What Lessons Can Be Learned from Failure?

What Lessons Can Be Learned from Failure?

Learning from failure is a crucial aspect of leadership, and to gain deeper insights, we've compiled twenty-two valuable lessons from CEOs and Founders. From setting boundaries for setback contemplation to the importance of discipline in avoiding failure, these seasoned leaders reveal how setbacks have shaped their approach to running a business.

  • Set Time Limit for Setback Contemplation
  • Take Ownership of Failures
  • Learn from the 'Why' Behind Failures
  • Focus on Cash Flow Management
  • Emphasize Importance of Agility
  • Grow Through Adversity
  • Take Responsibility for Team Mistakes
  • Be Flexible and Customer-Focused
  • Combine Transparency with Rapid Learning
  • Turn Challenges into Growth Opportunities
  • Learn from Project Estimation Errors
  • Use Setbacks for Reflective Improvement
  • Improve Crisis Management and Communication
  • Criticize Broadly, Praise Specifically
  • Reframe Failure as Growth Opportunity
  • Use Failures to Improve Processes
  • Admit Mistakes and Plan Improvement
  • Accept Criticism as a Leader
  • Document and Measure for Direction
  • Test Before Implementing Strategies
  • Analyze Failures for Better Leadership
  • Discipline is Key to Avoiding Failure

Set Time Limit for Setback Contemplation

In the early days of Bemana, I ruminated heavily on each and every setback. I thought that eliminating failure entirely was the only solution and worked toward perfectionism. But, of course, disappointments prevailed.

It was my mentor who pointed out that my mindset was the actual issue. Expecting smooth sailing all the time is unrealistic, and dwelling on mistakes with 20/20 hindsight is unproductive. The habit was holding me back. She advised me to set a time limit on contemplation. When setbacks occur, it's fine to spend an hour or two evaluating what went wrong. But when that consideration drags on for days and weeks, it becomes negativity for negativity's sake: a sort of mental punishment.

Implementing boundaries on this behavior helped immensely, and I'm now able to move on from failures quickly and stop playing the self-sabotaging blame game.

Linn Atiyeh
Linn AtiyehCEO, Bemana

Take Ownership of Failures

One pivotal leadership lesson I've learned through failure is the importance of taking ownership. It's only a true failure if you fail to learn from it. Learning leaves the room when we justify failures by blaming external factors and others, by seeking false comfort and validation. By honestly reflecting on our failures, what we would do differently, where we messed up, and where we did great, even within the ultimate failure or setback, allows us to reframe them as opportunities and respond with actionable personal changes.

I provided a way to embrace my vulnerability but refused to stay there. Instead, by 'owning' my role, actions, and results, I lift my growth mindset, strengthen my resilience, increase my knowledge, wisdom, and insight, and prepare for next time. Owning our failures and seeing them as a necessary part of learning ensures we are always moving towards becoming our personal best, remembering it's a journey, not a destination.

Cheryle Hays
Cheryle HaysFounder & CEO, InPower Strategists

Learn from the 'Why' Behind Failures

Find out the 'why' behind the failure instead of glossing over it. Admitting our mistakes can sting at first, but figuring out where we went wrong and learning how to avoid making the same mistakes again helps us grow a lot. When we see failures as chances to learn and really dig into what caused them, we build resilience and sharpen our decision-making skills for the next go-round!

Loren Howard
Loren HowardFounder, Prime Plus Mortgages

Focus on Cash Flow Management

One single leadership lesson I learned from a setback was to be extremely focused on our company's cash flow. There was a point in 2022 when we took on too many house-flipping projects and ended up losing a significant amount of money. One of those projects we decided to hold on to, and instead of renting it out, we let it sit vacant for a long period because we were worried about tenants destroying the property.

Due to that fear, we bled a lot of money every month, and so our cash flow essentially went away. Because I wasn't on top of the books, I put my employees in a position where I had to temporarily lay them off. If I had been more focused on our company's cash flow, I would have either sold that last property immediately, or I would have rented it out instead of putting my employees in a jeopardized position.

