The Right-Hand Roadmap

#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"

#21: Make The Most of Q4: Finish The Year Strong

Use Q4 strategically to set your company up for a successful next year with practical tips on operations, talent, finance, and business development.
As we enter the final stretch of the year, it’s tempting to push through Q4 in a rush to hit annual goals. However, at Second First, we believe that Q4 is the perfect time to slow down, reflect on the year, and plan strategically for next year. By taking a thoughtful approach, you’ll avoid feeling like you’re behind when January arrives.
In our latest podcast episode, we share a process to assess how your company has performed so far and how to shift into a long-term strategy. We recommend using the S.W.T. analysis—strengths, weaknesses, and trends—so you can identify key trends in the market and industry that could shape your strategy. We also provide actionable questions to assess four crucial categories: operations, talent, finance, and business development.
Take the time in Q4 to tighten up your processes, assess team needs, and strengthen relationships with partners. This will help you hit the ground running in January, ensuring that you start the new year feeling prepared and ahead of the curve.
You'll hear all about:
01:32: Q4 is the time to take an honest look at the past year and shift into long-term strategic thinking.
02:00: Introduction to the S.W.T. assessment: strengths, weaknesses, and trends.
02:26: How trends in the market, technology, and consumer behavior can influence your strategy.
03:04: Operations: Questions to ask about bottlenecks, processes, and vendor performance.
04:14: Talent: Where are team bottlenecks? Who is ready for a promotion? Where do you need to upgrade your team?
05:21: Finance: Ensure your prices, margins, and payroll are in check. Focus on profits, not just revenue.
05:57: Business development: Build better relationships with referral partners and explore strategic partnerships.
06:20: Example of creative strategic partnerships to boost sales.
07:09: Wrap up with key insights on setting up recurring revenue and starting next year strong.
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#20: Decode Your CEO: How an Entrepreneur Thinks

Understand and navigate your CEO’s entrepreneurial mindset and thinking habits.
Entrepreneurs are fast-moving visionaries who thrive on risk, resilience, and a willingness to fail forward. They have a unique set of thinking patterns that can be confusing or even frustrating to more operations-minded executives. By recognizing, understanding, and appreciating these traits, you can find the middle ground that allows you to work more effectively together.
In this episode, we break down the entrepreneurial mindset into key components—risk-taking, resilience, and views on failure—while also delving into common thought patterns that drive their decision-making. Understanding these behaviors will not only help you better support your CEO but also strengthen the partnership as a duo.
You'll hear all about:
00:39: Challenges operations-minded executives face with visionary entrepreneurs.
01:08: Key qualities of entrepreneurs: risk-taking, resilience, and views on failure.
02:07: Entrepreneurs’ unique relationship with risk and why they accept it.
03:25: The importance of resilience in entrepreneurial success.
03:59: How entrepreneurs view failure as a stepping stone to progress.
05:04: Common thinking habits of entrepreneurs that COOs should understand.
06:50: The anxiety-driven belief that everything could be lost, even during success.
09:10: The role of the Second-In-Command in managing and supporting these entrepreneurial traits.
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#19: The Four Mandatory Meetings

The Four Mandatory Meetings You Should Be Having as a Second-In-Command
In this episode of The Right-Hand Roadmap, we dive into the four must-have meetings every Second-In-Command of a founder-led company should be scheduling. Megan Long explains how these meetings not only drive company success but also strengthen your role as a COO. These meetings aren’t just about ticking boxes—they're about fostering alignment, driving strategic initiatives, and building strong relationships across the leadership team. From weekly one-on-ones with your CEO to quarterly planning sessions with your entire leadership team, each meeting plays a pivotal role in your success. We also explore the value of skip-level meetings, offering you a way to stay connected with all levels of your organization and truly understand the pulse of your company.
You'll hear all about:
00:55 - Meeting #1: Weekly one-on-ones with the CEO or founder; recommended structure and agenda.
04:35 - Meeting #2: Monthly same page meetings; fostering alignment and strategic planning.
05:52 - Meeting #3: Weekly one-on-ones with direct reports; building rapport and ensuring accountability.
08:07 - Meeting #4: Quarterly planning meetings; setting the strategic direction for the company.
09:32 - Bonus: The value of skip-level meetings for maintaining company culture and transparency.
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Links mentioned in the episode:
"Rocket Fuel" by Gino Wickman & Mark C. Winters
 

