Why is Anticipation a Crucial Skill for Executive Assistants?

In this article, author Jan Jones discusses anticipation and why it is a crucial skill for executive assistants.

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FlyPrivate: A group of assistants who are “investigating” your book in their book club are asking if you’ll expand on Anticipation, one of the crucial characteristics for assistants you discuss in your book. Is it still the most desired characteristic by executives as you say in the book?

Jan Jones: Assistants frequently ask me about anticipation. Probably because their executives value it so highly. A quick poll of executives reveals that anticipation continues to be much desired because it primes the executive to stay ahead and in control. It gives the executive a huge advantage to have a prepared, forward-looking assistant.

Importantly, good anticipation ability helps executive assistants become more strategic in their thinking. It is key to how they can function successfully in their role.

“When you are thinking strategically you are figuring out how to overcome a challenge. What actions are you going to take, and what forces are you going to deploy?” That comes directly from revered strategy expert Richard Rumelt, who wrote the book Good Strategy Bad Strategy.

Obviously that’s a thumbnail assessment, but I want to show it to you in relation to anticipation, because that’s exactly what you are doing when you anticipate, when you look ahead and chart a course. What actions are you going to take to handle a challenge, or take advantage of an opportunity? In order to anticipate, you have to know what you are facing. Then you can problem solve. Then you can make preparations so that you and your executive are not blindsided, or missing out on competitive advantages.

This is why I say Anticipation and Resourcefulness are identical twins, because in anticipating you also have to take into account “what forces you are going to deploy.” What resources will you need? Since I’ve been asked about anticipation, I’ll stay focused on that characteristic for this discussion, even though for me anticipation and resourcefulness are inseparable for performing the EA role effectively.   

Learning to look far out helps you to develop quicker mental reflexes, which strengthens your ability to respond. Don’t wait until a crisis is right under your nose before you give it your attention and take action. Be ready for what’s coming by constantly assessing situations. Get used to scanning the horizon and your environment in order to stay on top of what’s going on. Learn to recognize the signs that can guide your direction appropriately. Instead of always coming from behind, struggling with your workload and constantly playing catch-up, be ready to deal with whatever is coming at you.

Anticipation is an executive assistant’s best friend. It means events don’t overtake you. It buys us the precious commodity of time, so we aren’t always in a tailspin when situations are fast and furious. This may be one reason why assistants feel overwhelmed. They blame it on the pace of technology, but technology today is a given, so lack of preparedness may have more to do with it. Anticipation allows us to be on the offensive and get ahead of the game.

What do you need to have on your radar at all times? These are some guideline questions to ask yourself as you work on your projects and daily accountabilities.

  • What does your executive need now?
  • What will s/he need longer term?
  • What do they want? (Not always the same as what they need. This is where you really score anticipation points).
  • When will they want/need it?
  • How do they like to receive information? In what format? Make it easy for them, especially if there’s a lot of information to review.
  • Who else should be in the loop so I can quickly access what I need from them, or so they can be ready to respond if needed?

Remember, you need your own particular checklist to make sure you are in a good position for your own projects, or to meet your executive and your team’s needs. Be clear on what you are doing and why you are doing it.

  • What do I know so far?
  • What do I need to know?
  • How can I leverage the data I have?
  • What’s the deadline?
  • What resources are available to me?
  • Does anyone else need to be involved?
  • I continually ask myself, “what else?”
    • What else do I need to consider?
    • What am I overlooking?
    • Is everything accounted for?

To excel at anticipation, get into the habit of projecting yourself into the situation. In my book, I quote CEO Greg Renker who repeatedly remarked about how his assistant, Pat Shepherd, has this ability. As a result, nothing is overlooked. Everything is accounted for. Tech entrepreneur Josh Linkner talks about the hundreds of hours pilots spend in the simulator before taking command of the aircraft. This helps them to prepare for the unexpected and be ready for unforeseen circumstances. Same with race car drivers, astronauts, surgeons, athletes. They all use simulations to hone their skills so they are ready. The same for you. Walk through situations ahead of time. Look at them from every angle to make sure you’ve got everything covered.

