Winning Over Your New Boss

by Lew McCreary

Getting a new boss can be fraught with anxiety and risk, often making it hard to see the opportunities fresh leadership will bring to you and your organization. You’ll have to come to terms with whatever unpredictable changes she unleashes. Don’t expect the new regime to resemble the old one. Leaders are often brought in to shake up the status quo, so you’ll want to make it clear right away that you’re a valuable contributor.

If you get a new boss by joining another organization, you’ll have no immediate worries about job security. But you will need to figure out the culture (and its politics), meet with and impress new colleagues and direct reports, and above all create a successful partnership with your new boss. You’ll need to understand—quickly and in detail—exactly what you’ve been brought aboard to do, what key stakeholders you’ll need to please, what resources you can command, and how your performance in the job will be measured.

In either new-boss scenario, uncertainties abound— but you have a role to play in taming them. As Tom Gilmore, a principal at the Center for Applied Research (CFAR), points out, you’re just as responsible as your new boss for “the quality of the working alliance.”

What does that responsibility involve? Establishing yourself as someone the new boss can turn to for candid opinions, insight, and support—someone she can count on to perform. Here are some tips for doing that.

Prepare to Meet the New Boss

Because your first meeting with your new boss feels like a make-or-break encounter—especially if she’s the one who’s new to the company and presumably looking for things to change—you may be tempted to lead with your personal agenda. If you do, you’ll be part of a steady parade of petitioners, each bearing (as the leader sees it) a narrow set of demands.

Don’t arrive at that initial meeting with thick stacks of documents and a PowerPoint presentation. And don’t prepare an eager audition that recapitulates your LinkedIn recommendations. Instead, ask questions and listen to the answers. Find out who the new boss is, how she likes to work, what she doesn’t yet know that you can help her learn. Answer her questions candidly as well, and don’t be so tightly clenched that you fail to let the boss see who you are.

Gilmore, drawing on his experience and research at CFAR, offers the following advice for making crucial early encounters successful:

• Ease into the relationship. Think incrementally. Pick only a few vital issues to cover early on— ones that will help you lay the groundwork for an effective alliance with your new boss. For instance, initially brief her on your unit’s new open-innovation initiatives. Over time, you can discuss in more depth the projects that have been green-lighted so far.
• Observe her style. Does your new boss prefer short or long conversations? A buffet of options or one best recommendation? Hard data or soft? Use these indicators to shape the way you present yourself and your ideas.
• Consider others’ claims on her attention. It may be just the two of you sitting in her office, but you’re not the only one who wants something from her. Take account of how other key stakeholders might affect her agenda, and highlight how your issues fit into those overall priorities.
• Collaborate. Help her form opinions on issues of importance to you, her, and the group. Avoid simply seeking her judgment on your ideas. If, for example, you believe the group has grown too risk-averse, begin a broader discussion about risk. Share anecdotes about how the group has dealt with it in the past, and ask about her experiences and ideas.
• Be honest. Most leaders understand the difficulty of speaking truth to power, and yet they must depend at first on relative strangers for honest appraisals. Look for openings to provide helpful candor on some key aspect of the new boss’s agenda. Say your boss wants to launch an initiative that would require buy-in from two unit heads who don’t work well together. Diplomatically bring that dynamic to her attention and share stories of how others have been able to get the two to cooperate.
• Accommodate her preferences. Your new boss has inherited systems and processes tailored to her predecessor’s quirks. The more you can learn about how she would like to be supported, the faster you can help develop new systems that work for her. For example, if her style is to delegate, suggest a regular weekly meeting to review assignments and workloads. Let her know what sorts of tasks you’re best suited to take on and keep her apprised of your bandwidth.

Establish a sense of connection, says Gilmore, by “finding links between what you’d like to see happen and things the new boss wants to accomplish.” There will be time for your agenda after you’ve built a solid relationship.

Be Yourself and Be Transparent

J. Bruce Harreld, who now teaches at Harvard Business School, has both been a new boss and reported to one many times—at IBM, Boston Chicken, Kraft General Foods, and elsewhere.

Whether you’re getting a new boss at your current company or joining a different one, Harreld says, “The best advice I can give . . . is just to be yourself and be transparent. The more I think about ‘What should I say to the boss?’ the more he and I are both in trouble. I’m there for a reason—for my best opinion. And he’s there for a reason, which is to guide me and help me learn, and shape what my work agenda should be. And the more I posture to him, the less effective I am.” In effect, it lowers the value of the relationship.

