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7 Questions on Leadership with Avi Wolfson

Name: Avi Wolfson

Title: Professional Speaker

Organisation: Avi Wolfson

Avi Wolfson leverages a career as a licensed realtor, professional salesperson, 3-time axe throwing champion, and best-selling author to help audiences directly as a professional speaker. Wolfson, an expert in resilience, entrepreneurship, and self-discovery, inspires others with his story of overcoming childhood trauma and mental health challenges and finding work-life balance. In addition, Wolfson is a proponent of failure as part of the success process, giving back positivity into the universe by paying it forward. Audiences and critics find Wolfson “creative, humble, honest and smart” and adept at growing organizations by “helping people into better positions where they’re happy and flourish.”

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Avi's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

According to the Bible, Moses, one of the original leaders, neither sought nor enjoyed leadership. Nevertheless, he naturally emerged as a competent and well-regarded leader, essentially chosen by the people. While being a leader is not always easy, it constitutes a meaningful journey that transcends one's individual life. If you are chosen for a leadership role, the universe will find a way to communicate this to you. Rejecting this destiny may result in profound pain, regret, and unhappiness. Make a conscious decision to trust that, by taking proactive, positive actions in life, you will be guided toward a desirable destination, allowing you to achieve the goals inherent in the leader you were born and meant to be. Leave your mark on the world you were chosen to be a part of.

2. How did you become a leader? Can you please briefly tell the story?

"You stay back there. Don’t move. Stay put," commanded my older cousin, immersed in a game with me and one of his friends. I must have been around five years old at the time. The ongoing game was a Star Wars-themed blend of chess and checkers. Despite my lack of familiarity with the game, an inner drive compelled me to move my piece forward, defying his instructions. Even before the game began, I had mentally surrendered to the belief that being younger, smaller, and less experienced, I had no chance against my superior cousin. However, an internal motivation prompted me to make a move, and surprisingly, my cousin, absorbed in defeating his friend, overlooked my deliberate moves. In the end, I emerged victorious, triumphing over both opponents. Leadership qualities often manifest in unexpected ways. As Wayne Gretzky wisely stated, “You miss 100% of the shots you don’t take.” Even when faced with the belief that success is unlikely, it is highly important to seize the opportunity, move forward, and persist. This embodies the spirit of the "underdog." In my thirties, I went on to win three axe-throwing championships, once again emerging victorious as an underdog in my league. These triumphs propelled me to discover my true calling, which is speaking and inspiring others to reach their full potential and discover their inner champion. My childhood game taught me that taking a chance can lead to unexpected victories, emphasizing the importance of embracing opportunities even when the odds seem stacked against you.

3. How do you structure your work days from waking up to going to sleep?

"Beauty is in the eye of the beholder," is a familiar phrase suggesting varied perspectives. Yet, this concept extends beyond aesthetics. Experience, too, is subjective. In terms of workplace structure and organization, diverse platform solutions exist. Some organizations prefer HubSpot, while others lean toward Salesforce, among others. Although both facilitate organization, is there truly no difference between them? Indeed, there is a distinction, hinging on personal preference. What one person deems invaluable bells and whistles, another may perceive as impractical or worthless. Multiple methods exist for structuring your workday and determining the optimal routine involves testing until you find what works best for you. Popular methods include the “Pomodoro Technique,” the “3/3/3 Method,” the “Eisenhower Matrix,” “Eat the Frog,” the “Seinfeld Strategy,” and “Time Blocking.” Experiment with each method, take note, weigh the pros and cons, and ascertain which method or combination aligns best with your personal preferences.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

I worked for a best friend for several years, an experience that did not go well and ended on a sour note. What I learned from this painful episode of my life, is that respect begins with self-respect. If bitterness persists, you are likely to remain stuck or impede personal growth. Holding grudges throughout your life does not contribute to achieving goals, finding fulfillment, or healing wounds. If forgiving someone proves challenging, at least come to terms with the circumstances, acknowledging that the past cannot be reversed. Learn from the experience, remember the lessons, and move onward and upward. As Louis Smedes once said, “To forgive is to set a prisoner free and discover that prisoner was you.”

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

"Start With Why" by Simon Sinek significantly influenced my approach to business. For a significant period, my focus was solely on identifying opportunities for generating money or passive income. To cut a long story short, I encountered numerous unfruitful and wasteful ventures. In 2019, after investing immense effort into an e-commerce business, the challenges posed by COVID-19 led to its collapse. Witnessing the business I had worked so hard to build crumble was disheartening, leaving me with nothing. Fortunately, during this challenging period, I had a great mentor who suggested exploring Kindle Direct Publishing. It marked the first time I approached a business with my "Why" at the forefront. This project has become the most successful venture I've undertaken, and the work is not only meaningful and purposeful but also crystal clear in its alignment with my "Why." Childhood struggles fueled my desire to illuminate a positive future for parents striving to raise resilient kids and families that thrive. I make a deliberate effort to integrate my "Why" and the personal story behind my books into the fabric of my work. People aren't just purchasing my books for their value as parenting resources; they connect with the narrative and understand the purpose behind their creation.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Embrace humility. Demonstrating vulnerability among those you trust is not a sign of weakness but rather a true measure of courage. Lead with humility, be ready to engage at all levels, and treat others as equals and never as beneath you. Remember, respect is earned and not given. It's a valuable currency acquired through sacrifice, leading by example, displaying humility, and treating others as equals. The only time it's appropriate to look down on someone is when admiring their shoes. Authentic leaders, those who are genuine and natural, always lead with empathy.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

In my childhood, I recall my mother recounting an incident that occurred when she and my father took a taxi ride. She attempted to give the taxi driver a tip, but my father responded by hitting her hand, and the cab driver had to pick up the change from the ground. Despite being a highly intelligent and educated man, my father did not harness his education and intelligence for good. Unfortunately, he turned out to be a deceitful and selfish individual, a terrible businessman with no real friends. When establishing relationships, it's crucial to look beyond a person's accolades, and assets, and perceive them for who they are at the core of their soul.

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