The Right-Hand Roadmap

#32: Q&A: Measuring Your Success, Hiring a Second-In-Command, & Favorite Apps

Answering your questions about measuring success, hiring a second-in-command, and the best tools to streamline operations.
Feeling stuck in your role as a Second-In-Command? You’ve climbed as high as the org chart allows, achieved the “top” title in your company, and yet, the hunger for growth remains. In this episode, Megan Long dives into the unique challenges COOs and other seconds-in-command face when they’ve reached the top of the org chart in entrepreneurial businesses.
You'll hear all about:
00:28 – Listener Q&A kicks off! Learn how to submit your questions for future episodes.
01:28 – Question 1: How do I measure my success as an integrator?
04:32 – Question 2: What advice do you have for hiring a second-in-command?
07:29 – Question 3: What’s your top recommended tool or software?
09:33 – Closing thoughts: Submit your questions, find show notes, and subscribe to stay in the loop!
 
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Links mentioned in the episode:
Microsoft Loop Blog Post
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#31: What To Do When You've Hit Your Ceiling

Break through your ceiling and reignite growth as a Second-In-Command.
Feeling stuck in your role as a Second-In-Command? You’ve climbed as high as the org chart allows, achieved the “top” title in your company, and yet, the hunger for growth remains. In this episode, Megan Long dives into the unique challenges COOs and other seconds-in-command face when they’ve reached the top of the org chart in entrepreneurial businesses.
You'll hear all about:
00:38 – Why feeling "stuck" happens in entrepreneurial businesses and how flat hierarchies can limit traditional career advancement.
01:00 – Reframing career growth: shifting from climbing the ladder to expanding your scope.
02:02 – The lifecycle of a second-in-command: tactical beginnings to strategic partnerships.
02:45 – Transitioning from being in the weeds to coaching and mentoring your team.
03:11 – The strategic shift to organizational development and long-term planning.
04:08 – Becoming a thought partner to your CEO and taking ownership of new initiatives.
04:42 – Ways to upskill: hiring a coach, consuming high-quality resources, and joining peer groups.
05:21 – The value of structured training and small group masterminds like Second First’s membership program.
05:27 – Collaborating with your CEO through offsite discussions for personal and professional alignment.
06:08 – Developing external influence by positioning yourself as a thought leader and expanding your network.
 
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Links mentioned in the episode:
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#30: My Story & the Origin of Second First

The personal journey behind Second First’s origin and how COO support systems changed everything.
At Second First, we know that being a second-in-command in a founder-led business can feel both rewarding and isolating. Our CEO, Megan Long, knows firsthand the weight of responsibility that comes with such a role, and in our latest episode of The Right-Hand Roadmap, she opens up about her personal journey to building Second First as a haven for others in her shoes.
Megan’s story is one of resilience, perseverance, and a commitment to helping COOs, Directors of Operations, and Seconds-In-Command feel less alone. In 2020, facing everything from natural disasters to a pandemic, she realized how crucial it was to have a peer network that truly understood her role’s pressures. It was this experience—navigating uncharted waters with no place to turn—that sparked the creation of Second First. We wanted to build something more than a coaching framework; we wanted a community that lifts up each other through the toughest challenges.
If you've ever felt like no one understands the demands of being the "number two," tune in to hear the personal story that launched Second First and why we’re dedicated to building a strong, supportive community for second-in-command leaders.
You'll hear all about:
00:36 - Megan shares why she hesitated to tell her full story and discusses her gratitude for past mentors.
01:16 - Reflecting on the career experiences that shaped her perspective as a young entrepreneur and woman in leadership.
02:02 - Introduction to Megan Long and the founding of Second First.
02:46 - Background as a CPA and rise to COO in a founder-led company.
03:06 - Realizing the gap in professional development and peer support for seconds-in-command.
03:18 - Building a coaching framework for the second-in-command role.
05:15 - 2020 brings unexpected challenges: tornado, pandemic, and more.
06:13 - Leading the company through crisis: disaster response and financial adaptations.
07:28 - The pressure and personal isolation of crisis leadership.
08:18 - Facing depression and how it spurred her to seek support and start Second First.
10:10 - Founding Second First to prevent other seconds-in-command from feeling isolated.
11:32 - The importance of peer support for seconds-in-command and Second First’s mission.
13:28 - Highlighting member feedback on the Second First community.
13:51 - Upcoming opportunity to join the Second First membership
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Links mentioned in the episode:
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#29: AI Prompts to Make Your Life Easier as a COO

Use these powerful AI prompts to streamline your work as a COO and enhance productivity.
In this episode of The Right-Hand Roadmap, we explore how ChatGPT and other AI tools can streamline various aspects of a COO’s day-to-day responsibilities, from high-level strategic planning to task-focused productivity. Using the right AI prompts can save time and offer insights into decision-making without the need to open endless new applications or risk security issues.
We highlight practical uses for ChatGPT, including prompts to speed up decision-making by generating quick risk assessments and pros/cons lists for new initiatives. COOs can also offload admin work, asking ChatGPT to create executive summaries or time-block their schedules. For those diving into quarterly or annual planning, the episode also covers AI’s role in conducting trend analyses and drafting clear, concise presentations for team-wide meetings.
You'll hear all about:
00:28 - Addressing AI fatigue and common use cases reported by business leaders.
01:06 - Security concerns with open AI models; lessons from Samsung's data incident.
01:53 - Open-source vs. closed-source AI and their implications.
02:35 - App fatigue and tips for discerning new AI apps.
04:08 - Introduction to Palo Alto Networks' "Applipedia" for assessing app security.
04:54 - Prompt 1: Speed up decision-making with AI-based risk analyses.
06:17 - Prompt 2: Boost productivity by leveraging AI for summarizing reports, time-blocking schedules, and creating checklists.
07:44 - AI use case for personal organization, such as creating a self-care plan or meal planning.
08:39 - Prompt 3: Utilize AI for strategic planning and trend analysis.
09:54 - Breaking down priorities or “rocks” with AI for a 90-day plan.
10:38 - Use AI to draft presentations for a State of the Company meeting.
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Links mentioned in the episode:
Palo Alto Networks' Applipedia
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#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