Insights
LEADERSHIP CHALLENGES AND STRATEGIES
An Analysis of Trends and Implications
OVERVIEW
Leadership has always been a balancing act involving developing self, managing teams, meeting goals, and navigating external pressures. Over the past two decades, leaders have faced seismic changes and ever-growing complexity from the global financial crisis in 2008 to the digitization of industries, the emergence of social justice movements that have redefined workplace culture, and the rise of remote work accelerated by the COVID-19 pandemic. These events have consistently tested leaders' abilities to adapt and evolve.
Recognizing that the definition of successful leadership has long been shaped by external forces, we set out to explore whether the current environment has brought about new challenges—or simply shifted the existing ones. This article dives into our findings and offers insights into the evolving nature of leadership in this era of rapid change.
For this analysis, we examined the experiences of senior leaders within our collective business network. The study involved 24 participants—19 females and 5 males, predominantly over the age of 40—representing both the private and public sectors.
Each participant was interviewed in-depth about challenges they faced in the following areas: personal life, company culture, peer and direct report interactions, the broader environment, and how each factor impacted their ability to lead effectively. They were also asked to share stories about key growth experiences and how those experiences assisted them in navigating challenges and leading others.
The responses were analyzed to identify recurring themes and then further explored by how the themes interact and influence each other. The first section is a summary of participant responses by type of challenge, the second how they are interconnected, influenced, and impacted by one another, and the last outlines recommendations for how to move forward.
WHAT WE HEARD
“I'm reaching that age where age discrimination becomes a thing.”
Personal Challenges
The personal challenges faced by leaders reveal the deeply interconnected nature of home life and professional responsibilities. Many leaders highlighted the struggle to find a healthy ‘balance between home and work’, as they juggle parenting, household duties, and the emotional toll of being constantly available. Health and wellness issues, including mental health, caregiving for family members, and navigating physical health changes related to the normal aging process, also weigh heavily on them. Leaders expressed concerns about ‘career sustainability’, particularly in fast-growing companies where the pressure to remain relevant can feel overwhelming. Setting clear boundaries has proven difficult for some, while others emphasized the importance of saying “no” to extra work commitments early in their careers. The literal managing of tasks related to available time emerged as a major challenge, especially for those caught between caring for both aging parents and children. The emotional toll of leadership was also evident in the exhaustion many feel from constantly being available to their teams, coupled with a lack of confidence that their team members can handle responsibilities in their absence.
“I know that I’m pretty good about explaining expectations, but some people [are] going to do exactly what they’re told to do and no more…”
Challenges with Direct Reports
Navigating the complexities of a multigenerational workforce presents unique challenges, particularly with communication and work ethic disparities. Study participants describe a younger generation that often favors remote work, shorter hours, and clear boundaries, yet may struggle with emotional maturity and problem-solving abilities. And while many prefer remote work, it further exacerbates feelings of disconnection between the leaders and their team members, as well as team members with each other. Many younger employees also prefer checklists over critical thinking, tending to perform the bare minimum, which fosters a "box-checking" mentality rather than a drive for ownership and accountability. This is compounded by issues like a lack of professionalism, emotional intelligence, and public speaking skills, that lead to difficulties in client interactions and teamwork. Additionally, the cultural shift towards prioritizing personal well-being often clashes with organizational expectations of longer hours and personal sacrifice, increasing frustration for leaders and reducing motivation among team members. The leaders talked about setting reasonable expectations while offering training on essential skills in business etiquette and effective communication, as a means of support for younger employees.
“I had to learn to be very adaptable and flexible…if [I] didn’t, the market would be killing us…”
Challenges presented by the World at Large
The leaders interviewed shared a range of challenges they face with "the world at large" that affect their ability to lead. The most reported issue was mental health, with leaders noting heightened stress and anxiety influenced by external factors like climate change, political instability, and the lasting impact of the pandemic. Many mentioned the influence of AI and the necessity of helping clients adopt new technologies, which brings both opportunities and challenges. The unpredictable political environment and fluctuating economic conditions, such as interest rates and market volatility, also impact decision-making and organizational stability. Leaders expressed concern about aligning business values with broader societal goals beyond profitability, responding to shifts in workforce expectations from remote work, and the need for resilience to navigate these changes. Some leaders emphasized the importance of diversity, equity, and inclusion (DEI) in creating psychologically safe work environments. Additionally, generational divides were noted, with younger professionals seeking remote options while older professionals adapt more readily. These factors collectively underscore the complexity of leadership in an ever-evolving world landscape.