#18: Catch-Up From Summer Break: Behind the Scenes of Second First

We're Back!
Back from our summer break, host Megan Long fills you in on all of the exciting behind-the-scenes happenings at Second First, the company behind The Right-Hand Roadmap podcast!
In this casual, chatty episode, you'll hear all about:
You'll hear all about:
01:04 – The May launch of a Mastery class, our ten-week certification course.
02:00 – The second big project of the summer: our mastermind event, Exchange.
02:58 – How Megan wants to make Exchange “easy” for attendees compared to other conferences.
03:36 – An exciting, to-be-announced change to the Exchange program.
03:51 – Growing the Second First team.
04:03 – The changes in our podcast, and hard lessons learned when choosing software platforms.
04:43 – Some new and different workshops Megan Long is hosting for unique Seconds-In-Command.
 
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Links mentioned in the episode:
Second-In-Command Mastery – 10 Week Certification Course
Second First Exchange – Mastermind

#17: Reengaging Disengaged Leaders

Discover strategies to reengage disengaged leaders. In this episode, we’re taking a workshop-style approach to tackle the issue of disengaged leaders head-on. From identifying common reasons behind declining participation to offering actionable strategies for reengagement, we’ve got you covered. Whether it’s addressing managerial burnout, navigating the Peter Principle, fostering a compelling vision, or managing external personal issues, we’re here to guide you every step of the way. Throughout the episode, listeners will gain valuable tips on how to recognize signs of disengagement, ask probing questions to uncover underlying issues, and implement effective solutions to reignite passion and commitment in leadership roles. You'll hear all about: 01:08 - Common reasons for declining participation among leaders. 01:28 - Strategies to address managerial burnout are explored, including setting boundaries and practicing stress reduction techniques. 03:28 - The concept of the Peter Principle is introduced, along with strategies to navigate it such as the nine-box grid and dual career ladders. 06:15 - Lack of vision or "what's in it for me" (WIFM) is examined, emphasizing the importance of a compelling and relatable vision for all team members. 07:38 - The Pygmalion effect and its implications for leadership expectations and performance are discussed. 08:42 - External or personal issues affecting leader engagement are acknowledged, highlighting the importance of HR involvement in finding solutions. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: Nine Box Grid for Talent Management

#16: Q&A: Compliance Risk, Finding Employment, and Feeling Held Back

Listener Submitted Q&A: Compliance Risk, Finding Employment, and Feeling Held Back. In this episode, Megan Long, your host and owner of Second First, dives into the second quarterly Q&A of 2024. Each quarter, we address pressing questions submitted by our listeners. From navigating regulatory challenges to strategizing career moves, we cover a wide range of topics relevant to today's second in commands. Throughout the episode, we offer practical advice and actionable strategies to help listeners overcome common obstacles in their roles. Whether it's convincing a CEO to prioritize compliance, positioning oneself as an attractive candidate for new opportunities, or navigating disagreements with company owners, we provide valuable insights to empower COOs in their journey. You'll hear all about: 01:34 - Question 1: A listener expresses concern about their company's transition into advising work and the lack of focus on compliance. 04:04 - Question 2: A listener asks how to position themselves as an attractive candidate for their next role, tailored to the needs of the CEO. 06:14 - Question 3: Handling disagreements with the CEO about the company's growth strategy, emphasizing the importance of alignment and transparency. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: https://secondfirst.com/10 - The Right-Hand Roadmap Episode 10: Interviewing for an Executive Role

