Managing Conflicting Personality Types in Executive Teams

We’ve all heard the phrase that owning 80% of a watermelon is way better than owning 100% of a grape - apply the same analogy to the composition and interaction workflow of your core team. A team that has invested in optimizing their structure operates at ~100% efficiency is much more effective than a team that pushed this ongoing and critical topic to the side so they could continue operating at ~75% or even less efficiency. Startup management teams are composed of individuals with different backgrounds, experiences, and skills - and these folks are often introduced to the core management teams because they have experience building or running teams before. While that’s a great skill to have, it also often comes with a steadfast thought process that what they’ve been doing is the most ideal strategy, and that whatever their department is in this new firm with you, they must implement the same learnings to ensure success.

This desire for success is great, but when untamed, it can only augment what one can assume is an already non-optimized core team of equally-motivated individuals. And while diversity is a strength, it can also lead to communication and collaboration challenges. One tool that can help startup management teams navigate these challenges is the Myers-Briggs Type Indicator (MBTI). 

As a quick background, the MBTI is a personality assessment that categorizes individuals into 16 different personality types based on their preferences for certain behaviors and attitudes. By understanding their own personality type and the personality types of their team members, individuals can improve their communication and collaboration skills.

For example, an individual with a preference for thinking may have a difficult time understanding the perspective of an individual with a preference for feeling. By understanding this difference, the team members can work to bridge the gap and improve their communication. Similarly, an individual with a preference for judging may have a difficult time understanding the perspective of an individual with a preference for perceiving.

Moreover, MBTI can also help team members understand their own strengths and weaknesses, as well as those of their team members. This knowledge can help them work together more effectively and assign tasks and responsibilities that play to each team member's strengths.

In a startup, where resources are limited and the pressure is high, it's critical for the management team to work together effectively. The MBTI can provide a valuable tool for improving communication, collaboration, and overall teamwork. BUT, keep in mind: when using the MBTI to understand the personalities of a startup management team, it's important to be aware of potential conflicts between different personality types.

For example, individuals with a preference for thinking may have a difficult time understanding the perspective of individuals with a preference for feeling. These individuals may also have different communication styles and approaches to decision-making. Individuals with a preference for thinking tend to rely on logic and analysis, while individuals with a preference for feeling tend to rely on emotions and values. This can lead to conflicts if the team members are not aware of these differences and make an effort to understand each other's perspectives.

Similarly, individuals with a preference for judging may have a difficult time understanding the perspective of individuals with a preference for perceiving. Individuals with a preference for judging tend to like closure, structure and planning, while individuals with a preference for perceiving tend to like flexibility, adaptability, and spontaneity. This can lead to conflicts if the team members are not aware of these differences and make an effort to understand each other's perspectives.

To avoid conflicts and improve communication and collaboration, it's important for team members to be aware of these potential issues and to make an effort to understand and respect each other's personality types. This may involve learning about different communication styles, adjusting work processes, and making an effort to find common ground.

It's also important to remember that while there may be potential conflicts between certain personality types, these conflicts do not necessarily mean that individuals with these personality types cannot work together effectively. With awareness, understanding, and mutual respect, individuals with different personality types can work together to achieve common goals.

I’ll share a short story, for which I’ll replace the actual names of the people with generic ones:

In a prior company of mine, a multi-million dollar consulting firm, I had a management team composed of four very different individuals, with very different risk appetites (and definitions of risk): 

I was the CEO, with a preference for whiteboard, dreaming of creative methods to execute, and generally had a higher risk appetite than others in regards to new business and partnerships; We had Sarah, a CRO with a preference for feeling and “getting the sale” regardless of the risk it posed - immediate or future; Michael, a COO/CFO with a preference for structure, processes, and judgment, accompanied by a lack of appetite for any sort of risk; and Emily, a CTO with a preference for perceiving and iterating in real-time, at roughly the same risk appetite level as the CEO (but in a completely different style).

As the CEO, I had, or thought I had, a clear vision for the company and made decisions based on logic and analysis. I was always focused on achieving the company's goals and was not very flexible when it came to changes in the plan, but I was forced to be flexible when others’ plans changed that directly affected us. Sarah, the CRO, on the other hand, was more empathetic, but towards potential clients or partners, without considering the impact of the commitments on the employees and customers.

Michael, the COO/CFO, was a stickler for deadlines and was always looking for ways to streamline the company's operations. He liked to have everything planned and organized in advance. He often advocated for more of a human-centered approach in the company's decisions (and would say things like “I’m just trying to set you up for success” which would drive me bananas).

