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How AI-ready are you as a Chief of Staff?
Take our AI Readiness Diagnostic to find out where you stand and what to do next.
- Observer: You're aware AI exists, but it's not part of how you work yet and the window to start is closing.
- Experimenter: You're using AI for individual tasks, but you haven't rewired how you actually operate.
- Practitioner: AI is part of your workflow. Now the question is whether you'll lead your organization's transformation or just your own.
- AI Native: You're not just using AI, you're rebuilding the role around it, and the community needs what you've learned.
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If you haven’t yet realized that the way companies work has changed, it’s time to face reality. Off-the-shelf AI systems can now do a substantial portion of tasks that white collar workers do today, and the improvement curve is steep. Chiefs of Staff are not immune to that change.
At Chief of Staff Network, we view it as our responsibility to help Chiefs of Staff around the world connect and grow. Historically, that has been around skills like managing OKRs, running effective offsites, improving corporate culture, and optimizing internal communications. Some of these skills will still be important in a year or two.
Other skills will be entirely taken over, or made obsolete, by AI. Today - as in right now - it can generate a good first draft of your next board deck and write your next investor update. It can provide (good) advice on tough personnel issues with a little bit of context. It can create an internal web app to track and update OKRs and suggest new ones. It can generate a full plan for an executive offsite, gather venue options, and email those venues for quotes. It can create and update a financial model in Excel. It can take product usage data, qualitative input from your sales team, and customer feedback and create a PRD for a new feature, then build that feature and push it to production. And these are just a few examples.
You’re likely already thinking: if these tasks are taken off your plate, what will your role be? Your answer might be: “Well, I’ll work with our Exec team to move our strategic priorities along faster.” But, large parts of their jobs (and their teams’ jobs) will be done by AI, too. It will take longer for Chiefs of Staff in government and highly-regulated industries to feel the impacts (fax machines are still widely used in healthcare, after all). At larger companies, these changes will take a longer time to take hold, too, whether because of organizational inertia, employment law, time to get leadership buy-in, or data privacy and security concerns. Still, technological changes of this magnitude don’t leave any organizations untouched.
Indeed, there’s a case to be made that the Chief of Staff role will disappear entirely, with Principals instead being supported by always-energetic, instantly responsive agentic systems with the ability to extend the Principal’s capabilities without the back-and-forth that any human relationship requires.
To avoid that future, Chiefs of Staff must return to the fundamentals of the role, instead of clinging to the old ways of doing things. You must rethink how you can best serve your principal and fundamentally rebuild your organizations with your unique combination of insight and relationships, with the transformative capabilities that AI now offers.
Why do Chiefs of Staff Exist?
Fundamentally, Chiefs of Staff exist for two reasons: because their principals can’t be everywhere and make every decision, and because organizations of any real size experience coordination problems that are best solved by someone with broad context and significant direct (or implied) authority.
You can envision a company that’s just a CEO perched at the top of a massive army of AI agents, with complete transparency into all actions being performed and absolute authority to change the course of the business without the time-consuming work of cajoling human workers to change what they’re doing. For small businesses, this may be possible. However, for any organization that generates large amounts of data, requires a large number of decisions, interfaces with the physical world in any way, or requires sustained coordination with people outside the organization, human workers will still be part of the equation (for now, at least).
While large-scale layoffs now seem possible across most industries (and are already happening in tech), the most likely near- and medium-term future involves leaner teams that have both human and AI workers. Customer- or public-facing teams in particular are likely to continue to be more human-intensive, though their work will be supported with agents that help fewer, higher-performing individuals perform at their peak.
In this likely reality, here are the fundamental building blocks of the Chief of Staff role, how they are handled today, and what Chiefs of Staff should be working to build now to retain their roles and maximize the success of their organizations:
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As you can see, many of the task-level items that Chiefs of Staff (except for the most senior Chiefs of Staff at very large organizations) typically spend time on can instead be done by AI systems. With this additional bandwidth, Chiefs can now focus on two things: setting up and maintaining the systems that help their Principal and their organization perform at their peak, and doubling down on the tasks that only humans can (or should) do.
What should a Chief of Staff do to transition to this new reality?
To effectively set up and maintain the AI systems that help their Principal and organization, Chiefs need to take on the mantle of AI champion within their organization. That means continually learning about, and experimenting with, the cutting edge systems. It means leading by example and showing others what can be accomplished with AI. It means gaining buy-in to spread those systems throughout their organizations, even if it means full-scale transformation.
Being AI-first is no longer an optional part of the Chief of Staff job – it’s the core of it.
To double down on tasks that only humans can do requires more inner work. That means cultivating virtues like curiosity, wisdom, and equanimity in the face of unsettling change. It means spending more time with other people, listening to them, and learning from them. It means finding sources of information that AI doesn’t have access to, whether that’s rare books, off-the-record conversations, or talent that hasn’t been identified yet. It means becoming a better manager (of people and agents). It means becoming someone that people want to be around.
If that sounds a little more nebulous, that’s because it is. We don’t know the exact path that the next few years will take us on – few, if any, predicted we’d be where we are today – but spending time cultivating these traits will be worth it because they will make you a better Chief of Staff and because they’ll make you a better person.
Learning broadly – from books, articles, podcasts, music, art – will help you cultivate the virtues you’ll need. But, the most important thing to do is to spend time with other people in similar roles, ideally in person. Those conversations, complete with body language, social awkwardness, spontaneous epiphanies, and fun, are where real change occurs.
Will all Chiefs of Staff evolve to meet this moment? It’s unlikely. But, the role itself will persist: increasing organizational complexity will require highly capable, cross-functional operators and principals still need trusted consiglieres with broad context. For organizations to transition to becoming AI-first will require steering from trusted operators, too.
While this level of change and uncertainty can be frightening, the tools to navigate this uncertainty and shape the future of your Chief of Staff role are at your disposal. All it takes now is for you to face reality and step into that role today.
Convinced? Here’s what to put on your to do list for this week.
- Take one recurring task from your workload and automate it
- Block two hours to experiment with a frontier AI tool on a real work problem
- Have a conversation with your principal about how AI changes your shared priorities, and the priorities of the organization
Where do you actually stand?
We built the Chief of Staff AI Readiness Diagnostic to give you an honest assessment of your AI adoption across the core building blocks of the role — gathering information, managing projects and people, long-term planning, and supporting your principal. It takes ~5 minutes, scores you across four tiers, and gives you a clear next steps.
