Hands-On Advice

Chapter 2: Your Boss

You probably met your boss while you were interviewing for your new job. You had an extended conversation about your expectations (and his or hers) and your boss listened closely when you described your strengths and weaknesses. Almost certainly, you and your boss aren’t total strangers to each other.

In fact, there’s a good chance you were hired because you made a positive impression on your new boss. Don’t blow it now.

Over the next hundred days, how you interact with your new boss is likely to be the single most important day-to-day relationship in your budding career. Your new boss can be a source of advice and feedback on your performance, an influential advocate, and a primary decision-maker about the assignments that will help you show off your star potential.

But before this magic happens, you should recognize that there are two kinds of bosses: hands-on and hands-off. How well you get along with your new boss will depend greatly on whether you interact appropriately:

Hands-on bosses are primarily people managers. Their top responsibility in the company is to work with team members, enhancing overall performance and output of the group they manage. When the team generates what seem to be weak results, hands-on bosses often believe the best solution is to jump in and micro-manage everyone. Hands-on bosses like teamwork, staff meetings, and frequent status reports.

Hands-off bosses may manage a few employees, but their primary role involves working with clients or directly providing professional expertise (finance, law, creative services, medical care, etc.). Hands-off bosses tend to give their team members a good deal of autonomy, but getting the full attention of a hands-off boss can be frustrating. In some organizations—schools, for example—a nominal boss may relinquish so much authority to senior staff members that employees come to feel that they don’t even have a boss. In cases like this, it’s usually wise to treat the boss’s stand-ins as if they’re running the show.

Of course, you’ll need to discuss your boss’s specific expectations and management preferences during your first post-hiring conversation… and you should follow up by talking with other team members who also report to your new boss. The success of your new relationship will depend heavily on how well you engage with the boss’s personal management style.

If you haven’t had much experience working with a boss, you may be astonished by the diversity of management styles you’ll encounter even within a small company. One of the most important (and subtle) differences in style is how your boss processes new information. Management guru Peter Drucker argues that bosses are usually either “listeners” or “readers,” and he says they often ignore information that reaches them through the wrong channels. This kind of communication failure can be disastrous, says Drucker:

Lyndon Johnson destroyed his presidency, in large measure, by not knowing that he was a listener. His predecessor, John Kennedy, was a reader who had assembled a brilliant group of writers as his assistants, making sure that they wrote to him before discussing their memos in person. Johnson kept these people on his staff—and they kept on writing. He never, apparently, understood one word of what they wrote. Yet as a senator, Johnson had been superb; for parliamentarians have to be, above all, listeners.

Pay close attention to how your new boss handles meetings, decision-making, disagreements, stress, and missed goals. Since you’re the junior member of this boss-employee relationship, it’s largely up to you to make pragmatic adjustments to your own working style—do whatever works best, as well as you can. (As you build trust and personal authority, you can probably push back a bit. But not in your first hundred days.)

Regardless of your boss’s specific management style, however, there are some basic guidelines that will get your relationship off to a good start:

✔ First, never waste your boss’s time: Figure out the simple stuff on your own—how to find the supply cabinet or fill out an expense form. Use your face time with the boss to ask intelligent questions about project requirements, deadlines, resources, quality expectations, and workflow for your assignments. Plan your agenda carefully: You should never need to send a follow-up e-mail that says, “I forgot to ask you…

✔ Bring alternate solutions instead of problems: Here’s the kind of question bosses hate: “One of our bidders on the outsourcing contract just dropped out—what should I do next?” Bosses would much rather hear this: “Should I recruit a third bidder, or are we okay with just two bids?” Get into the habit of figuring out a Plan B for everything you do (and perhaps a Plan C, D, and E for important issues). When problems pop up—and they always do—your boss will begin to notice that you’re usually well prepared.

✔ Make sure your boss knows everything that matters: This is tougher than it sounds. Bosses are swamped with lengthy reports and raw data dumps, which typically contain little relevant, actionable information. Rather than add to this problem, identify key points that might require the boss’s action or a decision (a good rule of thumb is to present no more than two or three major points per report). Show trends and context (did customer satisfaction drop right after the new product hit the market, or do our scores always drop during the summer?). And never hide bad news—in fact, make a point of being direct and honest when there’s a problem. Many bosses ignore all the happy talk they hear and dig until they find a single obscure failing (one cranky customer, a 5% budget overrun for February) and then go nuts. This is called “management by exception” and it will make your life miserable if your boss thinks you don’t disclose the whole picture.

