“No plan of operations reaches with any certainty beyond the first encounter with the enemy's main force.” -Helmuth van Moltke

It's one of the oldest and most reliable truths of warfare: no plan survives contact with the enemy. As soon as bullets start flying, everything goes to hell, and it's up to the commanders on the ground to make as much out of the resultant mess as possible.
This is one axiom, however, that I am inclined to disagree with.
Making plans that will survive initial contact intact is not impossible. That's not to say it's easy, or it's something that can be boiled down to a few easy to remember steps. It's one of those things that very few people have any sort of intrinsic talent for, and even for them, it takes hard work and experience to hone that instinctive grasp into something usable.
For everyone else, the only way to get good at it is to study and practice, over and over again, until you get more right than you get wrong. You have to learn for yourself what works and what doesn't work, consistently reinforce good habits while minimizing bad, and above all else, be willing to push past the inevitable failures until you start to get the hang of it.
There's a reason that most military forces rely on established doctrine to determine how engagements are fought at the individual unit level. Having a set of preestablished plays, much like a coach in a football game, allows for junior leaders who haven't had the experience to come up with their own stuff on the fly adapt to just about any situation as it arises. Learning when to use which plays still takes some experience, but that's why junior officers have senior NCOs backing them up.
Unfortunately, you don't really have that option here on Chaos thank. Battles tend to be whole armies mixing it up or individuals duking it out. There's some unit level engagement, but not enough for any real sort of doctrine to have been established.
With all that in mind, I'm not going to be able to turn anyone into a master planner over the course of a single lecture. Instead, what I'm going to try to do is give you some tools to use in planning your operations, as well as some general advice to keep in mind. Just a heads up, this is going to be a long one, so I'm going to put each section behind spoiler tags to keep from bombarding you all with a solid wall of text. Also, apologies in advance, but this one is going to be fairly dry.
The first tool I'm going to go over is one that we've discussed briefly and used in other lectures: METT-TC.
METT-TC is a mnemonic popular in the US Military, as it's an easy way to remember what factors you should consider and their priority in relation to one another. It stands for Mission, Enemy, Terrain, Troops Available, Time, and Civilian Considerations.
We're going to briefly discuss each of these factors, how they relate to each other, and how to best employ METT-TC when planning a mission. When completing the METT-TC analysis, brevity is important. There's a time and a place for going into excruciating detail, but this ain't it.
Mission: What exactly it is you're trying to accomplish. Nearly any operation can be distilled down into a sentence or two, or at most, a short paragraph. While this likely won't open any magical windows into the future to determine the path to success, summing up the mission in a brief and concise manner does help cut away the extraneous crap we tack on in our heads. We have to go here and do this. End of story. Laying it out in stark terms has a way of clarifying exactly what it is you have to do.
Enemy: Who you're fighting, and approximately what numbers and with what equipment. Since the enemy forces in the area will almost certainly try to stop you from accomplishing your mission, you've got to take them into consideration. Note that there's no such thing as perfect intelligence. If you can guess with about 80% accuracy what you're facing, you're doing really, really well. In general, it's better to estimate high than low when dealing with unknowns, although estimating too high is also a bad thing. Being prepared to take on a stronger force than what you actually end up fighting is one thing. Paralyzing your fighting force with panic is quite another.
Terrain: Terrain matters a lot. The mission takes ultimate precedence. It has to be accomplished regardless of where you're fighting, and you'll obviously want to bring enough toys to handle whatever enemy you're going to have to face. But you have to take into account the terrain, because it will have a huge impact on how the mission is carried out. Fighting in a jungle is vastly different from fighting in a desert, which is different from fighting in a city. You have to tailor the force for the terrain, and using it effectively can give you a huge advantage. See the Hoth analysis for an example.
A good tool for analyzing the terrain is OCOKA: Observation and Fields of Fire, Cover and Concealment,
Obstacles (man made and natural), Key or Decisive Terrain, Avenues of Approach.
Troops Available: You would think this would be higher up on the list, but realistically, the mission, enemy, and terrain will have a greater impact on the mission than the troops you have on hand. Because, let's face it, you have what you have, and it's the job of the commander to make the best use of what's available rather than complain about what they wished they had. The real trick here is to make use of force multipliers to increase the effectiveness of a relatively small fighting force if necessary.
Time: How long you have to complete the mission. This includes planning and prep time. The longer out you start planning, the more time you have for things like gathering supplies, reconnaissance, etc. That said, you also have to take into consideration the amount of time the enemy has to prepare for you. While you want to make sure you have enough time to be as ready as possible, you also want to move before they have a chance to prepare for whatever you might cook up. Note that timelines that rely on extreme precision are to be avoided if at all possible. Try to build in enough leeway that the whole plan isn't screwed if a particular element doesn't make it to a particular position at exactly the right time.