“I’ll just say like I've been disappointed in the startup world to some degree, still not a lot of women [and] hardly any people of color at the top so…it [has] not been disrupted as far as I can see…”
Work Environment Challenges
Study participants are navigating a complex array of challenges in their work environments that significantly impact their ability to lead effectively. Bureaucracy, centralization, and slow decision-making create frustration as processes have become overly complicated. Many are facing constant change and instability, particularly in fast-growing industries, where change fatigue and poorly executed rollouts cause confusion and resistance among teams. The shift to fully remote and hybrid work has added another layer of difficulty, making it harder to maintain strong team member connections. Additionally, resource and workforce constraints, such as hiring freezes and lean teams, have left our participants taking on extra responsibilities without the corresponding reward and recognition, leading to resentment and burnout. Communication and collaboration issues, especially poor top-down communication during times of organizational change, add to the strain. Women leaders also report challenges with gender and age discrimination, feeling dismissed in meetings, and struggling for recognition in male-dominated spaces. Lastly, the pressure of heavy workloads and lack of prioritization in startups and fast-paced companies makes it hard for study participants to focus on long-term strategy while managing daily demands.
“I still haven't completely cracked the code on how to always work better with people who [have] different thinking preferences to [mine]”
Challenges with Peers
The most frequently reported challenge our participants are facing with peers is a lack of openness and professionalism, which often impacts collaboration and cohesion within teams. Many participants noted a decline in teamwork, citing siloed work environments, conflicting goals, and competition-driven dynamics that reduce the incentive to help others. Remote work has also created barriers to effective communication and connection, like navigating technical difficulties and colleagues who refuse to be on camera, making it harder to align on shared objectives. Additionally, participants reported issues with receiving and providing constructive feedback, which sometimes led to conflict rather than productive discussions. Less commonly, leaders mentioned challenges around transitioning responsibilities with retiring colleagues and navigating the dynamics of having previously subordinate colleagues as peers. Despite these obstacles, some leaders expressed positive experiences, highlighting flexibility, adaptability, and the support of collaborative peer relationships, which helped them overcome many of these challenges.
“It can’t just be work, work, work all day long…we are going to keep burning ourselves out if we don’t go take a walk, or once a week go to lunch…”
Growth Experiences
Our leaders’ journeys have been rich with growth experiences that have shaped their leadership capabilities. Most prominently, they highlighted the importance of personal, face-to-face interactions as a cornerstone for building trust and understanding within teams. Key character traits such as perseverance and commitment to your responsibilities were considered essential for successful leadership, and leaders discussed how they had strengthened these traits through continuing education and seeking out active leadership development opportunities. By embracing mindfulness, leaders have learned to maintain focus during personal and professional stressful situations. Through leadership training, they’ve also learned to develop an understanding of diverse leadership styles, which has helped clarify the reasoning behind decisions with which they had previously found confusing. The importance of patience and adaptability came to the forefront especially in navigating significant changes like business acquisitions. Many leaders drew insights from prior experiences in customer-facing industries such as hospitality, revealing that collaborative leadership can be an incredibly powerful approach. Lessons learned from deliberately leaving toxic work environments underscored the significance of emotional resilience, financial health, and the principles of minimalism. Finally, participation in leadership development programs like Mindful Command and Dale Carnegie enhanced leaders’ abilities to read people and situations and ask the right questions at the right times to gain clarity about, and confidence in, their own decision-making.
