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Leaders, Let Them Fail

Do not judge me by my success, judge me by how many times I fell down and got back up again.

Nelson Mandela

Mandela demonstrates resilience to the nth degree, defined as “the capacity to withstand or to recover quickly from difficulties.” Resilience stems from failure, resistance, and setbacks.

Readers, today I want to explore how leaders can build resilience in their teams by letting them fail. Done correctly, resilience strengthens problem solving which supports the successful functioning of a healthy business.

Let’s start by clarifying generational workforce divisions, understanding that generational behaviours at a macro level don’t, of course, preclude recognizing people as individuals.

Here’s how I’d sketch the perception of resilience by each generation:

  • Boomer: Pick yourself up and get moving! Persevere and you’ll overcome adversity.
  • Gen X: It’s up to you. Develop resilience to ensure your success.
  • Millennial: Take care of yourself. You’ll bounce back.
  • Gen Z: Resilience = change. Treat change as a positive so you can make your impact.

As a leader, identify your generation and decide if you perceive resilience according to your cohort. It’s possible you identify with another one. Pick the one that suits you best.

Now I want you to think about your team. Which generation(s) do they belong to? How does their generation interpret resilience?

Pause a moment.

Can you see the potential disconnect between how you view resilience and how your team might? Think about the possible consequences of misalignment based on how each party sees it.

If the capacity to recover from difficulties is what resilience is, knowing how each generation approaches it helps leaders navigate the murky waters of today’s topic, failure.

Dr. Mary Donohue researches how generations interact in the workplace, explaining that each generation shares common anchoring moments meaning “how you frame solutions to your problem.” 1

Anchoring moments, as the phrase implies, ground and instruct. They nurture resilience. Donohue argues if you don’t allow for failure, either as a leader, parent, or friend, you don’t allow for anchoring moments. Without anchoring moments, you don’t acquire the means to find solutions to your problems.

The parents of Millennials (Boomers) provided their kids with mentors and coaches. Millennials experienced Kumon and lots of organized after-school activities which only accelerated in the next generation, Gen Z (parents: Gen X).

With all that instruction and structure, failure was not an option. Failure became externalized (“it’s the teacher’s fault, not the student’s, that he was unable to understand the content”). Anchoring moments found in learning how to navigate tough or awkward conversations, for example, weren’t developed.

As Millennials and now Gen Z entered the workplace, they naturally turned to managers to solve their problems because they were used to parents stepping up on their behalf. Even though some managerial Gen Xers and Boomers resented the role of negotiator/parent in the workplace, that’s what some members of the younger generations expected. Boom! Here you see the clash of generational perspectives.

Failure fosters resilience. That’s why I urge you, leaders, to let your team fail. Trust your team to learn from their mistakes. Just ask Miss Frizzle from The Magic School Bus. Or my friend who says, “You don’t fail, you learn.”

Resist the urge to bail out your team at the first sign of struggle. Remind yourself that friction is inherent to the process of achieving goals. The satisfaction derived from achieving goals expands the capacity to withstand future challenges.

Leaders, let them fail.

You have to be open minded in order to grow. The coaching that Laura gave me opened my eyes to what and how I was doing things and allowed me to see the bigger picture. I am not done yet but I already see the changes in my everyday life.


I think coaching is a great way to help you clear your mind when you get stuck with overwhelming situations or when stepping into changes in your life.


Coaching is life changing. It pushes you outside your comfort zone and challenges your perspectives.  It is highly motivating and the exercises and techniques used are both fun and informative.  I think the main benefits of coaching are to see yourself, others and the world more clearly.  I think coaching is valuable to anyone regardless of where you are in your life or career.


I honestly never thought I’d need a coach. I thought coaching was for CEOs and industry VIPs. I didn’t think it was for the “little guys” (i.e. me). Now, I’m of the belief that everyone – yes, EVERYONE – needs a coach. Coaching has really benefitted me and I’m so grateful to have had that time with Laura. It’s changed my life!


Laura is very patient. She took the time to understand what was causing me to be stuck where I am today and help me build a better vision so I can continue to grow.


I think Laura’s coaching was what I had been waiting for. Laura was so approachable, kind, and open. Her willingness to help and support made a difference for me. I found in her coaching new strategies, ideas, and perspectives that I could incorporate into my goals and objectives that I didn’t see before.


Laura is an incredibly intuitive, positive and caring coach. Her techniques helped me recognize both my strengths and areas I might want to explore as I embark on the next chapter of my career. The exercises she employed were instrumental in providing self perspective and challenging my frames of reference.


Laura is a natural coach. Her probing and compassionate questions helped me learn about myself: my value system, interests, goals and strengths.


Coaching sessions with Laura gave me new perspectives on how to process specific feelings and situations in life.  She showed me how to sit with my emotions, acknowledge them, and then use visualization strategies to move through them.  I now feel more confident and in control of how I choose to walk through life.


From the beginning, Laura put me at ease, creating a safe, open space for me to talk and share freely without fear of judgement. I loved the variety of approaches she used depending on the topic we were working on and it was fun being able to try out things I wouldn’t have considered before! With Laura’s coaching, I substantially grew my confidence in the workplace, overcame fears, dealt with issues I’d been carrying around for many years and, most importantly, learned to value myself and define a path forward into the future.


Laura’s coaching was a breath of fresh air and EXACTLY what I needed at that point of my life. I didn’t realize how impactful coaching was going to be, but by the end of the sessions together, I left feeling refreshed, inspired and genuinely curious about what my future held for me. Because of Laura and her coaching, I believe I became a better person – someone who is more open-minded, someone with a clearer focus, and someone who is willing to explore opportunities and possibilities far more than I ever did before.


I engaged Laura for coaching as I took on an expanded role leading an asset management company in Canada. As a female, I knew I would be a role model and had high expectations of myself. I was feeling overwhelmed and anxious.

In our first few coaching sessions we worked through exercises that allowed me to reflect on my purpose, leadership style and what mattered most to me. I continue to be grounded by the clarity I achieve in my coaching sessions – allowing me to be resilient and confident when challenges came my way.