CEOs and other top-ranking executives these days are glued to their computers like the rest of us. But a high-powered executive assistant is still an essential fixture in the executive suite, even if her boss types his own memos.
In fact, she has taken on more important responsibilities in an increasingly fast-paced business world.
One thing has remained a constant. She still serves as the gatekeeper for her busy boss.
How to Present Yourself
How you present yourself to the executive assistant can make all the difference in your gaining access to the decision-maker. It amazes me when someone is condescending to an assistant. She holds the key to the executive suite and deserves your respect.
In trying to get your first appointment, be sure you know the correct spelling of the assistant’s name and her exact title. Don’t assume she’s “just” a secretary.
Learn all you can about her (or him). If you know other people in the company, ask them about her special interests. Does she like the ballet or is opera her favorite pastime? Does she have children?
Has he recently become an uncle or recently adopted a dog or cat? Is he a member of a band on weekends or on a sports team? Acknowledging these interests can be conversation starters. She may have a LinkedIn profile, always a good place to start when you’re researching someone.
Once you’ve landed an appointment, take your cues from the environment. You may see fresh flowers on her desk and pictures of her with her family on the credenza.
Everyone has an ego and likes to receive compliments. A simple,“What a lovely photo. Is that you with your family?” is sure to get a smile. When that happens you’re on your way to making a friend.
If at First You Don’t Succeed
It isn’t always easy to get past the gatekeepers and gain their trust. 
A number of years ago we were asked to provide presentation training for the partners of a management consulting firm at a meeting in Barcelona. It was our first project with the firm, which has since become one of our most valued clients.
Each partner had an executive assistant and none of them were happy with “this woman” telling their bosses how to speak. The hostility was obvious. We made a concerted effort to win them over. I took them all for drinks in Barcelona and didn’t treat them any differently than their bosses.
They finally recognized that I was there to assist their bosses in becoming better presenters and not to try and outshine them.
Build on Your Relationship
Once you’ve gained the trust of an assistant, build on your relationship by keeping her in the loop. Copy her on correspondence with her boss so that she’s aware of your appointments with him and the projects you’re working on.
An assistant may be reluctant to ask her boss for clarity when given an assignment.
If you see she is struggling, and you were present at the meeting, then explain what you heard. You might say, “Would you like to review the details of the project so we’re all in sync?”
Offer to prepare a memo summarizing the discussion. Make yourself the valuable resource she knows she can rely on for advice.
Keep top of mind by sending small gifts throughout the year. Send her a box of candy or a bottle of her favorite perfume to celebrate a birthday. Perhaps he likes gummy bears or dark chocolate.
It’s even nicer to receive a present when it isn’t a special occasion. We once bought every promotional gift box of Godiva chocolate that Lord & Taylor Manhattan had in stock. They only contained a few small pieces of chocolate. We sent them to every executive assistant we delt with on a regular basis. It wasn’t a big deal, just a reminder that we were thinking of them.
People appreciate and remember your thoughtful gestures. Just recently, an executive assistant told me that she still has the paperweight on her desk that I gave her ten years ago.
Initially, it’s a challenge to get past the gatekeepers. But over the years many of them have become good friends. I show them the respect that they deserve. And their bosses – my clients – appreciate that I do.
