You may have read the title to this piece and thought “Absolutely not!” and with some justification. After all, the Chief of Staff role has been around in the U.S. since at least the Eisenhower administration (though John Steelman, Assistant to President Truman, could make a compelling case that he was really the first). And going back a few more millennia, figures like Hemiunu, Pharoah Khufu’s second in command who helped manage the state, led the Royal Scribes, and oversaw the construction of the pyramids, filled Chief-of-Staff-like roles as early as 2580 BCE.
But AI may put a stop to this 4,600 year tradition. And it may do it soon.
How? Let’s get into it.
A little over a year ago, we put a stake in the ground. We argued that AI was a can’t-miss opportunity for Chiefs of Staff to use their singular skills, access, and agency to expand their portfolios, transforming their role into “Chief of AI”.
17 months later, we think it’s fair to say that we were right. Our most popular events center on the implementation of AI, more than 80 percent of attendees at our NYC Connect conference last year said that they were in charge of AI initiatives at their organizations, and we’ve collected dozens of novel AI use cases driving real ROI in our recent survey (participate here if you haven’t yet). We’re also using AI ourselves to make our work more efficient.
So what has this taught us?
Most Chiefs of Staff’s core tasks revolve around:
- Strategy & planning
- Leadership team management/wrangling
- Internal communications
- Special projects
These could be condensed into a one-line description: distill the executive’s vision into a plan and marshall the entire team’s efforts’ towards that plan.
Already, AI can transform substantial parts of each of these areas. For example:
Strategy & Planning: need help generating OKRs for every department? Upload your goals for the year, your org chart, your last four board decks, and any broad company strategy docs you have to a project in chatGPT or Claude and ask it to come up with OKRs - it’ll do a pretty good job.
Leadership team management: using the above OKRs generated above, your tool of choice can put together an agenda for an executive offsite, recommend venues and activities, and even draft emails announcing the offsite and describing any pre-work that the executive team needs to complete.
Internal Communications: keep your AI notetaker on during the executive offsite (turning it off, of course, during any legally sensitive conversations!). Combine the transcripts with the OKRs and any plans that emerge to draft talking points for the executives at their team meetings, agendas for any 1on1 conversations that they need to have with key staff members, and an email to the whole team recapping the offsite.
Special Projects: use Perplexity to create a monthly competitive intelligence report on your key competitors, partners, and customers for distribution to the executive team.
The work described above likely represents several weeks’ worth of work for an experienced Chief of Staff. How long would it take for someone experienced with these basic AI tools? Hours, if not minutes.
One could make the argument that these are cherry-picked examples, and that the true week-to-week work of a Chief of Staff is much more difficult and varied than what today’s AI tools could handle. Perhaps. But if you break down the fundamental units of work underlying many of these tasks, they share commonalities that AI tools are good at today and will be great at tomorrow.
Taking this at face value, a well set-up AI system could probably handle 75 percent of an average Chief of Staff’s workload.
Fair, you could say, but the magic is in the final 25 percent. The anticipation, the convincing and cajoling, the innovation - these things aren’t easily replicable. And besides, you’re far from average, right?
Perhaps, but with AI’s rate of improvement, how much would you bet on this staying true for the next ten years, especially if you’re not using the tools to make yourself better along the way?
Faced with this reality, you have a few options (if you set aside the non-choice of burying your head in the sand or getting out of the profession altogether):
Option 1: Situate yourself in a highly-regulated, highly physical, or extremely change-resistant industry. The AI future won’t be evenly distributed, and industry idiosyncrasies or government regulation could delay the change in your industry. But while this could put off the inevitable for several years, unless you’re near retirement it’s unlikely to take you through the remainder of your working years.
Option 2: Double down on the fundamentals of being an exceptional Chief of Staff, learning everything you can from peers in Chief of Staff Network and outside the community. Your value won’t come from automation, but from the relationships you build, intuition you develop, and influence you wield to keep the business moving forward.
Option 3: Fully embrace AI and try to put yourself out of a job, while taking the lead on AI initiatives internally. We call this the “Chief of AI” route.
Option 3 strikes us as the best approach. Predictions of what the world will look like in a post-AGI world will likely be wildly different and wrong, but proactively finding ways to make your organization stronger and making yourself more valuable at the same time is the real essence of the Chief of Staff role.
The old playbook, being the behind-the-scenes force that keeps everything running, needs an upgrade. Instead of measuring success by projects completed, meetings facilitated, or executive bandwidth saved, the resilient Chief of Staff must focus on creating AI-leveraged outcomes for their organization.
The strongest Chiefs of Staff will be the ones who turn AI from a passive tool into a force multiplier for the business. How much faster are strategic initiatives moving with AI automating execution? How much more aligned is the leadership team when AI can help to synthesize insights across the organization? Embracing AI gives Chiefs of Staff the opportunity to correct one of the core weaknesses of most Chief of Staff roles by tying their work to specific, measurable business outcomes.
What does a Chief of AI role look like?
If your current role involves wrangling people to do the things you need to get done, then stepping up into a Chief of AI role means continuing to do that, but adding a bunch of tools to your toolbox.
You’ll need to keep up to date with the latest developments in AI, testing them and evaluating whether new tools are right for your organization and its unique challenges. You’ll need to continue to understand your business deeply, looking for ways to grow faster, increase margin, and improve your competitive position. You’ll need to work with your CEO to more deeply understand her vision and push it further, helping them to understand the new frontiers unlocked by AI. And you’ll need to push AI into every corner of your organization, whether working with existing leadership or working around them, if the situation calls for it.
In a fully-formed state, you’ll sit at the control console of your business, tweaking processes, evaluating new systems, adjusting goals, and managing both humans and AI agents, all in service of your company’s ultimate objectives, set in partnership with the visionary leader at the helm.
Where to Start
If you agree with us, there are some things you should do, starting today.
First, continue to engage with your peers in Chief of Staff Network. Learning from peers (whether about AI or other topics) and building relationships will serve you well, no matter what the future holds.
Second, study our upcoming AI use case report to figure out how other companies are applying AI to solve their business challenges.
Third, think from first principles about the products, processes, and people that keep your organization running. How could you decompose those and rebuild them with AI? Would it be possible to do them faster, with higher quality, or less expensively?
Finally, stay tuned for much more content from Chief of Staff Network, including training and playbooks on incorporating AI into your organization and new ways to monetize those skills.
Chief of Staff Network isn’t going anywhere, but we will continue to evolve to keep pace with the times. We’re dedicated to helping Chiefs of Staff - and the organizations they work for - grow while cultivating a sense of belonging amongst our members, and that won’t change.
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