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14 Tips For Improving Your Relationship With Your Boss

This article is more than 10 years old.

Today is National Boss's Day; a secular holiday celebrated around the world on Oct. 16 each year.

It reportedly began in 1958 when a woman named Patricia Bays Haroski registered the holiday with the U.S. Chamber of Commerce because she wanted to designate a day for employees to show appreciation for their managers. Haroski chose Oct. 16 because it was her father's birthday, and she working for him at the time as a secretary for the State Farm Insurance Company in Illinois.

In 1962, four years after registering the holiday, the Illinois Governor officially proclaimed the day, which is now observed in the U.S. and countries such as Canada, Australia and India.

Millions of appreciative workers will take full advantage of the day; thanking their boss’ for their support, encouragement and guidance throughout the year. Others, however, have little to celebrate today. These are typically employees who have terrible relationships with their managers.

If you fall into that second group of workers, National Boss’s Day is the perfect opportunity to reflect on your employee-employer relationship, and think about ways to improve it.

“It’s very important to have a strong, or otherwise healthy relationship with your boss for a variety of reasons,” says Teri Hockett, chief executive of What’s For Work?, a career site for women. “First, your boss has a tremendous amount of influence over workplace stress, whether real or perceived. They can make the workplace exciting and something to look forward to each day, or a place that you dread visiting. In short, your health is at stake," she says. "Second, they typically hold the key to your advancement within the company, or sometimes outside as well. Without a good relationship, they may not speak highly of you or consider nominating you to other positions, departments or companies, regardless of your performance. And third, having a good relationship with your boss just makes sense. Work consumes most of your time usually, and having good relationships will make things more enjoyable and lead to opportunities.”

Joyce Maroney, senior director of customer experience and services marketing for Kronos, a Mass.-based workforce management software and services company, says the boss-employee relationship is much like others we need to manage in our lives. “We get out of them what we put into them – as long as both parties are committed to the relationship,” she says. “If both parties aren’t clear in communicating their expectations and giving feedback when expectations aren’t met, little issues can snowball to the point the relationship is no longer viable.”

Maroney says a recent Kronos survey revealed that 69% of employees believe their managers set a good example in the way they behave and 92% of those employees also believe their managers adhere to those values on a regular basis. “But setting a good example for behavior doesn’t always translate into a strong relationship. Employees might not get the direct and constructive performance feedback they need to elevate their career--or the boss isn’t all that invested so he or she doesn’t push the team to consistently achieve and grow.”

Sandy Mazur, a division president at Spherion, a recruiting and staffing firm, agrees. “In order to grow, learn and advance in their careers, employees need to be on the same page with their supervisors about their goals, objectives and career path,” she says. “And employees should start this dialogue so that they can open the lines of communication with their supervisor and engage them in this process.”

According to a recent Spherion “Emerging Workforce” study, most workers rate their relationship with their supervisor as good, great or excellent (84%). “However, for the small amount of people that rate their relationship as weak, it could be related to trust. Strong relationships are based on trust from both parties, and it takes an open line of communication from both the employee and the supervisor to make that happen.”

Other reasons some employees have such weak relationships with their boss?

Andy Teach, a corporate veteran and author of From Graduation to Corporation, says sometimes it’s simply due to the “very nature of the boss-employee dynamic.” “If an employee has someone over them who is constantly telling them what to do and in many instances, how to do it, this can easily cause friction and resentment,” he says. “An employee is always being held accountable by their supervisor and this just adds stress to the employee's already stressful work day. In addition, there are many employees who are jealous of their boss and perhaps feel that they, not the boss, should be the one in charge. Again, this causes resentment toward the one person at work who has the most control over your career.”

But Teach says it’s absolutely imperative to have a great work relationship with your boss “because they control your destiny.”

“You don't have to love your boss but you need to be able to work well with them. One of the main reasons employees leave their job is because of their boss. A troubled relationship with your boss can negatively affect your morale, your productivity, your happiness, and of course, your career. A positive relationship can improve your morale, productivity and happiness which could lead to more career success in the form of promotions, raises and higher self-esteem.”

Maroney says a “strong relationship” may mean different things to different people, but what she has seen again and again is that “it’s important to manage your relationship with your boss if you expect to prosper in a job.”

Here’s how to strengthen your relationship with your boss:

Put yourself in your boss’s shoes. Figure out the challenges your boss will encounter that day and be prepared to offer solutions, Mazur suggests. “Anticipate the questions that your supervisor may ask about your work or a project and have thoughtful answers or next steps for them to take. Thinking ahead can really show that you’re an invaluable team member.”

Teach says it's easy to be resentful of your boss, especially if they treat you a certain way, “but they have a job to do, just like you,” he explains. “There's a lot about their job that you don't know about or see, so don't assume that they're out to get you,” he adds. “Sometimes they act a certain way for a reason--perhaps their boss is putting a lot of pressure on them--so try to be understanding.”

Show value. “They hired you for a reason, so make sure that you’re adding value to the organization and/or position,” Hockett says. “Bosses want employees not only to agree with them, but also be willing to speak up about the realities and challenges in the business that need to be addressed. Be the person that speaks with facts, confidence and reasonable suggestions that produce results. This builds your boss’s confidence in you.”