WHAT WE LEARNED
“A system is never just the sum of its parts, it's the product of their interactions." – Russell Ackoff”
The challenges described by the leaders we interviewed reveal a complex web of interconnected issues. For instance, the struggle to balance home and work life not only affects individual well-being but also impacts leaders’ effectiveness and their team's morale. Similarly, as leaders navigate a multigenerational workforce, disparities in expectations and work ethic further complicate their ability to foster collaboration and hold team members accountable. These challenges are exacerbated by the ongoing pressures of remote work and rapid market changes, which create an environment ripe for interpersonal detachment, disengagement, and ultimately burnout. To effectively identify interconnected issues, we employed a systems-thinking framework to isolate factors that influence one another. Our analysis revealed four prominent and recurring leadership issues, and two distinct ways in which leaders grew their competencies and introduced stability into their leadership practices.
Work-Life Balance
The desire to find some semblance of a balance between work and personal life continues to be a focus for leaders, especially those who are 40+ and in senior roles with high levels of responsibility. Most of the study participants we spoke with were not only managing intense careers and leading teams but also sandwiched between children and ageing parents/in-laws, all of which require significant investments of emotion, time, and energy. In many cases these leaders either had had or were currently experiencing family illnesses or caregiving responsibilities of older relatives. This equates to more demands on their time than they can supply; they have literal time shortages, with them getting little to none of it for their own health and well-being. The lack of time for things like exercise, cooking vs. eating out, and just simply enjoying experiences with friends and family are leading to true exhaustion. In addition, with the continuation of remote work, professional and personal boundaries stay blurred, driven by feelings – and sometimes expectations – of needing to be continuously ‘on’. Other factors influencing this trend include organizational cultural norms, expectations about leadership commitment, the availability of organizational support structures (e.g., mental health resources), and the leader’s ability to establish and enforce boundaries for themselves. These dynamics are working together to amplify stress and increase the probability of burnout at a time in life where these individuals feel as if they should be at the peak of their careers.
Complex Communication
The leaders with which we spoke still grapple with communication difficulties, whether it’s giving/receiving feedback, addressing differences, or navigating team conflicts. These are not new challenges but have become more complex in today’s diverse and often virtual workplace. Communication challenges in virtual and diverse workplaces often stem from generational differences, remote communication barriers, and cultural expectations. These issues can result in misunderstandings around tone, intent, and delivery, leading to conflicts, especially during feedback sessions or virtual interactions. Influencing factors include the organization’s communication culture (whether the workplace encourages open dialogue, promotes active listening, and values constructive feedback or is more hierarchical and rigid in its communication); the effectiveness of conflict resolution mechanisms (the availability of formal processes such as mediation, the presence of HR support, or the use of peer-led conflict resolution strategies to address disputes); and, the strength of leadership engagement (leaders who actively model and foster clear communication across all levels, encourage diverse viewpoints, create psychological safety, and address issues promptly versus leaders who avoid difficult conversations or lack transparency). Generational differences in communication preferences also play a key role, as younger workers often prefer more direct, real-time feedback through digital tools (not in person), while older generations prefer formal or face-to-face interactions.
Ongoing Leadership Development
Leaders have long recognized the importance of continuous growth, and today’s dynamic workplaces require them to stay ahead by cultivating key competencies like change readiness, skill adaptability, and emotional resilience. This is evident in their participation in leadership training programs, such as the Mindful Command which cultivates emotional resilience and effective decision-making by being present and self-aware. Many leaders also use tools like the Myers-Briggs Type Indicator to help their teams understand individual preferences and working styles as well as 360-degree feedback surveys to identify blind spots and drive personal growth. Factors driving this trend include the rise of emotional resilience as a critical leadership skill in high-stress industries like tech and healthcare, the accessibility of advanced professional development resources, and a leader’s commitment to evolving with the changing demands of their role.
Change Management
The shift during Covid to remote or hybrid work models introduced additional challenges in fostering collaboration and maintaining productivity. This shift further exacerbated the deficiency in change management practices within many of our participants’ organizations. Practice weaknesses such as inadequate preparation and poor communication have led to confusion, frustration, and ultimately emotional detachment, resulting in reduced productivity. This manifests as leaders struggling to keep their teams aligned during transitions or rollouts of new policies, procedures and/or processes, especially when the team is dispersed as the lack of in-person interaction may reduce opportunities for asking/answering questions and informal problem-solving. Factors influencing this issue include the individual speed of technological adoption, varying employee preferences for and satisfaction with remote work, and an organization’s historical approach to change management.
