Using Personality AI to Improve Your Leadership

Leading a growing team with many different personalities is not an easy endeavor.

Scaling up

Leading a team of unique, diverse people can be challenging. There are not many jobs that contain so many ambiguous, difficult responsibilities each day, like encouraging, motivating, and delegating to coworkers, coordinating group communication, answering questions, and working through conflict, all on top of your individual contributions.

When Drew and I started our last business, an event management software company, we needed to assemble our first sales team. It wasn’t very difficult in the beginning; when we found a qualified candidate, we’d hold an interview, and then hire them if they felt right for the position. It was simple enough. Once they were hired, we naively figured the hardest part was behind us.

As we began to grow more rapidly, we were quickly scaling and adding sales reps to qualify leads and conduct demos of our software. We assumed that as we added more reps, our sales numbers would continue to increase proportionally, but quickly learned that was far from the truth. Instead, we found that as the sales team grew larger, our sales increased at a lower rate. 

It became harder to be productive, rather than easier.

Each sales rep seemed to perform in different ways, depending on the type of prospect they encountered. Some seemed to do well with big customers that required establishing a long, consistent relationship beforehand, whereas others did well in shorter sales cycles for smaller customers that were sold in a more transactional way.

Unsurprisingly, as we continued to expand swiftly in sales, we encountered many other challenges. Communication progressively became more difficult, which negatively impacted our overall performance. It became more strenuous to keep all of our sales reps informed about the nuances of product updates. Additionally, each member of the sales team appeared to respond uniquely to my natural management style. While it felt easy and natural to get along with some, it felt like a struggle to even be on the same page as others. 

We quickly began to understand what many seasoned leaders have learned through experience: leading a growing team with many different personalities is not an easy endeavor.

Why groups are so complex

Every group is composed of complex people with vastly different personalities, communication styles, motivations, and personal experiences. Unsurprisingly, this intricate mix often makes group communication far more difficult and stress-inducing than one-on-one communication.

Take our current company, Crystal, for example - our office is a melting pot of strengths, weaknesses, communication preferences, and backgrounds. Without an understanding of each other’s differences, we would put ourselves at risk for frustration, confusion, and significant interpersonal conflict.

Thankfully, we use our own product for daily management and collaboration, so each person on our team can understand the unique work style of everyone else. The result is a collaborative and communicative culture, where our team takes the default position of empathy over ignorance. We use personality profiles to help each other improve and grow, emphasizing our strengths and building systems to accommodate our blind spots. 

However, I have worked on teams in the past where this was not the case and you likely have as well. It’s easy to overlook the importance of team dynamics when you’re staring at your overflowing email inbox or the growing pile of bills on your desk. The problem is that when we forget how to effectively lead and manage people, everything else is much more likely to fall apart.

If we have a solid grasp on each person’s differences, strengths, weaknesses and communication style, we can operate much more effectively. In other words, to be better leaders and grow great companies, we need to understand the intricacies of personality.

Understanding personality

Historically, the only way you would be able to fully understand someone’s personality is by either getting to know them really well, which takes lots of time and emotional intelligence, or having them take a personality test. Both of these approaches require that you have an established relationship with the person, which doesn’t tend to work in the world of outreach communication, since we are often trying to connect with new people who we have never spoken with before.

Thankfully, there is a new technology that unlocks another way to learn about someone’s personality without an assessment - Personality AI. We wrote about this in detail in another ebook titled, Personality AI (which you can download for free). This new technology analyzes publicly available information on websites like LinkedIn to predict someone’s personality, using artificial intelligence and machine learning. We built our product, Crystal, to harness Personality AI and enable anyone to identify personalities online to improve their communication and build stronger relationships, all based on the core principle of empathy.

Without getting too technical, when Crystal’s AI predicts personality, it uses a framework called DISC to classify personalities into a few categories that we refer to as D (dominance), I (influence), S (steadiness), and C (conscientiousness). Each of us has a primary DISC type in one of these categories and sometimes a secondary DISC type in another. To keep things simple, we separate these into easy-to-remember labels called Archetypes. 

