Working the Crowd

My immediate supervisor was so disorganized that it drove me up the wall. He was so busy trying to find his way out from underneath his desk that he was unable to communicate any vision whatsoever. His style put me off so much that I started to get really bitter. Eventually I could see my attitude seeping into our interactions, and I think my boss could tell that I didn't like him. Soon he found subtle ways to let me know he felt the same way, and the next thing I knew, I was getting all of the most boring assignments. I didn't want to sabotage my career, so I tried focusing on my boss's strengths. I found that he was a great listener and that he could talk sports with greater finesse than my husband. By making a conscious effort to value what he brought to the table, I was able to turn things around between us.

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Dvora, 26, Florida

There are as many different types of bosses in the corporate world as there are people, and, hopefully, the manager you work for is a good fit for you. As the captain of your department's ship, your boss is responsible for the group's success and, to a great extent, your own. As such, it's crucial that you get to know your immediate supervisor early and determine her priorities. During your first days in the trenches, observe your boss in action. If you can, shadow her for a day to see how she interacts with junior and senior employees, and how she handles different situations. Business consultant C. Sam Benson, in his article “Your Management Success,” defines the following basic management styles:

• • Aggressive: competitive, decisive, direct, likes immediate results.
• • Persuasive: poised, optimistic, convincing, likes interacting with people.
• • Supportive: patient, reliable, a good listener, likes security.
• • Analytical: precise, prepared, plans thoroughly, dislikes mistakes.

It's difficult to slap a label on a complex person you barely know, but thinking about your boss's management style will help you determine how to proceed with the best chance of success. You may have heard that there are documented variations between male and female bosses. Supposedly, women are more nurturing, collaborative, and relationship-focused, but they may react emotionally when they feel threatened or insecure. On the other hand, men are presumed to be more generous and easygoing, but they tend to favor individual work on tasks and an autocratic approach to decision-making.

There has also been a lot of talk lately about generational differences among the various age groups that currently comprise the workforce. In his book Managing the Generation Mix, author and generational expert Bruce Tulgan defines the generations as follows:

• • Schwarzkopfers: Born before 1946 and now few and far between, their strengths are loyalty, dependability, responsibility, altruism, and a strong work ethic. Other generations can count on these seasoned workers for everything from historical perspective to an important document. Their attitude is “take charge” and “do what's right.”
• • Baby Boomers: The huge Baby Boom generation, born between 1946 and 1964, experienced a child-centered upbringing, a focus on individuality and youth, and a distrust of anyone in authority. Older Boomers admit they're competitive and self-centered, but have a strong commitment to the mission of their organizations. Younger Boomers see themselves as cautiously loyal and more realistic about life and work.
• • Generation X-ers: These independent, ambitious go getters, born between 1965 and 1977, are accustomed to taking care of themselves. Not obsessed with climbing the corporate ladder, these free agents are energetic, creative, and adaptable as they make lifestyle choices that contribute to their wellness, happiness and health.
• • Generation Y-ers/Millennials: Born after 1977, Y is the most outspoken and empowered of all the generations. Influenced by education-minded Boomer parents and fueled by their facility with technology, Gen Y-ers are poised to be lifelong learners. They're socially-conscious, have high expectations of organizations, and are constantly looking for ways to improve how things are done.

As members of the Millennial Generation, you may have noticed that some of these broad characteristics accurately describe you, your colleagues, and your managers. However, as you get to know your boss, I urge you not to put much stock in generalizations. I think you'll find that the way your boss operates will depend almost exclusively on her unique personality, and that gender or age seldom plays a major role.

It's a good idea to set up a one-on-one meeting with your new boss right away. You will need to be proactive about this because, in the crazed atmosphere of the corporate world, your boss may be too harried to make the suggestion. If necessary, block an hour with his admin or ask him to grab a quick lunch in the cafeteria. New York City career counselor Judith Gerberg suggests three strategies for this first encounter: 1) express gratitude and enthusiasm, 2) clarify roles and expectations, and 3) define the training and support you will need to do your job well. Additionally, you'll want to leave the meeting with answers to the following questions:

• • What are your daily responsibilities?
• • Are there department meetings he would like you to be a part of? Are there particular people he would suggest you meet?
• • What is the best way to get in touch with him if you need something (for instance, does he want you to drop by his office, would he prefer a voice mail, or is e-mail best)?
• • How should you document your work? How often and in what format does he want you to report on project status?
• • How should you go about suggesting new ideas or processes?
• • How will your performance be evaluated?