#15: Going Dark: Why We Ghost Our Boss

Understanding the Impact of Going Dark on Your CEO. In this episode, we're pulling back the curtain on a common but often unspoken habit: the tendency for COOs and executives to disconnect from (or “ghost”) our CEOs. We know firsthand the challenges of navigating the fast-paced, world of reporting to an entrepreneur. But as crucial as it is for us to keep up with their pace, we sometimes find ourselves falling into the trap of “going dark,” whether due to our busy schedules or fear of burdening our CEOs with bad news. But here's the thing: communication breakdowns can lead to a whole host of issues, from duplicated work to frustrated team members. That's why in this episode, host Megan Long is sharing insights on why we ghost our bosses, the repercussions of doing so, and most importantly, practical strategies for fostering open communication and stronger relationships.  You'll hear all about: 01:07 – The common occurrence of COOs “going dark” on their CEOs. 01:20 – Characteristics of entrepreneurs and the challenges they pose for COOs. 02:32 – Communication breakdowns between COOs and CEOs, leading to COOs “going dark.” 04:43 – Exploring the fear-based response of COOs to shield their CEOs from negative news. 05:40 – Strategies for improving communication and preventing “going dark,” including regular updates and same-page meetings. Rate, review & follow on Apple Podcasts CLICK HERE TO LISTEN! OR WATCH ON YOUTUBE If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

#14: Financial Moves to Impress Your CEO

Financial Strategies to Impress Your CEO and Contribute to Your Company's Bottom Line. In this episode we dive into some profit-adding financial moves that a Second-In-Command can make, even if they're not a CFO. Together we cover identifying and eliminating waste, renegotiating vendor contracts, and addressing revenue leakage. These strategies can help plug the holes in the financial bucket and pave the way for sustainable growth. By implementing these strategies, COOs can demonstrate their value and contribute to the financial well-being of their organizations.  You'll hear all about: 01:03 - The importance of auditing every expense line item to identify waste. 01:52 - Examples of areas where waste might occur, such as unused software licenses and unnecessary subscriptions. 02:28 - How and when to renegotiate vendor contracts to reduce costs. 03:26 - Addressing revenue leakage, including adjusting prices to cover credit card processing fees. 04:11 - Other areas of revenue leakage, such as inaccurate billing and late payment fees. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode.

#13: Avoid Burnout: The 7 Types of Rest

Navigating Burnout: Strategies for COOs and Second-in-Commands. In this insightful episode, we delve into the critical topic of avoiding burnout in the demanding role of a Second-In-Command. As COOs, our responsibilities often overwhelm us, leading to physical, mental, and emotional exhaustion. Host Megan Long shares her personal experiences with burnout and highlights the importance of prioritizing self-care. We explore the seven types of rest essential for maintaining our well-being and effectiveness in our roles. You'll hear all about: 01:16 - Megan's personal encounters with physical and mental burnout though her career, and its impact. 01:39 - Dispelling misconceptions about what "boundaries" mean and emphasizing self-care. 02:20 - An overview of the Seven Types of Rest 02:49 - Physical Rest: Beyond sleep, vital for preventing health issues. 03:41 - Mental Rest: Strategies for preserving mental resources. 04:13 - Emotional Rest: Validating emotions and fostering support systems. 04:58 - Social Rest: Curating positive connections and setting boundaries. 05:39 - Sensory Rest: Unplugging to reduce stimulation and rejuvenate. 06:04 - Creative Rest: Cultivating imagination and problem-solving skills. 06:31 - Spiritual Rest: Finding purpose and resilience. Rate, review & follow on Apple Podcasts Click Here to Listen! Or Watch on Youtube If you haven't already done so, follow the podcast to make sure you never miss a value-packed episode. Links mentioned in the episode: "What If There's More?: Finding Significance Beyond Success" by Traci Schubert Barrett