Do whatever it takes to make your boss look good. “Everyone cares about their work reputation, or at least they should,” Teach says. “If you can make your boss look good, they will be happy--and if they're happy, you'll be happy.”

He says this also means that you shouldn’t correct your boss in front of others. “There is almost nothing worse for a boss than to have a subordinate correct them in front of other people. This is embarrassing for them, even if they are wrong about something. You're better off mentioning their mistake to them after people leave.”

Hockett agrees. “At all times, display a level of professionalism that not only benefits you personally, but also reflects highly of your boss,” she says. You’re a reflection of their leadership.

Know when and how to communicate with your boss. Does your supervisor like one sentence e-mails or prefer a detailed account of what's going on? Does she want to receive an outline of where your project stands, or do you need to provide all of the details? “Learn how your supervisor likes to communicate and receive communication, and mimic this style,” Mazur suggests.

Hockett says you should also ask yourself questions like: "What time of day would my boss prefer to answer questions I might have?" and "What day of the week is the best time to approach him?" “Knowing this in advance can greatly improve the relationship,” she says.

Ask for feedback. “Don’t be afraid to ask your boss for feedback,” Maroney says. “Don’t assume that your work isn’t valued because your manager is juggling multiple deliverables and not spending as much time with you as you’d like.” Too many people shy away from speaking up for fear of the unknown, she adds. “Ideally your manager should already be providing feedback but this is your career so don’t be afraid to take the driver’s seat.”

Get to know your boss personally. You don't need to be friends with your boss or hang out with them on the weekends. However, it couldn't hurt to ask them how their weekend was, or find out what their hobbies and interests are outside of work, Teach says. “Bosses are human, so communicate with them on a personal level.”

Offer to help. Hockett says you should ask as your boss if they need help on any projects. “Many bosses have a full plate, and sometimes will not speak up about needing help. So during conversation, ask them if they need a hand with anything,” she says.

Maroney agrees. “We all feel like there aren’t enough hours in the day.  Demonstrating that you’re willing and able to take on more is one of the best ways to position yourself for advancement. And who knows, you might get the opportunity to tackle a project that will let you learn new skills, earn new fans in the organization, and position yourself for bigger and better opportunities.”

Keep your supervisor informed. “No one likes surprises, so if you are experiencing challenges in your work, communicate those,” Mazur says. Don't hide behind obstacles or mistakes; just keep your supervisor informed along the way. “Whether things are going well, or not so well, you're building mutual trust and integrity if you keep your supervisor in the know.”

Teach agrees. He says your boss doesn’t want any surprises--so if you keep her informed of your progress on major projects through e-mail, phone calls or office visits, she won't need to micromanage you and "everyone will be happy."

Under-promise and over-deliver. Put your best foot forward to exceed your boss’s expectations, Mazur says. “For example, if you are working on an assignment, be sure to provide a realistic timeline for when you’ll get the work done and surprise your boss by completing it earlier than expected. This will show that you are proactive, and that you can manage your workload.”

Ask for help and advice. Maroney says 61% of survey respondents indicated they’d prefer that management invest in their professional development rather than spending on creating a fun environment. “Clearly people want to acquire new skills,” she says. “Your boss will likely warm up to you if they see you as a possible protégé.”

Hockett says people also like to be seen as subject matter experts, especially your boss. “Make a point to ask for their advice every so often, and make it count. You don’t want to ask for advice on something trivial. By inviting them into the process of finding or validating a solution, you’re showing how much you value their opinion.”

Show your boss respect. Even if you don't like your boss, respect them, Teach advises. “Chances are they've earned their position for a reason. Whether you like it or not, they are your supervisor. They're higher up in the food chain than you and if you disrespect them in any way, this will definitely hurt your relationship with them.”

Be authentic. Don’t be the person that is perceived to be kissing up to the boss, Hockett says. “Be authentic in your approach.” For example, swinging by your boss’s desk each day with a cup of coffee might not be a good idea, unless that’s in your job description. But, if you’re on your way to the break room, extending the offer to grab them one too is a nice gesture, she explains.

Stay above office politics and gossip. Your behavior reflects on your manager, Maroney says, so avoid snarky commentary, “and when it doubt, be circumspect.”

Hockett concurs. “Whether you think you can trust coworkers or not, it’s best to never engage in gossip about your boss, nor anyone else for that matter. Word always gets out when you do, which can weaken your relationship with your boss and peers.”

Establish a line of open communication. If you are honest and communicate openly with your supervisor, this will help build transparency and trust in the relationship, Mazur explains. Hockett suggests scheduling a weekly or bi-weekly phone or in-person meeting (15 to 30 minutes). “Use this time to build rapport, share progress and seek advice. If possible, try to get out of the office for lunch or coffee every so often with them.”

“At the end of the day, it's all about building trust within the relationship between you and your supervisor,” Mazur says. “Employees need their supervisors to be a mentor, cheerleader, go-to person, and advocate all in one--and so it's important to instill trust so that this can happen.” Also, if you're working for a supervisor that lives and believes in the values of the company and recognizes and rewards their employees for adhering to those values, then it will be a successful relationship, she concludes.

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