✔ Meticulously organize your own work: If your boss drops into your office to ask about the Acme Explosives contract, you should never say, “I think it’s in my inbox. Or maybe in that stack over there…” Set up your files and records so you (or anyone else) can instantly retrieve active information. Record passwords, account numbers, contact names, software licenses, and other data. Document all your office procedures. Display project milestones on a bulletin board. Keep an appointment calendar that shows the status of every phone call and e-mail contact you’re responsible for tracking. And so forth. If you vanished tomorrow, your replacement should be able to step in immediately.

✔ Pick your time carefully: If your boss is concentrating on a major client presentation or complex budget projections, even a brief interruption can bust up his concentration. Try to schedule your urgent problems so they can be handled at routine project meetings. And if your boss has a poster on the wall that says “Your lack of planning is not my emergency”—well, you’ve been warned.

✔ Listen carefully to your boss’s advice: According to a large-scale survey by Leadership IQ, a coaching service, the single biggest reason why new hires fail is that “they can’t accept feedback.” The study found that 26% of failures (defined as people who were “terminated, left under pressure, received disciplinary action or significantly negative performance reviews”) ignored advice from their bosses, colleagues, clients, and others. By comparison, only 11% failed because they lacked necessary technical skills. Your boss may be a jackass, but at least try to take his or her advice graciously. Ignoring feedback brands you as negative and argumentative, and that’s almost always a big deal on your performance record.

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The First Conversation

It’s pretty standard practice for bosses to take new employees out to lunch (or make some comparable social gesture) to welcome them to the team and answer questions. Often, this conversation is just a formality: The new employee insists “everything is super, no questions, I’m glad to be aboard.”

That’s a bad way to get started. Your first extended conversation with your boss is an opportunity that may never get repeated. From now on, you and your boss will rarely talk about long-term expectations, your career, and other topics that aren’t immediately work-related. So be prepared with at least three or four issues that only your boss can address:

✔ What’s the highest priority for the team in terms of results? If your new boss says “Everything is a top priority,” probe for details. Who are the department’s most valued customers? Are deadlines more or less important than budgets? What metrics get the most attention from top management?

✔ How can I ace my first annual assessment? Be clear that you’re determined to become a top team member, so you want to understand how your boss measures performance. One reason why employees hate the assessment process is random, undocumented criteria for rating employees. By raising the issue up front, you’re giving your boss an opening to define a more objective approach.

✔ Do you see any areas where I could use more experience or training? Here’s where you get insight into your immediate career path within the company. Again, probe for details if you can. How would you get “more experience”? Can your boss recommend training or classes? How about tutorials on the company’s own products?

✔ What’s the department’s biggest obstacle? This question gives your boss a chance to open up and discuss personal frustrations, so be sure you’ve established some degree of trust before you ask it. If your boss has been evasive about earlier questions, move on.

Note that there is one question you should never raise during this first conversation: How and when do I get a raise? Wrong time, wrong place.

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Surviving a Bad Boss

If you’re lucky, you’ll get a boss who’s a wonderful character, likely to become a life-long friend. Great bosses are visionary leaders, their endorsements are influential throughout their industry, and they always find time to send thank-you notes when you’ve done a great job.

More likely, your new boss will be more or less adequate at his or her job and will be aware that taking care of you and the rest of the team is a responsibility that somehow has to fit into an already-crowded calendar.

And then there’s the boss who’s an incompetent jerk. Not just a hard task-master, but someone who sucks the air out of a room and makes you hate your job.

Sadly, a good many companies seem to have a high tolerance level for bad bosses, and their negative influence is remarkably destructive. According to an Inc. Magazine survey, “three out of every four employees report that their boss is the worst and most stressful part of their job and 65% of employees said they would take a new boss over a pay raise.” Bad bosses are said to derail innovation, annoy customers, play favorites, hog the limelight, drive away top talent, and create perpetual uncertainty among their employees. One management consulting firm even found that bad bosses help break up marriages and ruin weekends (anxious employees spend an average of 6.2 hours every weekend worrying about their bosses, the consulting firm found).

