Episode Number:

Ep 179: Navigating Challenges and Trust Building in Leadership with Jon Dwoskin

Ep 179: Navigating Challenges and Trust Building in Leadership with Jon Dwoskin

September 5, 2024 - Matt Reiner

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.

More Content For Financial Advisors and Wealth Management Firms

 
Subscribe, rate, and review Bridging The Gap here.   About the Show

Bridging the Gap is a financial podcast hosted by CEO Matt Reiner focused on bringing together leaders from the finance and the technology industries to focus on innovating the financial services industry.

Follow Matt on Social

Latest Episodes

Ep 262:Why Your AI Isn’t Delivering ROI

The reason most AI pilots fail isn't the technology — it's the execution. In this episode of The FutureProof Advisor, Shannon joins me for another round of listener questions, and the theme running through all of them is the same one I keep coming back to: change...

Ep 261: What Happens after the AI Hype?

  The gap between what AI can do and what most firms are actually getting out of it isn't a technology problem — it's a process problem. In this episode of The FutureProof Advisor, I explore why so many firms are stuck in what I call pilot purgatory:...

Ep 260: Q&A: Why Successful Firms Struggle to Innovate

There's a difference between being busy and actually moving forward — and most firms are doing a lot of the former while calling it the latter. In this episode of The FutureProof Advisor, Shannon joins me for another round of listener questions, and the thread running...

Ep 259: AI Isn’t Killing Jobs. It’s Creating a New Economy.

  The narrative around AI and job loss is louder than the data supports — and that gap matters for how we talk to clients. In this episode of The FutureProof Advisor, I dig into what's actually happening in the labor market, why the current moment looks more like...

Ep 258: AI Doesn’t Create Value. Your Process Does.

  The questions advisors are asking right now aren't abstract — they're urgent, practical, and rooted in the daily reality of trying to move forward without losing what makes their firms valuable in the first place. In this episode of The FutureProof Advisor,...

Listen to the Latest Podcast

Matt Reiner, CFA, CFP®

Matt Reiner, CFA, CFP®

HOST