Navigating the complexities of leadership, we’ve gathered insights from CEOs and founders on transforming setbacks into constructive lessons. From conducting team retrospectives for growth to inspiring teams amidst challenges, explore the diverse strategies shared by fifteen executives on leveraging adversity for learning, growth, and self-care.
- Conduct Team Retrospectives for Growth
- Foster Transparency and Reflect
- Embrace Vulnerability and Seek Support
- Learn from Hands-On Experience
- Recalibrate Strategies After Setbacks
- Align Innovation with Strategic Goals
- Reiterate Services for Client Satisfaction
- Sharpen Pitches After Investor Setbacks
- Refine Offerings After Contract Reductions
- Find the Gift in Setbacks
- Stay Committed to Core Principles
- Use Failure as a Learning Step
- Document Learnings for Better Leadership
- Build Trust and Explain Your Vision
- Inspire Teams Amidst Challenges
Conduct Team Retrospectives for Growth
We all fail from time to time, but how we handle failures is what determines our future growth. One must be honest with themselves and run a retrospective on the situation. In our organization, I do it with my team on projects when we run into an issue.
One example that stands out was when a client left dissatisfied with our services. We’ve built a case of facts and then discussed it with top managers to identify causes of dissatisfaction and reasons for losing a client. This has helped us revamp our strategy to make sure the same mistake doesn’t happen in the future.
By approaching setbacks as opportunities, you and your team not only improve the processes but also foster an agile environment and build resilience in both yourself and the team.
Michael Podolsky
Co-Founder and CEO, PissedConsumer.com
Foster Transparency and Reflect
I’ve encountered setbacks that tested both the business and my leadership. I handle failures by viewing them as learning opportunities rather than roadblocks. One key approach is fostering a culture of transparency—openly acknowledging mistakes and analyzing what went wrong without placing blame. This helps turn setbacks into moments for reflection and growth.
An example is when our initial ID verification product launch faced significant technical issues. Instead of seeing it as a failure, we took the opportunity to dissect the process, involving the whole team to identify weaknesses in development and communication. We revamped our approach, tightened quality control, and used the experience to improve our future releases.
Personally, I’ve learned the importance of self-care during these times. Taking breaks and maintaining a balanced perspective allows me to stay resilient. By treating failures as valuable lessons, I’ve become a better leader and built a stronger, more adaptive team.
Liudas Kanapienis
CEO, Ondato
Embrace Vulnerability and Seek Support
These experiences, though often painful, have been crucial in shaping me both professionally and personally. When faced with a setback or failure, I embrace vulnerability. I understand that setbacks are a natural part of the entrepreneurial journey, which allows me to approach them with curiosity rather than shame. I also conduct a post-mortem analysis after setbacks to identify root causes and learn from my mistakes.
Additionally, I seek support from a strong network of mentors, colleagues, and friends who provide advice and encouragement. Another important step I take is to prioritize self-care. I find that self-care is essential for maintaining my mental and physical well-being.
One of my favorite acts of self-care is long-distance running. Over the years, I’ve trained for and completed several marathons and a triathlon, gaining valuable insights into resilience. These races have pushed me to my physical and mental limits, but overcoming those challenges has taught me to bounce back from adversity and persevere through difficulties.
Ultimately, rather than viewing setbacks as failures, I see them as opportunities to develop resilience, adaptability, and a stronger sense of purpose.
Lisa Lanier
President & CEO, Lanier Law Group, P.A.
Learn from Hands-On Experience
When I started my company, my enthusiasm for cannabis far outweighed my knowledge. That gap led to some early missteps, like when I remember ordering a huge batch of CBD oil, only to realize I hadn’t properly vetted the supplier or understood the testing requirements.
Instead of giving up, I decided to turn it into a “back-to-school” type of learning opportunity, and I spent weeks on the road, visiting growers, extractors, and labs across California. Those were the conversations where I learned about the intricacies of cultivation, the importance of third-party testing, and the nuances of different strains. There’s really no substitute for hands-on knowledge.
Dennis Sanders
Founder, Burning Daily
Recalibrate Strategies After Setbacks
Facing challenges is a normal aspect of the business world, and as a leader, the key is your reaction to them. I view failures as opportunities to readjust, not as final stops. I see failures as moments to recalibrate, not as dead-ends.
