How To Master The Secret Art Of Getting Inside Your Boss’s Head

Helping your manager shine could be the key to accomplishing your own goals faster. Here’s how to do it with out looking like a suck-up.

How To Master The Secret Art Of Getting Inside Your Boss’s Head
[Photo: Pauline Frederick, “Potiphar’s wife” via Wikimedia Commons]

When it comes to job security and getting ahead, few things can go as far as being the employee who makes your boss look great. Anticipating what those in charge need—sometimes even before they realize it—shows that you understand the big picture in ways that many employees don’t.


“I give this counsel all the time, but it’s not the job you do, but how you do the job,” says Andrew Alfano, chief operating officer of The Learning Experience, a childhood development center franchise company. Alfano walks his talk, too—before joining the Learning Experience, he spent 15 years working his way from district manager to senior vice president at Starbucks.

But how do you get inside your boss’s head to anticipate how to make them look good when you’re just trying to keep ahead of your own to-do list? There are some savvy ways to do so—and spending the time gaining the insight and information you need could also help you become a better employee and reach your own career goals a little faster.

Ask The Right Questions

Too many people try to guess at what is important to their supervisors without actually sitting down and having a conversation about it, Alfano says. “I would never avoid that,” he says. But, sometimes, your boss may not be able to articulate exactly what you need to do or may simply be unsure, as well. In those cases, you have to find creative ways to get the information you need, he says. Ask questions like:

  • What does “success” look like in my role?
  • What do you need from the person in my role?
  • Who has had success in this role before me and what made them successful?

Figure Out What Your Boss’s Boss Wants

Remember that your boss is also trying to appease and anticipate the needs of her own manager, Alfano says. And, sometimes, looking to those higher-ups can give you valuable insight into how you can better manage your own supervisor, he adds. Of course, you don’t want to make your manager feel like you’re going over her head. However, good senior leaders typically want to get to know the people working for them to scope out potential talent in the ranks, he says. Look for opportunities to connect with your manager’s manager and take advantage of the encounter to ask questions about how you can better support the whole team.

See What Takes Up Most Of Her Time

The simple act of paying attention can tell you a great deal about your supervisor’s priorities, interests, and concerns, says executive and career coach Donna Schilder. Take note of the meetings that are taking up the most time and look at how you can help. During those meetings, listen to what people are discussing or requesting. Pay attention to what’s written on the white board in their office or analyze email messages on which you’re copied. Each of these interactions offers clues as to what’s going well, what’s not going so well, and where you might be able to prove your value in the form of assistance, she says.


You don’t want to overstep into eavesdropping or “spying,” she says. But, “any time your boss is talking to someone, you could be learning things about the company, about the assignments coming up, about what’s going on in the organization,” she adds. Use that information to focus efforts on streamlining workloads, providing additional assistance on certain important projects. You might even ask for a stretch assignment that would help your supervisor and provide you with valuable experience.

Do Their Homework

If you’re trying to think like your boss, you need to have a good understanding of the bigger forces at play in the company. Start by getting in the habit of reading industry news, relevant analyst reports, and your own company’s news release or internal reporting on business conditions. “It’s about research, research, research. The great people out there who move ahead are obsessed with research, says Sander Flaum co-author of Boost Your Career: How to Make an Impact, Get Recognized, and Build the Career You Want.

Alfano agrees. He says that emerging leaders typically focus too much on results and can lose sight of their broader role in the organization’s goals. Understanding what those goals are—whether they’re related to sales, innovation, culture, or other matters, for example—can help them get a clearer vision of how to help everyone be more successful. “It’s really just not about meeting the deadlines and it certainly is not winning at all costs, which I think, at least for myself, those are probably some of the mistakes I made early on,” he says.

Schilder suggests distilling relevant research into mini-reports for your supervisor. Become an aggregator of sorts, providing valuable insight when you find it, she says.

Think Ahead

Anticipating needs, large and small, requires thinking ahead, Schilders says. Are there busy seasons coming up? How can you help your manager prepare? Is she taking a vacation soon? Look for ways that you can help while she’s out.


Again, as you look at what’s coming up in the future, you can find ways to make yourself indispensable, and increase your opportunities to take on more responsibility in preparation for a promotion or a new job.

Get Input From Others

Outside perspectives can be valuable in helping you see areas you may be overlooking Flaum says. Ask your mentor or even other trusted managers and coworkers about how you can become invaluable to your boss. If you have the opportunity to speak with people who previously worked for your boss, such conversations can yield valuable insight about priorities, preferences, communication styles, and other areas.

“It’s really important because if you don’t make your boss look good, you’re out. You’re not getting promoted. People move up when the boss says, ‘Uh-huh. [they] really made an impact,” he says. The key is to find out what “impact” matters—and how to achieve it.

About the author

Gwen Moran is a writer, editor, and creator of Bloom Anywhere, a website for people who want to move up or move on. She writes about business, leadership, money, and assorted other topics for leading publications and websites