Candor goes hand in glove with confidentiality. Don’t share your boss’s comments with others unless he’s asked you to. And beware of carrying tales of your peers back to him. “A lot of people view their boss as someone they have to tell everything to,” says Harreld. “You have to be careful with that. In a complex organization, if you view the CEO as the kingmaker, you’re putting yourself at risk. If I wear my power with my boss on my sleeve, and people know I run back to him often, I’ve just cut out all these other relationships and made myself totally ineffective.”

When Harreld worked for Lou Gerstner at IBM in the mid-1990s, they didn’t always agree, but they never pulled their punches: “That’s part of the process, part of being on a team. You make your recommendation as forcefully as you can. And once the decision is made, you have to snap around and say, ‘OK, here we go.’ And sometimes people can’t [make that pivot]—they get strident. And sometimes they have to leave the team.”

That’s worth remembering. The agenda for change may stretch farther than you and others are willing to go. Many new leaders have transformational marching orders. Your job in the course of a leadership transition is to see how compatible the new boss’s plans are with your own agenda and career goals. If they’re at odds, you might have some thinking to do. And, of course, that thinking cuts both ways: If you’re on the edge of disillusionment, a new boss can be a breath of fresh air, helping to rekindle your enthusiasm and optimism.

Help Your New Boss Get Up to Speed

If she’s new to the organization, your boss has a lot of catching up to do. You can make it easier by:

• Saving her some time. Be generous with what and whom you know. Help your boss identify colleagues whose expertise will help her meet her goals.
• Saving her some trouble. Share shortcuts through the administrative mazes that drive every newbie crazy. This may seem like a small thing, but it’s not. Let her know that Phil in the IT user-services group is the only person to call when her technology goes on the fritz. Or that Maureen in Finance has developed an idiot-proof Excel template for expense reports.
• Saving her some work. Being new is a job unto itself. There may be something on the boss’s plate that you can take on or at least help with. If you see an opportunity, step up. Suppose your boss has been asked to honor her predecessor’s speaking commitment at an industry conference, and it’s clear she’s not happy about going. Since you know your way around the presentation material, volunteer to fill in.

Listen for Clues to the Future

In town-hall get-acquainted sessions, new bosses often default to being politic and careful. Sometimes, however, telling comments slip out. File these away as possible clues to the mysterious future. Some of them will doubtless be worth probing later when you have one-on-one meetings with the boss.

Also bear in mind that you may end up with a new boss who isn’t right for the business. Pay close attention to what she says (and how she says it). You may be able to spot trouble brewing early on. A former colleague and I, in our first joint meeting with a new boss, were surprised to hear him say, contentedly, that he really had “nothing to prove.” Since just about everyone in the company was energetically focused on proving something, the comment seemed discordant. In less than a year, the new boss and the company parted ways.

Remember That the Stakes Are High

Reuben Slone has weathered—and learned from—numerous new-boss transitions in his career. He recently left OfficeMax, where he was an executive VP leading the supply-chain organization, for a comparable position at Walgreens. While at OfficeMax, he had five bosses in eight years.

Each time he’s had to adapt to a new boss, Slone has reread the Harvard Business Review article “Surviving Your New CEO” (May 2007). He dusted it off again as he prepared for his new assignment at Walgreens, where his challenge is to take an increasingly complicated supply chain—with a growing set of channels, customers, and offerings—to the next level of sophistication.

Slone values the article’s tips on how to build a strong relationship with your new leader, whether it’s you or your boss who’s joining the organization. But he also rereads it for a reality check: It includes sobering research on the jeopardy executives face when a new boss takes over. In some cases, turnover among top executives is 33%—nearly double the normal rate. So every opportunity to make an impression matters tremendously.

Slone’s advice? “Make sure the boss knows he can count on you, what he can count on you for, and that you’re there to help make the transition as easy as possible. Be explicit about that. And get in early—don’t wait for him to come to you.”

Lew McCreary is an editorial consultant and a contributing editor to HBR. Working as a consultant means he gets new bosses regularly. He has learned that the most valuable attribute is to be flexible—up to a point.