Becoming Comfortable Being Uncomfortable

Edwin Covert
16 min readSep 16, 2022
Photo by Andrea Piacquadio:

Note: this article was my final, i.e. my portfolio project, in Decision Theory in a Global Marketplace (ORG 525) from Colorado State University Global.

Leadership is a key to any organization’s success. Taking this course showed however that there are various approaches to leadership, and each one provides its own unique advantages. This paper, through two sections, will discuss different challenges in leadership. The first section will focus on adaptive versus technical leadership as applied to the Harvard Business Publishing (2020) pandemic simulation we performed in Module 2. The second section will examine how virtual teams are bound by leadership, communications, trust, and motivation.

Section 1 — Applying Adaptive Versus Technical Leadership

Understanding the distinction and relevance of adaptive and technical leadership is important. Pak et al. (2020) define adaptive leadership as leadership that addresses problems with unknown answers. It requires new ways of thinking about a challenge. Technical leadership is about problems organizations can solve through existing solutions, procedures, tools, and expert guidance (Pak et al., 2020). Table 1 summarizes the characteristics of each type of problem.

The distinction between the two is crucial because if a leader does not comprehend the nature of the problem at the outset, they can present a technical solution for a problem that is actually adaptive. At best, the leader has wasted resources because they did not solve the problem. At worst, technical solutions to adaptive problems could exacerbate the issue leading to even more costly solutions in the future.

Table 1

Characteristics of Adaptive and Technical Problems

Note: Adapted from “Technical Problems vs Adaptive Challenges” by Network for College Success, n.d. Copyright University of Chicago, n.d.

Simulation Demographic Options and Characteristics

Harvard Business Publishing (2020) created a leadership simulation called Patient Zero. Patient Zero required a player to act as a “high-ranking advisor” (p. About you) to advise the leadership of a fictitious country as it manages a zombie-link pandemic. To begin the simulation, I made several choices about this country, called Edtopia: its style of government, type of economy and culture, and characteristics. I selected democracy, free market capitalism, and a progressive culture respectively. I selected these options as the starting point because they are what I believe they are characteristics of a modern first-world country.

Through randomization, Edtopia possesses a low population density of 221/km2 akin to Switzerland (World Bank, 2021). Next, the simulation randomly assigned a value of five points which I divided between five aspects of Edtopia: its economy, health, infrastructure, institution, and military. I awarded each aspect an equal one point because I lacked meaningful information about the role these values would play in the future. I was thinking technically about this decision since each sector was equally weighted.

Overview of the Decisions I Made

With Edtopia configured, the simulation required me to make a series of decisions around key events as the pandemic progressed coupled with random dice rolls to get results. The first was whether to allow a pilgrimage to a holy site in Edtopia. The decision led to fewer infections but did increase general unhappiness in the public (Harvard Business Publishing, 2020).

The next decision concerned a set of faulty test kits developed by a commercial company and whether to make their inefficacy public. I elected to reveal the existence of the bad test kids and decided the government would intervene to improve them. This decision resulted in Edtopia taking a short-term economic hit but no long-term effects occurred (Harvard Business Publishing, 2020). The third decision involved whether to subsidize antiviral drugs from a supplier that were ineffective. I decided to not subsidize these clearly faulty drugs. This decision led to ethnic tension and riots in the country (Harvard Business Publishing, 2020).

The fourth decision centered on the use of an information technology solution developed by a company that would have provided surveillance to the government about infections via surreptitious means. I elected to not use this software and instead work with the country’s public health organization to find better and more legal ways to improve the accuracy of its information concerning outbreaks. According to the simulation, people were upset by this decision (Harvard Business Publishing, 2020). The final decision I made involved whether to assault a part of the capital that contained many infected citizens holding a medical team. I decided to not order the assault (killing all plus the medical team) and instead increased military intervention and evacuated the team. This decision caused general unhappiness in the country (Harvard Business Publishing, 2020).

In the end, the simulation recorded a three percent infection rate, a medium level of morale, and only a four percent chance of societal collapse (Harvard Business Publishing, 2020). These were mostly positive results; I reran the simulation in Week Four using an authoritarian style of government and received markedly more negative results in terms of infection rates and societal collapse.

