We often hear about lessons learned from failed companies—issues like not prioritizing market validation or lacking financial discipline. While these are important and true, I’ve been reflecting on whether we take enough time to unpack the leadership lessons and behaviors that contribute to these failures. There is so much more to learn there. Failure, in my experience, is the gateway to success.
Over three decades of working with entrepreneurial companies in human resources, organizational development, consultant, and executive coach, I have witnessed a handful of successful liquidity events—but far more failures. I’ve managed massive reorganizations, layoffs, and shutdowns, all of which have shaped my understanding of what it takes to build high performing leadership teams and successful organizational cultures. Entrepreneurship is inherently risky, but within these challenges lie profound lessons.
Reflecting on my journey, I’ve distilled my insights into five key leadership lessons fundamental to thriving in today’s fast-paced, ever-changing environment.
Failure is your teacher
Having worked with countless high achievers, I’ve realized that failure, while often feared, is an unparalleled teacher. Personally, I’ve learned more from the adversities than from successes. The same applies to organizations: we push hard for wins but often fail to pause and reflect on the losses – it’s often the tragedies that define us. In fact, in times of discomfort, the most learning occurs. Failure fosters resilience and innovation – but only if leaders are willing to pause and reflect.
Unfortunately, I’ve observed that immature leadership teams often dismiss, excuse, or rush past failure. Where is the learning if we don’t pause? Where is the resilience when we ignore failure? Do you take the time to hold a blameless postmortem after a failure on your team? Or do you just point fingers, blame, and move on? Do you stop, pause, and engage in active listening when someone brings a failure on a project to you, or do you immediately start to find fault? Interesting questions to consider.
Blame and shame is an interesting study inside organizations. If I make a mistake, I might feel guilty. If my team fails, it does not define me as a failure (shame/identity). We don’t spend enough time examining our own relationship with shame especially around failure. Brené Brown explains this in her book, Rising Strong:
Shame is a focus on self, while guilt is a focus on behavior. This is not just semantics. There’s a huge difference between I screwed up (guilt) and I am a screwup (shame). The former is acceptance of our imperfect humanity. The latter is basically an indictment of our very existence.
For example, when a key employee leaves, do you make excuses for their departure, or do you take accountability and reflect on your role in it? Learning from failure requires strong leadership willing to look in the mirror. It fosters trust, drives engagement, and creates a foundation for innovation. Failure is an inherent part of the learning process, and it also fosters resilience. In Forbes Article, 20 Leaders Share Lessons Learned From Business Failure, 15 out 20 leaders mentioned learning from failure as part of their leadership lessons learned.
Slow down to speed up
This timeless lesson is particularly crucial for startups and entrepreneurial ventures. Having worked with so many serial entrepreneurs, I see this as both their greatest superpower and their Achilles heel. Leaders’ urgency to build and launch products sometimes eclipses the need for market validation. According to CB Insights, 35% of startups fail due to a lack of market need—a clear case for slowing down to strategize before moving forward.
I see the emphasis on speed and a sense of urgency as problematic for leaders in larger organizations as well. This drive for speed, urgency, and a relentless focus on results is evident in organizations of all sizes. Leaders often struggle with limited resources, making it challenging to navigate delegation, empowerment, and self-care, which can ultimately lead to burnout for both them and their teams.
Speed can become systemic within the organization, often turning toxic in the culture. It can lead to bad decision-making, misalignment the team, lack of vision, frustrated customers, and disengaged employees. Slowing down doesn’t mean becoming less productive; it means working smarter. Leaders who take time to plan, strategize, and reflect are more likely to make informed decisions. They are better equipped to adapt to the fast-paced changes in their environments.
Slowing down means building infrastructure, behavioral planning, and scalable practices. Slowing down means taking the time to build alignment in your leadership team and good hygiene around decision making. It means hiring slowly and firing quickly – and yes, this is coming from a senior HR professional. The team that starts the journey may not be the one that finishes it. Taking too long to terminate one senior leader in an early-stage organization can be a terminal decision.
Embrace conflict to foster productive teams
Tough decisions are inevitable. Noam Wasserman’s book, The Founder’s Dilemma, highlights that 65% of high-potential startups fail due to co-founder conflict. I’ve witnessed how unresolved conflicts among co-founders bleed into the leadership team and broader organization, creating misalignment and dysfunction throughout the system.
Leaders and teams often avoid addressing the elephants in the room, sidestepping tough conversations or confronting their own blind spots. This avoidance is frequently rooted in a results-driven mindset—focusing solely on getting things done without building a framework of trust and psychological safety. However, avoiding conflict tends to exacerbate problems. Without trust, people don’t feel safe enough to express their true thoughts or feelings. Healthy, respectful conflict is essential for challenging ideas, fostering innovation, and generating better outcomes. When trust forms the foundation, conflict becomes a constructive force rather than a destructive one. Ironically, by taking the time to develop this framework of trust and psychological safety, we ultimately achieve better results—a concept that has always seemed so straightforward to me!
