The Right-Hand Roadmap

#48: De-Risking the Business as a Second-In-Command

Protect the business and your team by identifying and eliminating risk before it derails your growth.
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. It’s not about fear—it’s about responsibility. We talk through how to evaluate operational systems, vendor dependencies, leadership bandwidth, and revenue streams with fresh eyes. Megan also shares a true story from a tornado that tested her own continuity plans, and an ADA compliance issue that could’ve quietly cost $20,000 if not addressed.
You'll hear all about:
00:28 – Why de-risking is a critical function for Seconds-in-Command in founder-led companies
01:03 – The three core priorities you must balance: growth, team health, and risk mitigation
01:33 – Understanding key person risk: what happens if the CEO—or you—can’t work?
02:01 – The value of cross-training, documentation, and succession planning
02:22 – Operational risk: how to spot single points of failure in systems and processes
02:47 – A business continuity exercise that lists every function, tool, and backup plan
03:32 – The real-life value of this work: how a tornado in 2020 tested their contingency planning04:17 – Payroll goes down? Here’s a backup plan that ensures no one misses a paycheck
05:01 – Strategic and financial risk: are you too reliant on one client, channel, or product?
05:51 – Vendor risk: how to evaluate suppliers and what to do when terms change unexpectedly
06:16 – The two-part vendor checklist: security protocols and financial terms
07:25 – How to approach worst-case scenario thinking without being a fearmonger
07:48 – Pitching risk-mitigation to your CEO: making it real with examples
08:00 – A real ADA website lawsuit story—and why a $20K surprise could derail your year
09:14 – Use storytelling and real-life examples to prioritize de-risking in your annual plan
 
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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

#47. Financial Planning for Six-Figure Earners & Compensation Plan Pitfalls with Brenton Harrison

Avoid the Hidden Traps in Your Compensation Plan and Financial Planning as a Six-Figure Earner.
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.
You'll hear all about:
00:41 – Meet Brenton Harrison: Financial planner for first- and second-generation high earners
02:25 – Why Brenton launched New Money, New Problems and the emotional baggage behind financial success
05:40 – The blind spots of compensation plans for seconds-in-command
07:55 – Why “you should be thankful” is a red flag in any compensation conversation
10:32 – When commissions and bonuses are more about control than reward
14:47 – How to recognize a toxic comp plan
17:10 – Planning for income that fluctuates (like commission-based roles)
21:18 – Should you accept equity? What questions to ask first
25:00 – The “six-figure lifestyle” trap
27:36 – How high earners can build a financial strategy that’s actually sustainable
30:41 – Why your net worth matters more than your income
32:19 – Tips for COOs navigating equity, risk, and career growth
36:03 – When to hire a financial planner—and what to look for
38:45 – Brenton’s advice for COOs in fast-growing companies
 
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Links mentioned in the episode:
New Money, New Problems website
Brenton D. Harrison’s Instagram 
New Money, New Problems Podcast
Second First Membership
Second First One-on-One Coaching
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#46: Employee-Generated Content & How to Start Building a Personal Brand Online

Encouraging employee-generated content and building a personal brand on LinkedIn can position your company and team as industry leaders (while also making hiring easier than ever).
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.
You'll hear all about:
00:29 – Introduction to employee-generated content and personal branding
00:41 – What is UGC (user-generated content) and how does it apply to companies?
01:08 – Two main types of UGC and how brands use it
02:13 – Applying the UGC concept to your employees and company
02:49 – Why the fear of employees posting too much on LinkedIn is outdated
02:55 – The benefits of encouraging your employees to post online
03:02 – How thought leadership from your team strengthens sales and hiring
03:49 – How to help employees start posting on LinkedIn
04:45 – Why Seconds-in-Command need to build a personal brand separate from their company
05:06 – Your company is a rented brand—so it’s critical to establish your own reputation
05:43 – Boz Saint John as an example of a strong personal brand
06:21 – Practical first steps for building your LinkedIn presence
07:12 – Your personal brand is more than just LinkedIn—it’s the unique value others expect from you
 
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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

#45: Q&A: Early Stage Priorities, Scaling in Anticipation of Growth, and Employees That Just Don't Care

Get practical answers to questions COOs are asking—about SOPs, staffing ahead of growth, and managing disengaged employees.
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.
You'll hear all about:
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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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

#44: Keep It Brief: Conciseness Is an Essential Leadership Skill

Want your CEO to actually read your emails? Master the art of concise communication.
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.
You'll hear all about:
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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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

#43: Quarterly Planning Prework

Prepare for quarterly planning with a structured prework process that ensures alignment, clarity, and execution for your leadership team.
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.
You'll hear all about:
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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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

#42: Being Second-In-Command to Your Spouse & How to Win in Family and Business with "Chief Matriarch" Amy Stasiukaitis

Secrets to success being a Second-In-Command to your spouse while balancing business and family life with Amy Stasiukaitis, Chief of Staff at Low County Case & Millwork and founder of The Helm.
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.
You'll hear all about:
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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Links mentioned in the episode:
 
Chief Matriarch - Amy's Website
Low County Case & Millwork
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn
Amy Stasiukaitis on LinkedIn
Amy Stasiukaitis on Instagram

#41: EA vs. Chief of Staff vs. COO & Maximizing the Partnership with Founders with Hallie Warner

Learn the key differences between an Executive Assistant, Chief of Staff, and COO, and how to maximize your partnership with a founder, featuring expert insights from Hallie Warner.
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.
You'll hear all about:
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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Links mentioned in the episode:
The Founder & The Force Multiplier
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn
Hallie Warner on LinkedIn
Hallie Warner on Instagram

#40: Why Am I Becoming Less Confident Over Time?

Feeling less confident in your role as a Second-in-Command? Learn how the Dunning-Kruger effect impacts your leadership and how to overcome it.
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.
You'll hear all about:
01:11 – Why COOs and Integrators often feel less confident over time.
02:17 – The paradox: the more you know, the more you realize you don’t know.
03:00 – Real-world examples from coaching engagements where confidence dips after deeper learning.
03:42 – Understanding "Mount Stupid"—why overconfidence is highest when knowledge is lowest.
04:11 – Three ways the Dunning-Kruger effect impacts Seconds-in-Command:
04:16 – Second-guessing decisions, even when you’re the most qualified.
04:44 – Assuming the CEO has all the answers (hint: they don’t).
05:22 – Holding back on leading boldly when your perspective is most needed.
06:03 – How to counteract self-doubt and embrace your role:
06:09 – Trust your expertise and recognize self-awareness as a strength.
06:32 – Assert yourself with confidence—your CEO needs your input.
07:34 – Embrace continuous learning, but don’t let it paralyze you.
 
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Links mentioned in the episode:
The Dunning-Kruger Effect
Second First Membership
Second First One-on-One Coaching
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#39: Strategic Networking as an Executive: Making Your Dream Connections

Want to connect with top industry leaders and expand your executive network? Learn how to make high-impact connections and build relationships that open doors.
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.
You'll hear all about:
00:48 – Why networking matters for executives and leaders, not just entrepreneurs
03:05 – The importance of owning your network and making your value transferable
03:58 – The power of bold introductions: How a simple conversation led to a career-changing internship
06:05 – The art of networking with high-profile individuals (without being awkward or pushy)
07:25 – The “one-degree separation” strategy: Using mutual connections to get introductions
08:14 – Leveraging conferences and events to meet industry leaders
09:14 – How to maximize company sponsorships to access exclusive networking opportunities
10:18 – The key to effective follow-ups and making connections stick
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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:
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn