Being Easy to Work With is the Single Most Underrated Career Skill

Be the employee every leader wants on their team

Jessica Donahue, PHR
5 min readFeb 17, 2022

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Being Easy to Work With is the Single Most Underrated Career Skill
Photo by Jud Mackrill on Unsplash

Have you ever been asked to “tell me about the most difficult coworker you’ve ever worked with and how you dealt with them” in an interview? The first time I recall being on the receiving end of this interview question, I was in high school.

I still remember the panic bubbling up inside of me as I searched the depths of my memory for a solid example. I hadn’t yet worked with many people, and those I had worked with were all relatively pleasant.

I was 16 years old and an aspiring summer camp counselor — what was there to be difficult about?

But after more than a decade spent working in HR, first in corporate America and now as a solopreneur and startup consultant, I would knock this question out of the proverbial park if asked today.

There are just so many examples to choose from.

We’ve all encountered people who are difficult to work with in our professional lives. We know how to spot them and what to expect from them.

It won’t matter what you do or don’t do; it will always be wrong in their eyes.

The problem with being perceived as someone who is difficult to work with is that over time, it won’t matter how good you are at doing what you do.

There will come a time when the headaches you cause for others will outweigh the value your [often very high-quality] work brings to the organization.

I recently read an interview with Molly Graham where she talked about how to thrive at a hyper-growth company. People working at companies like this often have the most to gripe about because things are constantly in a state of flux, but not Graham.

Molly helped the startup Quip go from pre-launch to a Salesforce acquisition, before pivoting to philanthropy with the Chan Zuckerberg Initiative. Now, she’s landed at Bloom Institute of Technology, as their COO.

Looking back on her success, Graham points out the importance of being the person that everyone wants to work with. “This is one of the most effective ways to get more responsibility and to grow inside of companies…

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Jessica Donahue, PHR

Fractional HR & People Ops for Startups & Early Stage Companies