Dealing with Difficult (and Sometimes Crazy) People

Dr. Miriam Reiss

February 03, 2019

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Miriam Reiss will be hosting the following webinar on February 21, 2019, from 12:00 p.m.–1:00 p.m. PT (3:00 p.m.–4:00 p.m. ET).

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As an executive coach for over 20 years—and WITI (Women in Technology International) webinar presenter and conference speaker for 12 of those years—I've come across a wide range of personalities. From the C-level IT'er who frequently scheduled last second, sunrise team meetings, to the executive who insisted that direct reports follow his own, specific format. I've seen bosses, employees, and co-workers create emotionally stressful, charged environments for those around them.

While it's hard being around difficult people, it's harder if that person is your boss or supervisor. According to a Gallup poll, more than 75% of employees in the United States quit their jobs because of their bosses—and not because of the job, the company, or a lack of opportunity. I've seen clients' work performance, sleep, health, home life, personal relationships, self-worth, and self-confidence negatively impacted by difficult bosses. Challenging supervisors can block otherwise high performers' levels of motivation and resulting success.

Over time, I've come to identify 13 classic, difficult personality types that show up regularly in organizational settings, along with six personality subtypes. And, just to keep things interesting, these types aren't always cut-and-dried. A difficult person may be a combination of more than one type. While you might be able to guess some of the types, such as the control freak and the gossip, other types are more subtle to the eye but still manage to do significant damage to organizational productivity and bottom line.

While each type has its own specific behaviors and needs to be dealt with in customized ways, here are some overall tips for dealing with difficult personality types:

Don't Try to Change Them

Difficult personalities often attract fixers, people who want to change their behavior. While the fixer may say that they're not trying to change the difficult person's behavior, their actions typically indicate otherwise. Know that trying to fix a difficult personality is a lost cause. It's not in the job description to fix difficult people.

One-Size Doesn't Fit All

For sustained effectiveness, each of the difficult types needs to be approached in specific ways. What works with one type may backfire with another.

Sensitivity Level

Difficult types of people are often more sensitive. A tough exterior doesn't equate to a tough interior.

Approach Matters

Success with a difficult person will be directly linked to neutrality. When acting reactive or judgmental, expect defensiveness or anger from the difficult person.

Dr. Miriam Reiss, DSS, MCC, executive coach, speaker, and WITI webinar leader, is a specialist in leadership development, neuroscience, psychology, marketing, and wellness. She specializes in working with women in technology. You may contact Miriam at

Opinions expressed by the author are not necessarily those of WITI.

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