Two coworkers are seating on the sofa in an office while talking about work. One of the colleagues is holding an open laptop and the other colleague is following and watching along the work shown on the computer.
Published in  
Personal & Professional Growth
 on  
December 9, 2021

Developing a Productive Relationship With Your Boss

Tips for how you can take to finesse the relationship with your boss and manage some of the anxiety and frustration you may be feeling in trying to make it work.
Would I rather be feared or loved? Easy. I want people to be afraid of how much they love me.”

This is 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 often bordered on the bizarre, but he ultimately did enough of the right things to win people over.

Photo by Pablo Varela on Unsplash

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 attempt to manage relationships with their bosses so they experience more appreciation and respect and less fear and frustration.

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

Many young professionals today are seeking more meaningful career experiences.

The global pandemic has prompted people to rethink what they want from their jobs. Things like frustrations with the team culture, inequities with promotions offered, lack of face time with management, and inadequately recognized accomplishments are all key reasons why many employees are considering other options.

Believe it or not, the most significant catalyst for a change of scenery isn’t so much what people want to move towards, but more often, what people desperately want to move away from—the boss!

In an ideal world, if given the responsibility of picking our boss, we may make a different choice. Unfortunately, most of us in the real world don’t get to make that choice.

Working with a Michael Scott persona daily may be nice and fun, 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, work schedule, salary, or benefits. It is actually the relationship with one’s boss.

Many workers 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.

‍Why are strained and challenging relationships with bosses so common in the workplace?

For starters, many organizations still promote people because of their technical success or revenue-producing track record, not their leadership skills.

Often, many new managers lack the necessary training and emotional intelligence before stepping 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 boss's responsibility. 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 also need to own the relationship.

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 them.

‍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 towards your boss and replace it with compassion. Accept that your boss has been given the power to direct your activities, even if you feel you possess superior technical and leadership skills. Accept the reality and work on increasing your influence with this individual.

Manage your expectations

Try to figure out exactly how and why their leadership style is causing you angst. It may be that your boss has a different operating style than you. Work on pinpointing the problems and developing strategies to navigate your boss’s deficiencies. Remember, bosses are people, not robots. They are not perfect, far from it. Like all of us, they possess endless quirks, nuances, and annoying habits. Try to avoid behavior that makes these habits rise to the surface.

Know your boss

Invest considerable time in getting to know how your boss may work differently than you do. It’s also crucial to understand how they work differently. Through close observation, 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 their plans?

‍‍Becoming more informed will likely lead to more conversations and make managing up less intimidating.

Photo by krakenimages on Unsplash

Develop empathy

See your boss as more of a person and less of a pure authority figure. When you do, you begin to appreciate their goals and challenges better, and you can develop more empathy for this person as your manager. Most bosses are motivated to do their best to support you, and it is best to internalize this. Once we let go of anger and see our bosses through an imperfect lens, we can begin to see the world through their eyes. We can better appreciate their workload, the competing priorities they constantly deal with, the direct report outliers representing roadblocks to team progress, and the work-life balance they frequently struggle with.

Take initiative and offer solution

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. Bosses want to hear solutions, and they want to know you have an opinion on the best alternatives. Demonstrating initiative is a highly coveted trait 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. 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.

By managing up, you will learn what kind of manager you want to be and what type you don’t want to be.

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