What’s behind this proliferation of bad bosses? Executive coach Bruce Tulgan claims that the core problem that many bosses face these days is simply finding enough hours in the day to do their job well. Bosses typically face relentless demands on their time, both from their own bosses and from the staff they’re supposed to supervise, says Tulgan. They’re perpetually stressed out.

One consequence of this time pressure, Tulgan adds, is “a shocking and profound epidemic of undermanagement”:

The vast majority of supervisory relationships between employees and their bosses lack the day-to-day engagement necessary to consistently maintain the very basics of management: clear expectations, necessary resources, real performance tracking, and fair credit and reward.

Ouch. That’s a pretty grim description of what’s supposed to be your most important working relationship.

In It’s Okay to Manage Your Boss, Tulgan goes on to argue that most of the management behaviors that drive employees nuts—micromanagement, confusing instructions, procrastination, lack of respect for top performers—are symptoms of this “undermanagement.” And undermanagement itself is what happens when bosses are too busy to hold up their end of a work relationship.

One solution that veteran employees use with stressed-out bosses is to cut them out of most decision-making. Just forge ahead, do what seems to be the right thing, and hope for the best. As the legendary Admiral Grace Hopper once said, “If it’s a good idea, go ahead and do it. It is much easier to apologize than it is to get permission.”

But for a newcomer, this is clearly a high-risk strategy. Better to keep your head down and hope that someone in your boss’s chain of command is listening to the rumors. (Senior managers usually have a private intelligence network that keeps them aware of the worst jerks. Your new boss may already be on the way out.) Build a solid record of accomplishments and make friends in other parts of the company who can recommend you for openings in their departments.

At the same time, bear in mind that not all tyrannical bosses are genuine jerks. You may end up with a boss who’s as green as you are—newly-promoted to a managerial job and overwhelmed by new responsibilities. If that seems to be the problem, giving your boss extra personal support may dramatically change the jerk-like behavior. It’s worth a try.

In addition, many highly competitive industries—including Hollywood, the Internet, the media, and high fashion—often put new employees through a rugged “boot camp” entry-level period. The purpose is to weed out people who don’t have enough passion about their careers for long-term success. If you think that’s the reason your badly-behaved boss gives you a hard time, then (assuming you really want to succeed in this world) treat this experience as a test of your grit and determination.

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The Loyalty Challenge

“I get along pretty well with my current boss, but my goal is to get promoted to a job in a different department,” a reader asks. “I’m worried that my boss won’t recommend me if I become too valuable to him.”

This is a fair question. No boss really expects to hang on to a talented employee forever… but at the same time, the cost and hassle of replacing you is not going to be trivial. Career guru Donald Asher points out that an in-house promotion ”creates two staffing changes; hiring from the outside involves only one.” If you have scarce skills, if you’re involved in a “critical, high-value project,” if you’ve developed relationships with important clients—your boss will probably hang on to you like Super Glue.

Moreover, it’s likely that you’ll need your boss’s enthusiastic endorsement for a promotion elsewhere in the company. In an insightful guide to upward mobility called Who Gets Promoted, Asher makes the point that companies are sometimes wary about hiring internal candidates who seem a bit too outstanding:

Top performers are by definition not like the rest of us. Many are difficult and temperamental people. They’ve lived in a world designed for the averages; they are often frustrated, or they may be rule-breakers. Are you known as reliable? Or are you a strong contributor with a tragic flaw, like a hot temper or a habit of blowing off assignments that don’t interest you? When managers do risk analysis, they must project worst-case scenarios. If the risk is too great, all the benefits in the world will be passed over in favor of a less risky alternative.

So how do you escape the clutches of a boss who thinks you’re terrific? Asher has some helpful thoughts:

On being easy to replace: “Irreplaceable people are never promoted,” Asher warns. “In every organization there are some people who withhold critical data from others, refuse to delegate anything but the most mundane tasks, and retain all decision-making authority. Their absence from work, for even a day, brings their unit or department to a halt.”

