7 Keys to Executive Success: A View from the Desk Outside Your Door

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Jana DiCarlo, Serco Inc.

Jana DiCarlo, Serco Inc.

I’ve been an Executive Assistant (EA) for so long that I’m not even sure I can recall the exact year I got my first EA gig.  Suffice it to say, I’ve been at this for nearly 25 years and during that time, I’ve supported a lot of executives, five of which were CEOs.  I have been fortunate enough to work for what I consider to be some of the finest CEOs in the DC area.  While they all have very different personalities, in terms of leadership skills, they all possess many of the same qualities.

Sitting at the crossroads where individuals both internal and external communicate with the CEO’s office has put me in the catbird seat to earn an on-the-job-MBA of sorts.  I’ve learned a lot in my career.  Below are some observations most worthy of a share to the senior executive.

Prior to writing this, I enlisted the help of my favorite search engine to see if my search string results would yield the same content found on the usual business websites and blogs.  It was not surprising that none of them offered the perspective from an EA, the person who spends more time, day in and day out with senior executives.

So, let’s get on with it.

Family first.

Live by it. Regardless of how many hours you’ve put into the office, your Board or boss can kick you to the curb tomorrow. You’ll be replaced in a heartbeat. What was once ‘your’ company will march on without you. No one will even have the time to miss you. On the other hand, your family will always be there for you. While standing curbside, however, you don’t want to find yourself just now learning your wife’s favorite flowers are stargazers, not the roses you usually send, or that trash day is Thursday, not Tuesday.  And, when inevitably, your time comes to leave this earth, those are the people who, regardless of how busy they are, will mourn your loss daily. Your family deserves at least the same effort and attention you put into the office.

Let your employees live by it too.  Tough family situations are only made worse when employees feel as though they can’t be away to attend to loved ones.  An employer can expect a very high degree of loyalty as a result of readily practicing what others need the Family Medical Leave Act to force them to do.  One of my favorite CEOs used to say, “Always do what is in the best interest of the employee.”

Be squeaky clean.

It probably seems unfair for you to be to be held at all times to the highest standards of principles.   Such is the reality of being a senior- or C-level executive.  You must have iron clad ethics and the strongest of morals and values.  Even behind closed doors with your most trusted confidant, you must choose your words carefully and temper reactions to the worst of news and the biggest of challenges.

You probably remember the Gillette deodorant slogan, “Never let them see you sweat.”  Actually, a little sweat in corporate America isn’t such a bad thing.  The troops like to see you roll up your sleeves and lock arms with them with some sweat on your brow.  On the other hand, getting ‘sloppy’ (a descriptor that covers a whole list of no-no’s) is professional suicide.  No one wants to see your warts.   It’s not acceptable for your employees and it is beyond unacceptable for the senior executive.  Your brand, good or bad, will define the culture of your company.

Keep a dotted line around you.

Every company has moths that want to fly a little too close to the flame.  It is said that being CEO is the loneliest job in the world (actually, being the EA to the CEO is).  You might be the one that built the sandbox but that doesn’t mean you get to play in it.  You have to find the fine balance between being approachable but not letting relationships with staff get too personal.  Your people truly want you to be a leader, not an officemate.

Develop a culture of confidentiality.

I’ve supported CEOs who consistently exercised the highest levels of confidentiality.  A senior executive must practice the strictest of confidentiality at all times.  He or she must regularly counsel those that have revealed themselves as less-than-confidential or, eventually bid them adieu.  Relationships in the DC area, especially in government contracting, are so closely intertwined that you shouldn’t find yourself in public with your husband, wife, best friend, what have you, discussing any business matter that could be overheard.  Additionally, it goes without saying that you can’t discuss just any business matter with them.

You remember Bud Light’s Real Men of Genius radio ad saluting Mr. Really Loud Cell Phone Talker Guy? Click here for a listen if not. I worked with that guy when I was at a software company some years ago.  He was in sales.  It just so happened, we both used the same dry cleaners.  As I walked out of the shop one day with my garments, I could hear a guy speaking very loudly on his cell phone about pricing and other confidential information that might be useful to a competitor.  Then, was appalled when I realized we worked for the same company.  I probably should have walked right up to him and suggested he finish the call from his car.  But, being that Sales tended to have a very high turnover, the inevitable took care of Mr. Really Loud Cell Phone Talker Guy in the end.  The bursting of the dot com bubble took care of the now non-existent software company.  And, it should come as no surprise that the company was not known internally for its confidentiality or ethics from the top down. Monkey see, monkey do.

