What to Do When You’re Stuck Between Your Boss and Your Boss’s Boss

May 2, 2018 Rebecca Knight

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Cathy Scola/Getty Images

It’s smart to have strong relationships with both your boss and your boss’s boss, but when there’s conflict between the two of them, you’re often in a tough spot. What’s the best way to navigate this situation? Should you align yourself with the person who has the most influence over your job and career? How can you be as transparent as possible without risking your relationships?

What the Experts Say
It’s no fun being caught between your boss and your boss’s boss. “It’s like when you were a kid and your parents would fight,” says Priscilla Claman, the president of Career Strategies, a Boston-based consulting firm and a contributor to the HBR Guide to Getting the Right Job. “You feel stuck in the middle.” Not only is the situation “awkward and uncomfortable,” but it can also be “very time intensive,” says Nancy Rothbard, the David Pottruck Professor of Management at the University of Pennsylvania’s Wharton School. “You’re managing different people and you’re trying to do it without making them angry.” Here are three common scenarios you might find yourself in and ideas on how to respond to these workplace tugs-of-war.

Scenario #1: Your boss’s boss asks you to do things without clearing it with your manager
“If your boss’s boss wants you to take on a project, he should talk to your boss, and then your boss should talk to you,” Claman says. “Those are the norms, but it doesn’t always happen that way.” When you’re put in this position, Rothbard advises, speak up. Be honest and straightforward: “This puts me in an awkward position vis-à-vis my boss. What do you recommend I do?” Depending on your relationship with your boss’s boss, you might also ask them to “run interference” so that you’d be freer to take on the assignment. Maybe they can pull rank and “find someone else to help, or swap in another person” to even out the workload.

Scenario #2: One boss shares information with you that the other isn’t privy to
“If your boss tells you something personal — say, she’s pregnant and not yet ready to disclose, or maybe she’s resigning in a month — it’s best to keep that information confidential,” Claman says. But “if your boss’s boss tells you something that your boss needs to know” or vice versa, such as information that pertains to the business, “that’s a more difficult one” to navigate. “If you tell your boss or boss’s boss, it will be obvious that the information came from you.” In cases like these, when you feel that the news you’re being told should be more public, focus on listening and asking questions rather than giving a decisive opinion,” Rothbard says. Help your bosses think through their decision-making processes by asking them: Do you think others ought to know this information? Are there risks in not telling them?

Scenario #3: Your boss and your boss’s boss are in a stalemate
If you’re close with both parties, and have “intimate knowledge of both their interests,” you are “uniquely positioned to bring them together,” Rothbard says. Claman recommends scheduling a meeting with the two of them and other colleagues to try to come to a consensus. She suggests saying something like: “I don’t think we are in agreement here. Can we have a meeting with the three of us — and maybe bring in Lucy and Eduardo to figure out our priorities?” She adds, “Inviting others broadens the issue and dilutes [whatever animosity] may be present in their relationship.”

But no matter what scenario you find yourself in…

Try not to take sides
When you’re dealing with two distinct personalities, it’s natural to “have a preference” for one over the other, Claman says. Maybe you have a longer professional history with your boss, or perhaps you’re simply more compatible with your boss’s boss. But aligning yourself too closely with either of them is potentially dangerous. “You have to be very careful about taking sides,” she says. Rothbard agrees: “Try to be neutral.” And when there’s obvious discord between the two of them, “don’t say too much.” Remember that getting too involved in their power dynamics could be damaging to your career. Instead, think of yourself “as separate from the people but engaged in the work.”

If you must pick, think carefully
If you’re forced to take sides, in most scenarios, you should prioritize “your relationship with your boss,” Rothbard says. After all, this relationship “matters materially to your day-to-day life: your raises, your promotions, and your assignments.” Claman concurs: “You never want to throw your boss under the bus.” Should you decide to align yourself with your boss’s boss, take precautions. Make sure “your boss’s boss has another place to put you,” Rothbard says. “You have to have options.”

