In this episode of The Daily Windup, we explore the surprising intersection between leadership confidence, self-doubt, and team dynamics in business. Our conversation uncovers how even seasoned CEOs wrestle with waves of uncertainty—despite producing thousands of deliverables over their careers—and how tools like StrengthsFinder and the Enneagram can help leaders better understand themselves and their teams. You will hear how strategic hiring, self-awareness assessments, and ongoing learning play a role in building a resilient organization, even when perceptions of leadership don’t always match the leader’s self-image.

Our discussion also takes a deeper dive into big-picture planning, mentorship, and knowing when it’s time to pivot. From setting a clear vision that aligns staff to reflecting on when—and why—you might sell your business, this episode delivers candid insights on navigating the entrepreneurial journey. Along the way, we hear how mastermind groups, mentorships, and strategic reflection can shape a company’s direction, and why having “what’s next” in mind is essential for both succession planning and personal fulfillment.