The Right-Hand Roadmap

#38: Gain 20% of Employee Time Back & Manage "Digital Chaos" with Shawn Lemon

Discover how to reclaim 20% of your team’s time and master your digital tools with Shawn Lemon, founder of The Digital Organizer.
In this episode of The Right-Hand Roadmap, we sit down with Shawn Lemon, founder of The Digital Organizer, to tackle the hidden costs of "digital chaos" in your organization. Shawn shares practical strategies for optimizing digital tools, streamlining workflows, and reclaiming 20% of your employees' time. Whether you’re drowning in a sea of Slack messages, struggling to find that elusive Google Doc, or wondering how to finally implement efficient systems, this conversation is packed with actionable insights you can start using today.
You'll hear all about:
01:20 – Introduction to Shawn Lemon and The Digital Organizer: Shawn explains his mission to help companies escape “digital chaos.”
03:45 – Identifying "digital chaos": Common signs your organization is losing efficiency due to poor digital organization.
06:15 – Reclaiming 20% of employee time: How systematizing your tools and workflows can unlock hours of productivity.
08:50 – Essential tools for digital organization: Shawn’s go-to platforms and why less is more when it comes to tech.
11:10 – Email mastery: Tips for managing overflowing inboxes and setting boundaries.
13:30 – Overcoming resistance to change: How to get buy-in from your team to adopt new systems.
16:00 – The power of a "single source of truth": Why a centralized platform is the foundation of digital clarity.
19:40 – Real-world examples: Stories of teams who regained control and boosted productivity through Shawn’s methods.
22:15 – Quick wins: Immediate steps you can take today to reduce digital clutter.
25:00 – Closing thoughts: Shawn’s advice for sustaining long-term digital organization.
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Links mentioned in the episode:
Download Your Free Guide from The Digital Organizer
The Digital Organizer Website
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn
Shawn Lemon on LinkedIn
The Digital Organizer on LinkedIn
The Digital Organizer on Instagram

#37: Three Phrases to Add to Your Toolbox

Simple yet powerful phrases to elevate your leadership, empower your team, and reclaim your time.
In this episode, host Megan Long shares three essential phrases every COO or second-in-command should master. These tools are designed to grow your team’s problem-solving skills, build trust with your CEO, and help you maintain focus by avoiding unnecessary urgency.
You'll hear all about:
00:29 – Introduction to the episode: three phrases to add to your leadership toolbox.
01:01 – Phrase 1: “What do you suggest?” — Empower your team to think critically and solve their own problems, boosting their confidence and decision-making muscles.
02:10 – Benefits of using “What do you suggest?” for your team’s growth and your freedom as a leader.
03:05 – Phrase 2: “How do you feel about that?” — Gain insight into your team’s and CEO’s perspectives while strengthening trust and connection.
04:13 – How asking your CEO this question enhances your partnership and provides a deeper understanding of their thought process.
04:29 – Phrase 3: “When do you need an answer by?” — A strategy for managing decision-making pressure and prioritizing effectively.
05:52 – The hidden benefit of teaching your team the difference between urgency and importance.
 
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Links mentioned in the episode:
“Who’s Got the Monkey?” by Harvard Business Review
Second First Membership
Second First One-on-One Coaching
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#36: Set Accurate Revenue Goals

Set realistic revenue goals for the year and create a strategic plan to hit them.
In this episode, Megan Long breaks down the process of setting accurate revenue goals for your business. If you’re tired of arbitrary revenue targets, this episode will teach you how to evaluate your sales funnel, crunch the numbers, and build a clear path to success. Whether you're a COO or second-in-command, this episode gives you actionable steps to help your company achieve its financial targets—and even exceed them.
You'll hear all about:
00:28 – The common pitfall: arbitrary revenue targets set by CEOs without sufficient planning.
01:20 – The importance of working backward to assess team capacity and realistic targets.
01:55 – Megan introduces the downloadable worksheet to guide listeners through the exercise.
02:12 – Start by analyzing your sales funnel and collecting five key data points.
03:36 – Calculating average deal size using historical sales data.
04:14 – Breaking down an example sales funnel with clear metrics and close rates.
05:45 – How to calculate your company’s revenue capacity based on your sales funnel.
06:17 – Adjusting team capacity or hiring needs to meet ambitious revenue goals.
07:26 – Evaluating individual salesperson capacity to handle increased quotas.
08:12 – Using sales funnel math to communicate actionable plans to your CEO.
 
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Links mentioned in the episode:
Second First Membership
Second First One-on-One Coaching
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#35: Building a Professional Membership

Discover how Second First designed and launched a membership model for COOs and Seconds-in-Command.
In this behind-the-scenes episode, Megan Long pulls back the curtain on creating a professional membership program tailored for Seconds-in-Command of founder-led businesses. Learn how Second First transformed their mastermind events into a dynamic, year-round membership with curated cohorts, expert workshops, and a user-friendly online platform. Megan shares the challenges, decisions, and strategies that brought this vision to life.
You'll hear all about:
01:04 - The inspiration: a Nashville mastermind event and the need for continuity.
01:51 - Transitioning from one-off events to a year-round membership.
02:14 - Three key projects: pricing structure, value proposition, and building an online platform.
02:35 - Designing the revenue model for affordability and predictability.
03:48 - Why monthly dues include the in-person event to simplify budgeting.
05:00 - Shifting from project-based revenue to recurring revenue for stability.
05:13 - Crafting value: small mastermind cohorts for accountability and growth.
05:52 - Added perks: tools, templates, expert sessions, and a member directory for connections.
09:00 - Choosing Circle as the membership platform for its intuitive design.
 
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Links mentioned in the episode:
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#34: Five Gifts I Gave Myself This Year

Five "gifts" that are impactful ways to prioritize yourself and your growth in 2025.
As the year winds down, we often focus on giving to others—but at Second First, we also encourage our community to invest in themselves. That’s why we’re excited to share the final episode of 2024, where we dive into five intentional gifts Megan Long gave herself this year. Each one represents a commitment to self-care, growth, and setting up for success in 2025.
You'll hear all about:
01:25 - The first gift: Pre-scheduled "choice days" for rest, focus, or catch-up time.
02:52 - The second gift: A "personal profile" setting on her phone to limit work-related notifications.
03:32 - The third gift: A premium subscription to the Finch app for gamified self-care and productivity.
05:47 - The fourth gift: The "10 Things to Be True" exercise for visualization and goal-setting.
07:16 - The fifth gift: Three new professional memberships for growth and accountability in 2025.
08:46 - Reflections on the first year of The Right-Hand Roadmap podcast and what’s to come in 2025.
 
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Links mentioned in the episode:
Finch App
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#33: REPLAY: Unlock the Power of Your Second-In-Command Webinar

Use the Three C's to unlock the COO's superpowers.
In this special replay of a webinar presented to the Entrepreneur's Organization, Megan Long unpacks how to use the Three C's: Communication, Coaching, and Community, to unlock the power of a strong Second-In-Command. Whether you're a founder looking to level-up your leadership team or a Second-in- Command seeking growth, you'll gain actionable insights and real-world examples from Megan’s presentation.
You'll hear all about:
02:15 - Common challenges founders face when scaling their businesses.
05:30 - The strategic role of a second-in-command in bridging vision and execution.
08:45 - How to assess whether your business is ready for a COO.
12:00 - Characteristics of a successful founder-COO partnership.
15:30 - Real-world examples of founder-second-in-command dynamics in action.
18:45 - Megan’s top strategies for empowering your second-in-command to drive results.
 
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Links mentioned in the episode:
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#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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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:
Palo Alto Networks' Applipedia
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn