Chief-of-Staff

How To Find a Great Chief of Staff?


The Connection: September 2024 Issue #09

When your business reaches a point where you’re feeling overwhelmed, hiring a chief of staff might seem like adding another task to your plate.

A Chief of Staff (CoS) is the CEO’s or executive team’s right-hand person. While finding the perfect candidate may require some initial effort, the long-term benefits of having a CoS by your side are invaluable.

If you’ve decided to hire your Chief of Staff from outside your company, you might be wondering where to start. We can help – this is what we do best!

Below is a comprehensive, step-by-step guide to help you find the ideal candidate.

1. Understand the Role

Before starting the search, you must fully understand what a Chief of Staff does and how they will fit into your organization. This role is not just administrative but highly strategic.

A Chief of Staff manages important projects and attends high-level meetings. However, the responsibilities of a Chief of Staff can vary depending on the company’s size and structure.

However, the primary purpose remains: to relieve pressure on leadership by handling day-to-day tasks.

Analyze Your Needs:

  • What are the key areas where leadership requires support?
  • Is it project management, decision-making, communication across departments, or all of these?
  • Do you need them to manage internal communication, oversee projects, or focus on external partnerships?

2. Look for Key Skills

A Chief of Staff must juggle multiple tasks and interact with people at all levels of the organization. He conveys ideas and strategies to leadership and employees. They often represent the executive in meetings, so they must understand complex information.

The CoS will often be required to tackle unforeseen challenges, so their ability to think critically and quickly is essential. They must also work collaboratively across departments to get things done.

Critical Skills to Look For:

  • Communication Skills
  • Problem-Solving Abilities
  • Organization & Time Management
  • Leadership & Teamwork

3. Focus on Experience

Experience is a significant factor in finding the right Chief of Staff. A candidate’s background should demonstrate their ability to manage multiple responsibilities, lead teams, and work alongside senior leadership. A Chief of Staff will have experience working directly with executives or senior leaders.

What to Consider:

  • Have they managed teams or departments?
  • Assess their ability to handle high-pressure situations, as the Chief of Staff often deals with crises or last-minute challenges.

4. Cultural Fit Matters

A Chief of Staff will work closely with leadership, so they must share the same values and work ethic as your executive team. If your leadership team operates in a high-pressure environment, you’ll want a Chief of Staff who thrives under similar conditions. If your company values work-life balance, find someone who respects that.

5. Find a Trusted Advisor

The Chief of Staff should be more than just an executor of tasks – they should be a strategic advisor to the leadership team. A good CoS provides honest feedback and helps the executive team make better decisions.

  • Ask about times they’ve had to give feedback to a superior. How did they handle it?
  • Look for candidates with a history of managing confidential information responsibly.

6. Use Your Network

Post the job online and let people know you’re hiring. Your network is often a great place to find suitable candidates. Tell your friends and colleagues what you need and ask if they know anyone who could be a good fit.

  • Draft a clear and concise job description and share it within your network.
  • Engage with potential candidates directly on LinkedIn or similar professional networks.

7. Ask the Right Interview Questions

The interview process is your chance to learn more about how a candidate will function in the role. Focus on questions about how they handle challenges, manage projects, and communicate with leaders.

Examples of Key Questions:

  • Problem-Solving: “Tell me about a time you had to make a critical decision under pressure?”
  • Communication: “How do you ensure that key information flows effectively between leadership and other teams?”
  • Crisis Management: “Give me an example of a time you had to manage a crisis. What steps did you take, and what was the outcome?”

8. Assess Their Adaptability

The business world is unpredictable, and priorities can shift quickly. A CoS must remain calm under pressure and pivot when necessary. They should also be open to acquiring new skills as the company grows and evolves. The Chief of Staff must often operate in situations with incomplete information and be comfortable making decisions with limited data.

9. Provide Clear Expectations

Once you’ve identified the right candidate, setting clear expectations is crucial. Clearly outline what you expect the Chief of Staff to manage, including specific projects, timelines, and leadership duties.

Create a 30-, 60-, and 90-day plan to help them transition into the role smoothly. It will give the CoS a clear understanding of what success looks like in their role. Schedule regular check-ins to review their progress, especially in the first few months.

Conclusion

Finding the right Chief of Staff can significantly impact your leadership team and the organization’s success. By understanding the role, identifying the essential skills, and focusing on experience, you can identify a candidate who will be a strategic partner to your executive team.