Secretary jobs in the age of AI

A guest post by Hollis Robbins

Photo by Jean-Louis Paulin on Unsplash

A lot of people are thinking very hard about the future of work right now, given the explosion in the capability and popularity of generative AI. I recently co-wrote a post about how large language models and AI art might change creative jobs, but that really only scratches the surface. Job roles and tasks have shifted continuously since the start of the Industrial Revolution, and I expect this trend to continue in the age of AI.

Today’s guest post offers a highly creative idea about what the jobs of the future might look like. Hollis Robbins is the Dean of Humanities at the University of Utah, and has studied organization theory and bureaucracy. In this post, she predicts that secretaries could be in demand in the AI-driven future — not as old-style administrative assistants, but as confidantes and advisors.

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The ‘secretary’ literally means ‘person entrusted with secrets,’ from the medieval Latin secretarius, the trusted officer who writes the letters and keeps the records. The secretarial role originally conceived was far more central than roles with the “assistant” title now standard. In the nineteenth century, the secretary was a prized role for young men: a diplomatic assistant, the overseer of correspondence, the superintendent of the files, and in many cases, an apprentice manager—well-positioned to learn at the elbow of the man in charge, someday to be the man in charge. The invention of stenography machines and commercial typewriters at the end of the century transformed the business world. Dozens of secretarial schools were established, most famously, the Katharine Gibbs schools, “the Harvard of secretarial education.”

Training for high paid secretarial roles in the mid-20th century was rigorous: a fifty hours-per-week workload to learn typewriting, stenography, business and social correspondence, organizational systems (office filing, business archives, inventory management, taxes), budgeting and finance, and social conventions. Top secretaries were expected to understand municipal administration, the relationship of business to government, local party politics. Cultural competence was critical. Art and music appreciation classes were required, as well as English literature (and grammar), and tasteful behavior (how to adjust a hat, how to greet guests, how to hold a cocktail in a crowded room).

Secretarial jobs propelled millions of 20th century women into financial independence, whether they spent their career in the role or advanced into management or executive positions.

I have been thinking about the “keeper of secrets” aspect of the old-school secretary now that ChatGPT is being touted as the final answer to a cheap, reliable assistant available to all, from job seeker to CEO. Indeed, ChatGPT is a kind of assistant, the way Google is, but let’s separate the assisting tasks from the assistant position, which is, still, woefully low paid. The general idea is: why hire a person when you’ve got an answer machine in your pocket? Not only is ChatGPT cheaper (even when it stops being free) but the very concept of ‘assistant’ is vexed, particularly among assertive Gen-Z and Millennial women who are expecting to start at the top.

And yet I predict that ChatGPT is going to drive a comeback of the “keeper of secrets” role, paid well to screens calls and emails, who will make whoever can afford a good secretary much more efficient. If you’re in a role of any importance, you’re going to be flooded with AI-written communication, much of which will be incorrect. You’re going to need to hire someone with a head of their shoulders to sort through it. Why not a secretary, if a culture shift could bring back both the job and title?

Second wave feminism is partly to blame for the scorn of the secretarial role by ambitious women. In 1971 Gloria Steinem offered the worst possible advice ever given to Smith College graduates: “perhaps a whole generation of us should fail to learn how to type.” With the doors of top universities, law schools, medical schools, and business schools finally opened to women, the secretarial role was sadly disposable.  

Steinem could not know that in just a few years, most professionals would become their own secretaries, as email and the internet, Expedia, OpenTable, Google Docs, Google Calendar, and TurboTax meant that you would be typing your own correspondence, keeping your own calendar, keeping track of your own documents, making your own lunch, dinner, and travel reservations. We all self-secretary now. Most of us do it badly, particularly when it comes to filing, which most people don’t do at all. A thousand software companies bloom every year with personal assistant apps for email, note-taking, personal and office filing systems and document databases. I know people in their thirties who have never owned a filing cabinet and who keep tax records as email attachments in the cloud.

Getting rid of ‘the secretary’ as both a person and portfolio of responsibilities has been bad for everyone. Imagine how productive you would be if you had beside you an entity (let’s say an individual) with the following functionality:

• Reviews and processes 90% of your email;

• Has a working relationship with all of your colleagues, your direct reports, your customers, your external stakeholders, and your immediate family;

• Embodies and models organizational norms and culture: intensity (high or low), formality (high or low), professionalism (presumably high).

• Organizes/files all correspondence and key documents methodically;

• Organizes and rearranges your calendar according to changing priorities;

• Tactfully communicates delays, postponements, cancellation of meetings;

• Ensures your preferences in travel, accommodation, entertainment, dining;

• Remembers birthdays and anniversaries; suggests gifts;

• Serves as a sounding board; advises caution when appropriate;

• Keeps secrets.