Work Culture
Our leaders are experiencing what they describe as a declining work ethic and professionalism that they attribute to generational differences, which continue to create tension in the workplace. Our leaders observe younger employees setting stricter boundaries between work and their personal lives, resisting traditional practices like working long hours, and/or the lack of desire to adhere to hierarchical structures. This trend often manifests as friction between leaders and employees over accountability, with some younger workers seen as ‘checking boxes’ without taking ownership of their full responsibilities. Other factors influencing this category include evolving career needs and expectations where employees seek meaning in their work and expect work-life balance, the rise of the gig economy, and differing views on the definition of professionalism (e.g., casual attire, flexible hours, and schedules). The organization’s cultural norms, approach to employee development, mentorship, and performance management all play key roles in shaping employee attitudes toward work ethic and accountability
Resilience, Commitment, and Alignment
The need for resilience, adaptability, and aligning work with personal values has always been crucial for leadership effectiveness. Leaders continue to face challenges in setting boundaries and maintaining commitment in a rapidly changing environment. The demand for resilience and adaptability has only increased in today’s fast-paced work environments. Leaders may struggle to maintain personal commitment and alignment with their values as they navigate rapid organizational changes, market volatility, or personal crises. This often manifests as leaders feeling burned out or disengaged, especially when there is a misalignment between their values and their company’s direction. Factors influencing this trend include external market pressures (e.g., economic downturns, industry disruption), the organization’s culture around work-life balance and support, and the leader’s personal strategies for stress management and setting boundaries. Leaders who demonstrate resilience are better equipped to maintain their commitment and lead effectively, particularly when their values align with the organization’s mission. When a company fosters an environment that supports personal and organizational value alignment, it reinforces a leader’s sense of purpose, making it easier to navigate challenges and stay committed to the work. Conversely, when this alignment is lacking, leaders may feel disillusioned, leading to burnout. For example, a leader in a sustainability-focused company may feel more energized and committed if their personal values align with the company’s environmental initiatives, while a leader in a misaligned organization may struggle to stay motivated despite resilience-building efforts.
RECOMMENDATIONS FOR MOVING FORWARD
“In systems thinking, the process of change is just as important as the outcome.” – Donella Meadows
Despite the disruptions caused by the pandemic and the shift to remote work, many of the core challenges leaders face today are not drastically different from those they have faced in the past. What is new is the way these challenges manifest in a more digitally driven, globalized environment. Perhaps most importantly, these challenges are deeply interconnected, reinforcing the need for a systems-thinking approach in understanding them.
Adopt Systems Thinking
The interconnected nature of these leadership challenges underscores the importance of ‘systems thinking’ —an approach that views issues as part of a broader, interrelated system. In practice, this means understanding that addressing one challenge often influences others. For example, a lack of work-life balance can negatively affect mental health, which in turn impacts decision-making and productivity. Similarly, communication gaps can hinder effective change management, leading to confusion and lower morale.
Systems thinking encourages leaders to view problems not as isolated issues but as part of a larger network of factors that influence one another. This perspective allows for more comprehensive and sustainable problem solving and solution testing by considering how a decision in one area will affect others, and then ‘pulling the most influential lever’ for the greatest impact.
A leader overseeing a transition to remote work might initially prioritize the technical and logistical components, such as ensuring that employees have the necessary hardware, software, and secure access to company systems. They may focus on setting up virtual communication tools, establishing clear guidelines for online collaboration, and addressing any cybersecurity concerns. However, applying a systems thinking approach would encourage the leader to expand their focus beyond these immediate operational tasks and examine how this shift impacts other critical areas.
