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Be Watchful for Derailing Personality Characteristics

Updated: Apr 8, 2022

The top reason people leave organizations is their relationship with their managers. Personality is a big people in positive relationships. An individual doesn't need to be gregarious, charismatic, or extremely outgoing. Those are often assumptions when thinking about personality in leadership. The key is that they don’t have derailing personality traits. We all have components to our personality that aren’t great. But take these to an extreme, and they create toxic work environments.

Hogan Assessments is an organization that has done brilliant work in personality. They produce an executive assessment that is, to my knowledge, the world’s most commonly used executive assessment. The comprehensive report summarizes the intensity against a number of different scales, such as how important recognition, power, etc. The reports are broken into three parts. First, the Potential or bright side report…attributes common to executives. The Values report illustrates various components that are commonly important to executives, such as hedonism, aesthetics, etc. Finally, the uniquely powerful report is the Challenge report. That is the one that outlines the common ways in which an executive will trip up…or derail.

Not enough focus is given to looking for derailers in candidates. I have found it is less the positive attributes and more the presence of derailers that tell the story of whether or not someone will be successful as a leader. The framework from Hogan is clearly articulated, so let’s use that to sort through common derailers because while there are other frameworks to think about such things, most of that fall within one of these categories. In this discussion, the thing to keep in mind is that too much of a good thing works against us. Whether it is being bold or cautious, each has its place. If you are consistently extreme in either one, it is simply limiting as a leader, and consequently, employees and organizations suffer. It is also important to note that when we are not our best selves because we are stressed, hungry, tired, etc., this behavior becomes even more extreme and further paralyzes an organization.

Here are several derailing personality traits you should be aware of and how to identify them in the interview process.


Someone who has a derailing characteristic of being bold is OVER confident. Confidence is often a trait people look for in leaders. Overconfidence is a turnoff and can often lead to bad decision-making. People who demonstrate this tendency have, as Hogan would describe, an inflated sense of self-worth and ego…they often show up as entitled. Take, for example, a former CEO who would drone on about how no one could get it right except for him. This hero complex did not play well with his team. The phrase “has to be the smartest person in the room” often surfaced around this individual, and as a result, people didn’t want to be around him. When people don’t want to be around you as a leader because they find you distasteful, you have limited yourself in your ability to impact things because, as I always say…by definition, leaders need followers.

You can look for this in an interview by listening for their word choice but also with questions such as:

  • Who is the smartest person you know and why that person?

  • How are you most misunderstood?

  • What frustrates you?

  • Where do you get your energy?


As much as being too bold is an issue, being too cautious is as big of an issue. Being too cautious looks like someone who doesn’t initiate things, is slow to make decisions, and is often resistant to change. Take the CEO who runs an engineering company and who cannot decide and stick to it. He’s extremely slow to make that decision, and everyone around him knows it is likely not to stick. It paralyzes the organization from moving forward on key actions. Leaders who behave in this way cause extreme frustration in those around them.

Questions to ask to flush out this derailer are:

  • When you think about growing an organization, what levers do you lean on?

  • Give an example of how you had to be flexible.

  • What was the biggest decision you made recently and why was it a big deal?

  • What is your approach and your philosophies regarding change management and change leadership?


Someone who has colorful as a derailer can be very dramatic, over playthings, and not listen. The last one seems to be the biggest detriment to leaders being effective. How often have you heard people express frustration because their leader wasn’t listening? The irony is that, in most cases, those leaders heard they are simply not using the input of others. Being too colorful doesn’t leave room for others. People want to be heard and want their input to matter. A common item on an employee survey is, “My opinion matters.” If this is low, you are sure to have morale issues, and shortly thereafter, you will have turnover issues. But, again, this is something set with the tone from the top.

Interview questions that help source for this are:

  • What do you do to maintain self-awareness?

  • What have you learned from others that were blind spots to you?

  • What are your frustrations/hot buttons and how do we know when you are frustrated? What does it look like?

  • What is some difficult feedback you have received in the past?


Diligent is defined as an extreme orientation to detail and overcommitment to precision. When leaders demonstrate diligence to a degree of detriment, they create an environment where it is difficult for employees to be successful. Nothing is ever good enough; nothing is ever completed. These leaders often grind their employees on points past the level of productivity. They can create a forum of “gotcha” based on the detail they require. Also, if leaders focus on these areas in the extreme, they are quite frequently not doing what they should be doing.

Useful questions to get to this in interviews are:

  • As a leader, what are things you are doing that others can and what are things only you can do that you should be doing more of?

  • On the scale of detail orientation (on the left) and strategic (on the right), where do you fall? (…and you can’t put yourself in the middle!)

  • What areas do you find people don’t work hard enough for your liking?

  • What are your hot buttons?


The derailing portion of someone who is dutiful is that they are overall concerned about what people think and, as a result, won’t be a contrarian and are viewed as eager to please. This is detrimental to a leader’s success. Employees are incredibly frustrated by leaders who won’t be brave and do the right thing by their assessment. Employees lose respect for leaders who won’t stand up for principals and, in turn, are conflict avoidant or are too pleasing.

Some questions to help identify these tendencies in an interview process are:

  • How do you handle office politics?

  • What is an example of where you had to take a stand about something with people at the next level leadership? What did that look like?

  • How would you describe your approach to conflict?

  • What is important to you in your relationships? What do you expect? What do you give to them? What are elements you try to avoid?

As mentioned, personality is a tremendous factor in the success a leaders enjoys (or not) in a leadership role. It is critical that we identify whether candidates, internal or external, have derailing personality traits as they are often largely unchangeable. The next blog will address an additional half-dozen derailers that we need to search for in potential leaders.


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