and tackling tactical responsibilities. They enable the CEO to focus on high-value activities, like scaling revenue or forging key partnerships, while ensuring no critical balls are dropped.
2. Driving Cross-Functional Alignment
As companies scale, silos and bottlenecks become inevitable. A skilled CoS is the glue, breaking down barriers and aligning teams toward shared goals. They ensure effective lines of communication and raw accountability.
3. Operationalizing Vision
A CEO’s vision is only as impactful as its execution. The CoS turns abstract strategies into concrete action plans, driving high-priority initiatives to completion and creating scalable systems that set the foundation for future growth.
4. Providing Actionable Insights
A Chief of Staff filters signal from noise. Whether it’s through competitive research, data analysis, or synthesizing internal KPIs, they deliver clear, concise insights that allow the CEO and leadership team to make better, faster decisions.
5. Catalyzing a High-Performing Culture
Culture is the invisible engine of a growing company. A Chief of Staff helps nurture team morale, reinforce core values, and ensure strong communication—even amid rapid growth. They’re the stewards of cohesion and champions of the organization’s DNA.
// JOB DESCRIPTION
POSITION OVERVIEW
The Chief of Staff (CoS) is a hybrid strategic and operational role, acting as the CEO’s right hand and an integrator across the executive leadership team. The CoS ensures organizational efficiency by managing administrative functions, driving cross-functional initiatives, and providing research and insights that support decision-making. This individual will handle high-priority projects, streamline processes, and oversee tactical and strategic initiatives, enabling the CEO and leadership team to focus on scaling the business.
KEY RESPONSIBILITIES
CEO Enablement and Administrative Support
Manage the CEO’s calendar, prioritize meetings, and proactively resolve scheduling conflicts.
Act as the CEO’s proxy in meetings, providing summaries and action items as needed.
Prepare presentations, reports, and briefing materials for internal and external engagements.
Handle sensitive and confidential information with discretion.
Coordinate logistics for CEO travel, events, and customer-facing activities.
Operational Excellence
Execute payroll, invoicing, and other recurring (and often sensitive) administrative tasks.
Manage meeting rhythms, including scheduling, agenda preparation, note-taking, and follow-ups for executive and cross-functional meetings.
Develop and maintain a centralized internal business wiki to house SOPs, KPIs, and workflows.
Identify opportunities to streamline operational processes through automation and delegation.
Cross-Functional Leadership and Team Support
Act as a liaison between departments to break down silos and resolve bottlenecks.
Support team-building initiatives, including cultural and morale-boosting activities like virtual coffees or lunch events.
Facilitate communication across teams by summarizing updates, decisions, and next steps.
Research and Strategic Insights
Conduct research on industry trends, competitor benchmarks, and ideal customer profiles to inform go-to-market strategies.
Design and execute customer surveys and product feedback loops, analyzing results to identify opportunities for improvement.
Aggregate internal data, build dashboards and provide actionable insights to the CEO and leadership team.
Sales and Customer Support Support
Assist the Sales Manager with pipeline reporting, demo preparation, and account prioritization.
Collaborate with the Customer Support Manager to track key support metrics and ensure timely resolution of escalations.
Summarize critical customer accounts and escalations requiring CEO or leadership attention.
Culture and Team Building
To foster engagement and cohesion, organize team-building activities, such as virtual coffees or lunch sessions.
Act as a cultural ambassador, ensuring alignment between team values and organizational goals.
SUCCESS METRICS
The Chief of Staff will be evaluated on their ability to:
Free up CEO / exec capacity by streamlining administrative tasks and managing tactical responsibilities.
Enhance efficiency and alignment across the team through improved workflows and meeting rhythms.
Deliver high-quality research, insights, and reports that enable strategic decision-making.
Maintain a well-organized, up-to-date internal business wiki and operational documentation.
Support team cohesion and morale through effective communication and cultural initiatives.
