Developing a Productive Relationship with Your Boss

“Would I rather be feared or loved? Easy. I want people to be afraid of how much they love me.”

One of the most-quoted catchphrases from the popular sitcom, The Office. Despite all of his workplace faux pas, Michael Scott was ironically universally loved because his warmth and presence helped him to earn people’s admiration and respect.

His operating style and decision-making behaviors often bordered on the bizarre, but he ultimately did enough of the right things to win people over.

Obviously, there is so much more to effective leadership than having a charming, engaging personality. Regrettably, though, the skill of earning people’s loyalty and praise is often missing in the DNA of some managers. Because of this, many employees wind up finessing relationships with their bosses to ensure their dynamic is one marked more by appreciation and respect and governed less by fear and frustration.

The folks at Dunder-Mifflin, where Michael ran the show, learned this over time! 

Many of the young professionals I have been working with seek more meaningful and stimulating career experiences. I often ask them to visualize the ideal business environment they would like to transition into. Inevitably, the dialogue often shifts to things like frustrations with the team culture, the inequities with promotions offered, the lack of face time with management, and the fact that people’s work is not being properly recognized.

The catalyst for a change of scenery isn’t so much what people want to move towards, but rather, more often what people desperately want to move away from—the boss!

I have seen it time and time again that, in an ideal world, if given the responsibility of picking our boss, we may likely make a different choice. Most of us in the real world, unfortunately, don’t get to make that choice. It may be nice and fun to work with a Michael Scott persona each day, but that is not the real world.

This is too bad because believe it or not, for most employees, the primary driver of job satisfaction is not the office environment, or work schedule, or salary, or benefits. It is actually the relationship with one’s boss. A recent study revealed that 65% of workers surveyed would choose a new boss over a pay raise.

In search of something new, many professionals often don’t quit their jobs—they quit their bosses.

Power struggles, mismanaged expectations, lack of open two-way communication, and concerns about offering a dissenting opinion can create strained relationships.

Why are these challenging relationships so prevalent in the workplace?

For starters, many organizations still promote people because of their technical success or revenue-producing track record, and not their leadership skills. Often, many new managers lack the requisite training and emotional intelligence before they step foot into the new role.

This clearly can make for many unhappy campers in the workplace.

Compounding the issue of leadership shortcomings is the fact that managing your boss effectively requires a great deal of finesse and skill. Many workers, unfortunately, don’t invest the time to assess how to be sensitive to their boss’s work style. Also, many employees feel that maintaining healthy two-way relationships is the responsibility of the boss. This is a misguided notion.

While you may have many days where you wish you could snap your fingers and magically overhaul your boss’s personality and communication style, you need to own the relationship as well. It’s a two-way street.

Instead of obsessing over how things could be different with the person you work for, and how you desperately wish they had a better personality, the better alternative is to work more effectively with the boss you have.

The best way to “manage up” and strengthen the relationship is to see your boss in a more balanced and human light, and then develop a mature and empathetic mindset towards her or him.

Here are some steps you can take to finesse the relationship with your boss and manage some of the anxiety and frustration you may be feeling.

De-escalate your frustration: It is wise to let go of any anger and resentment you may feel towards your boss and replace it with compassion. Accept the fact that your boss has been given the power to direct your activities, even if you feel you possess superior technical and leadership skills. You may feel you can do the job more effectively, but you are likely stuck with this person for the foreseeable future. Put yourself in your boss’s shoes. How would you want your team to treat you? Accepting reality and working to increase your influence with this individual will produce better results and keep you off the ledge.

Manage your expectations: Try to figure out exactly how and why their leadership style is causing you angst. Is it because they lack the proper experience? Do they not demonstrate sufficient emotional intelligence? Is their decision-making poor? Do they not hold people accountable for results? Maybe, it’s simply that your boss has a different operating style than you. Whatever the main reason, if you can pinpoint and prioritize the problems, you can create targeted strategies to try and navigate your boss’s deficiencies. It is important to remember that bosses are people, not robots. They are not perfect. Far from it. Just like all of us, they possess an endless array of quirks, nuances and annoying habits. Try your best to avoid behavior which makes these habits rise to the surface.

Know your boss: If you haven’t done so yet, the first order of business is to invest considerable time in getting to know your boss, however you are able, whenever you can. It’s not enough to know that your boss may work differently than you do. It’s also crucial to know how he or she works differently. This will help you not only identify the areas where you can fill in some crucial gaps, but it will also guide you in determining the best way to offer your perspective. Through close observation and probing dialogue pay attention to several strategic considerations: What is your boss ultimately trying to accomplish at this organization? What does your boss feel most challenged by right now? What is their preferred communication style? What role do you play in her or his plans? Let your quest for greater awareness push you to seize the opportunity for more conversations. Becoming more informed makes the process of managing up less intimidating.

Develop empathy: Once you begin to see your boss as more of a person and less of a pure authority figure, and once you have a better appreciation for her or his goals and challenges, you can begin to develop more empathy for this person as your manager. Most bosses are in fact motivated to try their hardest do their best to support you, and it is best to internalize this. Once we let go of anger and see our bosses through a more imperfect lens, we can begin to see the world through their eyes. We are able to better appreciate their workload, the competing priorities they constantly deal with, the direct report outliers who represent roadblocks to team progress, and the work-life balance they frequently struggle with. Often, being a manager means putting out fires. That’s not what they want to do with their time, but it’s easy for them to get overwhelmed if problems start to build up. If you better understand which of your responsibilities is most important to your boss, you are better positioned to help prevent fires from dragging you or your team down.

Take initiative and offer solutions: Don’t be passive about creating opportunities to collaborate with your boss. Always be looking to bring initiative to the table. Truly own the responsibility for keeping the lines of communication open. Make a habit of paying attention to when and where you might be able to pitch in more effectively. Find creative ways, independently, to address some of the goals your boss may be trying to accomplish. Even if your ideas are not acted upon, you have demonstrated respect for her or his time, and you have shown an ability to think beyond established patterns. Also, managers don’t want to hear all the problems you have—they want solutions. It is important that you have your own opinions on best alternatives. This demonstrates that you have carefully thought through a situation and avoided being reactionary and impulsive. When you are able to assist your manager in accomplishing her or his goals, you show you are dependable and can take initiative… two highly coveted traits managers look for in their employees.

Successfully managing up will make your time at work more pleasant and make it easier to accomplish your goals. Even with the most approachable boss, it might take you a while to feel comfortable with managing up. So many of us feel that it is our role to listen and not to question. You will have to let go of these misconceptions, for the sake of both your organization and your own career.  

Managing up allows you to practice navigating and influencing people who approach work differently than you. Learn how to look beyond your own needs and perspectives and consider the needs and perspectives of others. If nothing else, by managing up, you will learn what kind of manager you want to be and what kind of manager you don’t want to be.