You can see them all on this graphic called the Personality Map:

Below is a breakdown of common personality traits within each of the categories in DISC.

 D Personality Types: Captains, Drivers, Initiators, Architects

  • Motivated by control over the future and personal authority
  • Tend to prefer instant, concrete results and having an advantage over competition
  • Communicate clearly and succinctly

I Personality Types: Influencer, Motivator, Encourager, Harmonizer

  • Motivated by innovative, unique, creative ideas and excited by the future
  • Tend to prefer building new relationships and experiences
  • Communicate in a casual, expressive way

S Personality Types: Counselor, Supporter, Planner, Stabilizer

  • Motivated by peace, safety, and others’ wellbeing
  • Tend to prefer security, reliability, and trust
  • Communicate in a friendly and genuine way

C Personality Types: Editor, Analyst, Skeptic, Questioner

  • Motivated by logic, information, and problem solving
  • Tend to prefer accurate information and quality solutions (quality over quantity)
  • Communicate in a business-like, fact-based way

These differences are extremely important to understand when approaching a conversation with anyone. For example, someone who is a warm, people-oriented Supporter (S) is less likely to engage in a discussion about facts and data. They’d usually prefer to engage in a more personal, get-to-know-you conversation. An Analyst (C), on the other hand, tends to enjoy learning more about specific, concrete information. By identifying someone’s personality type, we can learn how to best communicate with them.

Understanding yourself as a leader

Being a leader carries tremendous responsibility to communicate well, understand others, and make sure everything that needs to be done is completed. It can be overwhelming for some, while others may find themselves naturally drawn to the challenge. As a leader, it’s important to be consciously aware of your own strengths and blind spots so you can use your talents effectively and avoid your natural pitfalls.

D Personality Types (Captains, Drivers, Initiators, Architects) 


  • Eager to take charge and provide clear direction.
  • Tends to challenge others with demanding tasks and high expectations. 
  • Provides high-level instructions that focus on the end result.  
  • Creates a competitive, dynamic work environment. 

Blind Spots

  • May immediately seek to resolve conflict by starting verbal disputes. 
  • Pace of work may be too fast for team members to complete their tasks with high enough quality for their standards. 
  • May not allow team members enough flexible time to get to know each other well and build trust. 

I Personality Types (Influencers, Motivators, Encouragers, Harmonizers)


  • Creates a casual, outgoing work environment. 
  • Focused on inspiring others with a bold vision of the future. 
  • More comfortable delivering important messages verbally, with group meetings. 
  • Gives others autonomy to find their own solutions to problems.

Blind Spots

  • May not maintain thorough notes and documentation for team members to refer to. 
  • May have a relaxed attitude towards risks, without carefully considering the costs and consequences of major decisions.
  • May not devote enough time for the team to analyze the details of a problem before jumping to solutions. 

S Personality Types (Counselors, Supporters, Planners, Stabilizers)


  • Typically leads by example.
  • Creates a peaceful, calm work environment. 
  • Expects team members to be stable, reliable, and cooperative. 
  • Focused on developing the team with one-on-one coaching and instruction.

Blind Spots

  • May be overly forgiving instead of holding team members accountable to deadlines, quality, and responsibilities.  
  • May allow interpersonal conflicts to sit beneath the surface without bringing them out into the open. 
  • May miss out on good opportunities for team development and advancement because of high sensitivity to risk.

C Personality Types (Editors, Analysts, Skeptics, Questioners)


  • More comfortable distributing important messages in writing. 
  • Focused on creating rules and processes for others to follow. 
  • Expects team members to make decisions with logic and supporting data. 
  • Provides detailed, specific instructions to solve problems.

Blind Spots

  • May encourage the team to spend lots of time researching and assembling information when immediate action is required. 
  • Might ignore the emotional or social impact of a decision, even when it is logical and practical.
  • May restrict more creative team members by requiring them to conform with standard practices, rather than allowing for flexibility.