// SIMULATION OVERVIEW
(CLICK HERE FOR THE FULL VERSION VIA NOTION)
This simulation is designed to provide a realistic preview of the Chief of Staff role while allowing us to evaluate your ability to perform at an elite level in the position. It mirrors the fast-paced, high-impact nature of the job and tests how you manage priorities, communicate effectively, and deliver results.
YOUR MISSION
As the CEO's Chief of Staff, your role is to act as a force multiplier. You triage requests, manage competing priorities, and deliver clear, actionable insights to support executive decision-making.
In this exercise, you will enter a “busy day” and handle simultaneous requests. You aim to demonstrate how you approach decision-making, problem-solving, and communication under time pressure.
STRUCTURE
Set the Scene:
See below for 4x scenarios representing typical requests that might land on your desk simultaneously.
Each scenario will include relevant information, such as attachments, calendars, KPI snapshots, or partial details to simulate the incomplete nature of real-world tasks.
Your Tasks:
Prioritize and Assess: Review each scenario and categorize it by impact and urgency.
Produce Deliverables: For each scenario:
Draft clear, actionable responses or internal communication.
Propose immediate next steps and any follow-up actions.
Synthesize & Summarize:
Provide a concise executive summary that includes:
Key issues requiring the CEO’s attention that day with desired outcomes and proposed next steps.
Additional context or supporting material (e.g., detailed deliverables).
Include a resolution plan for the remaining tasks with a target timeline.
EVALUATION CRITERIA
We’ll assess your performance across the following dimensions:
Prioritization & Decision-Making: How effectively do you distinguish between urgent and important tasks?
Information Synthesis & Insights: Can you distill complex information into clear, actionable insights?
Written Communication: Are your responses and summaries clear, professional, and complete?
Problem-Solving & Follow-Through: How well do you resolve challenges and drive tasks to completion with limited guidance?
Cross-Team Coordination: Are you able to address concerns spanning multiple teams (e.g., Sales, Marketing, Customer Success)?
SCENARIOS
“As Chief of Staff, you’ve just been looped in on an urgent client escalation. How would you proceed?”
“Sales urgently needs a client reference who matches XYZ Innovations’ profile. Who do you recommend, and how do you propose we handle scheduling or providing supporting materials?”
“Marketing is blocked on a major campaign for the Analytics 2.0 launch. Product has some unresolved items—both feature specs and final pricing. How would you, as Chief of Staff, break this bottleneck and align the teams?”
“Our CFO needs a high-level competitor scan, focusing on pricing models, feature differentials, and new market developments. We’ll use this to update our own pricing and packaging approach. Please review the documents and prepare a concise summary with recommendations.”
SYNTHETIC REFERENCE MATERIAL (SAMPLE)
(Click Here for All Scenarios and Associated Reference Material)
SCENARIO #1: An urgent support escalation from a key customer concerned about the team’s responsiveness and ability to resolve issues. — “As Chief of Staff, you’ve just been looped in on an urgent client escalation. How would you proceed?”
INTENDED DELIVERABLES:
An immediate action plan / email summarizing the situation to the CEO and relevant stakeholders (Customer’s complaint and urgency).
Proposed next steps for internal alignment (Engineering, Support, Customer Success).
Draft communication back to the customer (John Smith), reassuring them and outlining next steps.
PACKET OVERVIEW
Attachment A: Email from the Key Customer (Subject: “URGENT: Escalation – Major Issue Impacting Our Systems”)
Attachment B: Internal Slack Thread (Support & Engineering)
Attachment C: Support Ticket Overview (Key details, timeline, current status)
Attachment D: Internal Note from Customer Success Manager (Context and Additional Background)
ATTACHMENT A: Customer Email
From: John Smith (VP of Operations, Orion Tech)
To: [Your Company’s Support Alias], CC: [Candidate’s email as if they are included]
Subject: URGENT: Escalation – Major Issue Impacting Our Systems
Hello Team,
We’ve been trying to get an update on a critical issue logged in Ticket #9876 for the past 48 hours, but so far, we’ve only received a single automated response. The issue is causing significant downtime in our internal reporting dashboards. Our executives are becoming concerned about your responsiveness and our overall partnership.