Civilian Considerations: This section sits at the bottom of the list, but that doesn't mean it's not important. If you're going to be going into an area with a civilian population, there are several factors that have to be considered. Your rules of engagement will determine how and when it is appropriate to fire on civilians (the answer is usually never unless they present an immediate threat to the mission). You also have to consider things like whether or not you'll have embedded reporters, whether you'll be working with civilian or government agencies such as humanitarian groups, and what you have to do in regards to refugees, prisoners, etc.
When used correctly, METT-TC is a valuable tool for planning missions. It helps clearly define what it is, exactly, that you have to do, what you're up against, and how long you have to complete your mission. Once you've got all that figured out, planning the actual operation becomes a lot more straightforward. Not easy, but straightforward.
Operations Order (OPORD)
The Operations Order, or OPORD, is an Army tool for planning an operation. It serves two functions: it provides the leader in charge of planning the operation a format with which they can easily write down vital information, and it provides them with a universal means of conveying that information to those under their command. Now, I'm not going to go over the whole thing here, because it's long and there's a lot of stuff in there that simply doesn't have any bearing on Chaos. If you want a more in depth version, here's a link.
Instead, what I'm going to do is come up with an abbreviated version that can be used on Chaos for planning operations.
Situation: Explains anything your subordinates might need to understand the overall scope of the mission. For an invasion or a skirmish, think of it as the story setting up the encounter.
Mission: Exactly what it is you're trying to accomplish. You can basically copypasta the METT-TC version here.
Execution: This is the part where you write out a short narrative of your plan. You'll go into more detail in later portions, but what you're basically trying to do is give a brief outline of how you want things to go. Helps give some context to the later portions.
Enemy: Essentially a more detailed version of the METT-TC analysis. You want to try to provide as much useful information here as possible, with a minimum of guesswork. In an RP environment, it's important to not rely too heavily on metaknowledge. Anything you use here should be backed up by work in order to avoid problems.
Friendly Forces: Again, a more detailed version of what you did for METT-TC. You'll want to break this portion down into three sections:
  • Locations and Planned Actions: Where your units are, and how you expect them to move and interact with each other and the enemy. In other words, provide a brief summary of how you expect the battle to go for each unit.
  • Allied Units: Much the same as with the Locations and Planned Actions, but for your allies. Given recent events, it might be a good idea to come up with contingency plans in the event that they turn on you. It's also a good idea not to let them know about said contingency plans.
  • Fire Support: What you have on hand in terms of fire support, and how you want them to work with your line units. This can include everything from artillery to mortars to orbital bombardment or close air support. Ideally, each unit that is expecting enemy action should have some sort of on call fire support available, in the type best suited for their engagement. For instance, don't count on CAS if you can't guarantee air superiority.
OOC Considerations: It's impossible to conduct an operation in an RP environment without taking into account OOC. As much as we all like to pay lipservice to the idea of keeping IC and OOC separate, we all know it rarely works out like that. In this section, you'll need to briefly detail any potential OOC hangups that might influence the outcome of the battle. Is there a particular player on either side with a reputation for a temper, or for being flaky? Do you have someone who is monstrously good at dueling, or a team with excellent synergy that can reliably accomplish objectives? Do your best to be as honest as possible here, and play to your strengths. Also bear in mind that a key part to achieving victory in an invasion is quality story without drama. Try to pair off your writers with opposite numbers that they'll play well with. Doing so will make life a lot easier for everyone involved, and should cut down on drama while upping the fun.

When distributing copies of the OPORD outside of the faction's admin team, this section should probably be omitted in order to avoid hurt feelings. If you know someone is weak in a particular area, beating them over the head about it is not going to help them out any. However, if you know they're weak in that area but strong in another, you can place them where they'll have the most positive impact on the operation. In the event that this section does leak, try to avoid being mean. Be honest, but don't be an nerf herder.
Contingencies: In this portion, try to identify key points in the plan that are most likely to fail, and come up with ways to minimize the impact of failure. Even the best laid plans have portions where failure is not only likely, but expected. If you can identify them ahead of time, you can plan for that outcome and maybe even use it to your advantage. Example: if you know you have a portion of your line that's likely to buckle under sustained pressure, you can use that to make the enemy overextend themselves.
End State: Where you plan to be at the end of the operation. If you accomplish your objectives, what will the battlefield look like when you're done? If one or more objectives result in failure, how does that affect the outcome? Avoid pie in the sky dreaming here. Be as realistic as possible. A mark of a good plan is one that, at the conclusion of the battle, looks an awful lot like the desired end state.
Now, you'll note that the OPORD format represents a dramatic departure from the traditional invasion planning. And believe me when I say that it's not for everyone, or for every faction. If your faction leadership likes to maintain a hands off approach to how invasions are conducted, they're not likely to find it a very helpful tool. Many will argue that it's far too regimented for RP, and in those sorts of factions, they may very well be right.