What Type of Decisions Did I Make?

As I noted earlier, I leaned into deciding based on a technical basis, not an adaptive one. Each of the decisions I made in the simulation met the definition of technical answers: they were easy to solve, required minimal change to my assumptions, and fairly quick to implement (Network for College Success, n.d.). While this is perhaps an indictment of my abilities before I was more immersed in leadership theory, my decision process was also bound by the rules of the simulation.

In the first decision, I did not allow the pilgrimage to occur. I chose this path to prevent the infection in the simulation from spreading. This was a technical answer to what I saw as a technical problem, not an adaptive one. Adaptive leadership required me to consider more information than I did. If I had used experimentation (a key element of adaptive leadership according to Korengel (2019)), I might have allowed only a certain segment of the population to make the journey and only with protective gear (masks, etc.). This would have provided Edtopia with data about the exact transmissibility of the infection and provided an overall alternate course of action. This idea of playing with alternatives would repeat itself over the course of the simulation.

Of course, there is a downside to this approach; namely the possibility of illness from the infection. In the version I ran during Week Four, I allowed the pilgrimage and finished the simulation with an infection rate of 19 percent. Between these two extremes (few infections versus nearly one in five citizens becoming infected) lies the adaptive approach to leadership: getting additional data, understanding the complexity of the situation, and rethinking past ways of doing things are all key elements of adaptive leadership (Korengel, 2019). Of course, acting in a crisis does not always lend itself to deliberative approaches.

Making Complicated Decisions in a Crisis

During a crisis, it is important to be prepared (Sickler, 2022). Many times, that preparation means having a playbook that addresses particular aspects of the crisis or disaster as it unfolds. According to Rezaei Soufi et al. (2019) , such preparation is critical to surviving a crisis or disaster. Still, these are technical solutions: they are easy to implement mostly because organizations have gamed them out in advance, they are quick to deploy for similar reasons and they do not require significant change to the organization during the crisis; however, adaptive leadership requires us to think about if we have truly understood all the ramifications of the problem before we develop a technical solution. In short, organizations should use adaptive leadership to get to technical leadership so they are prepared to reach during the crisis. In the military there is a saying: if you train like you fight, you will fight like you train. This is the application of taking adaptive thinking and turning it into technical thinking.

Each of Ramalingam et al.’s (2020) five principles of leadership are a way of thinking about adaptive leadership. They need to be applied before organizations need them in a crisis as Sickler (2019) points out. For example, instead of reflexively trying to prevent a moral hazard in capitalism (defined by Marshall (1976) as excessive benefit beyond marginal value, in this case from the antiviral drug manufacturer), I could have looked at the problem differently leading to less ethnic tensions in Edtopia.

Becoming Comfortable Being Uncomfortable

As explained previously, understanding the distinction between adaptive leadership and technical leadership (or specifically processing adaptive challenges and technical challenges) is vital to make sure leaders are developing the right solution for the right problem. However, being comfortable with the uncomfortable nature of adaptive challenges is not something I can say I have achieved yet. It is an ongoing learning process for me.

During Week 3, I took the Clifton Strengths Test from Gallup (2022). The results indicated my top five strengths are: Intellection, Input, Activator, Communications, and Maximizer. Intellection shows that I “instinctively give good advice” (Gallup, 2022, p. 3). It implies that, being well read, I have a natural decision making instinct that draws on things I have learned in the past, not desiring to understand new ideas in the heat of the moment.

Input, according to Gallup (2022), allows me to counter my natural instinctive intellection abilities with new information. This trait, or theme, shows I acquire “lots of information by reading all kinds of written material” (p. 4). This trait amplifies the previous one by feeding the Intellection. Next is Activator; it is common in individuals that want to act and not just discuss (Gallup, 2022). The fourth of my top five traits is Communication. Here, it shows I am likely “adept — that is, talented, skilled, and knowledgeable — with language” (Gallup, 2022, p. 5). Once I have decided on a course of action, expressing that idea is not a challenge for me. My last theme is Maximizer. Here Gallup (2022) tells me I “seek to transform something strong into something superb” (p. 5). I want to change things for the better.

