Why this matters:

Change is a daily reality for any chief of staff. This executive is charged with managing people both upward and downward — and aligning their shifting abilities and circumstances with company goals and the various opportunities and requirements of the marketplace. This question provides insight into how your candidate will take charge of an ever-evolving landscape.

What to listen for:

  • Awareness of the changes and challenges that come with the job
  • A flair for and open-minded approach to problem-solving 
  • The ability to engage and involve others toward solutions

Why this matters:

A chief of staff must play an integral role in developing and executing company goals and priorities. The CEO depends on this person, not only to provide insightful input on where the organization needs to go, but also to effectively mobilize staff and translate a plan into real-world action and results.

What to listen for:

  • Experience contributing to company planning initiatives
  • Ability to translate plans into actionable staff decisions
  • A strong executive presence and communication skills

Why this matters:

As the leader primarily responsible for a company’s workforce, a qualified chief of staff must bring an effective hiring philosophy to the organization. Based on firsthand experience, they should know how to best attract, recruit, and ultimately hire and retain top talent. Their approach can greatly influence a company’s power to draw quality people.

What to listen for:

  • Extensive experience recruiting and hiring staff
  • Specific strategies for recruiting success
  • A personal approach to finding the right hire

Why this matters:

A good chief of staff understands people. More specifically, they can anticipate how key workers will either act or react in a given situation, and plan accordingly. If there are any potentially impactful conflicts or misalignments on the horizon, the chief of staff can help their teams navigate the shifting terrain — in a way that sets expectations, avoids confusion, and upholds positive morale.

What to listen for:

  • An ability to look ahead and foresee challenges
  • A practice of staying in touch with employees both regularly and manageably
  • An empathetic, yet strategic, disposition amidst change

Why this matters:

In addition to understanding how people will behave, a good chief of staff is also aware of their capabilities. They think through, and have taught their direct reports to think through, how to assemble teams whose members complement one another in terms of skills, strengths, knowledge, experience, perspectives, approaches, future potential, and any gaps that others can fill.

What to listen for:

  • Confidence in building effective teams
  • Knowledge of how to build and blend skills — and recognize a person’s future potential
  • Recognition of the importance of diverse perspectives

Why this matters:

As an executive team member, the chief of staff must have the capacity to execute long-term strategic goals. Defining key objectives alongside other leaders, creating a workable strategy, delegating responsibilities to all involved, and ensuring timely progress are all essential skills for a chief of staff who’s responsible for guiding critical objectives from conception to completion.

What to listen for:

  • Ability to translate high-level goals into practical tasks
  • Experience with receiving direction and delegating work
  • Skills for monitoring and improving staff efficiency and productivity

Why this matters:

A good chief of staff consistently promotes and acknowledges staff successes. Not only must they intuitively understand the value and importance of making workers feel appreciated, they must also be capable of doing so across a variety of personalities and situations — from recognizing an individual to celebrating the achievements of a larger group.

What to listen for:

  • Past examples of employee reward programs or initiatives
  • Strong interpersonal skills and an ability to motivate others
  • Familiarity with what incentivizes human performance

Why this matters:

The chief of staff role requires strong communication skills. In addition to sharing information and ideas with executive leadership and staff, the chief of staff must also interface regularly with board members, investors, and other stakeholders. A good chief of staff serves as a reliable communication channel for everybody engaged in the company’s success.

What to listen for:

  • Excellent oral and written communication skills
  • Ability to build strong, trusting relationships
  • History of managing company communications

Why this matters:

Difficult situations are inevitable in every role. But as an executive leader, the chief of staff deals with high-stakes conflict and other issues on a regular basis. A good chief of staff is able to navigate these challenges with poise and self-assurance. They can take a firm stance and make others feel heard and included as they skillfully guide teams toward resolution.

What to listen for:

  • Empathy and strong listening skills
  • Ability to identify the crux of an issue
  • A track record of successful conflict resolution
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