Sebastian Jania
Sebastian JaniaCEO, Ontario Property Buyers

Emphasize Importance of Agility

A key leadership lesson I’ve learned from setbacks is the importance of agility. When a major supplier suddenly went out of business, it underscored the need to have contingency plans and remain adaptable. This experience taught me to diversify suppliers and always be prepared for unexpected changes.

Nicolas Krauss
Nicolas KraussFounder and CEO

Grow Through Adversity

I believe Albert Einstein is the one who said, "Failure is success in progress," and I was only recently truly able to relate to this quote. You see, someone who hasn't failed has never truly had the chance to grow because growth and progress come via adversity, and what is failure but a challenge to overcome?

The very first time I set up my company, I failed. It was a devastating experience, but this is the greatest leadership lesson. You must be able to gain wisdom through your experiences and grow, and then mentor the next generation on how to be better. Many make the mistake of thinking that leadership is like a herder who directs his flock. No, it is more like a wolf who must train their cubs to grow strong and resilient. And resilience is learned when you overcome failure.

Phil McParlane
Phil McParlaneFounder & CEO, 4DayWeekJobs

Take Responsibility for Team Mistakes

Sometimes, failures are your fault as a business owner, even if you weren't directly to blame for the decision involved. Being a leader means delegating and managing your team, and when one of them messes up, you need to look at your own strategies carefully. Ultimately, it's your company, and the buck stops with you.

Recently, I had to remind myself of this. A worker made a mistake that set us back weeks, and my instinct was to place the blame at their feet.

But instead, I took a moment to consider the training I'd offered and assess where my advice might have fallen short. A quick review opened my eyes to the issue, and I realized that I hadn't adequately prepared them for every possible scenario. I can't expect my workers to read my mind and know what I would do on the fly—I have to walk them through hypotheticals and provide strict protocols.

Taking responsibility allowed me to adjust my onboarding process in a way that ensures future employees will know exactly what to do in similar situations.

Rob Reeves
Rob ReevesCEO and President, Redfish Technology

Be Flexible and Customer-Focused

As Director of Business Operations for Stallion Express, I’ve had my fair share of setbacks. One of the biggest lessons I learned from a failure is the importance of being flexible.

A few years back, we introduced a new cross-country shipping service that we thought would be popular based on early market research. We were wrong. The initial response was negative. We quickly realized that our expectations didn’t match up with what our customers were looking for. It was a frustrating experience, but also a valuable lesson: never ignore your customers and be prepared to change course.

Instead of replicating a failed approach, we conducted detailed customer research and analyzed shipping trends. Our customers preferred a new pricing model and quicker shipping times. By quickly adapting to these changes, we completely changed the service. Within six months, we saw a 30% improvement in customer satisfaction and a 25% increase in sales.

Adaptability in leadership is not just about changing course. It’s about listening to feedback and adjusting as the market changes. My experience has taught me that staying on top of customer needs and being able to make quick changes is essential for long-term success.

This lesson remains at the heart of all we do at Stallion Express to maintain our position as Canada’s leading e-commerce shipping company.

Jen Seran
Jen SeranDirector of Operations, Stallion Express

Combine Transparency with Rapid Learning

In business, strikeouts are part of the game. One leadership lesson that a past setback really hammered home is the importance of transparency combined with failing fast. When we faced a challenge, being upfront with the team about the situation was key.

Transparency builds trust and lets everyone collaborate on solutions. But we also learned to fail fast and learn faster. Don't be afraid to take calculated risks and experiment, but be ready to adapt if things don't go according to plan. It's all about learning from mistakes, adjusting your approach, and keeping the team in the loop – that's how you turn setbacks into stepping stones.

Beth Worthy
Beth WorthyCofounder and President, GMR Transcription Services, Inc.