Emilio, the CTO, was more open-minded, always looking for new and innovative ways to approach problems with him and his team, regardless if it was in line with what we had talked about in the meeting literally that same morning. As a CTO, he had a tremendous ego (my way or the highway) and he was not comfortable with strict schedules and preferred to be able to adapt to changes as they arose (“you guys wouldn’t understand, please let me do this since this is my area of expertise”) - an obvious red flag for the other C-suite executives who liked to have a clear-cut plan.

At first, the team was “fine”, but that’s when complacency started to creep in. We just assumed that everyone has their quirks and we moved past red flag warnings with blinders on. But by the end of the first year of everyone working together as C-level staff, we struggled to work together effectively. My focus on logic and analysis, along with bearing the stress of a rapidly growing (and expensive) organization, often clashed with Sarah's emphasis on empathy and emotions to clientele - promising them the moon, while Michael's preference for planning and structure often clashed with Emilio's preference for flexibility and adaptability and my habit of planning the next strategic move while he was still laying the plans for the current one.

My mistake (and impetus for writing this post) was that I didn’t utilize powerful tools like the MBTI (or other proven personality models) since I thought it was fluff-stuff / ice-breaker stuff that didn’t really matter. I lost a lot more than the 8-figure exit I had within reach, including valuable time and relationships I’m never going to get back. Had I known the MBTI types of each team member, I could have helped by restructuring the management team in a few ways:

Assigning tasks and responsibilities that play to each team member's strengths: By understanding each team member's personality type, the management team would have been able to assign tasks and responsibilities that play to each team member's strengths instead of having people pick up the slack in areas that just needed to be taken care of.

Improving communication: By understanding each team member's personality type, our management team would have been able to improve communication by adapting their communication styles to suit each team member's preferences. For example, with my preference for thinking, I should have communicated using facts and logic via analogies or metaphors that would have resonated immediately with Sarah, who preferred to communicate using emotions and values. Doing so would have struck a personal connection faster with Sarah, and she would have seen that decisions I was proposing/making did take into account her clients whom she cared so deeply about.

Finding common ground: By understanding each team member's personality type, we would have been able to find common ground and find ways to bridge the gap between team members with different preferences. For example, Michael, with a preference for judging, could have learned to appreciate Emily's, with a preference for doing whatever the hell creative structure she found on Stack Overflow that morning, flexibility and adaptability, and vice-versa: Emily could have learned to appreciate Michael's preference for planning and organization, knowing that he was just doing his job to execute on the many roadmaps I was creating in real time. Since Emily and I had a connection that was stronger than she did with any other team member, she would have lightened up the pushback on Michael since she would have realized he was doing it to help me.

This is just one of the many examples of a complicated internal power-struggle and issues that occur daily within management teams around the world. There’s a reason the world of I/O Psychology (Industrial & Organizational Psychology) has shot up in popularity, with I/O psychologists getting $500K+ recurring engagements with corporations to study the composition and interactions between key leaders to ensure a smooth running operation.

While it may seem like overkill to think about all of this for a startup management team, taking a Myers-Briggs Personality test can be a valuable tool for understanding not only strengths and weaknesses, but egos and intrinsic personalities as well as those of their team members and even themselves. Just knowing this information (the MBTI result type) isn’t enough - if you don’t have the time to dedicate resources or efforts to learning what the types mean, how they interact, & other important information, I highly recommend working with someone (even on a fractional basis) that has this domain expertise. Find an advisor (vs a consultant because that will just drain cash resources - doesn’t make sense to fix one problem by introducing another) that can design a plan/program for the current team and any proposed or future hires. Having this knowledge in house and easily accessible will help teams work together more effectively, assign tasks and responsibilities that play to each team member's strengths and improve the communication and collaboration environment overall.

Startup advisors with industrial organizational psychology (I/O psychology) knowledge can be extremely valuable to a startup management team. I/O psychology is the scientific study of human behavior in organizations, and it can provide a wealth of insights and tools for improving communication, collaboration, and overall team effectiveness. Advisors with I/O psychology knowledge can help the startup management team to understand the personalities of their team members, as well as to address potential conflicts and improve communication and collaboration. They can also provide guidance on how to design effective work processes, and how to create a positive and productive work environment. Additionally, they can assist the team in developing strategies for recruiting, selecting and retaining the best employees, and help to create an organizational culture that supports innovation and growth. With this knowledge, startup advisors can help the startup management team to optimize the performance of their organization and achieve their goals.

We’ve all heard the phrase that owning 80% of a watermelon is way better than owning 100% of a grape - apply the same analogy to all of the points mentioned above. A team that has invested in optimizing their structure operates at ~100% efficiency is much more effective than a team that pushed this ongoing and critical topic to the side so they could continue operating at ~75% or even less efficiency.

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