The Right-Hand Roadmap

#25: My First Business & Unequal Partnerships

Lessons learned from a childhood business, and how they apply to partnerships as a Second-In-Command.
In this episode of The Right-Hand Roadmap, we take a nostalgic trip down memory lane with Megan Long, as she shares the story of her very first business—Bodacious Beads—and the early lessons she learned about unequal partnerships.
As a young entrepreneur making beaded jewelry with a childhood friend, Megan quickly realized that not all partners contribute equally. This experience, while playful at the time, echoed deeply in her later career as a COO. Many seconds-in-command know the feeling of carrying the bulk of the workload while the CEO enjoys the spotlight and reaps the rewards.
Through this story, we encourage all second-in-commands to reflect on their roles and ask the tough questions: Are you fulfilled by the work you do? How can you reconcile your role to ensure it aligns with your personal goals? Tune in to hear how personal fulfillment plays a crucial role in long-lasting and successful partnerships.
You'll hear all about:
00:40 – The story of Megan's first business, Bodacious Beads, which she started with a childhood friend, diving into early experiences of partnership dynamics.
02:20 – Megan describes the process of making jewelry and her unexpected realization when her partner contributed significantly less.
04:03 – The moment of truth arrives at a craft show when Megan notices the difference in effort between her and her friend, introducing her to the concept of unequal partnerships.
05:00 – Drawing parallels to her experience as a Second-In-Command, Megan explains the unequal work dynamics COOs can face when managing the day-to-day while the CEO enjoys the spotlight.
06:05 – She emphasizes the importance of finding personal fulfillment and alignment with career goals as a COO.
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#24: Take Your CEO/COO Partnership to the Next Level

Unlock the full potential of your CEO/COO partnership with communication, coaching, and community.
We recently launched our Partnership Alignment Checkup, a quiz designed to help you understand where you stand in your CEO/COO relationship. Whether you’re in lockstep with your CEO, have a solid foundation that needs improvement, or are struggling to align, this tool provides valuable insights to help you strengthen that bond. From there, we offer practical advice on improving communication, coaching each other for better clarity, and seeking community support from peers in similar roles. Together we cover the Three C's—the three key factors—communication, coaching, and community—that can take your partnership to the next level.
You'll hear all about:
00:37 – How to assess your relationship with your CEO using the new "Partnership Alignment Checkup" quiz available on the Second First website.
01:16 – Possible outcomes from the quiz: You’re either in lockstep, have a solid foundation with room for improvement, or need significant alignment.
01:58 – The role of the COO as a "force multiplier" and how the relationship with your CEO impacts your effectiveness.
02:26 – Introduction to the "Three C's" of improving your partnership: Communication, Coaching, and Community.
02:51 – Rapid-fire communication tips, including setting big-picture one-on-ones, creating a shared idea list, and documenting roles and responsibilities.
04:19 – Coaching: How repeating back what your CEO says can improve clarity and alignment.
05:06 – Understanding different priority systems and working together on what’s urgent vs. important.
06:14 – Why exploring leadership and executive coaching can help bridge the gap between vision and execution.
06:44 – Community: The importance of having peers in your vertical and connecting with other seconds-in-command for support and insight.
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Links mentioned in the episode:
Partnership Alignment Quiz

#23: 2024 Second First Exchange Mastermind Recap

Wrap-up of the 2024 Second First Exchange mastermind for Seconds-In-Command.
At Second First, we recently wrapped up our highly anticipated 2024 Second First Exchange mastermind in Nashville, Tennessee. It was an incredible experience, bringing together Second-In-Command leaders from across various industries for two days of in-depth learning, sharing, and connection. Megan shares key moments, takeaways, and the importance of creating a safe, yet valuable space for Seconds-In-Command to thrive.
This mastermind wasn’t just another business conference; it was a transformational experience where leaders left feeling heard, understood, and empowered. We're excited to bring even more value to the Second First Exchange in the coming months, so stay tuned for exciting updates!
You'll hear all about:
00:28 - Recap of the Second First Exchange mastermind held in Nashville, Tennessee.
03:25 - Megan discusses the value of surrounding yourself with the right people and setting a positive, supportive tone for the cohort.
03:36 - Guest speaker Duane Marshall shared insights, and was impressed by the immediate camaraderie of the group.
05:30 - A recurring theme from attendees was the relief in finding peers who understood their unique challenges as seconds-in-command.
08:49 - Megan emphasizes the importance of curating the best experience and not taking the path of least resistance when organizing events.
09:58 - A member appreciated the balance between offering value and creating space for peer-to-peer learning, a key goal of the mastermind.
11:09 -Exciting changes to the Second First Exchange program will be announced in the coming months.
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Links mentioned in the episode:
Second First on LinkedIn
Second First website

#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