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Workplace Relationships – Are You and Your Boss Compatible?


Workplace Relationships – Are You and Your Boss Compatible?

Great strategies for developing workplace relationships with different personality types.

By Bridget Quigg and Lydia West, special to

Every relationship has its own set of issues – even, and maybe especially, the work relationship you have with your boss. The secret to developing workplace relationships is discovering the best ways to work with your particular boss and all the preferences and personality traits they bring to the table. Whether your boss is a charming hand-shaker or prefers spreadsheets to people, we have some advice on how to motivate different types of workplace personalities, and create the best possible working relationship with the person who holds the fate of your paycheck in their hands.

Boss Type: The Performer – New client dropping by in five minutes? Sounds great! Last-minute presentation? No problem! This extrovert thrives under pressure and loves to entertain clients (and everyone else). He’s very comfortable taking center stage, whether it be in the board room, at a client dinner or around the water cooler.

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The Pros:
•    Keeps the office atmosphere more fun and lively.
•    Very good at reading others and making them feel at ease.

The Cons:
•    May try too often to jump in and “help you” during a presentation or meeting.
•    Prefers to leave the details to someone else.

Most Compatible Employees for The Performer: Detail-oriented planners who know just when to bring the boss in to charm big clients or partners.

Best Strategies for Working with The Performer: If you’re less than comfortable speaking in public or schmoozing with clients, take the opportunity to learn from your boss. He’ll likely be happy to help you grow in an area where he feels strong. On the other hand, if you find you’re regularly being edged out of the spotlight in meetings, have a quick conversation to let him know you’re trying to improve your leadership skills and would like to have the floor more often.

Boss Type: The Planner – Does your boss not only have a 5-year plan but a 10-year and 20-year plan as well? Planners embrace details and deadlines. And, if you ever saw their email inbox, we’re willing to bet there’s a level of organization going on there that would rival Martha Stewart.

The Pros:
•    Keeps projects organized and delegates tasks well.
•    Is reliable and determined to meet every deadline.

The Cons:
•    Can get upset when unexpected changes come up.
•    May not leave room for other opinions.

Most Compatible Employees for The Planner: Those who take direction well and can see how each individual task fits into the bigger picture.

Best Strategies for Working with The Planner: Before a plan gets finalized, suggest a brainstorm meeting or two to ensure your ideas are represented as well. She is more likely to listen to new ideas before the wheels are in motion and you’re driving toward a deadline. If you want to make a change to an existing project, make sure to articulate your reasons for each change and why you feel it will create a more successful outcome.

Boss Type: The Dreamer – From new locations and bigger profits to more employees and brand new product lines, this person is great at coming up with new, creative ideas.

The Pros:
•    Always willing to push the envelope and innovate.
•    Inspires other with their enthusiasm.

The Cons:
•    Does not always consider the logistics needed to turn their “big ideas” into reality.
•    Is ready to move on to another project before the last one is complete.

Most Compatible Employees for The Dreamer: Realists with vision. If your boss has their head in the clouds, they need employees who will help them focus their energy on the best of their ideas and develop plans to make those dreams a reality.

Best Strategies for Working with The Dreamer: If it doesn’t already exist, suggest a process for vetting ideas before they make it to a planning stage. If an idea holds up to close scrutiny, do the work needed to set a schedule and keep the project moving forward. Keep your boss engaged and excited about the project by scheduling regular progress meetings. Be sure to enlist their help to work through interesting challenges that arise.

Boss Type: The Cheerleader – Your email to that client? Fantastic! Your comments during that meeting? Brilliant! Your boss thinks that everything you do is wonderful or at least, that’s what they tell you.

The Pros:
•    Helps boost your confidence about your skills and potential.
•    Does not wallow in difficulties or obstacles and keeps morale high.

The Cons:
•    Hides more critical feedback that could help you learn your job better.
•    Does not predict potential difficulties and plan for them.

Most Compatible Employees for The Cheerleader: Independent workers who don’t require a lot of hand-holding or specific direction to do their job well.

Best Strategies for Working with The Cheerleader: Everyone likes to feel appreciated, so that shower of compliments about your most recent presentation can be wonderful to hear, but if you’re never challenged to improve, it’s easy to get bored…or worse, blindsided. The danger here is that your boss may have issues with your performance and just has a hard time expressing it. While asking for critical feedback can seem like a foolish endeavor, ensuring that you truly know how your boss views your job performance is critical to your success. Be as specific as possible about what you want to know. Ask questions like, “I feel like I let that meeting get a little off-topic. Do you have any tips for me to handle things better next time?”

Boss Type: The Super Achiever – Another spreadsheet? More meetings? Tighter deadlines? This person loves to say, “Sure, we can do that!” They’re happy to hustle and keep the business coming in.

The Pros:
•    Helps increase everyone’s earnings by attracting customers.
•    Is confident that anything is possible.

The Cons:
•    Can lack realistic expectations about timelines and deliverables.
•    Has a hard time setting boundaries with clients.

Most Compatible Employees for The Super Achiever: Good communicators who aren’t afraid to push back, especially when they think taking on additional work might put other projects in jeopardy.

Best Strategies for Working with The Super Achiever: The key to working with a Super Achiever is knowing when to rein in expectations and when to just roll with the extra work. You don’t want your boss to view you as a naysayer. Rather than exclaiming, “there’s no way we can take that on,” help your boss see how everything can be achieved in a more realistic timeframe. Another good idea is to keep a running list of your projects and schedule a regular meeting with your boss to review and prioritize them. This way both of you know what you’re working on and hopefully, you can collectively set more realistic expectations that won’t have you working an 80-hour week.

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