The Right-Hand Roadmap

#28: Staying Focused on the Big Picture

Learn six practical strategies to keep your focus on long-term success while managing daily demands.
Being a COO or second-in-command in a founder-led company is no easy task. With so many day-to-day responsibilities, it's easy to lose sight of the bigger picture. That’s why in this episode of The Right-Hand Roadmap, we focus on strategies that will help you stay aligned with your company's long-term vision while managing immediate needs.
Listeners will gain insights on decision-making, setting priorities, and collaborating with other leaders, all while keeping the company’s long-term vision in mind.
You'll hear all about:
00:44 – First strategy: Will the solution work five years from now?
01:37 – Second strategy: Consider multiple perspectives within the organization.
02:16 – Third strategy: If a decision negatively affects one employee, does it benefit the rest of the team?
03:10 – Fourth strategy: Always focus on your "rocks" – the key priorities.
04:22 – Fifth strategy: Monthly big-picture meetings with the CEO.
05:04 – Sixth strategy: Create a list of 10 things you want to be true about the business in 10 years.
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Links mentioned in the episode:
The 7 Habits of Highly Effective People by Stephen Covey

#27: Setting Boundaries with a CEO as their Second-In-Command

How to set boundaries with your CEO to create a productive and balanced work relationship.
At Second First, we know that managing the delicate balance between supporting a visionary CEO and maintaining your own work-life harmony can be tricky for seconds-in-command. In this week’s episode of The Right-Hand Roadmap, we focus on how to set clear, mutually beneficial boundaries that ensure you’re delivering your best work while protecting your time.
Boundaries are not about restricting access or flexibility. Rather, they’re about creating clear expectations for how to achieve the best results in your role. We encourage COOs to think about what work-life fit looks like for them personally and what hours they expect to be available to their CEO. It’s equally important to recognize your "sacred time" – moments that should remain completely off-limits, whether for family or personal rejuvenation.
Today, Megan walks through practical steps to clarify expectations, navigate difficult conversations, and set yourself up for long-term success in your role, while still being available when it truly matters.
 
You'll hear all about:
00:44 – Framing boundaries as a way to enhance productivity, not limit flexibility.
01:35 – Get clear on what work-life balance or work-life fit looks like for you.
02:19 – Establishing expectations for availability between you and your CEO.
02:52 – The importance of setting boundaries to protect personal relationships.
03:17 – Creating agreements for handling communication outside of normal work hours.
03:40 – Identifying and protecting your "sacred time" where you are completely unavailable.
05:05 – Addressing misaligned tasks that don’t fit with your natural abilities or goals.
06:00 – Commit to staying refreshed and recharged to perform at your best.
 
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#26: How To Create Your Perfect Schedule

Take control of your weeks by designing the perfect schedule.
Today we dive into practical strategies for taking back control of your time by creating the perfect weekly schedule. A schedule that not only aligns with your priorities but also helps you minimize distractions, maximize productivity, and avoid burnout.
The framework Megan Long discusses in this episode, is called the "Ideal Week", based on Todd Duncan’s book Time Traps. By the end of the exercise, you'll walk away with a weekly schedule that includes all the essential activities -- team meetings, one-on-ones, and strategic work -- while also making room for personal development, self-care, and focus time. Once you’ve crafted this schedule, it’s about sticking to it and protecting your time from last-minute disruptions.
At the end of the episode, Megan also shares four of her favorite hacks to help you maintain control over your calendar (including how to avoid Sunday Scaries!)
You'll hear all about:
00:32 – Avoid the trap of always being available. Constant distractions reduce your effectiveness.
01:10 – Protect your calendar—don’t allow last-minute appointments or impromptu meetings.
01:55 – Introducing the ideal week framework from Todd Duncan’s book, Time Traps.
02:18 – Step one: Identify your top “must-do” activities like team meetings, one-on-ones, and priority work.
03:03 – Step two: Identify the “want-to-do” activities like personal development or self-care.
03:45 – Fill out an ideal week template to map out your day-to-day activities, from meals to work priorities.
05:16 – Focus on revenue-producing and value-creating activities like client proposals.
06:04 – Hold yourself accountable to your ideal week by printing it out or using a digital calendar.
06:45 – Megan’s top tips: 1) No meeting Mondays, 2) Group one-on-one meetings, 3) Block time for travel, 4) Leave protected blank space for deep work.
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Links mentioned in the episode:
Time Traps: Proven Strategies for Swamped Salespeople by Todd Duncan

#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