Risk Taking Versus Risk Avoidance

The question becomes how I apply this process in the face of a crisis i.e. do I use it to take risks or avoid them? I believe the first two key elements of the process are the most indicative and follow Sickler’s (2019) advice: Intellection and Input. Both require that I have a solid base of knowledge to work from and that I seek a lot of additional information that I can synthesize when needed.

Only with solid and trusted information will I become an Activator and decisively act moving the process forward. Thus, I believe I am risk avoidant because, contrary to the description for the Input theme, I only act when I feel I have the information. As Gallup (2022b) notes in a follow email to the Clifton Strengths report, I will not be at my best with a sudden requirement for brainstorming.

Gilovich, in a video interview, said of decision making, “it’s all about figuring out how to make the best judgments and decisions” (SAGE Publications, 2016, p. 5). I can only make those ‘best’ decisions when I have the information. In crises, that means planning. Trumer and Virine (2019) would label this a concave utility function. Coming back to my previous point about the Patient Zero point distribution, I dispersed the points across five aspects of Edtopia evenly. It was a risk-avoidance strategy because I didn’t feel I had enough information at that point in the simulation to allocate them differently, e.g. loading up one sector of the country at the expense of others. My Input theme was feeling short-changed. This lack of information made me uneasy about making potentially life and death decisions albeit simulated ones. This is how I know I am not quite comfortable being uncomfortable yet. Hougaard et al. (2022) says this is a journey and I am still on it.

One area I feel that contributed to my overall unease was the time constraints in the simulation. The simulation only gave me seven minutes to decide between the different options (with a countdown timer flashing on the screen to create even more anxiety). Of course, this mimics real life in the sense that crises are rarely slow-moving. They typically require immediate action to mitigate. This brings back my previous point about using adaptive leadership to develop thoughtful solutions and then turning them into technical solutions that are easy to deploy. For me, my Input trait would not be helpful in the moment. Therefore, it is always best to take the time to be insightful when you have that time i.e. not in the actual crisis and then apply what you have learned during this downtime to the actual situation at hand.

Section 2 — Leadership in a Global Virtual Team

What is Required to Make an Effective Virtual Team Succeed on a Project?

This section of the paper will discuss the idea of leading a global virtual team and what is required to be successful during a project. According to the Project Management Institute (PMI), projects have five distinct phases: initiation, planning, execution, monitoring and controlling, and closure (Kissflow, 2022). While each phase is unique, what ties these phases together in a virtual team are leadership, mediated communications, trust, and motivation as shown in Figure 1. Of course, these concepts apply equally well to non-virtual teams as well.

Figure 1

Demonstrating how leadership, mediated communications, trust and motivation all interact in virtual teams


Leadership undergirds every phase of the project management process. It is key to the success of any team, regardless of that team’s purpose (Brownlee et al., 2019). Depending on the project, the leader has various types of leadership available. Selecting the right one at the right moment is called situational leadership. According to Rabarison et al. (2013), situational leadership theory says leaders must change their leadership approach according to several criteria in the scenario: “the readiness, current skills, and developmental level of team members” (p. 1).

As leaders, we operate in complex environments of evolving needs and requirements. Having the ability to shift approaches to one that best suits a particular situation at a particular time is critical to not only accomplishing the task but providing the support to the team you are leading. In a virtual environment where team members come from a global pool of talent with different cultures and customs, being able to apply the right approach to the right situation is key; this could include a leadership approach for individual team members.

In Figure 1, the leadership styles start with a transformational nature (orange bar). This is because transformational leadership focuses on big ideas according to Bright et al. (2019). Middleton et al. (2015) says transformational leadership is effective in implementing changes. In the planning and initiation phases of the project, it is important to get all parties on the same page with the change that needs to occur. Having a transformational leader will assist with this particularly where virtual teams are dispersed throughout the global. As the project progresses, it is important to adapt the leadership style to the new normal of the project: execution and beyond.

