“Fail. Fail fast.”

How often, if at all, does your organization practice failing safely? 

That’s the goal of a tabletop exercise. You simulate a cyber attack against your organization, not to win, but to expose security, communication, and personnel gaps. It allows you to test the decision-making of leadership, and promote effective communication before chaos strikes. 

The cost? A few hours of people’s time. 

The value? Potentially millions saved when a real incident happens. 

What We’re Trying To Avoid

Imagine with me: it’s Friday afternoon and you are about to set the “Out Of Office” status on your calendar, and your SOC alerts leadership that ransomware has spread to your shared drives. Employees can’t access critical resources. The SOC and IT Helpdesk phones are ringing off the hook. Legal wants to know if this should be reported. PR is panicking about social media leaks. 

In too many instances, the response is silence, or worse, conflicting answers. This is the confusion that leads to mistakes, delays, and unnecessary loss. 

A tabletop exercise fixes this. 

What Exactly Is a Tabletop Exercise? 

A tabletop exercise is a discussion-based simulation of an incident, disaster, or other service interruption. Participants gather to go through specific “what would we do if…” scenarios. No systems are touched, no exploits or tools are launched, it’s about shining light on the people and processes. 

Participants usually include:

We can think of a tabletop exercise as a war game for business resilience.

Why They’re Worth It

1. Expose Hidden Gaps

Tabletop exercises reveal blind spots in day-to-day operations. From an outdated escalation process, to leadership thinking that restoring from backups is easy as flipping a switch and IT knowing it would take weeks. It’s important to clearly see where any potential “gotcha” exists. 

1. Build Cross-Department Collaboration

Security cannot exist in a vacuum. Tabletop exercises force leaders across the entire organization to practice cross-departmental communication.

1. Compliance & Insurance Expectations

Insurers, regulators, and auditors have increasingly come to expect organizations to show that they have tested their incident response program. Running tabletop exercises demonstrates due diligence and preparedness. 

1. Reduces Cost of Failure

IBM’s 2025 Cost of Data Breach Report puts the average cost of a breach to be at $4.44M (https://www.ibm.com/reports/data-breach); let’s contrast this by looking at a tabletop exercise, which may cost $10K

Common Pitfalls 

Unfortunately, not all tabletop exercises are created equal. Here are some common traps to avoid:

• Checkbox Mentality: treating it like another annual requirement without genuine engagement. 
• Too Narrow Participation: Only security & IT show up; executives and managers skip. 
• Unrealistic Scenarios: extra-terrestrial species stealing data isn’t helpful. Stick to attacks that are common for your organization’s vertical (if you’re unsure, ask your security/IT team). 
• Not Following Up: One of the worst outcomes is to go through the process of a tabletop, expose your weaknesses, and then ignore them. 

Tabletop Exercises. Let’s Make Them Effective

1. Define Clear Objectives

Are you testing response speed? Incident triage/IR procedure? Decision-making authority? Communication to correct parties? Have a clear understanding of your goal before you start. 

1. Pick Realistic Scenarios

Use common, high-impact threats (like the ones listed below) that are realistic for your organization. 

• Ransomware targeting file servers or shared drives.
• Cloud provider outage affecting critical applications. 
• Phishing campaign leading to account compromise. 
• Insider theft of IP or sabotage 

1. Debrief the Right People 

If the CEO, CIO, CISO, CTO, CFO and any other alphabet title doesn’t show up, your exercises misses the point. Security can detect, but the executive team makes the final calls. Cybersecurity is as much a leadership challenge as it is a technical one. 

For tabletop exercises to be effective, you need the right stakeholders (upper management, C-suite, etc.) to be invested in the exercise. Their buy-in isn’t just for financing the exercise, but ensuring follow-up action items get the traction they need to be remediated, especially when involving other departments. And if the tabletop goes perfectly, you want them to know how great your team is doing!

1. Don’t Lecture, Facilitate 

Ask probing questions (“What if this happens during a holiday weekend? What happens next? What if certain key stakeholders can’t be reached? What then?”)

1. Document, Document, Document

Assign a scribe (or your favorite AI meeting bot) to capture what worked, what didn’t, and what decisions caused stalling in incident de-escalation. 

1. Closing the Loop 

Turn the lessons learned during the tabletop into action items: update playbooks, contacts, escalation paths, and training. Go as far as to schedule follow-ups to ensure changes are made.

Conclusion

In cybersecurity, with today’s threat landscape, hope is not a strategy. 

You won’t rise to the occasion, you’ll fall to the level of your preparation.

Tabletop exercises are the cheapest and safest way to prepare your teams for the hardest day your organization may face. If your company hasn’t run one in the past year, start planning now. 

It has the potential to be the most valuable half-day you spend all year.