What’s So Hard About Planning Projects?

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When you make a marketing plan, or a 5-year strategic plan, or even just a plan to complete a complex project, you sometimes don't know much. You know what you wish would happen. You know some things you need to do so you can make that happen. Everything else is hypothetical.

The first time you make such a plan, it is quite satisfying. But if you've done much long-range planning, you know that the military saying "no plan survives contact with the enemy" is too often applicable.

What you want is not just a plan, but a good plan. A good plan motivates you and helps you execute each step until you're finished. With a good plan, you don't get stuck in indecision enroute to the goal. You did the thinking up front, and then you just execute the steps in the plan 1-2-3, with maybe a little adjustment along the way. You can only achieve this kind of effectiveness when you're confident the steps will take you to your destination — and they do in fact take you there.

How do you plan with that kind of confidence when you're dealing with the unknown? Classical planning tools can help.

Classical planning tools help with certain kinds of projects

Let's look at the common methods of planning.

Working Forwards, Working Backwards, and Planning for Contingencies

One way to identify steps is to start at the beginning and make a list of things you need to do, then put them in order they need to be done, start to finish. This is called working forward. Another way is to look at the end state, and say, "what would have to be done before that." This is working backwards.

It's good to do both. When the two methods meet in the middle, you can be pretty confident in your plan. You see your way clearly and concretely from here to there. If you want to make it even better, identify some possible problems that might come up, and plan for those contingencies.

Sometimes this is all you need for your project, even if it's very complex. Boeing has a very detailed step-by-step plan for assembling their next 747. They've done it before, and they know all the steps, and what order to do them.

But if your project is all new, you may find that the steps don't meet in the middle. If your third step is, "come up with a brilliant marketing campaign," it's hard to see forward beyond that point. You can't figure out the next steps until you've come up with the campaign.

Assemble the Parts

Another way to plan a complex project is to break it into pieces, then assemble the pieces at the end. This works well for a preparing a potluck dinner, not so well for writing complex software.

The difference is the complexity of the integration. Sometimes the biggest challenge is to figure out how everything interconnects. If you save that work to the end of the project, you dramatically increase risk.

The Waterfall Method

This is also called stage-gating. You break the project up into major stages, such as: concept, design, build, debug, release. Then you set strong tests for determining whether you are ready to move to the next stage.

This works well for projects that follow a well-established pattern. For example, in building a house, you need to finalize the plan, build the structure, finish the interior, then landscape. Or, a marketing plan may move through well-known phases: needs assessment, creative idea generation, mockup, go-ahead, rollout. Sometimes a loop (iteration) is added. For example, you might loop through several ideas and mockups before one is approved, permitting you to move on to the rollout stage.

The waterfall method breaks down if your original time and money estimates were way too low, and you can't extend the time and budget. For example, if the design stage takes much longer than expected, you can't just relax standards for the design to speed it up. That will guarantee more costly and more time-consuming problems downstream. The better alternative is to design something smaller and less complex instead — but this could mean starting over.

You need more power to plan complex projects with many unknowns

When a complex project involves many unknowns, planning it becomes mind-boggling. None of the above methods work — there's too much guesswork. If you try to spell out a detailed plan regardless, you wind up overdriving your headlights. You make decisions without the knowledge to base them on.

The guesswork makes the plan a disaster. The purpose of a plan is to fulfill your and your team's mental need for clarity and confidence during the project. You need to know that you are going in the right direction. If there are too many guesses, you never get that confidence. When you discover a significant mistaken assumption in the plan, the project becomes chaotic.

You need a plan that serves your mental need for clarity and confidence. To do that, you need logical and tactical thinking skills to meet two challenges:

Challenge #1: It's hard to see progress on a complex, long-term project with many unknowns

For a plan to serve its mental purpose, you need to see for yourself that the plan is working. You need to see you're making objective progress, that your hard work is paying off. That's what makes you confident about each step, and motivated to continue.

There's only one way I know to do that on a complex, project with many unknowns. You need to build the end into early results: plan to finish a scaled-down, stripped-down, very basic version of the project immediately. Then flesh it out, add on features, and scale it up in later stages.

This is an organic planning process. You start with a baby version of the project, and grow it into the mature version.

This kind of organic planning is seen in many areas. It's what you do when you outline before you draft, when you build a prototype before you build a production model, and when you do a full read-through of a play before you start placing actors on the stage.

But figuring out an organic plan for your own unique project takes some hard thinking. It is not obvious, and it's not easy. In particular, you need skill at essentializing: that's the key to figuring out that basic version to aim at first. I have developed a step-by-step process I call "planned evolution" that teaches people this crucial logical skill, which is not taught in school.

Challenge #2: You need to be able to incorporate new information as you go, with as little backtracking as possible

When you are dealing with many unknowns, you can't ignore them. You need to fill in those holes, so you don't spend time and money based on false assumptions.

But you also can't wait to get all the information you'd like before taking action. In many cases, you can't get information until you do some work. For example, when you're developing a new product, you need something to show prospective buyers before you can get useful feedback from them.

Therefore, you need to plan the growth of knowledge into the project. The best way I know to do this is to manage your thinking the same way manufacturers manage quality. To achieve high quality, they find and fix the problem causing the most quality defects first. Once that's fixed, they find and fix the problem causing the next most quality defects. By always tackling the biggest problem first, they achieve the greatest quality improvements in the short-term, and the highest quality in the long term.

You can take a similar approach to managing your own thinking to deal with ignorance. That's what my thinking tactics help you do. They help you marshal what you know, make good judgments about it, and discover the additional information you need. They help you untangle confusion and conflict, identify what you need to know, and then brainstorm ways to figure it out.

When you add managed thinking to an organic planning process, you get even better results. Every time you finish a stripped-down, scaled-down basic version, you get new information and a chance to assess how you're doing, and learn from what you've accomplished. You build in a chance to adapt to new information.

And when you add logical tools for discovery (how to differentiate, how to identify fundamentals) you can shape the organic planning process to provide natural experiments that help you discover exactly what you need to know, all while making observable forward progress.

A combination of managed thinking with organic planning can optimize your effort on a new, complex project

If common-sense planning is not enough to guarantee you success on your projects, you probably need some form of organic planning.

Depending on the kind of work you do, there may be a ready-made body of knowledge to tap into. This exists in writing, software (agile programming and related disciplines), performance arts (the rehearsal process), startups, and science (the experimental method). Unfortunately, these processes seem to be taught mainly by the master/apprentice model, so I have very few book recommendations. (There are certainly other books, but I only recommend books I think are both clear and true.)

Over time, I have developed my own general approach to this problem, drawing on my experience in all these fields. I call my basic organic planning process "planned evolution" and it can be adapted for any kind of complex project. I have used it or facilitated clients to use it on projects they were bogging down and burning out on, including:

  • Planing a major event (a workshop, a wedding)
  • Making a strategic plan (for a budget, for a business)
  • Reorganizing information (on a computer, in a paper filing system, books)
  • Prioritizing large quantities of material (a to-do list, a stuffed attic)
  • Creating information products (a proposal, a report, a website, a book, a presentation)

This material is now available in the Thinking Lab or my course on Motivating the Next Step.

Book Recommendations on Project Planning

Little Bets by Peter Sims is the most accessible book I know which discusses aspects of organic planning.

The Lean Startup by Eric Reis is an excellent book which discusses organic planning in more detail. However, it may be too technical for the average person. I will probably re-read Reis's book to see if I can write a general recommendation for it.

None of my 5-star book recommendations concern organic planning per se, but two offer excellent advice on contingency planning:

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