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As virtual assistants become all the rage, should human chiefs of staff be worried for their jobs?

I saw a question on Quora.com recently about the best virtual assistant programs, such as HeyEdgar.com. Naturally, it made me think, as virtual assistants become more and more popular, will it be very long before the tasks that I performed as a chief of staff can be “outsourced” to a machine? Just how smart are machines becoming, and when every other (clickbait) headline on social media is about the millions of jobs people will lose to computers, how worried should I be?

The short answer is this: chiefs of staff, breathe easy. For now. It will be a while. Even HeyEdgar is a human-assisted model. For chief of staff work, Maddy Niebauer is doing some interesting (mostly human) work at VChief. Perhaps Anthony Goldbloom, in his TED talk, The jobs we’ll lose to machines – and the ones we won’t, sums up as well as anyone what I found in a cursory glance at the literature on machine learning and human jobs:

We have no chance of competing against machines on frequent, high-volume tasks. But … where machines have made very little progress is in tackling novel situations. They can’t handle things they haven’t seen many times before.

At least today. Tomorrow might bring a different picture as machines, well, learn. What I’ve begun to form a stronger opinion about, however, is that chiefs of staff should be paying more attention to how machines can help us. What are those frequent, high-volume tasks that we’re still holding on to? Reviewing departmental reports for keywords or trends? Looking at what your [insert department here] said they could deliver versus what they did deliver, over time, and comparing that against what others predicted to find out who’s most accurate? Finding keywords in contracts or patents that signal negative outcomes later? Identifying the rhythm of your business, comparing it against local school calendars, religious holidays, and industry events to indicate when people are likely to be out of the office and creating your annual calendar for leadership team meetings accordingly? The list goes on. What else could you do with that time if a machine did these tasks for you? For one thing, you might spend more time on the “novel situations.” Here are some examples of novel situations that came up in interviews with chiefs of staff for my book, Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization:

  • How to handle internal and external messaging when a wildly popular former employee is suing for wrongful termination
  • How to tell your leadership team that the entire division, including your position and the principal executive’s position, has been defunded, and how best to help people in the division after that
  • How to handle the conflict between the president and the CFO, and the allies they’ve enlisted against one another, over a seemingly trivial issue that has escalated beyond reason
  • Helping the head of HR figure out how to handle the viewing of porn on work computers, in violation of HR policies, by the company’s founder

What are the situations you’d give up to a machine in a heartbeat, and what are the things you’d do instead? Please share your thoughts in the comments or message me separately.

I help C-suite executives and board members assess whether a corporate chief of staff can help them be more effective, find the right people, and manage the first 90–100 days with a chief of staff. I also help chiefs of staff be as effective as they can be.


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