For example, team communication dynamics may change when in-person interactions are replaced by virtual meetings and messaging platforms. A systems thinker would anticipate potential challenges, such as reduced spontaneity in communication, misunderstandings due to lack of non-verbal cues, or feelings of isolation among team members. To address these, the leader might introduce regular virtual check-ins, establish clear communication protocols, or foster a culture of openness where employees feel comfortable reaching out for support.
Similarly, the leader would consider the mental health implications of remote work. Without the natural structure of an office environment, employees may struggle with feelings of disconnection, increased stress, or difficulty maintaining boundaries between work and personal life. A systems thinker would proactively offer resources like virtual wellness programs, access to mental health services, or flexible work hours to help employees manage these challenges.
Additionally, the leader would recognize that the shift to remote work can blur the lines between professional and personal time, potentially leading to burnout or decreased productivity. By incorporating this understanding into their strategy, they could implement policies that encourage healthy work-life balance, such as promoting regular breaks, setting clear expectations for work hours, or providing training on time management in a remote setting.
Through this holistic approach, the leader not only ensures a smooth operational transition but also fosters a supportive, resilient, and productive remote work environment that addresses both the immediate and long-term needs of the team. In essence, systems thinking helps leaders “work the problem” by staying open to various solutions and considering the broader organizational context, rather than jumping to quick fixes.
"You can’t understand a system until you try to change it." – Kurt Lewin
To effectively address today’s complex leadership challenges, organizations, and leaders need to move beyond traditional problem-solving methods and adopt a more holistic approach. These interconnected challenges—ranging from work-life balance and change management to communication breakdowns and generational divides—require a systems-thinking mindset that considers how various elements influence and reinforce one another.
Prioritize Well-being
The well-being of leaders and their teams is not just a personal issue; it's a critical organizational priority that impacts performance, engagement, and resilience. To foster a healthy work environment, organizations should assess their current workforce to understand employee challenges at all levels, as well as thoroughly think through what they want the organizational culture to ‘look and feel like’. Once having a clear target and understanding the current challenges, as well as understanding how they interrelate, brainstorming solutions can begin. Possible solutions might be implementing robust well-being initiatives, such as employee assistance programs, wellness resources, or mindfulness practices. These initiatives not only reduce stress and burnout but also enhance leaders' ability to make thoughtful decisions and maintain high levels of productivity. When well-being is integrated into organizational culture, it creates a ripple effect—leading to higher retention, better collaboration, and a more motivated workforce. Well-being isn't a one-time fix but an ongoing commitment to supporting the mental, emotional, and physical health of leaders and teams.
Improve Change Management
Organizational change is inevitable and holds a significant opportunity for individual and team growth. Most changes are poorly managed though and therefore immediately lower productivity, erode trust, and create resistance. Effective change management requires communicating with clarity, empathy, and a forward-looking vision that aligns the organization’s strategic goals with the needs of its people. By combining systems thinking with sound change management practices, leaders can navigate the uncertainty that comes with transitions, reducing friction and fostering a culture of adaptability. Leaders who anticipate the ripple effects of change and proactively manage its impacts are better equipped to build resilient organizations.
Foster Thought Partnerships
Leadership is not a solo endeavor. Tackling these complex challenges often requires thought partnership—collaborating with experienced advisors who can offer fresh perspectives and solutions grounded in systems thinking. By engaging with thought partners, leaders can analyze specific hurdles, brainstorm innovative strategies, and implement solutions tailored to their unique organizational contexts. This collaboration helps to break down silos, increase cross-functional cooperation, and ensure that all aspects of a challenge are considered. At Kisley & Wild, our team is committed to helping leaders address their toughest challenges through a systems-thinking lens, empowering them to build stronger, more resilient teams and organizations. In today’s evolving landscape, leaders face many of the same challenges that have always existed—such as navigating uncertainty and managing diverse teams—while new pressures, like remote work and generational shifts, add layers of complexity. By adopting systems thinking, prioritizing well-being, improving change management, and leveraging thought partnerships, leaders can create more resilient organizations capable of thriving in a rapidly changing world. To explore how we can help you implement these strategies, reach out to us at info@kisleyandwild.com. Together, we can cultivate a leadership approach that sees the whole picture and creates lasting success.