Blog Post

The Top 6 Skills Every Chief of Staff Must Master (and Where AI Can Lead the Way)

Eddie Wang
Aug 4, 2023
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As the right-hand person to a high-level executive, the Chief of Staff typically plays a pivotal role in ensuring the smooth functioning of cross-functional teams and the effective execution of strategic goals.

As the right-hand person to a high-level executive, the Chief of Staff typically plays a pivotal role in ensuring the smooth functioning of cross-functional teams and the effective execution of strategic goals and risk management. 

This multifaceted position demands a diverse skill set, encompassing both hard and soft skills. In this article, we will explore the top skills every Chief of Staff must master. We’ll also explore which of these roles emergent technology such as Xembly’s AI Chief of Staff can take on and which ones are better left for humans.

As the scope and challenges of the average office job continue to grow, the need for highly effective support for every individual - not just the C-suite - has only risen, leading to a new wave of demand for best-in-class work assistance.

Scheduling Expertise

One of the most important things that an executive does is to convene teams together to collaborate in regular or ad hoc meetings. To provide effective leverage to their leader, a Chief of Staff must be a master scheduler, adept at managing complex calendars and coordinating appointments. Efficiently scheduling meetings with various stakeholders while taking into account the executive's availability and priorities is crucial. Anticipating scheduling conflicts and finding creative solutions to find time with multiple team members is a crucial skill. 

Verdict: Win for AI, thanks to the speed of AI

In this area, an AI Chief of Staff is well positioned to augment or even replace a human’s support efforts. By inputting your meeting preferences, an assistant like Xena can quickly suggest meeting times from a simple Slack or email message, much faster than any human assistant could. 

Reviewing 10 calendars for an open timeslot would be any assistant’s nightmare. In these cases, AI can provide instant scheduling suggestions by incorporating a user's natural language prompts to solve even the trickiest calendar Tetris puzzles.

Scheduling workflow with Xena

Meeting Note-Taking Proficiency

One of the critical responsibilities of a Chief of Staff is to attend meetings alongside the executive and take comprehensive notes. These notes serve as a record of important decisions, action items, and key takeaways from the discussions. The ability to capture and organize information accurately ensures that nothing falls through the cracks and that all follow-up tasks are appropriately assigned and executed.

Verdict: Best with humans + AI together (AI for accuracy, with added human context)

AI executive assistants like Xena are capable of taking over the critical responsibilities of note-taking in meetings. Rather than relying on human memory and cognition, AI assistants can leverage transcriptions to create concise bullet point Summaries alongside delegated Action Items. For participants seeking exact recollection, Xena can also produce a full transcript alongside a full video recording, enabling easy reference and searchability of important details.

However, sometimes a little bit of additional context can make meeting notes even richer. By leveraging AI, human Chiefs of Staff can stop worrying about tactical note-taking processes and tracking action items and focus on participating in the meeting. A little human review of the AI generated summary and action items after the meeting ensures that the results of the meeting are appropriately contextualized and keep the business moving forward.

Summary notification from Xembly in Slack

Priority Management Skills

Given the dynamic and fast-paced nature of the role, a Chief of Staff must possess exceptional priority management skills. They must help the executive identify and focus on the most critical tasks and initiatives. This involves constantly evaluating competing demands and aligning the executive's time and efforts with the organization's strategic goals.

Verdict: Best with humans + AI together (humans for prioritizing, AI for tracking)

In this area, humans excel at truly proactive strategic level thinking. A new quarterly initiative might involve a complete reinvention of an individual’s calendar. For more one-off needs like scheduling a follow-up meeting or a follow-up task, Xena can help ensure that nothing falls through the cracks by meticulously organizing information and action items, making it easy to track and follow up on tasks. 

Putting it all together, an AI Chief of Staff can provide efficient timely support that translates into a dynamic schedule that meets the challenge of every workday while a human approach can add that extra layer of cultural and contextual awareness to better align broader shifts in priority management.

Xena works proactively and reactively to help you manage everyday tasks

Effective Communication

Clear and concise communication is a fundamental skill for any Chief of Staff. They must be able to articulate the executive's vision and objectives to various teams and stakeholders. Moreover, being an effective communicator helps in facilitating collaboration and maintaining open lines of communication throughout the organization.

Verdict: Humans outperform AI, but AI is great at creative draft generation

As tools like ChatGPT become mainstream, smart workers are exploring how they can make text communication (and even image or video) better with AI support. An AI Chief of Staff like Xembly can also draw from GPT-4 as well as proprietary data sets to help conjure written communication such as emails, blogs, and even meeting agendas.

Of course, communication doesn’t exist solely over email, blogs, and Slack. In places where human delivery and interaction are necessary to overcome the hurdles of office politics, there’s no replacing the human touch.

If you haven’t explored the potential of AI in this space, we recommend using a tool for generating some initial ideas / first drafts. A very common example that we see at Xembly is the use of our AI Chief of Staff for drafting agendas for meetings and workshops.

Drafting an agenda with help from Xena

Problem-Solving Aptitude

Chiefs of Staff often encounter complex challenges that require quick and effective problem-solving. These everyday work crises are unpredictable and require a high degree of expertise to navigate. A proactive problem-solving approach can often address issues before they escalate and impact the executive's agenda.

Verdict: Human

For truly one-off problems, human Chiefs of Staff have far greater contextual awareness and autonomy to troubleshoot a situation and identify the right remedies. A general purpose AI-system that could run your business for you may work for a simple e-commerce business, but it’s not a viable solution for the needs of most complex businesses with multiple inputs and outputs.

Networking and Relationship Building:

Building strong relationships with internal and external stakeholders is essential for a Chief of Staff. Networking helps them gain support for the executive's initiatives, fosters collaboration, and facilitates smooth operations across different departments.

Verdict: Human

The timeless art of “schmoozing” and “water-cooler talk” is not easy to navigate and often ignored in the modern workplace. Building a relationship involves understanding what different people and building relationships during low-pressure situations in order to create an environment of trust and effective communication. As every individual who’s ever worked in a big company knows, having the right answer is frequently less important than knowing the right people to talk to and knowing how to convince them that you’re right. 

Having a human chief of staff enables executives to amplify their relational reach and help foster the soft and hard consensus needed to move projects forward. 

Ultimately, the decision between AI Chief of Staff and a human Chief of Staff is less a matter of either/or and more a matter of both/and. Both AI and human support provide unique value that cannot be easily replicated or replaced and the smartest executives and their teams are embracing AI accelerants to help get the job done.

The need for a generalized AI Chief of Staff solution for every knowledge worker is only becoming more and more clear while the need for human chief of staff support for executives is still undeniable for individuals with extensive responsibilities and reports. Better yet, a well-equipped team with a human chief of staff knowledgeable on how to work alongside AI support may yield the greatest productive impact. 

To get started incorporating an AI Chief of Staff into your team’s processes today, visit and try Xena for yourself.

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