What You Need to Know About Workplace Personalities – Lessons From the Gilmore Girls

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This post was updated to bring you the most up-to-date tips, October 2020.

Journeying to Stars Hollow has taught us many lessons on love, friendships, and life over the years. The Gilmore Girls’ multitude of personalities has given everyone someone to relate to — but managers have the challenging task of connecting with every personality type in the office without the drama. 

Leaders must connect with employees, but it’s challenging with so many different workplace personalities in the office. In fact, a 2017 study by Ultimate Software found that for 93% of employees, trust in their direct boss is essential to staying satisfied at work. More than half of employees surveyed say if they aren’t satisfied at work, they can’t put forth their best effort.

Gilmore Girls has provided perfect examples of varying workplace personalities — here’s a look at how to create a relationship with each one:

The control freak (Taylor)

Taylor owns many different businesses throughout Stars Hollow and is the head on multiple committees. He likes to be involved in every aspect of the workplace by micromanaging and ensuring each rule is followed precisely.

Sometimes these types of people can seem overbearing, but we can’t forget their primary goal — making sure everything goes well. Listening is key to building a relationship with those who like to be in control. Start by understanding what they want to do and why. If you disagree, you will know exactly how to make them understand why there’s a more efficient way to go about things. 

The overreactor (Sookie)

Sookie can be found running around the kitchen freaking out because the turnips Jackson delivered aren’t symmetrical. To her, this wasn’t just an inconvenience. It would ruin the entire meal.

Overreactors can be found preparing to make sure every tiny detail goes as planned — if it doesn’t, watch out. These employees are genuinely invested in their work but can get overwhelmed with the details. This personality type needs to hear that they’re not only doing a good job but exceeding your expectations.

Formal meetings may be too stressful for an overreactor because they like to keep busy, making things happen. Consider scheduling a brief walking meeting to discuss progress and gain feedback on what you can do to help make their workday run smoothly. 

Also, be present just by popping in to reassure them they’re on the right track — even if something does go wrong. Knowing management has their back will help ease the pressures they put on themselves. 

The negative Nancy (Luke)

It may be difficult to understand why Luke’s diner is continuously full of people. He tends to be rude, irritable, and somewhat unpredictable — but the coffee is just that good. 

Almost any leader can point out a person with this attitude on their team. This personality type can be harmless, but their negative outlook also can bring down the entire team’s morale. 

Transparency is the best way to deal with these types of people. Showing them how their daily tasks positively affect the company, and what management does once these duties are complete, can potentially curve their negative tendencies. 

Give their frustrations a safe outlet by letting them know they can come to you with any issue, so you can work together to solve it. Schedule weekly meetings to promote leaving the negativity in your office, rather than with other co-workers, or worse — clients.

The perfectionist (Rory)

Rory took her smarts all the way to Yale where she continued to give 110% — with only a few meltdowns along the way. Luckily, she had an unconventional mom to throw her pizza and candy parties when she needed a break from her mind. 

Perfectionists probably make up most of your A-Team. They have excellent communication skills and are always on top of their tasks. So, why is it important to focus on building relationships with these types of people? 

Striving for perfection every day is exhausting. These overachievers tend to overwork themselves, which can lead to both mental and physical breakdowns. 

Help limit perfectionists’ anxiety by creating weekly checklists. Make sure team members understand that once they check off these tasks, their workweek is over. Also, be sure they have the tools to succeed, so they do not stress over perfecting little details. 

You can always recognize their hard work with benefits that will help them take necessary breaks, as well. Start with a half-day once a month or add an extra day of vacation, and encourage them to take those essential breathers. 

The free spirit (Lorelai)

The proud owner of The Dragonfly Inn is as laid back as a business owner can get. Lorelai Gilmore knows how to run a business well and doesn’t allow the small stuff to bother her. 

Some may view a free-spirited employee, like Lorelai, as someone who doesn’t care about their work quality. On the contrary, they are very invested, but refuse to let little bumps in the road affect everything — or everyone — else around them. 

These go-with-the-flow attitudes will work well in a one-on-one setting where you can express your expectations and freely discuss any issues. Rehash a few of the mishaps from the previous month, take a look through their eyes at the problem, and work out a prevention plan together. These meetings provide leaders with the opportunity to learn what makes this personality type tick and what they’re trying to accomplish in the way they handle their workflow.    

Your relationship with these different types of workplace personalities may be on again, off again. So remember, always keep the communication — and coffee — flowing.


What tips do you have for leaders who are struggling to connect with their employees? Let us know! 

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Val Matta
Val Matta
Val Matta, Managing Director of CareerShift, co-founded the company in 2005 to help individuals bridge the gap between education and employment.  As a recognized expert in the field, Val is a frequent speaker on career management, networking, and job hunting strategies.  You can connect with her and the CareerShift team on FacebookLinkedIn, and Twitter.