Turn Challenges into Growth Opportunities

Embracing adaptability is crucial for leaders. From my experience at ZenMaid, when a customer finds a bug in our software, I see it as a chance to improve our product and demonstrate our commitment to service. This mindset is a lifesaver, especially during setbacks. For instance, losing a key team member is tough, but it forces us to distribute responsibilities more evenly. Simple perspective shifts turn challenges into growth opportunities.

Amar Ghose
Amar GhoseCEO, ZenMaid

Learn from Project Estimation Errors

One critical leadership lesson I’ve learned from a setback is the importance of accurate project estimation and billing. Early in my career, we undertook a large roofing project without fully accounting for all potential costs. We underestimated the materials needed and the labor hours required, which led to a significant financial loss once the job was complete.

This experience taught me the value of thorough planning and detailed cost analysis before committing to a project. Now, we invest more time in the initial assessment phase, considering every possible expense and contingency. This approach not only helps us avoid financial pitfalls but also ensures we can deliver on our promises without compromising on quality.

This setback underscored the necessity of clear communication with clients about potential additional costs. By being transparent and setting realistic expectations from the start, we build trust and avoid misunderstandings. This lesson has been instrumental in refining our processes and improving our overall business operations.

Tyler Poole
Tyler PooleOwner, White Oaks Construction

Use Setbacks for Reflective Improvement

One of the most enduring lessons I've learned came from an early setback when we failed to meet our recycling targets. Initially, I was incredibly disheartened, but this experience taught me the power of reflection. By critically assessing our processes and strategy, we recognized the need for more robust community engagement and innovative technology to process materials efficiently.

This reflection not only led to substantial improvements in our operations but also instilled a culture of continuous learning and adaptation within our team. Now, we see every setback as an opportunity to refine and evolve, ensuring we stay committed to our mission of minimizing environmental impact.

Gil Dodson
Gil DodsonOwner, Corridor Recycling

Improve Crisis Management and Communication

One significant leadership lesson I've learned in my 20 years in the vehicle-transport industry came from a severely delayed shipment due to unforeseen weather conditions. Though it was an uncontrollable factor, the incident led to considerable client dissatisfaction. This setback became a turning point in my leadership journey. It was a wake-up call about the importance of crisis management and proactive communication.

For instance, I realized that it's essential to keep customers well-informed about potential delays, provide regular updates, and develop contingency plans tailored to possible scenarios. Since then, I've implemented more proactive communication protocols and heavily invested in weather-tracking technology to better anticipate disruptions. Failure is a bitter pill to swallow, but it often contains the seeds of important lessons for growth and improvement.

Chris Estrada
Chris EstradaCEO & Founder, Nationwide United Auto Transport

Criticize Broadly, Praise Specifically

Criticize broadly and praise specifically.

I worked with a manager who singled out employees when they made a mistake. I remember the guy singling out a colleague of mine because her sales record was below what was expected. It was in front of the whole group of salespeople, too. The girl ended up crying and leaving early that day, not to mention the effect it had on the morale of the whole sales team.

After all, if you have a leader dealing with someone else like that, what's to stop them from doing it to you when you inevitably make a mistake?

I've taken this story with me once I moved up into management, and now I live by the rule of criticizing broadly and praising specifically.

When you criticize broadly, you don't make anyone feel small, and if anything, it brings the whole team together. Giving feedback this way allows you to highlight what's going wrong, but not make anyone feel small and resent you.

When you praise specifically, you see people light up. You make the person's day and also set an example for the rest of the team to follow. You tend to see an uplift in morale, as people want to be singled out next time for something great that they have achieved.

Janet Perry
Janet PerryMarketing Manager, DigiSurf

Reframe Failure as Growth Opportunity

Failure is not failure; it's an opportunity for growth. By learning from our setbacks, we increase our chances of success. Success rarely comes overnight. It takes time and perseverance. While we always hope that things will run smoothly, it's important to instill in those we lead that they should never stop playing or pushing the boundaries.

In doing so, we encourage them, and ourselves, to be creative and think innovatively, and to not fear untried ideas but to embrace them. Adaptability and reframing failure into opportunities for growth are the keys to longevity in business. Having a growth mindset will allow you and your business to stay ahead of these changes and your competition.