If you can accomplish one thing in this initial meeting, make sure you and your boss agree on how to move forward. All of your efforts to impress him with your expansive knowledge of the field and your creative ideas will be fruitless if the two of you are going in different directions. Find out what he wants from you first, and then brainstorm ways to surpass his expectations. You can also establish a good rapport by making your new boss feel needed. Show him in the very beginning that you are ready and willing to be guided, and bond with him over the fact that he has some years on you, and, therefore, has a treasure trove of career advice to offer.

How else can you get started on the right foot? Here are some other hints:

1. Be humble. Don't approach your boss with a sense of entitlement, as though he is personally responsible for furthering your career. Instead, focus on learning what you can do to make his life easier, contribute to your company's goals, and make him look good to his boss.
2. Be realistic. Keep in mind that your boss is a human being and that he is going to make mistakes. He is not trying to make your life difficult. The two of you are on the same team, so don't be overly sensitive or critical. Listen without judgment, make a sincere effort to understand your boss's position, and patiently explain your ideas. If you're unclear about something, ask for clarification rather than expecting him to read your mind.
3. Be honest. Admit if you do something wrong, and then ask your boss how you can rectify the situation. Don't allow yourself to get caught in a maze of lies or excuses that will result in a loss of credibility.
4. Be respectful of your boss's time. Appear in his office with a checklist of things you need to cover, and don't dwell too long on any particular subject. Your boss will be more receptive to meeting with you if he knows you'll be in and out of his office quickly.
5. Be self-sufficient. Only approach your boss with a problem or complaint if you've explored all options for resolving it yourself. When you do, be prepared to have a solution at hand that you could implement with his help. Choose your battles wisely, and decide carefully if bringing an issue to your boss's attention is really necessary or if you would be better off letting it go.
6. Be friendly. Encourage your boss to genuinely like you. If he expresses an outrageous political opinion or offers unsolicited advice about your personal life, nod and smile. You don't have to agree, but you don't have to disagree either. Your boss's feelings should be protected at all times. Compliment him on his tie or presentation, if it's appropriate, and thank him profusely for any efforts on your behalf. Do personal favors for him and brownnose all you want, but make sure you do it sincerely. Your boss will smell phoniness a million miles away—and believe me, he won't appreciate it. Even if your boss isn't someone you'd choose as a friend, focus on the things about him you do like, and do your best to establish a positive working relationship.
7. Be a “can-do” employee. When your boss asks you to do something, accommodate him, if possible. The words I don't have time should never escape your lips. If you know something needs to be done, do it without being prodded, and if your boss asks for help in a group setting, be the first to volunteer. Your boss will quickly come to see you as a huge asset to the team and as someone he can count on.

An important caveat to the “can-do” mantra: You have to set reasonable boundaries for your new manager. There is a fine line between being a hard worker and letting people take advantage of you. Some managers, even good ones, fall victim to the gofer syndrome. If you've ever made a photocopy for a boss who has a Xerox machine in his office, you know what I'm talking about. The gofer syndrome involves a stream of barked orders to the tune of, “Do this, do that, get me this, get me that, tell this person ABC, and get an answer from that person on XYZ.” Pretty soon, you're spending so much time on silly errands that you don't have time to get any real work done. Cure your boss of the gofer syndrome by telling him that you're happy to make those copies if he will give you permission to de-prioritize the report you're working on for the CEO. Your boss will see for himself how he should best utilize your time.

Also, don't let your boss catch you staying until 10 p.m. or obsessively responding to e-mail on weekends unless you want her to expect that behavior from you for the duration of your career. Along those same lines, you shouldn't impose a performance standard on yourself that is impossible to maintain. If you return all of your boss's messages within 5 minutes of receiving them and complete assignments way ahead of deadlines, you run the risk of disappointing her when you can't deliver.

One more piece of advice: Get to know coworkers who report to the same manager quickly so that you can probe them about your boss's pet peeves, preferences, and expectations. Be careful how you phrase your questions, though, because you don't want to launch a discussion that criticizes your new boss in any way. Ask a colleague to fill you in on the chain of command in your department. Use this information to introduce yourself and explain your function in the office to your boss's boss and the other managers you'll be working with. Establishing strong relationships with the department higher-ups will accomplish the dual functions of making your boss look good and strengthening your overall position in the company.