Nothing gave me more satisfaction as an executive assistant than anticipating what my boss would need before she asked for it.  On several occasions I walked into her office holding a file of information I predicted she would need. Just as she said: “I need…” I placed the file on her desk. Her exclamation, “Excellent!” made my heart jump for joy. Those moments of harmony and sense of partnership were valuable to both of us.  They cemented the feeling that we were in this together.

There is no magic in this anticipation or foresight. The EA’s prescience is not that of a soothsayer.  Rather, it is a skill honed by deep study of the person she is serving and the circumstances at hand.  Experience and the desire to make the executive’s work life as effective as possible contribute to prescience. But there is another element of foresight: intuition – the “gut feeling” sharpened by the cultivation of awareness and concentration.

Travel itinerary preparation is a perfect example of the value of foresight.  While making travel arrangements and preparing an itinerary may seem like a straightforward and simple task, it is an exercise in paying attention to the minutest details of the traveler’s preferences and expectations.  For what airlines does he have frequent flier memberships? How will departure and arrival times affect his personal life and work?  How does he prefer to travel to the airport and how soon does he want to leave the office to ensure he has plenty of time for security and boarding?  Is he a last-minute person or a plenty-of-time person?  Where does she prefer to sit on the airplane and why?  What kind of hotel does she prefer?  Have all the registrations been made for the conference she is attending?  Are there meetings to be scheduled in the city or country she is visiting?  What kinds of advance materials does she need and are they included in the travel briefing folder? How do time differentials affect any conference calls scheduled during the trip?  How quickly does she recover from jet lag?

It can take months to years to learn the traveler’s preferences and needs, and the above is only a small sample of the kind of detail the EA internalizes to lay a clean, polished, and complete itinerary before her boss at the exact moment he or she needs it before departure. Once internalized, of course, this kind of detailed anticipation becomes second nature, even rote, perhaps, for the executive assistant.

Highly developed intuitive anticipation, however, is a different matter.  It comes into play, for example, when a staff member, or perhaps an executive’s peer walks into the office with a problem.  If the EA knows her executive well, she will intuit if this is a problem he will want to deal with immediately, even welcoming an interruption.  Or is the issue something that, for various good reasons, he will want to delay.  Will the assistant handle the situation respectfully and sensitively? Can she anticipate her boss’s reactions and motivations?  Is her intuition a refined and reliable tool transferable to various circumstances?

Anticipation is fifty percent preparation and fifty percent intuitiveness.  Honed by learning from one’s mistakes, it requires constant awareness and concentration. It is one of the executive assistant’s most valuable skills.



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