3 Difficult Personalities That Are Great Hires


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The concept of personality types, temperaments and working styles has been foundational in organizational behavior for years. As entrepreneurs or managers, we frequently assess personality to determine ideal team composition and workflows. While toxic personalities certainly exist, many others that seem difficult can offer severe advantages to start-up organizations. Oppositionality, non-conformity, perfectionism and the fickleness that often accompanies abstract thinking should not be deal-breaking traits.

As a founder, I tend to have strong opinions about the working styles and personalities of those I consider creative, resourceful and hard-working people. At the same time, certain characters tend to clash within small teams, creating a challenging work environment. However, hiring managers can quickly write off people who are “difficult” as toxic — which can cost a startup its competitive edge. I, for one, appreciate the contributions that seemingly “difficult” people make. Here are three challenging personalities that frequently make great hires and give startup teams the edge they wouldn’t have without them.

Related: Smart Advice for Networking With These 4 Personality Types

1. Demanding yet artistically brilliant

Just about any founder or CEO would appreciate a genius as part of their team, yet these rare outside-the-box thinkers can be notoriously difficult employees. They can be prickly, fiercely individualistic, anti-team players and have fragile personal lives.

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At my former design retail business, a set stylist we worked with fit the bill perfectly. Not only did he demand twice the market rate, but he also wanted my constant attention and would not allow anyone else on the team to address his concerns. That said, he successfully delivered the most beautiful sets in the most unlikely and underwhelming locations: he could turn a cave into a castle for the camera.

In today’s ultra-competitive consumer product market, where hundreds of versions of every item are available, the differentiation of brilliant design can make or break your brand.

Despite the obstacles, hiring a category-defying genius paid off for us. The key is to manage these individuals with empathy, awareness and appreciation for their unique contributions — while still setting the requisite boundaries for your sanity. Set your expectations that these hires will be individual contributors — not necessarily team players — and budget your time accordingly.

Related: Are You Asking for Employee Feedback? If Not, Good Luck With Retention.

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2. Absent-minded abstract thinker

For rational, linear thinkers who prioritize planning and organization, absent-mindedness can drive you crazy. Yet the same mental process that leads to fickleness can fuel fresh ideas and uncharted solutions.

According to a study published in Psychological Science, mind-wandering spurs what neuroscientists call “creative incubation,” allowing a disjointed train of thought to make unlikely and uncommon connections that yield unique and creative solutions.

Although one of the most inspired web developers I worked with often didn’t know what day of the week it was or where to find the printer he used every day, he figured out how to fashion a basic Shopify ecommerce system to deliver a fully custom site with sophisticated and unique UX features, flexible navigation and a robust backend–the likes of which even enterprise-level systems don’t often offer.

The key to working with these absent-minded gems is to pair them with a colleague who can provide extra operational support.

3. Problem-finding contrarian

While working with someone forever finding problems can be discouraging and morale-crushing, a team that enthusiastically supports an unrealistic product idea is headed for failure. The right balance is hiring that smart contrarian: “Someone who looks for business practices that don’t make sense, who’s not too reliant on a small group of like-minded people, who can embrace diversity, and who’s happier on the sidelines.”

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A founder I mentored shared with me that she only hired people who showed extreme enthusiasm for her product — a scheduling app. She wanted to avoid negativity. As a result, no one on her team paused the beta launch to address a known glitch, and her app experienced a significant feature failure.

Having that smart contrarian to call out real concerns at the right time, even if it’s not the popular or politically correct move, can help ensure problems are addressed before too many resources are invested, or larger issues ensue. While contrarians can be frustrating, they spot critical gaps others might fear speaking out about. To work effectively with contrarian personalities, practice prioritizing their observations and be prepared to translate unsolicited criticism into better ideas and more innovative solutions.

Related: 5 Ways to Make Your Company’s Hiring Process More Fair

The final decision

Ultimately, you’ll need to weigh the costs and benefits of working with challenging personalities in your organization. While many demand special accommodation, buffering and hand-holding, I have found that their contributions are worth the investment.



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