As you know, Orion Tech is in the middle of rolling out a major upgrade for our Q1 initiatives, and this downtime is negatively impacting our timelines. If we don’t receive a concrete update and resolution path by end of day tomorrow, we may need to explore alternative solutions.
Please prioritize this request. Let me know what additional information you need from our side, or if a call with your engineering team would expedite the process.
Thank you,
John Smith
VP of Operations | Orion Tech
(555) 212-9876 | j.smith@oriontech.com
ATTACHMENT B: Internal Slack Thread
Channel: #support-escalations
Participants: Alex (Support Specialist), Priya (Head of Customer Support), Dan (Lead Engineer), [Candidate or “You” as Chief of Staff], CEO (brief cameo)
[9:02 AM] Alex (Support Specialist):
Hey team, just flagged an escalation from Orion Tech (Ticket #9876). They’ve been waiting on an update for 48+ hours. They’re apparently a Tier 1 account. Anyone know the status?
[9:05 AM] Dan (Lead Engineer):
We looked into it, but we can’t replicate the bug on our staging environment. We asked them for logs, but apparently they haven’t provided them yet. Without logs, it’s tough to diagnose.
We’re swamped with the new product sprint, so it could be another 2–3 days before we can dedicate more resources.
[9:07 AM] Priya (Head of Customer Support):
We need to expedite this. Orion Tech is one of our biggest logos. They’re paying ~\\$30K MRR. Any chance we can escalate resources from another project?
[9:10 AM] Alex (Support Specialist):
I’ll see if I can ping them for logs again, but they’re upset about the delay. Could we set up a real-time Zoom call with them and engineering?
[9:12 AM] CEO:
This is a priority. Let’s coordinate an immediate plan. [Candidate’s name], can you jump in and help align everyone on next steps?
[9:14 AM] Alex (Support Specialist):
Looping you in, [Candidate’s handle].
ATTACHMENT C: Support Ticket Overview
Ticket Number: #9876
Customer: Orion Tech (Account Tier 1)
Issue Category: Dashboard reporting error / data not syncing
Date Opened: Monday, 10:15 AM
First Response SLA: Within 24 hours
Current Time Elapsed: ~48 hours (no substantial update after initial automated response)
Last Update:
Automated response sent Monday at 10:16 AM
Customer requested status multiple times on Tuesday afternoon
No new internal notes from the engineering team.
Summary of the Problem:
Orion Tech reports that the analytics dashboard times out whenever they try to fetch data for large date ranges.
They also report data discrepancies (numbers not matching across different sub-reports).
The issue surfaced after they upgraded to the latest version of our reporting module.
Next Steps (Per Internal SOP):
Confirm environment details, request error logs from customer if not already provided.
Reproduce the issue in staging to identify the root cause.
Provide daily status updates to Tier 1 accounts until resolved.
ATTACHMENT D: Internal Note from Customer Success Manager
From: Sarah Kane (Customer Success Manager)
To: [Candidate], CC: CEO, Priya (Head of Support)
Subject: Additional Background on Orion Tech Escalation
Hi [Candidate],
Here’s some extra context on the Orion Tech account:
Annual Contract Value (ACV): $360K (~$30K MRR)
Renewal Date: 6 months from now. They’re due for renewal and an expansion conversation in Q3.
Stakeholder Risk: John Smith, their VP of Ops, has been our internal champion. If he loses faith in our ability to deliver, it might jeopardize the entire relationship.
Past Escalations: They’ve historically been patient, but this is the second major issue they’ve reported in as many months. Last time, we resolved it quickly, but that was a smaller bug.
They’ve also hinted at wanting a bigger feature set around advanced analytics, which was going to be a big part of the upcoming renewal pitch. If we fail them now, it’ll be much harder to justify expansion later.
My recommendation:
Schedule a live call with the engineering lead, John Smith, and me ASAP—ideally within the next few hours.
Provide daily written updates to John until resolved.
Investigate whether this is a known bug or an edge case. If engineering can’t replicate, push for logs or screen-shares.
Let me know how else I can help.
Thanks,
Sarah
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