The Drop In CEO

In this solo episode of the Drop-in CEO podcast, host Deb Coviello shares personal updates and dives deep into the art of navigating challenging conversations with confidence. Deb introduces a practical framework for handling difficult discussions, explores why these conversations are often so tough, and emphasizes the importance of language and empathy. Through relatable stories from both family and business, Deb equips listeners with actionable strategies to improve their communication and leadership skills.   Episode Highlights The Framework for Challenging Conversations [10:39]Deb outlines a step-by-step framework for approaching difficult conversations, focusing on establishing common ground, identifying gaps, and taking mutual action. Why Challenging Conversations Are Difficult [7:30]An exploration of the emotional and systemic reasons that make tough conversations so challenging, and why most organizations don’t teach these essential skills. The Power of Language in Difficult Conversations [13:27]Deb discusses the importance of word choice, empathy, and respect in maintaining relationships and moving through workplace challenges. Personal Connection and Icebreaker [2:00]Deb opens the episode with personal stories and updates, setting a relatable and engaging tone for the discussion.   For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/See omnystudio.com/listener for privacy information.

In this solo episode, Deb Coviello, the Drop-in CEO, shares a heartfelt reflection on the importance of pausing and reassessing your leadership journey. Deb opens up about her own experiences, the challenges leaders face, and the critical need to invest in yourself, stick to your strategy, and avoid burnout. Tune in for actionable insights and stories that will help you lead with intention and leave a lasting legacy.   Episode Highlights 6:30 - Defining Planetary LeadershipDeb introduces the concept of planetary leadership and explains the risks of waiting for the "planets to align" before taking action. 11:20 - Real-World Example: Delayed Risk MitigationA story from Deb’s career highlights the consequences of delayed decision-making and the importance of addressing risks early. 15:40 - Building a Culture of Proactive LeadershipDeb offers actionable advice for leaders to foster environments where risk identification is celebrated and team input is valued.   For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/See omnystudio.com/listener for privacy information.

In this episode of the Drop In CEO podcast Join host Deb Coviello as she welcomes David Jenyns, entrepreneur and founder of Systemology, to discuss how business owners can free themselves from daily operations by building effective systems. David shares his journey from selling the Melbourne Cricket Ground to systematizing businesses, and offers actionable insights for leaders looking to scale and optimize their organizations.   Episode Highlights: 01:12 — David’s entrepreneurial journey: from selling the Melbourne Cricket Ground to founding Systemology 12:01 — The seven-stage process for systematizing a business and why “process first” matters 27:14 — Real-world impact: How systemization saved a business 1,000 man-hours and empowered team members 41:01 — Building a culture of systems: Overcoming resistance and the role of the “systems champion”   David Jenyns is an experienced entrepreneur who sold the Melbourne Cricket Ground in his early twenties and founded Melbourne SEO Services. He systemized himself out of that business in 2016 and founded SYSTEMology to help business owners implement systems to scale their business. Today, he supports a growing community of certified SYSTEMologists, delivers workshops, keynote addresses, hosts a podcast, and is on a mission to free business owners worldwide from daily operations.   Connect with David Jenyns: Company Website: www.systemology.comLinkedin: www.linkedin.com/david-jenyns   For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/See omnystudio.com/listener for privacy information.

In this episode of the Drop In CEO podcast, Deb Coviello welcomes Shane Barker, CEO and founder of TraceFuse, the first Amazon TOS-compliant negative review removal system. The conversation covers entrepreneurship, the importance of focus, lessons learned from business growth, and the value of work-life balance. Shane also discusses the origins of Trace Fuse, the challenges of working with Amazon, and his commitment to helping business owners protect their reputations and feed their families.   Episode Highlights: 02:00 Shane’s Backstory: From restaurants to digital marketing and influencer education 07:00 Lessons from early businesses and the drive to help others 13:00 The origin and mission of Trace Fuse 18:00 How Trace Fuse helps Amazon sellers proactively and reactively 22:00 Relationship with Amazon and the challenges of review removal 27:00 Growth, focus, and the future of Trace Fuse 32:00 Work-life balance, personal growth, and building a high-performing small team 38:00 Shane’s life outside of work and the importance of family 44:00 Final advice, how to connect with Shane, and closing thoughts   Shane Barker is the CEO and founder of TraceFuse, the first Amazon TOS-compliant negative review removal system. With over 25 years of marketing experience supporting Fortune 500 brands, Shane has been recognized as a leading influencer. His recent focus is helping Amazon sellers combat negative reviews through TraceFuse’s innovative, white-hat solution.   Connect with Shane Barker: Twitter: https://twitter.com/shane_barkerFacebook: https://www.facebook.com/ShaneBarkerConsultant/Instagram: http://instagram.com/shanebarkerLinkedIn: https://www.linkedin.com/in/shanebarkerCompany LinkedIn Page: https://www.linkedin.com/company/tracefuse/   For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/See omnystudio.com/listener for privacy information.

