AI and the chief of staff

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Navigating the Jagged Frontier: A Special Report from the Chief of Staff Association Executive Education Programme at Harvard Business School

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2025 was the year AI went mainstream. It was no surprise then, when Time Magazine named ‘The Architects of AI’ their 2025 person of the year. Not a day goes by without an attention-grabbing headline (possibly run through AI in advance) signalling its value or threat.

The cohort came to Harvard Business School with mixed experiences and familiarities with AI systems and agents. Some were already integrating AI tools into their daily workflows, others barely used them, and a minority were unsure where to start or which tools to use.

AI as a chief of staff thought partner

Participants had the advantage of tackling AI under the guidance of Mitchell B. Weiss. In addition to leading the seminar Teaching with AI, Weiss is a former chief of staff, ideally placed to understand exactly the challenges chiefs of staff face and how AI agents can help them organise and prioritise their time and workloads. Weiss’s key ‘prompt’ for participants was ‘stop thinking about AI as a threat to your judgement, or a shortcut around it, and start thinking of it as a thought partner: something you can work with and not something that works for you.’ The concept of thought partner was familiar to those in the room, given they performed that role for their principal, challenging assumptions and generating options which had previously not been considered. Weiss’s framing shifted the room. Participants who had approached the session cautiously began to see a different kind of question, not ‘will AI replace what I do?’ but ‘how do I use it to do what I do better?’

Informed curiosity

With AI reframed as a thought partner, Weiss led the cohort through a practical exercise where they used generative AI tools to tackle real problems. On one hand, participants saw how AI could accelerate the kind of work chiefs of staff do constantly: synthesising information, generating options, stress-testing arguments and drafting communications at pace. On the other hand, the exercise was also designed to show where AI fails: where it confabulates, where it produces confident-sounding responses that are simply wrong and where uncritical use leads to poor output. As one participant put it, ‘The exercise clearly demonstrated AI's limitations.’‘Knowing when AI is correct and successful or incorrect and unsuccessful is part of the informed curiosity a CoS must bring to the table. Put another way, the capacity to use AI tools effectively also involves understanding how and where they fall short.’

Where chiefs of staff are using AI

The session surfaced a candid picture of how the cohort was using AI in their roles. Usage ranged from basic drafting and summarisation to more considered applications in meeting preparation, stakeholder analysis and decision support. A number of participants were using AI to research before briefing their principals; to structure thinking on complex problems; and to save time on tasks that would otherwise consume hours of their week.The appetite to do more was clear. Several participants identified specific areas where they planned to act directly after the programme. ‘I will double down on AI implementation to create more structure and efficiency,’ said one, ‘helping us both save time and focus on higher-value priorities.’ Another was already planning to help their principal become proficient in at least one AI tool. A third spoke of using AI to generate ideas, then deploying different tools for different scenarios; a sign of a more mature and considered approach than treating AI as a single solution.Chiefs of staff operate at the intersection of information, people and decisions. They are asked to synthesise fast, advise well and communicate clearly, often with incomplete information and limited time. Those are precisely the conditions where a well-used AI tool can bring value in filling the gaps and speeding up delivery.

The advantage goes to those who start

The chiefs of staff who will lead most effectively in the years ahead are not necessarily the ones with the most technical knowledge. They are the ones who combine curiosity with judgement; who know how to work with AI tools, question their outputs, and apply these results to decisions that still require human insight and accountability.Weiss frames this well. He uses AI the way he might work with a capable research assistant; with clear direction, genuine engagement and a healthy scepticism about what it produces. AI adoption has real-term consequences for businesses, as well as for chiefs of staff in their careers. The 2025 PwC Global AI Jobs Barometer, based on analysis of close to one billion job advertisements across six continents, found that roles requiring AI skills now command a 56% wage premium, up from 25% the year before. As a result, it benefits chiefs of staff to develop their skills in this area. The advantage, as this cohort understood, goes to those who start.ReferencesPricewaterhouseCoopers, The Fearless Future: 2025 Global AI Jobs Barometer, AI makes people more valuable (2025, PwC), p. 2.