How to Hire a Chief of Staff? 7 Steps, Tools & Strategies

Hiring the wrong Chief of Staff might result in misalignment, unclear communication, or missed strategic opportunities. Still, many hiring teams rely solely on CVs or gut feelings to make hiring decisions.

In today’s fast-paced business world, top Chief of Staff candidates are in high demand. They don’t last long on the market. You can’t afford to get this role wrong.

This research-backed hiring guide is for CEOs, founders, and HR leaders. From defining the role to sourcing, screening, and onboarding, here’s how to hire a Chief of Staff the right way.

7 Proven Steps to Hire a Chief of Staff

A structured hiring process reduces the chances of mis-hires. It helps you find a chief of staff who can streamline operations, align priorities, and be a trusted advisor. Here’s a 7-step guide on how to hire a chief of staff:

Step 1: Define Your Hiring Needs and Set a Budget

Before creating a job post, clarify what you want your chief of staff to do.

Define:

• Primary focus (e.g., strategy execution, operations oversight, leadership support).
• Decision-making scope: limited to advisory roles or authority over specific departments.
• Reporting structure and success metrics (e.g., project delivery, alignment across teams, leadership efficiency).

After you outline these requirements, set a realistic budget that should cover:

• Competitive salary based on market data from sources such as Glassdoor, Payscale, and industry benchmarks.
• Performance-based incentives tied to organizational growth or project outcomes.

Stat: In the U.S., the average salary of a chief of staff is around $124,409 a year. However, it can go up to $171,500 annually.

Step 2: Write the Perfect Job Description and Post It Online

Your Chief of Staff job description should define the role's strategic focus. Focus on outcomes, not just tasks.

A high-performing JD includes:

• Specific job title (e.g., Chief of Staff to CEO or Strategic Chief of Staff).
• Purpose of the role, such as streamlining operations, aligning cross-functional teams, or supporting executive decision-making.
• Key responsibilities (e.g., leading strategic initiatives, managing executive communications, preparing board materials).
• Must-have skills such as business analysis, stakeholder management, leadership, and strategic planning.
• Preferred background (consulting, operations, strategy, or executive support).
• Benefits, salary range, and work setup (remote, hybrid, or in office).

Once crafted, post your JD on platforms like:

• Skima AI (AI-powered job posting distribution across top boards)
• LinkedIn and specialized leadership networks
• Executive and strategy job boards (e.g., ExecThread, Ivy Exec)
• Your careers page

Important Stat: According to LinkedIn, 91% of U.S. professionals say that including a salary range in a job post impacts their decision to apply, and 82% say it gives them a more positive impression of the company

Step 3: Source Chief of Staff Talent and Parse Resumes

To hire the right Chief of Staff, relying only on inbound applications won’t help much. Proactive sourcing ensures you attract high-caliber strategic leaders.

Here’s how to find qualified Chief of Staff candidates:

• Search Your Internal Resume Database: High-potential employees in operations, strategy, or product often transition into strong Chief of Staff roles.
• Ask for Referrals: CEOs, VCs, and executive recruiters often know skilled candidates who have held similar positions.
• Explore Professional Networks: Check LinkedIn and groups like Chief of Staff Network or ExecThread to spot skilled talent.
• Target Consulting Backgrounds: Former management consultants or strategy leads often do well as Chief of Staff. Their strengths lie in problem-solving and effective communication with executives.

Once you’ve gathered resumes, start evaluation with Skima AI’s resume parser, which transforms raw resumes into structured, searchable data. It highlights leadership experience, strategic impact, stakeholder management, and other critical skills, helping you shortlist faster and smarter.

Step 4: Screen Applications and Shortlist the Best Profiles

After you have the structured resume data, manual screening can be time-consuming. Top recruiters use Skima AI Search to speed up hiring. It screens and ranks candidates in just seconds based on your needs.

It assigns a match score out of 100 to each Chief of Staff profile. It highlights key areas like leadership, strategic execution, and operational alignment for clarity.

When screening manually, go beyond job titles. Focus on proven impact and adaptability.

• Strategic outcomes: Aim for results such as “Cut operational costs by 15%” or “Led cross-functional OKRs for a team of 200.”
• Executive partnership: Evidence of supporting CEOs, founders, or senior executives in decision-making and communication.
• Cross-functional leadership: Experience coordinating teams across operations, HR, finance, or product.
• Analytical strength: The ability to use data to streamline processes and drive business outcomes.

📊 Insight: Research shows the average recruiter spends 23 hours screening resumes for a single hire. AI scoring tools, like Skima AI, cut this down to minutes. This helps you find high-potential profiles faster.

Step 5: Conduct Structured Interviews to Assess Skills

Once you’ve shortlisted the top Chief of Staff candidates, it’s time to engage them. Use Skima AI Campaigns to send automated, personalized outreach across email, LinkedIn, and SMS, keeping candidates engaged while saving recruiters hours.