Understand your team

Within the team, people are likely to receive direction and leadership in different ways. As a leader, it becomes your job to be adaptable to many different communication styles and preferences. This is important to establishing trust, building connections, and communicating effectively. By understanding your employee’s preferences and adapting your communication style to match, you are likely to have more engaged employees who are happier and more productive.

D Personality Types:
Captains, Drivers, Initiators, Architects

Meetings: Should be very brief, to the point, and only scheduled when necessary.

Emails: Should be brief, business-like, and concise.

Feedback: Should be direct, actionable, and focused on the most important points.

Conflict: Essential for improvement, as long as it is actionable and objective.

Team: Teams should have a leader with clearly defined authority and effective distribution of responsibilities.

I Personality Types:
Influencers, Motivators, Encouragers, Harmonizers

Meetings: Should be done in-person when possible, without a rigid agenda.

Emails: Should be friendly, casual, and personal.

Feedback: Should be focused on the high level and delivered with encouragement.

Conflict: Can be a powerful tool to discover new solutions and ideas, but can also lead to people arguing in circles.

Team: Collaboration is essentially for teams to build relationships and achieve goals together.

S Personality Types:
Counselors, Supporters, Planners, Stabilizers

Meetings: Should be done in-person when possible, with a prepared agenda.

Emails: Should be warm, sincere, and expressive.

Feedback: Should be thoughtfully explained and delivered with empathy.

Conflict: Should be handled with caution, as it can escalate and result in hurt feelings.

Team: Should support each other and make sure everyone is always on the same page.

C Personality Types:
Editors, Analysts, Skeptics, Questioners

Meetings: Should be minimal, formally scheduled, and with a prepared agenda.

Emails: Should be clear, detailed, and factual.

Feedback: Should be specific, detailed, and delivered with logical reasoning.

Conflict: Conflict is a useful way to discover truth and bring underlying issues to the surface, as long as emotions are kept out of it.

Team: Should allow individuals to make their own independent contributions and create their own processes.

Energizing vs. draining behaviors

When delegating tasks, it’s important that you keep in mind the activities that will give someone energy and activities that may drain them.. If people are constantly given tasks that exhaust or overwhelm them, they’re likely to be much less happy and productive. 

For example, if you asked an Analyst (C) to host a big party for potential investors, they’re likely to be:

  • Surprised by the request
  • Overwhelmed by the amount of socializing
  • Completely depleted of positive energy

However, if you made the same request of an Encourager (Is), they’d likely be:

  • Excited by the opportunity
  • Motivated to do a good job
  • Brimming with creative ideas

By giving your team members tasks that are aligned with the strengths in their personality, you’re ensuring that their work doesn’t feel like work. People are happy, energized, and productive when they are in a role that allows them to do work that motivates and excites them.



D Personality Types

Types: Captains, Drivers, Initiators, Architects

Completing ambitious projects on a tight deadline.

Communicating with quick conversations and messages, only when necessary.

Taking primary responsibility and ownership over large projects.

I Personality Types

Types: Influencer, Motivator, Encourager, Harmonizer

Regularly interacting with a large, diverse group of people.

Providing verbal encouragement and telling stories.

Explaining things with emotional, expressive language.

S Personality Types

Types: Counselor, Supporter, Planner, Stabilizer

Paying attention to the needs and concerns of other people.

Playing a supporting role on the team and staying out of the spotlight.

Responding to difficult situations with empathy and compassion.

C Personality Types

Types: Editor, Analyst,

Skeptic, Questioner

Solving problems with thorough analysis of the existing data.

Taking time to meditate on a problem before making a

final decision.

Working on projects independently and bringing results back

to a group.

When people are placed in roles that require them to perform tasks that overwhelm, bore, or exhaust them, they tend to feel frustrated and weary. While it’s absolutely possible for people to perform well in roles that are outside of their comfort zone and require them to complete tasks that are considered “energy draining” for them, they will likely have a difficult time performing consistently well, unless there are other aspects of the position that allow them to engage in more energizing behaviors.