One example that stands out is when we overestimated demand for a product line, leaving us with excess inventory. At first, it felt like a big hit, but instead of dwelling on it, we shifted focus to creative ways to move the stock, like bundling and offering limited-time discounts. It worked, but more importantly, it taught us the value of being adaptable and listening more closely to market signals.
The lesson was clear: flexibility and fast decision-making can turn a setback into a win. Self-care in these moments is key, too—it’s easy to get consumed by the problem, but stepping back helps you gain perspective and make smarter choices.
Jordan Adair
CEO, ShirtMax
Align Innovation with Strategic Goals
As a CEO, I’ve learned that setbacks aren’t just challenges; they’re opportunities cloaked in disguise. One vivid example was when our team, buzzing with enthusiasm led by the previous CEO turned head of innovation, ventured into a product line that strayed from our core vision. Despite my reservations about stifling creativity, I greenlit the project, hoping to harness the team’s energy.
Unfortunately, the project tanked. It didn’t resonate with our customers, costing us time, money, and effort. This experience was a hard pill to swallow but a crucial lesson in leadership. It reinforced the importance of adhering to our vision, even when tempting diversions arise.
This setback taught me to balance fostering innovation with maintaining a clear focus on our strategic goals. Now, when faced with new ideas, I weigh them against our vision, ensuring they align before moving forward. This approach has not only prevented potential missteps but has also strengthened our team’s understanding and commitment to our collective goals.
Pete Srodoski
Business Coach, Roll With the Punches
Reiterate Services for Client Satisfaction
As a CEO, particularly in the dynamic field of digital marketing, I consider setbacks not as failures but rather as valuable learning opportunities. A key lesson I’ve learned over the years is the significance of reiteration. For instance, during the initial years of my company, we took on multiple projects we were unfamiliar with. It led to several revisions, late-night brainstorming sessions, and even lost clients.
Instead of being disheartened, we leveraged these experiences to build a more focused service delivery model, emphasizing areas where our technical competence was high. This perspective shift didn’t just reduce redundancies but also improved client trust and satisfaction. Today, our approach of “testing-learning-improving” has become a cornerstone of our organization’s growth, reminding us that there is no substitute for learning from our own experiences and that setbacks are only stepping stones to improvement.
Jim Kreinbrink
CEO, Hyper Dog Media
Sharpen Pitches After Investor Setbacks
As a CEO, setbacks and failures are inevitable, but I see them as opportunities for growth and resilience. One experience that stands out is when an investor backed out of a crucial funding round at the last minute. It was a tough blow, but instead of letting it derail our momentum, we took it as a challenge to sharpen our pitch and refocus our efforts. We rallied, reached out to new investors, and ultimately secured even more support than we initially expected.
That experience taught me the power of persistence and adaptability—sometimes a setback is simply a redirection toward an even greater opportunity. It also reminded me to take care of myself and the team during high-pressure moments, because clarity and focus come from within.
Nyasha Gutsa
CEO & Founder, Billy
Refine Offerings After Contract Reductions
As a leader, setbacks are inevitable, but they’re also where growth happens personally and for your company. I’ve learned to embrace failure as a necessary part of the journey. One of the most valuable lessons I’ve taken from a tough situation was when one of our enterprise clients unexpectedly reduced their contract. Initially, it was a financial and emotional hit, but it pushed us to reassess our value proposition and tighten our focus on building stronger, more resilient client relationships.
Instead of seeing it as a loss, we treated it as a chance to innovate and refine our offerings, ultimately leading to new opportunities and more aligned partnerships. That experience reinforced the importance of staying adaptable and trusting that every challenge can spark growth if approached with the right mindset.
Candice Durham
Founder & CEO, The B/Suite
Find the Gift in Setbacks
Be real. Nobody likes getting kicked in the junk and setbacks are hard to swallow. We lost a monster client to an acquisition this year. The modality I try to employ in these situations is to “look for the gift.” And then express that gift to my people. In this case, we learned a new industry, and are over-prepared for our next opportunity in that space. There is no past—only the present and what we carry with us into that moment. To carry the baggage of a loss is of greater harm than the loss itself, for your mental health. Find the gift.
