Oh Captain, My Captain


Hey there, I’m MistressVenom, and I have spent a considerable amount of time leading teams. Whether it be professional, sport related, or (most importantly) for CyberSecurity competitions, I have loved every experience. I have played National Cyber League (NCL) for four years, and was the captain of Ken’s Little Pwnies, for three of those four years. In doing so, I have played on over 20 different cybersecurity teams, captained many, and had the honor of working with many different team compositions that led to very different team styles.

What is a captain and what is a leadership style?

A captain is in command of your ship (well, team) and will be in charge of making the various decisions that influence how your team operates. There are an infinite number of ways to be a successful captain, and those ways of leading are often called a leadership style. Below, I will go through the five I have seen and experienced, as well as ways to pair them with the style your team operates with best. 

Does my team even need a captain?

That is a wonderful question for your team and your faculty coach to decide. Some teams work best with minimal leadership, and merely want a dedicated point of contact. 

Leadership styles and why I do/don’t use them: 

The Autocrat

At my first technical job, the manager had a belief that those in management should never ask a subordinate to perform a task that they were not willing to do themselves. If either the manager or the subordinate did not know how to complete the task, then one would work with the other, train them, and share the knowledge, the complete opposite of an autocrat. Conversely, at my next job working helpdesk, I was introduced to an environment that in almost every way was a polar opposite. Rather than this teamwork mentality that I had been part of for three years, I was faced with stressed, unhappy coworkers and management unwilling to collaborate as “There’s a reason I’m the director and you all are where you are. ” This ‘do as I say’ mentality defines an autocrat. An autocratic environment often leads to a loss of morale, diminished productivity, and a cold atmosphere. Having experienced this first hand, this leadership style is something I never wish to be part of again as it led to a loss of joy doing what I loved.  

The Strategizer

The strategic leader emphasizes planning and collaboration, but this may prolong the overall amount of time they dedicate to the NCL games. However, it is good to have one person help everyone see the forest through the trees and choose the one plan of attack that best suits your team dynamic. This does require a theoretical approach and the captain’s time may be taken away from the games, but it also has the potential for high payoff.

The Coach

A coaching leadership style is the one most often seen in the industry. The person deemed to be most knowledgeable takes the lead and works to support, direct, and train the other team members to be more effective. During the NCL team game, this position is used to help teammates find the answers on their own, a more accessible version of the faculty advisor. 

The Briber

A bribing leader requires the least amount of effort but encourages people to participate. The most common example of this is, “If you join the team and work on questions during the game for X number of hours, I will provide food, soda, entertainment, and company.” A bribing captain may choose to involve themselves in the organizational process, but it’s not required. This format works with multiple team styles, but this loose captaining may work for some groups better than others.

The Lassiez-Faire

This style is very similar to the coach, however, it is more hands off and less intensive. A lassiez-faire leader essentially functions in name only and may or may not be involved in the competitive aspect. Most often, this is seen as someone who wants to assist, but may be overburdened outside the games and doesn’t have the ability to participate as they would like. They generally provide assistance with resources but are uninvolved during the team game directly. Alternatively, the lassiez-faire leader may just be a teammate who only steps into the leadership role when needed for important decisions, paperwork, or other official representation.

Now, what is your team style?

The Golf Team

Individuals working alone toward a common goal with minimal communication.

The Think Tank

All eyes on all puzzles at one time. High levels of communication, but often low productivity.

Divide and Conquer

Each team member or pair will be assigned a section or two of the challenges and only focus on that.

The Advanced Hivemind

Each individual member does a separate investigation of puzzles. Everyone communicates on issues and questions, but the team only submits an answer if everyone/majority comes up with the same result.

My Personal Ranking of Capitan and Team-Style Combinations:

The Golf Team + The Autocrat

Overall Grade: F

This pairing is one of the most isolating combinations that I have experienced. There was a minimal amount of teamwork and a terrible atmosphere. For NCL, where there is a sense of community and camaraderie, this directly contradicts with the spirit of the competition and team game. After experiencing this and not seeing a reward, as everyone wanted to stand out on their own and not work as a team, it pushed me to create a team in a positive environment for the upcoming NCL season.  

The Golf Team + The Briber

Overall Rating : D

A Golf team style along with a transactional leadership style is highly volatile, and may cause high tensions, similar to functioning with an autocratic leader. Pending the division of questions or categories, this may leave team members unhappy and forced to go down rabbit holes on their own without a teammate to pull them out or work through a problem that someone else may have experience completing. 

The Coach + The Think Tank

Overall Rating : C- 

The Think Tank team combined with a coaching style is great when a veteran competitor is working with a team of people new to the industry or competition. This team and leadership combination functions similar to a small group class where everyone works together, and the captain functions similar to a teacher’s assistant. This combination often works best before the season begins. The team captain can hold practices and teach theory, tools, and problem solving techniques before the Gym, Preseason, and Individual games open. This will also help create an excitement surrounding the games, however, during the team game, this will likely slow down productivity, as everyone is focused on one small set of challenges at once. 

Lassiez-Faire + Divide and Conquer

Overall Rating : C

This combination is the other highly volatile pairing in this list, as the divide and conquer team style combined with a lack of clear leadership will either allow many people to shine, or will lead to an upset team with members who are either working on a category they are not interested in or not skilled in. 

The Coach + The Advanced Hivemind

Overall Rating : B-

An advanced hivemind approach with a coach style leader often requires a team that has known each other for a while and knows when to reach out and needs firm leadership to tell them what to do, and how to go about doing so, before they set off on their own to work on their targeted challenges. 

The Strategizer + The Thinktank/Divide and Conquer

Overall Rating : B+

I had the pleasure of working with a blended team style where approximately half of the team were new to cybersecurity and very eager to learn, and half of the team were seasoned NCL veterans. This required a strategic plan that I began preparing before the game officially began based on what I knew from previous seasons, what I knew about each member of the team, and whether or not it would be wise to pair a veteran with a newbie or find an alternative solution. This required a considerable amount of effort and turned out fairly acceptable. Team members were happy, and it was nice to see veterans imparting knowledge to the newer folks in their areas of expertise.

The Strategizer + The Advanced Hivemind

Overall Rating : A

This combination is wonderful for a team that knows each other well. An advanced hivemind lead by a strategizer will often be a team developed by the entire team. This has been the frequent successful leadership team style for many of the teams I have led. This style allows for individuals to focus on what they love to do during the games. A hivemind is highly successful with a strategist to give a directional outline for the entire team to take as well as the individual members. This allows the team to function without much intervention unless reorganization is needed during the games. Outside of the games, a strategist will likely set up meeting times, or a messaging server to allow for in-game collaboration and prepare strategy before the games begin.

Final Thoughts

Depending the composition of the team, these ratings may not apply, but a team and their leader are entirely what you chose to make of it. Take as much or little information as you wish from this blog, but my one request is that you compete in the team game one time, let yourself have fun, and work in a (hopefully) laid-back collaborative environment. As a captain, if you are struggling to find a good team or leadership style, get input from your fellow teammates! At the end of the day, you are all there to support each other.

Mistress Venom

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