When scheduling interviews, clearly explain the process and expectations. The Chief of Staff role is very strategic. So, skip the usual “tell me about yourself” questions.

Instead, design structured interviews that test leadership, problem-solving, and alignment with executive goals.

Ask questions like:

• How would you prioritize competing projects for the CEO when resources are limited?
• Give an example of how you helped a leadership team improve decision-making.
• How do you handle sensitive communication between executives and staff?

Assess candidates with:

• A business case exercise (e.g., streamline a process that saves 10% in operating costs).
• A scenario role-play where they must advise the CEO on a high-stakes decision.
• A stakeholder alignment exercise to test cross-functional communication skills.

📊 Stat: Harvard Business Review found that structured interviews are twice as effective as informal ones in predicting job success. This is crucial for strategic roles, such as Chief of Staff.

Step 6: Check References and Send a Competitive Job Offer

Before you finalize your Chief of Staff hire, conduct thorough reference checks. This role serves as a trusted advisor to leadership. Focus on integrity, strategic judgment, and how you collaborate.

Ask former managers and executives about:

• Their ability to manage cross-functional teams and drive alignment.
• How they handled confidential or sensitive information.
• Examples of influencing decisions without formal authority.
• Consistency in delivering results under pressure.

If the feedback aligns with your expectations, move quickly with a competitive job offer. A strong package should include:

• Base salary.
• Executive-level benefits (equity, performance bonuses, healthcare, retirement contributions).
• Professional growth opportunities (mentorship, leadership training, exposure to board-level decision-making).
• Flexibility in work setup and direct access to the CEO or leadership team.

Step 7: Onboard Your New Chief of Staff Effectively

Once your offer is accepted, proper onboarding is critical for a Chief of Staff. This role involves strategy, operations, and leadership alignment. Setting the right foundation early helps ensure long-term success.

Onboard Checklist:

• Provide access to company strategy documents, OKRs, and board decks.
• Clarify the reporting structure, decision-making boundaries, and CEO expectations.
• Introduce them to key stakeholders across departments and external partners.
• Share leadership communication norms (cadence of updates, escalation protocols).
• Set a 30-60-90 day roadmap

(e.g., shadow CEO meetings, lead one cross-functional project, implement an operational improvement).

💡 Insight: Structured onboarding is key for Chiefs of Staff. They serve as an extension of leadership. When done properly, it builds trust and establishes them as a reliable thought partner from the first day.

Now that you know how to hire a chief of staff, the next challenge is ensuring a good fit. Behavioral interview questions help you gain the insights needed to make a confident choice.

6 Behavioral Interview Questions To Ask

Hiring a Chief of Staff is one of the most important decisions an organization can make. The role isn’t just about operations. It’s also about strategy, trust, and being part of the executive team. That’s why traditional interview questions often fall short.

Instead, recruiters and executives should lean on behavioral interview questions. These uncover how candidates have handled real-world challenges in the past, which is one of the best predictors of future success.

Here are the top 6 behavioral interview questions to assess a Chief of Staff candidate:

1. Strategic Judgment & Prioritization

"Tell me about a time you had to prioritize multiple high-stakes projects with limited resources. How did you decide which to support?"

Why this matters: A Chief of Staff is constantly balancing competing priorities. The best answers show clear ways to make decisions, align stakeholders, and consider trade-offs.

2. Executive Partnership & Trust

"Describe a situation where you served as a trusted advisor to a senior leader. What was your role and impact?"

Why this matters: At its core, this role is about trust. Look for candidates who display good judgment and discretion. They should have the skill to influence results without being in the limelight.

3. Problem Resolution & Crisis Handling

Share an example of when unexpected challenges disrupted an executive’s plans. How did you adapt and support them?"

Why this matters: Disruption is inevitable. A strong Chief of Staff demonstrates composure, adaptability, and resilience when things don’t go as planned.

4. Cross-Functional Influence

"Give an example of a time you helped align conflicting priorities across departments. What steps did you take to build consensus?"

Why this matters: Chiefs of Staff often bridge gaps. Their answers should reflect diplomacy, communication skills, and the ability to gain buy-in from teams.

5. Ownership & Initiative

"Tell me about a time you identified a problem that wasn’t part of your role, then drove a solution. What was the result?"

Why this matters: The best Chiefs of Staff don’t wait to be told what to do. They proactively identify gaps, take ownership, and create measurable impact.

6. Alignment with Mission & Culture

"Describe when you had to embody company values during a challenging situation. How did you act?"

Why this matters: Skills can be trained, but cultural alignment is non-negotiable. This question reveals whether a candidate truly embodies your mission and values.

Behavioral interviews show if a candidate is a good fit. Once you find top talent, the next step is to evaluate the cost of hiring them. Let’s look at the numbers and find ways to lower them.