As the project moves forward, leadership should change to a more servant-based approach (the second orange bar). Servant leadership, developed by scholars in the 1970s, is an outgrowth of prior behavioral leadership models. In behavioral leadership theory, researchers state effective leadership depends not on specific characteristics but on learnable behaviors (Uslu, 2019). Servant leadership focuses on a specific set of behaviors by noting a leader should work “selflessly with followers to achieve shared goals that improve collective, rather than individual, welfare” (Bright et al., 2019, p. 134). It is about helping others grow and develop while still achieving the goal. Here, servant leadership allows the team to collaborate to achieve their shared goal of successfully completing the project.

Mediated Communication

Mediated communications refers to the devices that enable communication when not communicating in-person. Communication mediators include Group Decision Support Systems (GDSS)/Group Support System (GSS) that “support communication, coordination processes and information processing” (Hacker et al., 2019, p. 4). In virtual teams, this ability to communicate and share information is vital according to researchers (Hacker et al., 2019). The ability to collaborate with other project team members through all phases of the project allows the project to move forward in terms of schedule and ensures the project does not change. Figure 1 shows mediated communications as the yellow bar spanning the length of the project lifecycle as it affects the whole lifecycle.


Trust is critical in projects, particularly in those executed by virtual teams. Hacker et al. (2019) note there are various types of trust (gray in Figure 1). Several of the types they list are foundational types of trust: dispositional and institutional. Dispositional trust comes from the trustor having a pre-existing characteristic towards trusting, perhaps from having known someone from a long time who has not abused their trusted position (Hacker et al., 2019). Institutional trust comes from believing in the “norms and rules created by institutions that guide individual behaviour” (Hacker et al., 2019, p. 7). Another variation of trust the one can consider foundational is swift trust. Researchers describe it as “trust that is built quickly based on surface-level cues rather than interaction or knowledge of the trustee” (p. 7). In figure 1, each of these, being foundational, exist in the initiation stage of the virtual team’s project. The project is just starting and there is some innate level of trust, if it exists at all, in the team.

As the project moves through its lifecycle, the type of trust matures. As virtual team members come to know each other better and have to rely on each other in the planning phase, they experience multi-faceted trust, defined as trusting people to do specific things only (Hacker et al., 2019). Those levels of trust continue to build until they reach the time-based type of trust that comes from working extensively with other virtual team members in furtherance of the project goals (Hacker et al., 2019). Only in the trenches of a project can members learn to trust each other. Team members earn this trust.


In figure 1, motivation (green circular arrows) surrounds the entire project encompassing the project lifecycle, leadership, communications, and trust. It sustains the project for the virtual team. It is a cornerstone of the team’s performance because it gives them the shared vision for success articulated by the transformational leadership expressed earlier (Aubé et al., 2018). For virtual teams, this concept of motivation is even more important in that the team, being dispersed in some fashion, must believe in what they are doing on the project for it to succeed. As Aubé et al. (2018) note “a shared understanding of the work to be done is particularly important in complex and dynamic environments that required flexible work arrangements” (p. 804). Virtual teams, dispersed around the globe with varying cultures, customs, and time zones certainly qualify as ‘complex’ and ‘dynamic.’


Understanding the differences between adaptive challenges and technical problems is foundational to effective leadership. Applying technical solutions (fast and uncomplicated ones that do not require significant changes) can lead to disaster. If an organization is in crisis mode however, it is not the time for adaptive solutions. Organizations should have developed those before the crisis and turned them into functionally technical solutions. This will ease deployment during the actual event.

In virtual teams, it is important to comprehend the roles that leadership, mediated communications, trust and motivation play particularly regarding a project lifecycle. With a foundation of effective situational leadership, the project team can use its communication methods to increase trust from dispositional to multi-faceted to time-based. Leaders can use their skills and increasing trust to maintain the motivation necessary to sustain the project. Both ideas (understanding the role of adaptive leadership in crises and how leaders can maintain virtual teams) will serve leaders well.


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Edwin Covert

Cybersecurity, guitar, jazz, bourbon, rye, enterprise security architecture, current trophy husband. CISSP-ISSAP, CISM, CRISC, SCF, PMP at