Leadership During Times Of Prolonged Uncertainty - part #2

Remember The Stockdale Paradox

As we seek this deeper wisdom within paradoxes, we also need to remember The Stockade Paradox. Jim Collins writes about this paradox in his book, Good to Great: Why Some Companies Make the Leap. . . and Others Don't (HarperBusiness, 2001). The paradox originated from Navy Vice Admiral, James Stockade’s experiences as a POW during the Vietnam War, where he survived years of torture and deprivation by balancing his harsh and painful reality with a strong belief in a better future. As Collins explains, this paradox is based on the ability to “retain absolute faith that you can and will prevail in the end, regardless of the difficulties, AND at the same time confront the most brutal facts of your current reality, whatever they might be.” 

By combining a realistic acceptance of our current challenges, i.e. working within a VUCA environment, with a stedfast and optimistic outlook, i.e. we can, and we will over time prevail in the midst of this prolonged uncertainty, we can, and we will generate successful outcomes. In short, by holding two contradictory truths at the same time, and with regular coaching and support, leaders can get better at leading in the midst of these challenges. 

Still, we need to remember one other key point from the aforementioned book. As Collins writes, “Good is the enemy of great.” Right now, many leaders and managers can, to a degree, embrace The Stockdale Paradox, but when it comes to the point that they need to make a decision, I often hear them defer to a that’s good enough mentality. This is a major problem when dealing with prolonged uncertainty. It often reflects decision fatigue, cognitive overload, and a touch of just wanting to give up and go with the path of least resistance. 

I can not fault leaders who choose this path. That would be an example of grit gaslighting. As Tasha Eurich in her book, Shatterproof: How to Thrive in a World of Constant Chaos (And why resilience alone isn’t enough) (Little, Brown Spark, 2025), explains: “… grit gaslighting, a common phenomena, where, instead of validating our stress or distress, our commitment to coping with it is questioned. Often, grit gaslighting comes from people in positions of authority or well-meaning but unaware family and friends.” I have met many people who are deeply committed to the work they are doing, and completely overwhelmed and exhausted by the complexity and uncertainty that surrounds them. To solve this problem in the world of leadership, we need to approach this as a team problem, not just an individual effort problem. 

Surround Yourself With The Right People

Patrick Lencioni in his book, The Four Obsessions of an Extraordinary Executive (Jossey-Bass, 2000), writes about the importance of building and maintaining a cohesive leadership team. As he notes, “cohesive teams build trust, eliminate politics and increase efficiency by knowing one another's unique strengths and weaknesses,  openly engaging in constructive ideological conflict, holding one another accountable for behaviors and actions, [and] committing to group decisions.” In this kind of team environment, grit gaslighting would not be permissible or accepted. Instead, there would be open and engaging discussions about what are, and what are not acceptable, behavioral choices.

But, upon reflection, I think leaders jump too quickly to a focus on improving teamwork during prolonged uncertainty, and miss a key point of Lencioni’s work, namely to build the team, not just improve or maintain the team. The focus on building the team is often skipped over in the rush to get things done. 

Martine Haas and Mark Mortensen in their article called “The Secrets of Great Teamwork” from the June 2016 issue of the Harvard Business Review, writes, “Today’s teams are different from the teams of the past: They’re far more diverse, dispersed, digital, and dynamic (with frequent changes in membership).” From my perspective, given this important insight, we need to make sure we have “the right people in the right seats on the bus,” referencing the work of Jim Collins in his book, Good to Great: Why Some Companies Make the Leap. . . and Others Don't (HarperBusiness, 2001). 

The difficulty of this metaphor is that Collins did not initially define what are the characteristics of “the right people.” It was not until he wrote the book, How The Mighty Fall and Why Some Companies Never Give In (HarperCollins, 2009), that he gave a clear answer to the question, “What makes for the ‘Right People’ in key seats?.” In this book, he gives the following answer: “the right people fit with the company’s core values; the right people don’t need to be tightly managed; the right people understand that they do not have ‘jobs’, they have responsibilities; the right people fulfill their commitments; the right people are passionate about the company and its work; the right people display ‘window and mirror’ maturity.” The outcome of choosing the right people when building a team and later maintaining or improving it, is that you create a culture of discipline and a shared mindset based on a common understanding of what matters most. You also are choosing people who have a combination of technical and social skills that can handle uncertainty. 

Nevertheless, we as leaders need to make some tough choices when it comes to people. First, we must stop hiring and retaining people who routinely screw things up, or create levels of disruptive toxicity at the team level. If we tolerate these poor and misaligned behaviors, we will consistently have issues and problems that take our time and attention away from focusing on the right things, operationally and strategically. Having the right people in place reduces distractions and increases engagement and healthy teamwork, all of which is vital to coping with prolonged uncertainty. 