In this episode of the Drop In CEO podcast Dr. Denise Brown, a transformative leader in healthcare with over three decades of experience, shares her journey from medical school to becoming a Chief Strategy Officer and eventually a CEO. She discusses how she chose personal satisfaction over traditional success metrics, emphasizing the importance of making conscious, heartfelt decisions in both personal and professional life. The conversation also explores Dr. Brown's book, 'The Fairy God Doctor's Guide to a Good Life,' focusing on the seven prescriptions she outlines for living a fulfilled life. Both hosts discuss the challenges and rewards of embracing one's true self in leadership roles.   Episode Highlights: 05:19 Choosing Satisfaction Over Success 11:06 Insights from 'The Fairy God Doctor's Guide to a Good Life' 14:37 Balancing Life and Leadership 20:47 Mentorship and Legacy   With over three decades of experience in healthcare as a physician, CEO and Chief Strategy Officer, Denise S. Brown, MD is a transformative leader who helps women in business learn how to prioritize and avoid maternal overwhelm. A thought leader in self-care activities for women, she brings her expertise to books for successful women. A graduate of The University of Chicago's Pritzker School of Medicine, with training at Stanford and Vanderbilt, she lives with Alex, her childhood sweetheart of 28 years, and their sons Will and Hank.   Connect with Dr. Denise Brown: Instagram: @thefairygoddoctor Company Website: https://www.sagepartners.net/   For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/See omnystudio.com/listener for privacy information.

In this episode of the Drop In CEO podcast Ashish Gupta, founder and CEO of ScaleUpExec, shares his journey from co-founding a wireless technology company acquired by Qualcomm, to working at Apple, and eventually starting his own firm focused on fractional leadership for small and medium-sized businesses. They discuss the importance of understanding the needs of both the business and its team, the challenges and strategies involved in transforming distressed businesses, and the benefits of having a versatile COO. Ashish emphasizes the value of introspection for entrepreneurs to clearly define their business goals and align their teams accordingly.   Episode Highlights: 02:28 Ashish Gupta's Journey: From Wireless Tech to Apple 03:44 Entrepreneurial Challenges and Successes 05:52 Transforming a Distressed Business 08:55 Insights on Leadership and Team Building 17:29 The Role and Impact of Fractional COOs   Ashish has had a long journey in business and tech - selling 2 businesses where he was founder-level, managing a $2B/year budget at Apple, and now running a fractional COO firm that has turned around over 20 businesses. He is an expert at helping leaders and businesses reach their potential.  Connect with Ashish Gupta: LinkedIn: https://www.linkedin.com/in/ashish-gup/ Company Website: https://scaleupexec.com/   For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/See omnystudio.com/listener for privacy information.

In this episode of the Drop In CEO podcast Michelle Drolet, Founder and CEO of Towerwall, to discuss the complexities of cybersecurity and her journey as a leader in the tech industry. Michelle shares her personal and professional background, detailing her rise to CEO, overcoming significant challenges, and her strategies for building robust cyber defense programs for clients. The conversation highlights her resilience through personal adversities, the significance of trustworthy relationships, and the importance of giving back to the community through initiatives like the Towerwall Cyber Summit. Michelle emphasizes the need for organizations to be proactive and vigilant in their cybersecurity efforts, offering insights into how Towerwall partners with clients to secure their digital infrastructure. The episode concludes with inspiring words on leadership, resilience, and the importance of community impact.   Episode Highlights: 02:15 Michelle's Journey in Cybersecurity 07:05 Challenges and Resilience in Leadership 14:40 The Importance of Cybersecurity 27:08 Family and Business: A Personal Insight   Michelle Drolet is the Founder and CEO of Towerwall, a leading cybersecurity firm serving clients like BOSE, Smith & Wesson, Brown University, and UMass Memorial Health. Recognized as one of CTO Magazine’s "Top Women in Cybersecurity" and named to Forbes’ "50 Over 50," Michelle brings decades of experience helping organizations protect what matters most. With a client roster that spans industries and borders—including the Insurance Board of the Bahamas—Michelle is a sought-after thought leader and speaker. She’d be honored to join The Drop in CEO podcast to share actionable insights from the front lines of cybersecurity leadership and strategy.  Connect with Michelle Drolet: LinkedIn: https://www.linkedin.com/in/michelle-drolet-a926b79/ Company Website: Towerwall.com   For more information about my services or if you just want to connect and have a chat, reach out at: https://dropinceo.com/contact/See omnystudio.com/listener for privacy information.