Red Teaming Made Simple

By Kimani Upshur, M.Ed.

Red Teaming Made Simple is about a discipline borrowed from the military: deliberately assigning someone to attack your own plan as genuinely as a real adversary would, before the plan ever meets one. Your plan looks solid, the book argues, because no one has tried to break it yet. The point is not to be negative. It is to find the actual, exploitable weakness while there is still time to fix it, rather than discovering it the expensive way — so the first real test your plan faces is not the one that costs you something.

Thirteen chapters build the practice in order: what red teaming actually is, why your own plan feels more solid than it actually is, and building a genuine red team. It then gives techniques for stress-testing a plan, finding blind spots you did not know you had, and red teaming solo when you do not have a team. Applications follow for business strategy and for security and risk, along with receiving criticism without getting defensive, when red teaming goes wrong, working under time pressure, and the common mistakes that undermine the discipline, ending with a habit of self-challenge.

It serves planners, leaders, and teams who want examined confidence instead of praise from people hoping the plan succeeds. Written from a Christian worldview — Scripture first.

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