© Geery Howe 2026

Geery Howe, M.A. Executive Coach in Leadership, Strategic Planning, and Organizational Change

Leadership During Times Of Prolonged Uncertainty - part #1

Introduction

In 2011, Jim Collins and Morten Hansen in their book, Great By Choice: Uncertainty, Chaos, and Luck - Why Some Thrive Despite Them All (HarperCollins, 2011), wrote: “Given this rise of complexity, globalization, and technology, all of which are accelerating change and increased volatility, we must come to accept that there is no ‘new normal.’ There will only be a continuous series of ‘not normal’ times.” Fifteen years later, their words seem prophetic. They also could have been written yesterday about the events that are happening today. 

Currently, we are living in a VUCA environment, borrowing a term from the US military. This is a time period where things are volatile, uncertain, complex, and ambiguous. The implications are that instability is chronic, uncertainty is permanent, change is accelerating, and disruptions are common. All we know for certain is that we can neither predict nor govern most events.

Furthermore, we are worried about the possibility of phase transitions (wide-reaching disruptions triggered by small shifts, like market crashes or social movements), and the possibility for compound extremes (multiple co-occurring disruptions like a natural disaster during a recession). We also are concerned about the convergence of AI, advanced sensors, and biotechnology. Simultaneously, many people are experiencing chronic, compounding, and highly stressful challenges across multiple areas of their life (work, family, health, etc.). 

When we step back and look at all that is happening, and all that has happened, we come to realize that our challenges have become more difficult and complex, and that our organizational systems, and personal and professional mindsets have not evolved as quickly as the changes that are happening all around us. Thus, we are confronted with an important question: How can we strengthen our capacity to adapt during this period of prolonged uncertainty?

Embrace Paradox

Brene’ Brown in her book, Strong Ground: The Lessons Of Daring Leadership, The Tenacity Of Paradox, and The Wisdom Of The Human Spirit (Random House, 2025), writes: “Paradoxes embrace ambiguity, expose our intolerance for uncertainty, push our boundaries, and, if we hang on long enough, often force us to deny the comfort of our ideologies for a deeper wisdom that is a more honest reflection of the human experience and the human spirit.” As she continues, “In its original Greek, paradox is made up of two words, para (contrary to) and dokein (opinion). The Latin paradoxum means ‘seemingly absurd but true’.” And right now, there is a lot that is seemingly absurd but true. Therefore, we need to embrace these paradoxes.  

Wendy Smith, Marianne Lewis, and Michael Tushman in their article called, “Both/And Leadership,” in the May 2016 issue of the Harvard Business Review, write that the source of our uncertainty in the business world comes from three questions. The first question is: “Are we managing for today or for tomorrow?” This is the innovation paradox where we are challenged to balance today’s needs vs. tomorrow’s needs. The second question is: “Do we adhere to boundaries or cross them?” This is the globalization paradox where we are challenged to balance global integration vs. local interests. The third question is: “Do we focus on creating value for our shareholders and investors or for a broader set of stakeholders?” This is the obligation paradox where we are challenged to balance social mission vs. financial pressure. In each of these questions, we have to seek the concept of both/and rather than the more comfortable choice of either/or. 

From my perspective, the first step in this process of embracing paradox is to check our perception. There are two ways to see the world, namely the observing eye and the perceiving eye. Ryan Holiday in his book, The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph (Penguin, 2014), explains that the observing eye sees what is there, while the perceiving eye sees more than what is there. The goal for leaders during prolonged uncertainty is to see things as they really are, without any of the ornamentation, or self-imposed stories we project on to what is happening. 

Yet, as we choose to see in this manner, we must recognize that our perspective on the problems we are dealing with is always missing something, namely an in-depth understanding of our own history and “baggage.” And, at the same time, we must recognize that when we hear of other people’s perspectives or problems, we always see their history and baggage. 

So, when we choose to see things as they are, we must always check our perspective with others who we trust and can offer grounded insights and perspective over time. This check-in with trusted mentors, coaches, allies, and confidants requires us to step back from the press of current events, and instead choose to see the larger picture of the world. We need to do this step back in order to prevent and/or limit any level of myopic thinking, i.e. a short-sighted way of thinking that focuses on immediate problems and concerns, and short-term gains while neglecting long-term consequences and broader implications for the business. Myopic thinking always lacks foresight and the ability to consider how current actions will affect future growth and innovation. We do all of this, because the most dangerous perspective to hold is one where we think we can change everything, or something specific that is not ours to change. This is the tenacity of paradox, and the reason why we must seek “a deeper wisdom that is a more honest reflection of the human experience and the human spirit.”

