In this episode of the Chirp Podcast, Lee-Anne Scott welcomes Dennis Daigle, founder of Sidecar CTO Coaching.
The conversation revolves around the highs and lows of running startups, the evolution of the CTO role, and the significance of personal branding.
Dennis, a former startup founder and current CTO coach, shares his journey, lessons learned, and how he pivoted towards CTO coaching post-startup to guide other CTOs and tech leaders.
He emphasizes the need for CTOs to cultivate a strong vision, improve communication with their teams and CEOs, and establish a strategic approach to increase their brand visibility.
Lee-Anne & Denis also discusses the necessity of obtaining external coaching to foster progress, ensuring a smooth transformation path for different clients, and building a sustainable future with employees vested in the company's goals.
00:04 Introduction and Guest Presentation
00:38 Dennis's Journey as a Startup CTO
02:03 The Importance of a Coach in Startup Journey
02:55 Dennis's Current Role and Responsibilities
03:53 The Transformation Path for Startup CTOs
04:42 Dealing with Startup Failure and Lessons Learned
07:17 The Role of CTOs in Startups and the Need for Support
10:58 The Importance of Connecting CEO and CTO Roles
18:55 Challenges and Misconceptions for First Time CTOs
22:19 Overcoming Communication Barriers in Teams
22:40 The Power of Inclusion and Participation in Decision Making
24:20 The Importance of Team Alignment and Shared Vision
24:38 Connecting Team Efforts to Financial Outcomes
25:19 The Role of Feature Flags in Product Development
26:58 The Importance of Team Awareness in Business Sustainability
27:31 Innovative Approaches to Team Motivation
31:00 The Value of Personal Branding for CTOs
32:47 The Importance of Delegation and External Facing Roles
35:49 The Role of Coaching in Leadership Development
36:22 The Power of Personal Branding and Social Media Presence
38:03 The Importance of Servant Leadership and Transformational Coaching
38:49 Closing Remarks and Future Conversations
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Connect with Denis here: linkedin.com/in/daigledenis