Cost of Hiring a Chief of Staff & How to Reduce It

Hiring a Chief of Staff is a major decision, and it often comes with a significant investment. While the average cost of hiring an employee ranges between $4,000 and $20,000, hiring for an executive-level role like Chief of Staff can be even higher.

Costs cover finding top talent, paying executive search fees, long interview cycles, and the time senior leaders spend.

Here’s how you can reduce these costs with an all-in-one hiring solution like Skima AI:

• Eliminates individual job board listings with one click, auto-distributes AI-optimized listings across high-visibility channels.
• Saves 30-40 hours per hire through automated resume screening and shortlisting.
• Replaces costly assessments with built-in skill tests tailored to each role.
• Reduces dependency on external recruiters or agencies by automating sourcing & outreach.
• Includes built-in ATS and analytics. Also, it cuts the costs of multiple software subscriptions.
• Its integrations allow you to connect your existing stack seamlessly.

By streamlining sourcing, screening, and assessments, Skima AI enables you to hire a Chief of Staff faster while saving thousands in recruiter fees, tech costs, and executive time.

Recognizing the costs helps you plan the hire, but determining ROI allows you to justify it. Let’s look at the long-term value a chief of staff can bring.

The Long-Term ROI of Hiring a Chief of Staff

Bringing a Chief of Staff (CoS) on board is a strategic investment. Companies that effectively utilize this position tend to notice improvements in leadership efficiency and overall growth.

1. Streamlined Decision-Making

A Chief of Staff collects information, manages priorities, and guides executives in making crucial decisions. This reduces challenges and facilitates execution.

Impact example:

Many employees waste their time on administrative tasks. A skilled CoS can reclaim most of this time for strategic initiatives.

Faster decision-making translates to quicker product launches, market responses, and stakeholder alignment.

2. Increased Team Alignment and Productivity

Chiefs of Staff act as connectors across departments. They ensure teams understand leadership priorities and execute initiatives efficiently.

A CoS keeps an eye on workflows, solves conflicts, and ensures accountability. This helps teams meet deadlines without needing constant executive oversight

Stat: Gallup research shows that companies with highly engaged employees are 18% more productive. This leads to 23% higher profitability.

3. Better Stakeholder Management

A CoS helps board members and cross-functional teams communicate better and have more impact. They prepare briefings, anticipate questions, and facilitate decision-making.

Stat: McKinsey's analysis of over 500 projects revealed that cost overruns averaged 79% and delays averaged 52%, indicating that poor stakeholder management can contribute to significant project delays.

4. Cost Efficiency and Resource Optimization

Hiring a Chief of Staff brings salary costs. But the ROI comes from preventing misalignments, inefficiencies, and project failures. By coordinating initiatives and reducing duplicated efforts, a CoS can save organizations thousands of hours annually.

They also ensure that key hires, projects, and partnerships match strategic goals. This reduces unnecessary spending.

5. Strategic Growth and Scaling

A Chief of Staff doesn’t just support, they scale impact. They identify growth opportunities, prepare executives for expansion, and ensure operational scalability.

Companies with a CoS scale more smoothly. They also retain senior leaders better and onboard them faster.

6. Enhanced Organizational Agility

A Chief of Staff enables your organization to swiftly address market changes or internal shifts. By acting as a strategic navigator, they anticipate challenges, realign resources, and ensure that leadership decisions are executed efficiently.

This agility helps businesses grab opportunities, reduce risks, and stay competitive in fast-changing environments.

Stat: PwC's Agile Project Delivery Confidence report indicates that Agile projects are 28% more successful than traditional approaches.

Legal Requirements for Hiring Employees

Hiring in the U.S. involves key federal and state-level legal criteria that every employer must follow. Below are the six essential requirements

1. Get an Employer Identification Number (EIN)

All businesses with employees must obtain an EIN from the IRS. This unique 9-digit tax identification number is required for payroll and tax reporting. You can apply for it online for free through IRS.gov.

2. Verify Work Eligibility using Form I‑9

Every employer in the U.S. must fill out Form I-9 for each new hire. This form confirms the employee's identity and their legal authorization to work. Both employee and employer portions are mandatory, and Section 2 must be completed within three business days of the start date.

3. Report New Hires to the State

When you hire staff, federal law says you must report all new hires or rehires within 20 days. You need to send this information to the state’s “Directory of New Hires." This supports child support enforcement and unemployment systems.

4. Comply with Federal and State Labor Laws

Employers must adhere to:

• The Fair Labor Standards Act (FLSA) governs minimum wage, overtime, and recordkeeping.
• Equal Employment Opportunity (EEO) protections.
• OSHA rules for workplace safety apply especially if you have five or more employees in the private sector.