Emily Maguire
Emily MaguireEntrepreneur and Career Consultant, Reflections Career Coaching

Use Failures to Improve Processes

I learned not to be too hard on myself. Even when recapping how the project went and what could have been done differently, know that hindsight is always 20/20. Be at peace knowing that you did your best at the moment with the information you had, and don't get stuck in a negative place thinking about how it went wrong or how it could have been done better (or perfectly!). Just use that project debrief/post-mortem to keep improving and moving forward in a positive way, and keep refining your processes for the next projects.

Jessa Farber
Jessa FarberDirector of Creative Operations, Bristol Associates, Inc.

Admit Mistakes and Plan Improvement

I’ve learned that owning your mistakes is crucial. During a major campaign flop, I tried to deflect blame, which only made things worse. I realized that admitting the failure, analyzing what went wrong, and showing a plan for improvement builds more trust and respect. I think people appreciate honesty and accountability far more than finger-pointing and excuses.

Andrew Lee Jenkins
Andrew Lee JenkinsOwner, Catalyst RVA Marketing Agency

Accept Criticism as a Leader

Success belongs to the team; failure belongs to you. It's a tough lesson to learn, but a necessary one. When you're leading a business and things are going well, it is important to remember that you are a cog in a machine and only part of the reason for its success. As a leader, however, when things are going less well, you have to understand that your role changes. You are the magnet for criticism, and rightly so—these things happened under your leadership, after all. Being a leader can be a thankless job if you practice selfless leadership, but these leaders are the best of the lot, in my experience.

Kate Kandefer
Kate KandeferCEO, SEOwind

Document and Measure for Direction

Processes are important; procedures are needed. Document everything. Work with objectives; measure what you're doing; benchmark. If you don't track and measure, you don't know if you're going in the right direction. For me, doing all of these things is a key part of being a leader and something I've had to learn the hard way over the years.

As the CEO, it is my responsibility—and only my responsibility—to understand and guide the company as a whole. This means that having all of the facts and figures constantly on hand so I can be the most knowledgeable about how we're doing at any given time is a must.

Dragos Badea
Dragos BadeaCEO, Yarooms

Test Before Implementing Strategies

From a failed marketing campaign at Online Solitaire, the lesson was clear: always test before fully implementing. We launched a broad advertising strategy without adequate pilot testing, leading to subpar results. This taught me the value of incremental, data-driven decisions. We regrouped, initiated smaller, targeted tests, and gathered detailed feedback. The revised approach not only improved our marketing effectiveness but also reinforced the principle that careful testing and adjustment are essential for successful leadership.

Holger Sindbæk
Holger SindbækFounder, Online Solitaire

Analyze Failures for Better Leadership

Some say 'don't dwell on failures, look forward,' but I disagree. Dwelling on failures is a necessary exercise for becoming a better leader. Instead of just moving on, take the time to analyze the failure or the setback. What caused it? What could have been done better? What lessons can you draw from this?

Whenever we fail at something, I ask my team to write out an analysis of what happened and what lessons they learned and share it with the company. The purpose is to utilize the failure, and understand how to avoid it in the future. Just ignoring it only sets you up for repeating it again.

Elyas Coutts
Elyas CouttsCEO, Connect Vending

Discipline is Key to Avoiding Failure

One of the most significant leadership lessons I've ever learned from difficulties is the need for discipline. I can share an example of a project that seems like it was yesterday. We forgot about the specifics since we were too enthused about the new product we were creating for a client.

Disaster struck as we hurried into production without giving it enough testing. The product was rife with defects and fell short of our client's expectations. Our reputation and a substantial sum of money were ultimately lost. In retrospect, I see that the failure sprang from our lack of discipline. One important thing I took away from the event is that we were so preoccupied with the outcome that we overlooked the process.

Kartik Ahuja
Kartik AhujaDigital Marketer,

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