D Personality Types

Types: Captains, Drivers, Initiators, Architects

  • Listening to questions from other people and responding thoughtfully.
  • Building long-term trust and loyalty with consistent, predictable behavior.
  • Responding to difficult situations with compassion and empathy.

I Personality Types

Types: Influencer, Motivator, Encourager, Harmonizer

  • Solving problems with thorough analysis of the existing data.
  • Spending a lot of time researching the root causes of a problem.
  • Creating procedures, rules, and guidelines for other people to follow.

S Personality Types

Types: Counselor, Supporter, Planner, Stabilizer

  • Making decisions on behalf of other people without much group input.
  • Communicating with quick conversations and messages.
  • Critically questioning existing practices and procedures.

C Personality Types

Types: Editor, Analyst,

Skeptic, Questioner

  • Discussing abstract ideas instead of concrete ones.
  • Taking the time to understand how someone else thinks.
  • Bouncing between multiple ideas at once.

Delegating the right tasks and addressing people in a way that energizes and motivates them boosts overall morale and engagement. Not only will your team be more productive and efficient - they will be happier while working. That’s the point of all of this: communicating in someone’s preferred style and giving them work that energizes them will make them happy, safe, and comfortable and, in turn, lead to a more productive, healthier, positive environment for everyone.

What not to do

I have to admit, I haven’t always been the best at managing people. 

A few years ago, we hired a Supporter (S), who we’ll call Wendy. Wendy was kind and encouraging, but would take a few days to weigh the risks and benefits necessary to make important decisions. As a direct and assertive Architect (Dc), I tend to prefer fast-paced, efficient work environments and did not have an easy time accepting Wendy’s slower pace. When I made my expectations clear, she seemed hurt and offended. Similarly, I would address any problems I had with her work as quickly as possible and in person, in order to effectively discuss them. Wendy always seemed to have a difficult time doing this and would often seem to agree quickly with me, offering no defense for her own actions and perspective. Though, I’d later find out that Wendy did not necessarily agree with me after all; she was just avoiding conflict.

We seemed to have a very different understanding of how our relationship should function: while I prioritized direct leadership and clear expectations, Wendy preferred supportive and collaborative leadership. By treating Wendy the way I would want to be treated by a leader, I had pushed her away and stressed her out. She grew to feel uncomfortable in the office and, as a result, became less productive.

What to do

When I realized what was going on, I put a great deal of effort toward making Wendy feel more comfortable. For starters, I offered support by sharing recognition for the good work she had put into the company. I took the time to show appreciation for her contributions and set aside time to get to know her more personally through a team lunch. She seemed to really appreciate everyone going out to eat together. I began being less overt and blunt in my feedback; instead, I focused on addressing the good work she had done first, followed by a more soft, gentle expression of what I felt could be improved. I continued offering support, encouragement, and community day-to-day, and her productivity began to increase. Though she didn’t seem to enjoy the first couple of weeks on the job, a simple change in management style helped her thrive.

To be sure, this doesn’t mean I used that adjusted management style for everyone. To the contrary, we had a Questioner (CD) on the team, who we’ll call Robert. For Robert, my style of direct, assertive management was effective. Though Robert still took his time making well thought-out decisions, he didn’t take my need for efficiency too personally. He usually liked clear feedback and appreciated when I skipped over small-talk. As long as I gave him plenty of space to work independently, Robert worked well with my natural leadership style. 

Importance of leading with empathy

Leadership isn’t a cookie-cutter one-size-fits-all act; it requires a great deal of patience, understanding, and responsibility. If you’re not adjusting your communication for the different personalities of the people you’re leading or delegating responsibilities at least partially based on personality, you’re not utilizing your workforce efficiently. 

You’ve been entrusted with a position of authority and guidance, it’s so critical to understand who the people you’re leading are and how their tasks affect them. Tools like Crystal can tell you what someone’s personality type is, how to best communicate with them, and what tasks will be energizing for them. 

By making an effort to learn about your employee’s unique identities and using personality insights to help you communicate more successfully, you can create a cohesive, united, smoothly-running work environment.

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