The Right-Hand Roadmap

#52: No Bullsh*t Strategy: How to Clear Competition and Craft a Profit-Driven Strategy with Alex M H Smith

Most companies don't have a real strategy. 
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. Learn how to avoid the trap of generic positioning, unlock strategic leverage, and bring a real strategy to the table.
 
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Links mentioned in the episode:
Alex's LinkedIn
Basic Arts Website
"No Bullsh*t Strategy" Book
Second First Membership
Second First One-on-One Coaching
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#51: Determine What to Delegate to Scale & Successfully Work with a Remote VA with Kimeran Johnson

Unlock time and scale smarter by learning what to delegate and how to successfully partner with a remote VA
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 for building trust and engagement with remote team members. Whether you're overwhelmed or trying to unlock new growth, this conversation offers a step-by-step approach to making your first or next VA hire successful.
 
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Links mentioned in the episode:
Kimeran's LinkedIn
Nexus Point Website
Second First Membership
Second First One-on-One Coaching
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#50: Fifty Things I Wish I Knew as a COO (Rapid Fire)

50 Lessons for 50 Episodes
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 COO or integrator, this episode will speak directly to your experience.
 
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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

#49: The Lead-Gen Blueprint for SMBs & Perfecting an Outsourcing Partnership with Cindy Dodd

Scaling Smarter: What Every COO Needs to Know About Lead Gen
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, overseeing growth initiatives, or just trying to help your CEO hit ambitious targets, Cindy delivers clear, practical advice every Second-In-Command needs to hear.
You'll hear all about:
02:07 – How PEMA.io helps entrepreneurial businesses
03:08 – The biggest mistake entrepreneurial companies make with lead gen
04:52 – What to do when you’ve been placed over sales with no sales experience
05:26 – The difference between delegation and abdication
06:00 – How to get ROI from outsourced marketing and sales partners
07:20 – How to vet lead gen vendors (hint: demand proof, not promises)
08:24 – The importance of aligning expectations with partners
09:12 – Leading vs. lagging indicators in outbound sales
10:28 – Lessons learned from client delivery and expectation management
12:11 – Why having a strong internal sales process is critical for outsourced partnerships
14:04 – What COOs should focus on to scale their business in 2025
16:12 – How to set realistic revenue goals based on data (not CEO wishes)
18:33 – Why quarterly reviews with your sales team help spot and replicate what’s working
19:51 – Cindy’s backstory: from Johannesburg to asset management to entrepreneurship
21:57 – The ups and downs of cofounding a business with your spouse
23:52 – Sneak peek at Cindy’s expert session for Second First members
25:29 – Where to find Cindy online and get her free resources
26:14 – Free downloads: Outbound Sales Playbook & LinkedIn Guide
 
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Links mentioned in the episode:
FREE Outbound Sales Playbook
PEMA.io website
Cindy Dodd's website
The Takeover Podcast
Cindy Dodd's Instagram
Cindy Dodd's LinkedIn
Second First Membership
Second First One-on-One Coaching
Second First on Instagram
Second First on LinkedIn
Megan Long on LinkedIn

#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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Click Here to Listen!
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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