In this episode of Bridging the Gap, Matt sits down with business coach Jon Dwoskin to explore his journey from an aspiring entrepreneur to a successful business coach. Jon shares the pivotal moments that shaped his career, including managing a real estate office through the challenges of the 2008 market crash and transforming it into one of the top offices in the country. His experiences underscore the importance of facing obstacles head-on and learning from them, which has informed his approach to coaching, emphasizing self-awareness, vulnerability, and effective communication in leadership roles.

Jon delves into key skills crucial for entrepreneurs and leaders, such as time management and intuition. He offers practical strategies to enhance productivity, including breaking tasks into 15-minute increments and color-coding them for better visualization. He also touches on the importance of prioritization, advising leaders on how to say no to opportunities that don’t align with their goals. Jon advocates for continuous learning and self-improvement, suggesting practices like meditation and journaling to strengthen intuition and enhance decision-making. Listeners will gain valuable insights on how to improve their business acumen.

Jon highlights the power of a consistent calendar system, where tasks are meticulously organized to boost efficiency. He also encourages adopting small, daily habits that can lead to significant personal growth, such as dedicating a few minutes each day to a new task until it becomes second nature. Lastly, Jon emphasizes the importance of embracing vulnerability in leadership, encouraging a balance between being emotionally connected with your team and maintaining a composed, confident demeanor that prioritizes their needs.

Timestamps From This Episode

[14:25] Active listening and responding, rather than reacting impulsively, is crucial for effective communication. Keeping a calm and composed demeanor, even in difficult situations, is vital for maintaining a positive personal and professional image.

[17:46] Jon opens up about strategy to engage colleagues using food incentives.

[23:23] Evaluate commitment, execution, sales skills, and intuition for coaching success.

[26:32] Commit to daily practice, quiet the mind, trust instincts, and focus on execution. Recognize weaknesses and hire help if needed.

[28:24] Jon talks about successful entrepreneurship necessitates self-awareness and effective delegation strategy.

[31:29] Enhancing time management by adjusting calendar settings can help to elevate your daily communication with team members and clients.

[37:24] Examining the challenges of time and client management across professional fields. Tailoring coaching support to foster personal growth.

Host

Matt Reiner, CFA, CFP®

I’ve been fortunate to be around the wealth management business for over 25 years. Along with this, I’m also the CEO of a tech startup. These experiences have given me a bird’s eye view of both the technology and financial services spaces.