EP132 – Rehearse the Chaos — Why every MSP should be running tabletop exercises with their clients — with Adam Pilton, Heimdal Security episode artwork

EPISODE · May 16, 2026 · 32 MIN

EP132 – Rehearse the Chaos — Why every MSP should be running tabletop exercises with their clients — with Adam Pilton, Heimdal Security

from It's a Numbers Game

Daniel Welling welcomes back cybersecurity advisor Adam Pilton (Heimdal Security) for a masterclass on cyber tabletop exercises. Adam defines a tabletop as a staged rehearsal where senior leaders and key responders use the organisation's incident response procedure while a facilitator introduces evolving information, aiming to build confidence, stress-test decision-making, and improve communication. They discuss common failures like missing or outdated incident response plans, the facilitator's role in preparing and tailoring scenarios, and differences between SMEs (often using pre-made exercises) and enterprises (more tailored). MSPs should participate, with the on-the-day MSP representative not knowing what comes next, and facilitation can be segmented to reduce bias. Success means surfacing lessons learned, and Adam recommends at least annual exercises, ideally quarterly, including smaller segments within QBRs. He outlines six pillars of effective incident response and highlights the MGM incident as a communication case study.   00:00 Welcome and Guest Intro 01:20 Tabletop Exercises Defined 03:13 Game vs Serious Stress 04:20 Incident Plan Pitfalls 06:29 Facilitator Prep and Tailoring 10:51 SME vs Enterprise Approach 12:26 MSP Role and Independence 15:10 What Success Looks Like 17:01 Where and How Often 19:40 Packaging as Recurring Service 22:21 Six Pillars Framework 24:48 Communication Case Study MGM 28:27 Selling Security Upgrades 30:32 Wrap Up and Contact   Connect with Adam Pilton on LinkedIn by clicking here –https://www.linkedin.com/in/adampilton Connect with Daniel Welling on LinkedIn by clicking here – https://www.linkedin.com/in/danielwelling/ Connect with Adam Morris on LinkedIn by clicking here – https://www.linkedin.com/in/adamcmorris/ Visit The MSP Finance Team website, simply click here –https://www.mspfinanceteam.com/   MSP Glossary: MSP Finance Glossary Explained | MSP Finance Team We look forward to catching up with you on the next one. Stay tuned!

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EP132 – Rehearse the Chaos — Why every MSP should be running tabletop exercises with their clients — with Adam Pilton, Heimdal Security

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