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 plans that sound good on paper but leave you over-leveraged, underpaid, or misinformed.

This episode is a must-listen if you’ve ever second-guessed your bonus structure, wondered whether equity is really worth it, or felt embarrassed not knowing what questions to ask about financial planning. Brenton’s insights will challenge how you think about money, and give you the tools to build a smarter, more sustainable financial future.

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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 should start developing their own personal brand online, separate from their company. You’ll learn how to leverage LinkedIn without feeling cringey, encourage your team to become thought leaders, and strategically position yourself as an expert in your industry.

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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 employees who are just clocking in and out, this episode has guidance you can apply immediately. Megan draws on years of experience working inside and alongside founder-led businesses to help you set smart priorities and avoid common missteps.

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00:00 – Introduction to the Q&A format and how to submit your own questions

01:47 – Q1: Prioritizing SOPs and processes at an early-stage company with ambitious growth goals

02:11 – Why sales and marketing systems must come before internal process-building

03:10 – Strategic planning example: focusing on partnerships and lead gen over documentation

04:08 – A warning: 300% growth will break your current systems—so build flexibly

05:08 – Story: Megan’s mistake of over-documenting accounting procedures too early

06:47 – Challenge your CEO on whether SOPs are the most urgent need right now

07:08 – Q2: Should you staff up in anticipation of growth or wait until overwhelmed?

08:16 – The cultural and operational risks of premature hiring

08:46 – Megan’s rule of thumb: distinguish between proven vs. unproven growth

09:04 – Second First benchmarking data: turnover and revenue trends across members

10:07 – Forecasting in the post-2020 era: why historical data can be misleading

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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 acted on). If you’ve ever written a detailed email that went ignored, this episode is for you.

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00:28 – Why conciseness is a must-have leadership skill

00:40 – A real-world example: The director with PhD-level emails

01:36 – The manager whose messages were unreadable walls of text

02:32 – Have you ever written an email that was ignored? Here’s why.

02:53 – The #1 rule of communicating with CEOs: Get to the point

03:05 – The power of clarity: Trial lawyers and plain English

03:28 – How to write emails your CEO will actually read

03:35 – Start with an executive summary (2-4 sentences)

03:47 – Use bullet points for key facts

03:58 – Cut the fluff: Eliminate filler words and phrases

04:39 – The golden rule: Give CEOs access to supporting details, but don’t make them hunt for the key takeaways

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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 reviewing financials to aligning with your CEO, these steps will help you walk into the room prepared, confident, and ready to lead a productive strategy meeting.

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00:28 – The purpose of quarterly planning: alignment, focus, and execution

00:36 – The impact of preparation on a successful planning session

01:15 – Review last quarter’s results

01:56 – Evaluate last quarter’s rocks (goals)

02:47 – Review key business metrics and trends

03:17 – Meet with department heads

04:32 – Personal pre-planning session

05:19 – Align with your CEO

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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 County Case & Millwork and founder of The Helm, to discuss what it takes to balance leadership, marriage, and motherhood.

Amy also shared how she carved out her role as “Chief Matriarch” in a growing company, managing operations while supporting her husband’s vision.

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02:15 – Amy’s background and how she became the Chief of Staff at Low County Case & Millwork and “Chief Matriarch” in life as a whole.

05:30 – Defining the role of a Second-In-Command in a family-run business

09:45 – The biggest challenges of working with a spouse and how to navigate them

14:10 – The benefits of setting boundaries, or not setting boundaries!

19:30 – Why communication is the key to success in business and marriage

23:50 – The importance of trust between the entrepreneur and Second-In-Command

27:40 – How Amy’s experience led her to create The Helm and share her expertise with other Second First members.

32:15 – Advice for anyone stepping into a leadership role alongside their spouse

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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 role serves a founder differently, what makes for a successful right-hand partnership, and when it’s time to level up. If you’re a COO, EA, or Chief of Staff (or you’re thinking about hiring one) this episode will give you a clear roadmap to making that partnership thrive.

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03:12 - The distinct roles of an Executive Assistant, Chief of Staff, and COO—and how they evolve over time

08:45 - How a founder’s needs dictate the right-hand role they should hire for

12:30 - The biggest misconceptions about EAs, Chiefs of Staff, and COOs

17:55 - What makes a right-hand partnership successful, from both the founder’s and the operator’s perspective

23:40 - When it’s time for an EA to step into a Chief of Staff role—and when that might not be the right move

29:10 - Key skills that Chiefs of Staff and COOs need to develop for long-term success

34:50 - Hallie’s advice for founders looking to hire their first right-hand

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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 killer. Learn how to push past self-doubt, trust your expertise, and lead with confidence...even when you don’t have all the answers.

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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 grow in your role. Megan Long shares actionable strategies for getting in front of decision-makers, breaking into exclusive circles, and maximizing networking opportunities at events. Whether you're looking for mentorship, new opportunities, or simply a stronger support system, this episode will help you make the right connections.

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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.

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