© Geery Howe 2026

Geery Howe, M.A. Executive Coach in Leadership, Strategic Planning, and Organizational Change

The Importance Of A Good Day

On most mornings, people get up and get ready for work. As they go through their morning routines, they all want the same thing, namely to have a good day. While this varies to a degree by person, most people just want a day where they can make progress on things that are important to them, know that their job matters, and to work with people who are kind, thoughtful, and respectful. And if, by the end of the day, all of this has happened, then they can feel like it was a good day. 

Nevertheless, this is not the typical experience for many people. Most people encounter problems that are difficult to define, and have no easy solutions. Most people work with other people, who, at times, do not treat them or others well. And finally, most people don’t feel like they are making progress on things that matter the most to them. Instead, they feel like they are battling poorly designed systems, technology that is not helpful, and a company culture that says one thing, but does something completely different. In short, many people find their work life, frustrating, boring, and unsatisfying. And they feel powerless to change it. 

Yet, in the midst of this, most people hope for something better. They want a life and a job where they feel connected with others, and a sense of belonging that comes from doing things that make a difference in the lives of others. They also want a life and a job where they feel heard, and respected for what they know and what they do. At the same time, they want to be seen as a person, rather than just a warm body filling a box on the company’s org chart. And finally, most people want to feel like they have a life of choice and integrity, where they do not need to compromise their beliefs and values in order to make ends meet at the personal and family levels.

As leaders, I think we underestimate the importance of people wanting to have a good day. Typically, we are focused on getting things done, and, if we are honest, the sooner the better. We also are focused on generating positive KPI’s (key performance indicators) that show we are doing the right thing and generating the right outcomes. Then, the people who we report to will be pleased with us, and reward us in various ways, be that a promotion, positive feedback, or some monetary amount. 

But, most people do not have this option. They just wake up in the morning, get ready for the day, and then go to work. And everything that they did not get done the day before is still sitting there on their desk, wanting their time and attention. Meanwhile, a wide variety of new problems have surfaced that also call for their time and attention. 

So, how do we as leaders create a good day for those we work with on a daily basis?

First, leaders need to invest their time and energy in getting to know the people that they work with on a daily basis. As Marcus Buckingham in his book, The One Thing You Need to Know ... About Great Managing, Great Leading, and Sustained Individual Success (Free Press, 2005), explained: “great managing is not about transformation - if you dedicate yourself to transforming each employee into some predetermined perfect version of the role, you will wind up frustrating yourself and annoying the employee. Great managing is about release. It is about constantly tweaking the world so the unique contribution, the unique needs, the unique style of each employee can be given free rein.” As he continues, “To excel as a manager you must never forget that each of your direct reports is unique and that your chief responsibility is not to eradicate this uniqueness, but rather to arrange roles, responsibilities, and expectations so that you can capitalize upon it. The more you perfect this skill, the more effectively you will turn talents into performance.” And when we turn talents into performance, we create the conditions for someone to have a good day. 

Second, leaders need to help people achieve their goals on a regular basis. Teresa Amabile and Steve Kramer in their article called “The Power of Small Wins” (Harvard Business Review, May 2011), report some interesting results after a decade of research which included a deep analysis of daily diaries kept by teammates on creative projects. What they discovered is something they call the Progress Principle, namely “Of all things that can boost emotions, motivation, and perceptions during a workday, the single most important is making progress in meaningful work…. And the more frequently people experience that sense of progress, the more likely they are to be creatively productive in the long run.” From what they shared, I am convinced that making progress in meaningful work is vital to people experiencing a good day. 

Third, leaders need to be able to work at multiple levels within the company. As F. Scott Fitzgerald pointed out, “The test of a first rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” I think the best leaders, who create the conditions for optimal performance and positive work engagement, approach the future with three questions in mind, namely Where are we now?, Where do we need to prepare for the future?, and Where do we need to innovate?. This three way approach helps them work on the organization, and in the organization as needed. It also helps them to focus on making current operations better, and focus on preparing everyone for the future. 

While leaders may not be able to control everything about the work day, they can take steps on a daily basis to make the work environment a positive and respectful place. As I have learned over the years, leaders get what they exhibit and what they tolerate. Starting this week, we need to get to know our people better, and we need to help them achieve their goals on a regular basis. Finally, we need to ask ourselves the aforementioned three questions to make sure we are working on the organization and in the organization. The weeks and months ahead may be stressful, challenging, and complex, but the importance of people having a good day is a powerful and rejuvenating experience. And we all need to experience more good days rather than fewer good days.  

© Geery Howe 2026

Geery Howe, M.A. Executive Coach in Leadership, Strategic Planning, and Organizational Change