One book club assistant asked if anticipation is more important than critical thinking. I think that anticipation can loosely be considered an aspect of critical thinking. “Critical Thinking” is a term coined by John Dewey in 1910. He said it is “reflective thinking.” A Stanford article suggests that in part, critical thinking is “careful goal-directed thinking.” While I’m not saying they are the same thing, I am saying anticipating has elements of critical thinking. Anticipating is weighing up all the options, it’s thinking towards a goal, towards outcomes. Some of the components of critical thinking include observing, supposing, assessing, deciding. All these are factors in the process you go through when you are anticipating.

To meet the needs of the executives and teams you support, your goal is to keep them in a state of readiness. Make sure they have what they need for good decision-making, including time set aside on the schedule for thinking and reflection. Your job is to handle and keep away from them any minutiae that would be a distraction, so their focus is on challenges that they alone are best positioned to solve. That’s how you help them to keep their strategic focus. That’s what working strategically with your executive means, and it’s why anticipation must be a skill you develop and master.

The high level of inflation America is experiencing today has not been seen since 1982. That means many CEOs today have not had to deal with such a crisis before. The game has changed radically for these CEOs, new priorities have emerged and they are being urged to make hard decisions faster. Preparation is essential. With things moving fast you need to rethink how you can keep your executive ready to meet the challenges they are facing. You’ll need to sharpen your working knowledge of your company’s business. Pay attention to what your executive, your team, your customers, your competitors are paying attention to. This will help you understand the direction things are headed and help you to keep up with the pace of change.

Have frequent conversations with your executive – whether they are a CEO or not. Ask what you can do to keep them in ready mode as your company makes the necessary adjustments to cope with the consequences of today’s business climate. Hybrid and remote working is definitely an impediment to good anticipation since nothing will replace the advantage you get from being in proximity so you can observe, see and hear firsthand. This means you must make a concerted effort to communicate frequently with your executive. Sharpen your instincts and your ability to read between the lines.

Once in a while, despite your best efforts, things will happen that will be outside of your control even though you did your best. Life is like that. My tennis coach used to say that sometimes someone hits such a good shot that there’s nothing you can do about it, so just accept it and move on. In my book, Peggy Grande, former assistant to President Reagan said that once in a while if something went wrong, he’d give her a look that said “I know you did your best.” If something goes wrong, despite your best efforts, in that moment just accept it, knowing you did your best. It’s how you rectify the situation that makes all the difference. Figure out where it went wrong so it doesn’t happen in future.

You know the saying “Stay ready so you don’t have to get ready.” That’s what anticipation is all about. You are in a state of readiness – ready to take advantage of opportunities, or head off challenges. Anticipation is a business must-have; a strategic tool that keeps fine-tuned executive assistants out in front and gives their executives a winning edge.

©The CEO’s Secret Weapon. The ideas expressed in this article and any text extracted from “The CEO’s Secret Weapon” are the intellectual property and copyrighted to Jan Jones. All rights reserved. No unauthorized usage or duplication by any means is permitted without the express consent of the author.

Author: Jan Jones

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Jan Jones is the author of “The CEO’s Secret Weapon How Great Leaders and Their Assistants Maximize Productivity and Effectiveness.” The book has received widespread acclaim from executives and executive assistants worldwide. Jan spent 20+ years as an esteemed international executive assistant to well-known business people, including Tony Robbins, the world’s #1 business and life strategist. Jan continues to champion the executive assistant profession with her writing, consulting and speaking. She offers timeless, practical advice that is relevant to the day-to-day role of the executive assistant. 

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Visit Amazon to purchase Jan Jones’ book and visit her website: The CEO’s Secret Weapon.

The CEO’s Secret Weapon: How Great Leaders and Their Assistants Maximize Productivity and Effectiveness

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