If leaders avoid difficult conversations, they often lack the skills needed to address performance issues in real time or to reset expectations consistently which leads to productive teams. High performers, in particular, benefit from clear feedback stay engaged continue growing. When leaders lean into difficult conversations to navigate conflict and set boundaries, they foster a culture of accountability. This culture not only addresses immediate challenges but also encourages transparency, trust, and personal development, all of which contribute to long-term success.
In the absence of a culture of accountability, organizations often face a cascade of negative outcomes that can lead to failure. Without accountability, poor performance goes unchecked, creating frustration and resentment among high-performing team members. This lack of recognition for effort and results can lead to disengagement and turnover among top talent, weakening the organization’s overall capability.
Moreover, when leaders fail to set and enforce clear expectations, misalignment becomes systemic. Teams lose focus, resources are misallocated, and goals become increasingly difficult to achieve. This lack of clarity and ownership often fosters a blame-shifting culture, where problems are ignored or passed around rather than solved.
In startups or early-stage companies, the stakes are even higher. Without accountability, leaders may fail to address critical issues, such as product misalignment with market needs or operational inefficiencies, until it’s too late. Toxic behaviors can take root, eroding trust and collaboration. In some cases, this absence of accountability contributes to the erosion of company culture, making it difficult to attract or retain employees who can drive the business forward.
Accountability acts as a foundation for sustainable growth. It ensures that everyone, from individual contributors to senior leaders, is aligned and committed to the organization’s goals. Companies that embrace accountability not only mitigate risks but also position themselves for resilience and long-term success.
Emotional agility during change
Change and uncertainty are constants in organizations, especially during periods of growth or crisis. Companies that prioritize organizational resilience—not just in response to crises but as a proactive strategy—gain a lasting competitive edge. In today’s hybrid and post-pandemic organizations, empathy is perhaps the most important leadership skill as evidenced by this article from the Center by Creative Leadership, The Importance of Empathy in the Workplace. Leaders must recognize and address the emotional side of change. Compassionate leadership, which includes empathy and emotional intelligence, is critical in navigating these challenges.
Susan David, expert on emotional agility and award-winning Harvard Medical School psychologist says the following:
We often lose sight of our shared humanity in the midst of our dogged pursuit of productivity and profit. But success isn’t possible if we’re building upon an unstable foundation. The ability to help others be present with their own emotions is the core to effective teaming and leadership.
Unfortunately, failing companies often prioritize financial performance at the expense of team health. Leaders who neglect the emotional impact of change risk disengagement, resentment, and backlash from their teams . There are people behind products. Emotions and impact behind a message. Too often, the focus is placed on the result or the thing we are trying to change without considering the emotional impact on individuals involved. Whether due to a lack of emotional literacy or feeling ill-equipped, leaders frequently deliver tough messages without accounting for how their teams might feel. This oversight can lead to significant backlash, as evidenced by negative reviews on Glassdoor or social media following layoffs.
Cultivate culture and values
Successful companies build strong cultures rooted in clearly defined values. Establishing these early on is critical to sustaining growth. Organizations with a values-based culture experience greater alignment, engagement, and ultimately, financial success. Gallup reports that companies prioritizing culture see a 33% increase in revenue.
Founders and CEOs who prioritize culture lay the groundwork for long-term success. Culture and values should be clearly defined and integrated into measurable Objectives and Key Results (OKRs). CEOs must ensure leaders and managers are held accountable for achieving OKRs related to culture and values.
Values should reflect an organization’s identity, not aspirational goals. They should guide hiring, decision-making, and behavior. Involving the team in defining values ensures buy-in and alignment. Values should be behavioral rather than results-based, serving as an anchor during times of change and uncertainty.
Organizations that compromise culture and values for short-term gains often pay the price in the long run. By prioritizing culture and aligning it with strategic goals, companies lay the foundation for sustainable growth.
Final Thoughts
My career has been punctuated by wins and losses, each offering valuable insights into leadership and culture-building. While success is never guaranteed, leaders can significantly improve their odds by letting failure be their teacher, learning to pause, embracing conflict, fostering accountablity, building emotional agility and cultivating culture and values.
Leadership isn’t about perfection; it’s about being intentional, adaptable, and human. By embodying these principles, leaders can build resilient organizations and impactful teams. Entrepreneurship is a journey, and leadership is a continual evolution—but with the right lessons in hand, success is within reach.
Melanie is the Founder & CEO of Radical Ignition, bringing 30 years of C-level executive and consulting experience across a broad range of industries. She has coached hundreds of executives and teams across six continents, from startups to Fortune 50 firms, and is a sought-after speaker on topics including resilience, change, culture, confidence, leadership, and empowerment. Melanie has partnered with leaders from top brands such as Fresenius Medical Care, CVS Health, Microsoft, Johnson & Johnson, Google, Accenture, ServiceNow, Cedar, and Airtable.
