The Right-Hand Roadmap
The Right-Hand Roadmap is the only podcast for Seconds-In-Command of founder-led companies. I’m your host Megan Long, an award-winning executive & entrepreneur, pro athlete, and owner of Second First. Together we explore the unique world of being a #2 Leader in entrepreneurial companies. This is the place where we dive into the challenges, opportunities, and strategies that can help you excel in your role. Our mission is clear: to transform the relationships between entrepreneurs and, you, their Second-In-Command. We’ll cover a wide range of topics, from navigating your relationship with the founder to mastering the role through best practice knowledge, tools, and insights you need to thrive in your position. But this podcast isn’t just about learning; it’s also about being part of a community. This role is lonely and often misunderstood - together we’re stronger and supported in ways we can’t find within our companies or at home. If you’re ready to embark on a journey of growth, l...
Episodes
At Second First, we hear this all the time from seconds-in-command: “I’m running the company. I’m making the decisions. I’m keeping the team on track… but I don’t feel seen.” It’s a hard feeling to name, but it’s real. You’re essential to the business, yet your impact is often invisible.
This invisibility shows up in two ways. First, your contributions don’t always get recognized, because smooth ...
In this short but powerful solo episode, Megan Long addresses the all-too-familiar excuse: “I’m too busy.” Whether you're putting off professional development, skipping strategic planning, or just stuck in back-to-back meetings, it’s time to ask what that busyness is really costing you. This is a pep talk for every second-in-command who’s running on fumes—...
Before you chase aggressive growth targets, you have to ask yourself a hard question: Is your business actually ready to scale?
We work with leaders every day who are stuck in the messy middle: growing revenue while cash gets tighter, roles get blurrier, and the founder still has a hand in every decision. In this week’s episode of The Right-Hand...
What’s the difference between being the “best” in your industry and being the only one of your kind? In this episode, bestselling author and street strategist Alex M H Smith joins Megan Long to break down the myths of business strategy. If you’re a COO or second-in-command trying to steer your company toward a clear, scalable, and profitable future, this conversation is your shortcut. Lea...
In this episode, Megan Long sits down with Kimeran Johnson, COO of Nexus Point, to dive deep into how executives can offload the right work, reclaim their time, and scale their companies using offshore virtual assistants. Kimeran shares practical delegation frameworks, red flags to avoid when outsourcing, and best practices f...
In this special 50th episode, host Megan Long reflects on the hard-won wisdom gathered from years of working as (and with) Seconds-In-Command at founder-led companies. She shares 50 rapid-fire lessons she wishes she could give her younger executive self, ranging from mindset shifts and leadership tactics to strategic guidance and personal boundaries. If you’re navigating the complex and rewarding role of ...
In this episode, Megan Long interviews Cindy Dodd, the powerhouse COO and cofounder of PEMA.io, an Inc. 5000 B2B appointment-setting firm. Cindy breaks down the most common lead generation mistakes, shares how to hold outsourced vendors accountable, and reveals the revenue planning process that helps her team scale with confidence. Whether you're managing a sales team, ov...
One of the most powerful (and often invisible) things you can do in this role is proactively de-risk the business. That means thinking ahead, planning for disruptions, and removing single points of failure that could knock the business off track.
In this episode of The Right-Hand Roadmap, we unpack the real meaning of de-risking. I...
In episode 47 of The Right-Hand Roadmap, we sat down with Brenton Harrison, a Certified Financial Planner who specializes in helping first- and second-generation high-income earners. Brenton pulls back the curtain on the emotional baggage that often comes with financial success, and how easy it is to fall into the trap of compensation pl...
In today’s episode of The Right-Hand Roadmap, we’re diving into employee-generated content (EGC) and why it’s one of the most powerful tools for attracting top talent and building a strong company presence. We’ll also explore why Seconds-in-Command shoul...
In this Q&A episode of The Right-Hand Roadmap, Megan Long tackles real-world questions from second-in-command leaders navigating fast growth, resource constraints, and team dynamics. Whether you're wondering when to systematize your startup, how to staff for a 30% growth forecast, or what to do with employ...
As a COO or second-in-command, you don’t have time for long-winded explanation, and neither does your CEO. In this episode of The Right-Hand Roadmap, Megan Long shares why brevity is an essential leadership skill in founder-led companies. You’ll hear real-life examples of communication failures and learn how to craft messages that get read (and act...
Quarterly planning isn’t just about setting goals—it’s about ensuring your company is focused, aligned, and equipped to execute effectively. In this episode, Megan Long breaks down the essential prework every second-in-command should complete before heading into a quarterly planning session. From...
Being a second-in-command in any business is a challenge, but when your CEO is also your spouse, the dynamics become even more complex. In Episode 42 of The Right-Hand Roadmap, we sat down with Amy Stasiukaitis, Chief of Staff at Low Cou...
In this episode of The Right-Hand Roadmap, we dive deep into the evolving roles of Executive Assistants, Chiefs of Staff, and COOs with Hallie Warner, founder of The Founder & The Force Multiplier. Hallie shares her expert perspective on how each ro...
Ever feel like the more you learn, the less confident you become? You’re not imagining it. This is the Dunning-Kruger effect at work. In this episode, we break down how this psychological phenomenon affects Seconds-in-Command and why gaining experience can sometimes feel like a confidence k...
As an executive, your network is one of your greatest assets. In this episode of The Right-Hand Roadmap, we dive into the art of strategic networking: how to connect with key industry leaders, build meaningful professional relationships, and leverage those connections to gro...
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...
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...
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 t...
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