#22: Q&A: The Entrepreneur Stereotype, Must-Read Books, & Leadership Mishires

Navigating entrepreneurs that don't fit the stereotypes, reading recommendations, and the importance of a new leader's onboarding.

In this quarter's Q&A episode of The Right-Hand Roadmap, we dive into the complexities that COOs and Seconds-In-Command often face when leading alongside non-traditional entrepreneurs. Not every CEO fits the visionary, fast-paced stereotype. We explore how to navigate these dynamics while still implementing the tools and strategies from Second First.

Megan also shares three business books for any second-in-command looking to level up. These reads offer practical, no-nonsense advice on strategy, leadership, and client retention.

Finally, we tackle a common leadership challenge—what to do when you've hired someone who isn’t performing as expected. With strategies on how to reset expectations and establish a clear onboarding plan, this episode is a must-listen for any COO navigating similar leadership or strategic hurdles.

You'll hear all about:

• 00:44 - How to submit a question for future episodes

• 01:40 - Question 1: What to do when your CEO is not a typical visionary?

• 02:40 - How some entrepreneurs are content with maintaining a lifestyle business

• 03:18 - The seven types of second-in-command roles, including "the other half"

• 04:03 - CEOs as technical experts who prefer not to lead marketing and sales

• 04:26 - Applying CEO-level strategies as a second-in-command

• 05:00 - Question 2: Three must-read business books

• 05:59 - Megan shares her thoughts on long business books and recommends 3 titles

• 08:02 - Question 3: How to handle a leadership misfire after hiring someone new

• 08:37 - Importance of creating a detailed 90-day onboarding plan

• 09:36 - Pitfalls of hiring new leaders without a plan

• 09:59 - How to hit the reset button and realign a new leader with a 60-day plan

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Links mentioned in the episode:

• No Bullshit Strategy by Alex M.H. Smith
• The Power of Moments by Chip and Dan Heath
• Never Lose a Customer Again by Joey Coleman
• The First 90 Days by Michael Watkins
• 2006 Harvard Business Review article: "Second in Command: The Misunderstood Role of the COO"