The Right-Hand Roadmap

#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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Links mentioned in the episode:
Second First Membership
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#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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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 One-on-One Coaching
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn