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10 Lessons From My Time as Assistant to the Big Boss

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It's graduation season, and many of the nation’s brightest college graduates will soon leave leafy college campuses to work on the often less leafy campuses of the national security agencies that dot the national capital region. Some of these grads will take jobs as assistants to high-level officials, often called “principals.” While the titles and particular duties of such assistants may vary, at the root, an assistant supports his principal’s decision-making by managing paper flow, helping him get the information he needs and protecting his time.

I held a post along those lines in my 20s, first as a special assistant and then as an executive assistant in the Office of the Director of National Intelligence, and a friend recently asked what kind of advice I had for someone fresh out of college who was starting such a job. With full realization that the lessons I learned, like the jobs themselves, can be idiosyncratic and context-dependent, I offer 10 takeaways that may be useful starting points for anyone taking a position as an assistant to a chief. (Please note that I use male pronouns merely for ease.)

1. Come to understand what your principal needs and tee up decisions clearly. How does he process and assimilate information? How does he make decisions and what kind of information does he require to make them? Figure out his methods and develop mechanisms to suit them. For instance, if he prefers written recommendations, create clean options papers. If he processes information textually, prepare briefing books. If he prefers oral briefings, schedule in-person presentations. Remember: Your principal’s job is to decide; your job is to make that job easier by handling the staff work that goes into that decision and by making the choice before the principal as salient as possible.

2. Remember your principal’s time is his dearest resource. Guard it well and use it judiciously, even for your own purposes. Don’t confuse access with license to bother him with questions that you can get answered elsewhere.

3. Know three bullets down. Often, an assistant’s job is to synthesize a lot of information and explain it quickly and compactly to the principal. But don’t synthesize so much that your understanding is merely skin-deep. To resolve this problem, I came up with a helpful rule of thumb: If I was going to tell my principal one thing, I needed to prepare three other things about the issue to tell him, just in case he asked follow-up questions.

4. Keep a tight lip. You can never re-earn trust if you lose it. Things said in the heat of the moment in your presence are not for public consumption. Foster an environment of candor with your principal, and don’t keep notes for your memoirs.

5. Offer advice. Be confident and candid but humble. Don’t pester if your advice isn’t taken. Be a reality check on your principal’s presumptions. Your perspective may be closer to on-the-ground reality than your principal’s, who occupies a rarefied realm.

6. Maintain a public persona with the rest of the office. An assistant may start to view himself more like a principal than a staffer—but don’t be fooled. You’re a minion not a master. Walk the turf, be seen. Don’t just make phone calls and issue directives—that can lead to alienation and resentment from the people you need to help you do your job. Furthermore, sometimes it’s difficult for your principal to make the rounds and accurately understand the atmosphere in the trenches.

7. Don’t abuse your position to speak on behalf of your boss. Be firm but fair when asking for things from (what are often) more senior colleagues. Explain the motivations behind a last-minute memo, and say thank you when it comes through. Conduct yourself humbly and with respect.

8. Don’t get rolled. Politeness isn’t passivity. You’ll find lots of powerful people will want to step around you. Don’t let it happen; your principal’s time is too precious.

9. Don’t take credit. Even if you wrote the memo that everyone likes or proposed the plan that is now law of the land. Modesty is the watchword for the successful assistant.

10. Don’t stay too long. The proximity to power and responsibility may lull you into staying in a plumb assistantship forever. Don’t do it. These kinds of jobs are best held for a few years. Once you’ve learned as much as you can, go do something else. Take the experience and perspective you’ve gained and make your own mark, not as an assistant but this time as a principal.

And here’s a bonus: Have fun. These are great jobs that probably come along only once in a career. Enjoy the opportunity to do well and do good.

Matthew F. Ferraro served as special assistant and executive assistant in the Office of the Director of National Intelligence from 2006 to 2009. 

(Image via Ed Samuel/Shutterstock.com)

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