Plus, it's a lot of work. This version doesn't include a tenth of the stuff you would put in a real world OPORD, and I'm willing to bet that it would still take a team of admin hours, if not days to fully fill out.
If you're willing to put in the work, and your players are willing to take direction, it can be an invaluable tool for planning. Winging it is not an operation plan, but it seems to be the default method for conducting invasions. If you manage to change that, even just within your own faction, you might find that invasions go a lot more smoothly.
Do's and Don'ts
And now some Do's and Don'ts to consider when planning.
  • Be thorough. The more you can plan for ahead of time, the less likely you are to be surprised in battle. It's impossible to plan for every possible contingency, but there's no harm in trying.
  • Be flexible. Be willing, at all times, to adapt to change. No one is perfect, and even the best planners make mistakes. A good leader knows how to react to surprises effectively.
  • Be realistic. It is far, far too easy to over or underestimate the enemy, and even easier to do it to yourself. You have to know how to be honest with yourself if you're going to successfully plan anything.
  • Be professional. Always assume that the plan will leak, especially in an RP environment. You can be honest about your enemy without being an nerf herder.
  • Be scared of failure. Because you will screw up at some point. No one has a 100% success rate. When learning how to plan, expect to fail early and often, and be willing to push past that failure until you start to get it right.
  • Overthink it. Remember when I said you should be as thorough as possible? Know the difference between being thorough and overthinking things. It's hard to know exactly when to draw the line, but a good idea is to set a deadline for coming up with the plan. If you're fast approaching the deadline and you're nowhere near finished, you're overthinking things. Focus on the important details and most likely outcomes.
  • Scare yourself out of victory. During the planning phase, it's very easy to get sucked up in the perceived impossibility of a task and defeat yourself before the battle ever even begins. The harder the task, the more satisfying it will be to complete it. Focus on that rather than despair over long odds.

Miscellaneous Advice:
Some other things to consider that don't fit neatly into any other category.
  • Have a chain of command. Most factions have some sort of IC chain of command, but realistically, there's never much of one OOC. You have your fleeters, your grounders, and everyone else just sort of fits in where they want. Past the initial planning phase, there's rarely one person in charge of a particular area, and while that allows each individual player to have a great deal more freedom with their writing, it doesn't necessarily make for a cohesive team.
With an increased emphasis on teamwork and quality of story, having an established chain of command can make working as a team much easier, and the results should speak for themselves. On top of that, it makes it a hell of a lot easier to come up with a plan for any given operation if everyone knows where they're going to be, who they have to answer to, and what their responsibilities are. Some people might rankle at the idea at first, but success breeds success. Even if you have to deal with a few problem children in the early days, once people see you're winning, they'll be more likely to go along.​
  • Maintain discipline. Look. No one wants to have to be the bad guy, but sometimes, you've got to step on someone when they start getting out of line. This is something that a lot of admin teams are afraid to do, because they think it makes them look bad. Trust me, it is far worse to have someone actively undermining your authority and getting away with it. Likewise, if you seem someone being consistently bullied, stomp on that crap hard. "It's all in good fun" only works so long as everyone is actually having fun.
On the other hand, going to far in the other direction is just as bad, if not worse. No one should be afraid to offer honest, constructive criticism, so long as it's done in a reasonably polite manner. Accept that arguments will happen and that people will make mistakes, and don't hammer them for the little things. But if you're going to function as a cohesive whole, you cannot afford to accept someone willfully and maliciously sabotaging that effort.​
  • Recognize and reward talent. This is something that has bugged me about just about every faction I've ever tried to get involved with. Far too often, the players that make it into the upper ranks of the faction aren't necessarily there because they're good at any particular thing. Sometimes, they're just loud and charismatic, or they're friends with the current admin. I can think of a few examples where a particular faction admin actively hurt the faction because they had no business being trusted with the authority they were given.
Instead of falling into that trap, promote people based on actual skill. Having an established chain of command outside of the admin team makes it a lot easier to do that. If you know someone is a good planner, bring them into planning sessions. Bestow some trust on them. If someone is a good leader, let them lead. The more you reward hard work and talent and make an effort to keep nepotism to a minimum, the stronger your faction will be.​
  • Keep an open mind. Your plan may be good, but if someone has a better idea, let them speak. What's more, listen to them. Players are far more likely to invest their time and energy in a faction if they feel that their voice matters. It gives them a sense of ownership. There's a time and a place for ruling with an iron fist, but during the planning phase, you want to get as much feedback as possible, and your players need to know that their feedback matters.

So there you have it folks. I know this one was a long one, and if you took the time to read it all the way through, I sincerely appreciate it. As always, the comments section is open, so feel free to chime in if you have input.