Erik Radle
CEO, Miller Ad Agecny
Stay Committed to Core Principles
Valuable lesson: Stay committed… stay the course!
When our leadership team chose to implement EOS in 2016, we had a team of 10 people. Soon after establishing our core values, vision, and creating “rocks” for each person on the team, we lost five players who decided they didn’t “fit” in our new operating system. I had big-time second thoughts and regrets about moving forward with EOS, but we stuck to our principles and hired people who did “fit” into the new company. It took some time and patience, but our team/company is bigger (17 employees), better, and stronger than ever before.
EOS works!!
Stay committed…stay the course!!
Bruce Hagberg
CEO
Use Failure as a Learning Step
Failure is often viewed as a negative, but I believe we need to shift our mindset around it. In reality, failure is just part of the testing and learning process. It’s only true failure if we give up. When something doesn’t work the way we expected, we shouldn’t view it as the end, but rather as a data point—an opportunity to dig deeper and understand why things unfolded that way.
One of the most valuable lessons I’ve learned is that every “failure” gives us more information to improve. By shifting the focus to learning and refining our approach, we can create a much healthier relationship with failure. For example, we had a sales campaign that just didn’t produce the leads we thought it would. Instead of scrapping everything, we used it as a test case, analyzing what went wrong and adjusting our strategy accordingly. That learning helped us refine our future campaigns, leading to more success.
When we view failure through this lens, it becomes less about setbacks and more about the steps we take toward progress.
Chad Ramos
Chief Executive Officer, Privado Health
Document Learnings for Better Leadership
There is no such thing as a setback or failure as a CEO. They are learning experiences, and you have to look at each negative experience separately as a way to make you a better leader. It is critical to ask yourself this question: “What did I learn?” Then, as a remembrance, write the answer down so you don’t forget. The same should be done even with positive experiences.
As the CEO of a former non-profit organization, I was deeply involved with local government when we uncovered fraud and corruption. It was very disruptive to me and the organization. Yet, we did the right thing, which garnered trust and respect with my employees and in the community. Making hard decisions should be done in the best interest of your employees and the community, despite the consequences, because you know it is the right thing to do. Plus, it should allow you to sleep better at night.
Mark Lewis
CEO and Owner, Communique LLC
Build Trust and Explain Your Vision
My approach to setbacks as a CEO is to step back and be curious so I can understand what’s going on. Asking questions and fostering discussion doesn’t just help me diagnose the situation—it builds bridges, relationships, and trust to resolve the situation and work better as a team.
For example, when I started my company, I had a clear vision of what I needed to do and thought I could move quickly and bring my new team along easily. But I quickly realized that the automatic trust I’ve experienced in previous cultures wasn’t a part of my new organization’s culture—and I needed to slow down, build deeper relationships, explain the “why” behind my thinking, and actively listen to their concerns to gain buy-in and move the organization forward.
Bridgette Gray
CEO, ideas42
Inspire Teams Amidst Challenges
One of my biggest setbacks came three months into my new role as CBO of a global media conglomerate. We were entering into a global pandemic; on top of that, the company found its name in the press with a continuous parade of crises.
The challenge…how do I get the team motivated to perform when there is so much affecting us on a personal level and consistent chaos? Instead of freezing, how do I get them to focus? I knew the team needed to consistently hear from me. They needed a consistent, calm voice, acknowledging the challenges we were in but not letting them stay there.
For 155 weeks in a row, I sent out an 8:30 AM Monday morning email focused on taking ourselves to the next level…acknowledging the opportunities/challenges, setting the tone for the week, and inspiring the future.
That team went on to continuously crush their goals, build massive new businesses, close record-breaking deals, form strong bonds together, and develop talent into incredible leaders.
HOWEVER, what resonated the most with the team as I was moving on to my next adventure, was not the business successes we achieved together. Almost every note was thanking me for those Monday morning emails. Many of which said those emails helped them (and their families) get through COVID, often reading it together as they sat around the breakfast table looking for inspiration for the week.
It was a great reminder it’s not just about what you do, but how you make others feel. Resulting in loyal, happier, more effective teams that also know how to have fun.
Jennifer Mormile
CEO, RavenX Ventures