5. Post Required Labor Law Notices

U.S. employers must display federal and state labor law posters in a visible workplace location. Posters include rights under wage, safety, and anti-discrimination laws. The Department of Labor provides these for free.

6. Obtain Workers’ Compensation Insurance

Most states, including California and Florida, require workers’ compensation coverage when you have employees. This insurance helps pay for medical expenses and lost wages from work-related injuries. It also protects you from liability lawsuits.

3 Best Hiring Software to Hire a Chief of Staff 

Top recruiters use intelligent hiring platforms to automate tasks, match candidates, and make smarter decisions. Below are three top-rated tools widely trusted by the best hiring teams in the U.S.

1. Skima AI

Skima AI is an end-to-end AI hiring software built for recruiters who value data-driven, high-quality hiring at scale. Its in-house AI models help you streamline job posting, talent sourcing, resume parsing, candidate matching, personalized outreach, and analytics.

Plus, it is designed to integrate seamlessly with your existing ATS, payroll, VMS systems, and more. Skima AI enables teams to hire faster without sacrificing quality or increasing the learning curve.

Key Features of Skima AI:

• One-click multi-board job posting
• Accurate AI Resume Parsing
• Powerful AI Search (Trained on millions of resumes)
• AI Matching Score & Reasoning
• Custom AI Matching Models
• Local Database Search (talent rediscovery)
• Talent pipeline management
• Branded Careers Page
• Seamless Integrations to ATS, LinkedIn, Job Board, Chrome, etc.
• Enterprise Grade Security & Compliance (SOC 2)
• Advanced Analytics & Reporting
• Dedicated Infrastructure Options (Cloud, On-premises, Hybrid)

Skima AI's Impact: Teams using Skima AI report up to 40% faster hiring cycles and 2x higher-quality applicants, based on internal case studies.

2. Greenhouse

Greenhouse is a leading ATS and recruitment software. It centralises all hiring stages, from sourcing and structured interviews to onboarding and analytics.

The platform includes AI-powered tools, custom workflows, and numerous integrations. These features help companies streamline hiring and enhance decisions with data-driven insights.

Key Features of Greenhouse:

• AI-Powered Recruiting
• Talent Sourcing & CRM
• Structured Interview Management
• Diversity & Inclusion Tools
• Reporting & Analytics
• Onboarding & Candidate Experience
• Integrations

3. Lever

Lever combines an ATS with a CRM, helping hiring teams nurture passive talent just as effectively as active applicants. Its intuitive UI and automation features make it easy for recruiters and hiring managers to stay in sync.

Moreover, businesses can customize workflows to improve collaboration and decision-making. This leads to quality hires and cost savings over time.

Key Features of Lever:

• Applicant Tracking System centralizes all candidate data.  
• AI Interview Intelligence provides structured interview guides.  
• Recruitment analytics, such as time-to-hire, offer acceptance rates, etc.  
• Recruitment tasks automation, like candidate outreach, scheduling, etc

Summary - Hire the Best Chief of Staff

A skilled Chief of Staff provides clarity and alignment for your leadership team. They empower your team to execute plans effectively. Still, many companies struggle with defining the role, running costly hiring cycles, or hiring someone who lacks the right strategic fit.

This hiring guide took you through the step-by-step process of how to hire a Chief of Staff. It covered everything from defining responsibilities to sourcing, evaluating, and onboarding the right candidate. Now you have a proven framework to streamline hiring, improve decision-making, and boost long-term organizational impact.

Having the right system lets you find a Chief of Staff. That strengthens leadership and fuels growth. Skima AI helps hiring teams source, screen, and assess strategic talent with AI-powered automation. Start your 14-day free trial today.

Frequently Asked Questions

1. When to hire a Chief of Staff?

You should hire a Chief of Staff when the CEO spends over 40% of their time on coordination instead of strategy. This hiring guide helps identify the right timing and approach.

2. What are the key steps to hire a Chief of Staff?

Steps to hire include defining responsibilities, sourcing strategically, evaluating leadership potential, and onboarding effectively. Tools like Skima AI streamline sourcing and screening so you can focus on assessing true leadership fit.

3. How do I find a Chief of Staff for my company?

Finding the right Chief of Staff goes beyond resumes. Look for candidates with influence, adaptability, and strategic thinking. Skima AI’s AI-powered shortlisting helps you find qualified candidates faster with data-driven accuracy.

4. What skills should I prioritize when hiring a Chief of Staff?

Focus on strategic thinking, emotional intelligence, and strong project execution. These skills ensure your Chief of Staff can manage priorities, influence stakeholders, and support leadership effectively.

5. Is a Chief of Staff only for large companies?

No. Startups and mid-sized firms also benefit from this role to streamline decision-making and scale faster. Using a hiring guide and tools like Skima AI, founders can assess needs, follow clear steps to hire, and find the right Chief of Staff efficiently.