Listen to your ‘No-man’.

A good executive must possess excellent, expeditious, problem-solving and decision-making skills.  From time to time, he or she may find themselves seeking a weigh-in from their executive committee on an issue.  As the top dog, they are surrounded by yes-men.  Just as a really good EA should have the guts to tell their exec in the most discreet of settings that they just might need to consider a different opinion, you need one or two lieutenants that are capable of doing the same.

Hire the best people.

You’ve heard the saying, ‘Hitch your wagon to a star’ by Ralph Waldo Emerson.  I’ll assume your wagon is bigger than Emerson’s.  It is the very secure and smart CEO who knows that he can’t be good at doing everything and makes a conscious effort to add several stars to his hitch to form a galaxy of them.  You might need to utilize a search firm to find the right stars for your galaxy.  And if your Board won’t cough up the money to buy that star outright, get creative and be persistent.  Every candidate, ‘actively seeking’ or not, loves to feel wanted.  If you’ve built a good company, you won’t want the candidate that wants to come over because of price alone (I’ve seen many an expensive guy fail at delivery).  You’ll want the candidate that understands what you’re trying to build, wants to come over and make his mark and knows that he’ll be rewarded for it down the road (he’ll want that in writing of course).  The best people are not always the most expensive ones.

Have a strong right arm

I really should have put this at the top of the list, but, having it in the vicinity of ‘Hire the best people’ should suffice.  It cannot be stressed enough how important a good EA is to your success.  He or she is essential to your hitting your performance targets each year and they should be compensated accordingly.

If you don’t feel your EA maximizes your performance, you need to strongly consider finding a new one.  In today’s market, most companies are operating with the leanest of staffs which means everyone needs to be able to pull their load plus a few others.

Yes, it is tough to find a good EA.  It would be easier for you to lose an SVP and get along without him until you find his replacement than it would be to fill the chair of a good EA.  I’d hazard a guess it is the one requisition your recruiters most loathe the task of filling. Aside from maybe finding a candidate that holds a TS/SCI Lifestyle Poly clearance.  Why?  When an ad for an EA position surfaces, recruiters can expect to sift through hundreds of resumes before separating the wheat from the chaff and even then, determining the quality of that harvest is tough.  Because on paper, most EAs look the same.  As an executive, you don’t quite know what you’ve got sitting outside of your door until you’ve spent some time in the trenches together.  It’s a crap shoot.

What you should expect to see from the exceptional EA, truly the most important hire you will ever make, is one who is keen enough to watch how you do your job.  They must be an astute observer of how you and your direct reports interact with each other.  They should ask a lot of questions to learn the business and get a feel for where your focus is trending.  They should listen to open discussions to understand current issues that affect the business.  You should see a consistent pattern of that individual tracking just a few steps ahead of you.  They should exercise extreme confidentiality and possess traits of loyalty.  Lastly, they must cultivate skills to protect you, not from other people, but from yourself.

After reading this, if you believe you’ve met your 2012 targets with the help of your EA, congratulations.  You found a good one.  If you feel you met those targets without the help of your EA, shame on you.  You’re not properly utilizing a valuable resource whose sole purpose is to help you.  Conversely, if you didn’t meet your targets, time to stop by Recruiting with a box of donuts and apologize in advance for the unicorn hunt they’re about to go on.


Since 2008, Jana DiCarlo has held the post of Executive Assistant to Ed Casey, Chairman and Chief Executive Officer of Serco Inc.  Prior to that, for five years, she supported Brad Antle during his tenure as President and Chief Executive Officer of SI International, until it was acquired by Serco.  She was the founding chairperson of the WashingtonExec Assistants (Group 1).  Also an accomplished equestrian, she enjoys besting her boyfriend of 15 years at Yahtzee and just completed seasons one through five of Breaking Bad.  Downton Abbey is next.

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