Planning can be overwhelming. A lot can go wrong during this critical stage of an assessment or operation. I’ve written about this before, but I thought maybe a simple, deeper post was needed.

Like I mentioned in the article linked above, everyone in the team should be involved in the planning. Each team member should be heard and his/her opinions weighted towards having a good, simple plan that fits the project. We usually have a very straight forward way of doing this, steps of sorts, that we follow. At the end of these steps, the team leader runs the options by the team, we red team the plan/s and we come out with a possible one. That becomes the base for what we want to do.
The steps are nothing special, but over the years this system has helped a lot in organizing our thoughts and methods.

There are 4 initial steps to planning:

  1. Know the project or end goal
  2. Analyze the problems
  3. Red team the plans
  4. Perform a dry run

The first step is to identify what the project is all about, what is the end goal of the project or assessment. During this phase, we really try to analyze what we need, what is the information we have, what is the ultimate goal of this project. It is important to have a clear view of what’s expected. The first draft of the plan is usually created here.
The second step is used to identify the potential problems, trying to focus on the overall plan as well as each part of it. A solid self red teaming of the draft plan is performed here.
In the next step, we focus on finding the solutions to the problems found in step 2 and further polishing the plan. In this stage, and the next one as well, remember Rule 17: Use ACTE: assess the situation; create a simple plan; take action and evaluate your progress. It is important to look at the whole plan with each possible solution, because many things can change in the process of fixing a problem. Each issue identified has a solution, if it doesn’t, then you have to rethink that part of the plan altogether.
The final step is a dry run. This is important to test the solutions, tools needed, gear, etc. A good dry run can identify more problems (as mentioned ACTE). Go back to step 3 as many times as you need, but be careful not to get your team in an endless loop. At some point decide it’s good enough and commit.

Keep in mind something:

Rule 54: Plans are useless, but planning is indispensable.

Plans are something you have to have, however once you're in the field, chances are you will have to change the plan. That’s the reality of this business. Be ready for that, have a simple plan that can be modified.

Simple and light equals agility and mobility.

Red Teaming and the Adversarial Mindset: Have a Plan, Backup Plan and Escape Plan | ITS Tactical

Red Team Mindset Course Slides