Accountability, Inspiration, Passion, and Feedback

With Chaim BerkovicEP 189

Growing up in Williamsburg, Chaim Berkovic learned the importance of having a vision; years later, as the president and founder of Skyscraper Insurance, he was able to actualize that vision, even though the ways to achieve it were sometimes unclear. In this fascinating conversation, Meny asks Chaim about some of the methods he used to create and grow his business, as well as his strategies for being an effective leader. Listen in as they talk about transmitting passion to employees, how to maintain “brutal accountability” while also creating a positive company culture, the role of inspiration in leadership, what can be learned from failure, why feedback is indispensable, and more.

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Key Highlights:

[00:01 – 05:00] The Visionary’s Journey

Chaim’s transition from early failures to founding Skyscraper Insurance
The importance of learning from mistakes and taking calculated risks
How personal challenges fueled Chaim’s entrepreneurial spirit

[05:01 – 15:00] Risk Management and Client Trust

How Skyscraper Insurance approaches risk management differently
The significance of understanding client needs and building trust
Insights into the complexities of the insurance industry

[15:01 – 25:00] Leadership Beyond the Boardroom

The role of inspirational leadership in building a successful team
Balancing company culture with high performance and accountability
Strategies for nurturing a positive, growth-oriented workplace

[25:01 – 35:00] Mastering Growth and Scalability

Chaim’s perspective on business growth and strategic acquisitions
The impact of community and relationship-building in expansion
Learning from industry shifts and adapting for scalability

[35:01 – 46:08] The Mastermind Effect

The benefits of participating in mastermind groups for business leaders
How shared knowledge and accountability drive success
Chaim’s personal experiences and gains from mastermind involvement

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Practical Pointers
Don’t simply enter a particular field because you see others doing so; instead, ask how you can add value to the marketplace in that specific area. Adding value opens up a new market for the product or service you’re trying to advance.
A good leader doesn’t have all of the answers, and a good leader doesn’t always cover for you. But a good leader will inspire you, both by his actions and by demonstrating that his employees will benefit from unlimited opportunity and from sharing in the success of the company.
It’s not enough for a leader to try to inspire his employees; you also need a feedback reporting system to find out what’s working and what’s not. For example, consider having a meeting with team leaders every week to ask questions about your leadership.
Remember that accountability goes both ways: just as you hold your employees accountable for their failures, you also need to hold them accountable when they do their job, giving them credit for excellence. Maintaining both aspects of accountability is an important tool in creating a positive company culture without losing your ability to criticize poor performance when it’s necessary.
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Guest Bio
Person Image
Chaim Berkovic

Founder and president of Skyscraper Insurance. A visionary in the insurance arena, Chaim has extensive management expertise and has developed keen insight into the industry. Chaim is known for identifying opportunities in the insurance marketplace to create products, services and startup companies that address market opportunities, with a keen focus on high-risk populations which have been historically underserved.

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