I have a confession. I have read a lot of business books, sat through a lot of leadership programmes, and listened to a lot of consultants talk about frameworks. Most of it is forgettable.
What has never left me is a decision-making method I first encountered as a young Army officer — a structured set of seven questions designed to cut through uncertainty, align a team, and move from chaos to action.
It is called the Combat Estimate. And I have been adapting it for product and technology organisations ever since.
Why you need a playbook
Every leader faces the same recurring problem. You are handed a situation — a new project, a failing programme, a strategic pivot, a business that needs fixing — and you have too much information, too little time, and too many opinions in the room.
Without a playbook, most people do one of two things. They either freeze in analysis, waiting for certainty that never arrives. Or they jump straight to solutions, skipping the diagnosis entirely.
Both are expensive mistakes.
A playbook is not a rigid process. It is a set of guiding questions that force you to think in the right order — to understand before you decide, and to decide before you act. It is a discipline, not a template.
The best leaders I have worked with, in uniform and in boardrooms, all have one. They may not call it a playbook. But they have a mental model they return to when things get complex. Mine happens to be adapted from a method that has been stress-tested in some of the most hostile decision-making environments imaginable.
Where it comes from
The Combat Estimate is the British Army's primary mission planning tool. It comprises seven questions, designed to be answered in sequence, that take a commander from a blank page to an executable plan under pressure.
Others have noticed its relevance beyond the military. The APM have written about it for project managers. Mark Hewett applied it across five years of consultancy work. Chris Kitchener has shared it with leadership teams. The insight is consistent: the method works because it is structured around how good decisions actually get made, not how we wish they did.
My version has been refined through years of working with SaaS businesses, technology organisations, and leadership teams navigating growth, transformation, and change. It is the backbone of how I work through Headmark — and it is the framework I return to every time a client puts a complex problem in front of me.
The 7 questions
1. What is the situation, and why does it matter?
Before anything else, you need a shared, evidence-based picture of reality. Not assumptions. Not anecdotes. What is actually happening — internally, externally, and across your stakeholders — and what does it mean for what comes next?
Most organisations skip this. They go straight to solutions. The result is a plan built on sand.
2. What have we been asked to do, and why now?
Understand the intent of leadership one and two levels above you. What are they actually trying to achieve? What depends on this working? What trade-offs are they prepared to make?
This question changes everything. When you understand the why behind the ask, you can make better decisions at every level below it.
3. What effects must be achieved to succeed?
This is the pivot point. You are not listing tasks here — you are defining the intermediate changes that must happen for success to become inevitable rather than aspirational.
This is also where you make your first Go / No Go decision. Not at the end. Early, while you still have room to change course.
4. Where should work happen to succeed?
Place work where it can succeed. Understand your teams — their strengths, their constraints, their decision authority. Assign ownership through outcomes and boundaries, not task lists. People commit when they understand what they own, not when they are handed a to-do list.
5. What resources and contingencies are required?
Plan for disruption. It will come. The question is whether you have designed for it or are reacting to it. A RAID analysis — Risks, Assumptions, Issues, Decisions — done early is worth ten done under pressure.
6. How do actions interact over time?
Stress-test the plan before you commit to it. Walk through it stage by stage. Find the dependencies, the failure modes, the handoffs that will break under pressure. Change the plan now. Adapting at this stage is a strength. Adapting in execution is expensive.
7. How do we maintain control without slowing delivery?
The final question is about governed execution. Not micromanagement — governance. Clear communication, active coordination, and proportionate control that enables progress rather than constraining it.
Control is the glue. Without it, even the best plan fragments as conditions change.
Applying it to product organisations
The reason this framework translates so well to product and technology work is that the problems are structurally similar. You are operating under uncertainty, with incomplete information, across multiple teams with competing priorities, trying to create outcomes that matter to people who are not in the room.
The Combat Estimate was designed for exactly that environment — just with higher stakes.
When I work with a leadership team through these seven questions, something shifts. Decisions that felt stuck become clear. Priorities that felt contested become aligned. Teams that felt overwhelmed start to move.
That is what a good playbook does. It does not replace thinking. It structures it.
You already have a playbook
Here is the thing. Every experienced leader already has a version of this. A mental checklist. A set of questions they return to. A way of working through complexity that they have refined over years.
The difference is whether yours is explicit or implicit. Whether you can hand it to a new team member and say: this is how we think about hard problems. Or whether it only exists inside your head, inaccessible and unscalable.
Write it down. Refine it. Use it consistently. That is what turns a good leader into a replicable system.
Mine has seven questions. It started in a lecture room at Sandhurst and has been refined across two decades of military service, SaaS boardrooms, and technology programmes.
It works. I am still improving it.