The Right-Hand Roadmap

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

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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 planning
    • 04:17 – 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
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      The Right-Hand RoadmapBy Megan Long