On training and cross-training your staff: “Teaching, training, developing, guiding, and mentoring your subordinates can be career-advancing practices,” Asher says. Pay special attention to training your own replacement in case you do get promoted, he adds. “If you’ve done a good job of developing a subordinate, you may get the nod even if your rival for the promotion is a much better performer.”

On developing an internal resume: Maintain a secret “brag sheet” of your current accomplishments that are tied to “an overarching organization goal or strategy.” Constantly update this internal resume with your latest accomplishments, Asher adds. “If you hear about a great opportunity in a related department, you can drop your internal resume on that decision-maker and prevent him from posting the position, or you may become the frontrunner and keep him from seriously considering others.”

On following the rules: “Rules govern internal job-seeking at most organizations. Some of these rules may be official, codified policies, while others are just prudent practice.” One prudent practice, Asher adds, is always to notify your current boss when you’re applying for an internal job. “No gossip travels faster than a story about someone applying for a new job.”

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Too Many Bosses

“I’ve started a new job in a small firm that’s run by a husband and wife. The husband is the CEO, and his wife is general manager. Both keep giving me orders that contradict each other, and I’m about ready to quit. Is there any way to fix this awful situation?”

How hard have you tried to solve this problem? New employees can be surprisingly timid about confronting their bosses about relationship issues. You don’t need to throw a temper tantrum, but your first step ought to be a polite, low-key discussion about your new company’s chain of command. Avoid saying things like “awful situation” and “ready to quit” at this point—that’s not going to solve the problem (you know that, right?). Instead, stick to the facts: “Last week, Helen asked me to reorganize all our client files by date, and then George said to put everything back into alphabetical order. And sometimes I’m covering the phones at lunch for Helen and then George sends me to the deli for sandwiches. I’m trying to do a good job here, but it’s hard when I get conflicting instructions.”

By describing actual incidents rather than generalities, you may make an astonishing discovery: The root cause of your problem is that you’re too timid about talking with your boss (or bosses). Unless Helen and George are incredibly stupid, they’re likely to acknowledge the problem and try to solve it with minimal confrontation. George may say, “You work for Helen—that’s official. If I ask for a favor or make a suggestion, clear it with her if there’s any conflict. Okay?” The rest is up to you.

Now, sometimes an employee ends up working for multiple bosses and the problem isn’t just poor communication. Many firms have adopted a “shared resources” approach—employees with specialized skills are expected to work for whichever departments happen to need their services. These “shared” employees usually report to an administrative boss for assignments and scheduling, but their day-to-day work is supervised by other department managers or partners. Bigger companies call this arrangement “matrix management,” and the jury is still out on whether it creates more efficiency than chaos.

The problem with matrix management, not surprisingly, is that multiple bosses tend to have multiple agendas. A programmer who’s a “shared resource” on a big project may get orders to finish the job by the posted deadline no matter what gets in the way; meanwhile, the boss in charge of testing insists on rigorous quality assurance no matter what happens to the deadline. It’s the Helen and George show all over again…

And sometimes the situation gets worse. Unlike Helen and George, your individual “matrix” bosses typically don’t have much stake in you as an employee. You’re expendable, like a shared printer. Stress and long hours are just part of your job description. And your nominal boss—a project manager, an IT team leader, a resource coordinator—almost certainly has little authority to resolve conflicts.

Some advice for surviving matrix management:

✔ Keep a close eye on the schedule: A project that’s running a week late in August doesn’t look like a crisis. But if there’s a hard deadline at the end of December, somebody will have to work like crazy at year-end to make up the lost week. And forget about Christmas with your family. You and Santa Claus are both going to have a busy night.

✔ If you spot a potential problem, alert your admin boss: At least you’ll be on the record—and your admin boss now has to find a manager with the authority to resolve the issue.

✔ Find out who signs the check: Divided authority often means that you’ll run in circles trying to get a decision about spending money. Make sure it’s clear from the beginning who’s in charge of project budgets and who approves change orders.

✔ Find out which boss controls your performance review: Multiple bosses can mean multiple badly-informed perspectives on your value as an employee. The reward for your long hours and burnout may be that your great results become almost invisible.