One of my first jobs out of college in the 1980s, secretary to the liquor sales advertising executive at The New Yorker magazine, taught me more about how the world works (and how the magazine business worked) than most of my college education. My boss was courtly, exacting about which table he wanted at particular New York restaurants, wryly generous regarding the birthdays of ex-wives, and fantastic at his job. While I kept meticulous account files, the details were also in his head. When I would pull up comparisons for him, it was for confirmation of his own memory and to tell stories about how to “upsell” a client and when. But if he had suddenly vanished, the records would remain, perfectly organized, in the files.

Before the pandemic, there was a spate of think pieces about the role of the office support staff: about the vanishing executive assistant, and low-paid and beleaguered assistants. Loss of information flow and loss of culture have been the biggest reported casualties of a fragmented work force, as colleagues were separated and isolated in their home offices. As we rethink and rebuild office culture, it’s worth considering how self-secretarying contributed to office fragmentation long before remote work. The old-school secretary role is in fact essential to information flow and establishing cultural and professional norms—even in a virtual workspace—not to mention serving as a productivity multiplier and a training ground for future managers and leaders. A good secretary will use ChatGPT to help manage information flow but will focus most working hours tasks that are unique to each leader – the highly specialized tasks, including sensitive correspondence, that generalized intelligence can’t accomplish. Everyone wants a secretary so competent that if you say “get me a live elephant for the board meeting this afternoon” you will get an elephant (with guidance from a chatbot on the best vendors), but who also might say to you, “really? Is that really a good idea?”

The mid-20th century Gibbs training speaks to the competence, intelligence, and cultivation expected of top secretaries as well as the indispensable role secretaries played in the companies that hired them, which was simultaneously to keep an organization productive and human. Good secretaries are repositories of information and enablers of backchannel communications. Secretaries know where the files are, where there is an extra five minutes on a calendar, when brusqueness is not targeted at you but rather indicates anxiety about a sick child or indigestion, how and when to reschedule a meeting and how and when to smooth rough waters. One can’t imagine this sort of secretary working for Sam Bankman-Fried at FTX. This absence might have been an early warning sign in an era where one expects a CEO to have a highly competent personal gatekeeper.

The secretary as confidential advisor has never had a place on organizational charts. The secretary’s purely functional role began to fragment with advances in telephone and computer technology and the copy machine. With the exception of Rosabeth Moss Kantor’s Men and Women of the Corporation (1977), which spends a chapter characterizing secretarial power as “patrimony,” organizational theory and management books from Douglas McGregor’s The Human Side of Enterprise (1960) onward ignore the role or, in the case of Robert Townsend’s Up the Organization (1970), argue for doing without staff altogether. Clerical tasks that could be replaced by automation should be replaced, in large organizations and small. The trend played out on television. While Perry Mason (1957-1966) was supported by Della Street and Joe Mannix (1967-75) by Peggy Fair, in 1974, The Rockford Files opened with an answering machine. Jim Rockford worked alone.

How much more productive would you be with a good secretary? Consider an executive earning $1.5 million per year. A secretary earning $120,000 who works for one executive alone needs to save that boss only 5 hours of a 60-hour work week (8% more productive) to make the numbers work. As Melba J. Duncan argued almost a decade ago in the Harvard Business Review, a good executive assistant will more than make up that deficit. The key tasks? Managing a schedule, triaging email, organizing files, overseeing workflow, and perhaps the most time-saving function of all: taking dictation (throw out those terrible voice apps). There are also the harder-to-define tasks, like maintaining a general sense of order during a stressful week or managing the little things that can chip away at an executive’s time and focus.

What does the secretary get out of this role? Does the job provide a real springboard for leadership, or is it fulfilling in and of itself? Both. For a young Michael Ovitz, founder of Creative Artists Agency, working as an assistant to a top executive at the William Morris agency in the 1960s, with unhindered access to the corporate files, the secretarial role was foundational for his future success.  

Like many in higher education leadership, I’m concerned about ChatGPT but I’m more concerned about student readiness, the decline of corporate training programs, and the general economic future for college graduates, particularly in the humanities. I wonder about the role colleges and universities could play in training students to practice skills that AI can’t deliver and that employers value—how to show up early, how to deliver bad news, how to give and accept criticism, how to deal with an office visitor the team leader does not want to see, how not to be flaky, how to organize files, how to handle confidential information, and most importantly, how to write and answer emails promptly, swiftly, briefly, and with tact. These skills cannot be automated, cannot be outsourced, and may provide a competitive edge to businesses that value them. The first step is to put the position on the org chart and value it.

The idea of posting a job ad for a “secretary” sounds comically old-fashioned, potentially embarrassing for both the employer and the applicant. A snappy new name—enterprise administrator, management apprentice, organizational attaché—would undoubtedly make the role more appealing. But to be the person literally entrusted with secrets seems fundamentally more accurate to the role.  

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