Know your limits
Being caught in the middle of office drama is both tedious and stressful. So, in the interest of your sanity, do your best to keep some distance. “Don’t make yourself too vulnerable to anybody at work,” Rothbard says. And don’t allow yourself to get consumed by office politics. Remember, Claman adds, “these are working relationships; these people are not your family or close friends. You need to preserve your personal life.”

Principles to Remember

Do:

  • Ask questions. This is especially important if either manager wants you to keep a work-related secret that the other manager should know about.
  • Bring your boss and your boss’s boss together. Schedule a meeting with them and other colleagues to come to a consensus.
  • Keep some distance from workplace drama. Don’t align yourself too closely with your boss or your boss’s boss.

Don’t:

  • Shy away from taking action. If either boss puts you in a compromising situation, speak up.
  • Alienate your boss. Your relationship with your manager should be your top priority.
  • Lose sight of the fact that these people are colleagues. Be engaged in your work, but not overly engaged in your workmate’s scorekeeping.

Case Study #1: Consider the broader consequences of keeping a boss’s secret
Early in his career, Josh worked at a boutique New York City–based public relations agency. Josh knew one of the company’s founders, Dave, from a previous job. He did not have as long a history with his direct boss, Bill, who reported to Dave. (The names in this story have been changed.)

“The agency was not that formal or hierarchical, so Dave, Bill, and I were pretty close as colleagues go,” he says.

One day, Josh attended a prospective client meeting with Dave. During the meeting, Josh realized that Dave was quoting prices that were well under the rates given to other clients. Josh’s alarm bells went off.

“I thought this might be a problem, so after the meeting I talked to Dave about my concerns,” he says. “I asked probing questions because I wanted him to understand the bigger picture and where I was coming from.”

Josh learned that no other managers — including Bill — knew about the difference in pricing offers. “Dave’s perspective was that we were a private company and it was well within his rights to do this,” he recalls. “But at the same time, Dave implied that he didn’t want me to tell my manager.”

Josh felt conflicted. He didn’t want to lose Dave’s trust, but he was concerned for the health of the business. “I decided that I needed to be transparent and open,” Josh says. “I went to Bill and told him the situation. I said that I was looking out for the long-term success of the organization and that I thought it was important for the three of us to talk.”

Not long after, Josh, Bill, and Dave had a conversation about best practices for charging clients. After much discussion, they came to a consensus.

“Both Bill and Dave later told me that they appreciated the way I handled the situation. They saw that I wasn’t playing politics. I think both realized that I was an honest broker.”

Case Study #2: Avoid picking sides if you can help it
Alison is a professor of finance at a small college, but earlier in her career, when she was a management consultant, she had an experience of being caught between her boss and her boss’s boss. (The names have been changed here, too.)

At the time, Alison had been with the firm 12 years and knew most of senior management, including her boss’s boss, Harry, who ran the U.S. practice for the company. “Harry had originally been my boss when I first joined the firm as an analyst. We had both risen through the ranks: him to partner and me to middle management,” Alison says. “But during the intervening years, I was promoted to the London office and then promoted back to the New York office.”

When Alison returned to the U.S., she had a new boss, Charlie, who reported directly to Harry. “Charlie was new to the company,” she says. “He didn’t have established relationships, and he and I certainly didn’t have the rapport that I had developed with Harry over a dozen years.”

Because of her relationship with Harry, Alison often became privy to inside knowledge that Charlie hadn’t yet learned. Once, for instance, Harry shared some highly confidential information about individual team performance without making it available to any other senior managers. “It was awkward and uncomfortable knowing this information,” Alison says.

But she didn’t want to betray Harry’s trust, so she kept the information secret. “I had planned to feign ignorance, if necessary, to avoid being placed in the middle,” Alison says. “My goal was to avoid the topic. I assumed the situation would work itself out if I could manage to avoid being sucked into the fray. And it did.”

Alison says that the key for managing the relationship was “to stay honest and respectful of Charlie” while maintaining her deep connection to Harry. “From my point of view, I wasn’t sure whether Charlie would be successful at the firm,” she says. “But I knew Harry was in it for the long haul. Plus, I had loyalty to Harry, who had looked after me over so many years. I knew if there was a side to take, I would have sided with him.”

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