On Planning

Dreams die between idea and execution—Jocko Willink

Ideas are thrilling, exciting, and fun. They are usually not the problem—execution is. Imagining the success of your ideas obfuscates the messy reality of bringing them to completion. This is the same type of problem as “Do you find this idea interesting?”¹ Both are surface-level, and our brains tend to look for shortcuts. The real question is, how do we get there?

The upside of planning

Ideation, though not trivial, is cheap. If done in excess, it is like daydreaming; it feels good, but it is a means of analysis paralysis. To turn ideas into reality, we need to plan. You might object that nothing will go according to plan. You are right.

Plans are useless, planning is helpful—Eisenhower

The point is not having the plan; it’s about the process. Planning should force you to make all assumptions explicit, reduce the burden of the end-goal into bite-sized steps.

Planning is about figuring out what can fail and figuring out how to prevent that.

If you cannot devise a good plan², the idea might not have been that great. Thus, you can pull the plug before wasting a lot of time.

Procrastination, deadlines, and planning

You have seen people accomplishing many things before a deadline. Perhaps you have done that too. The second wind is real; performance can get a boost close to the finish line. The question is

Are you using deadlines intentionally to boost focus and productivity?

While reading Labwork to Leadership, I became aware of the distinction between active and passive procrastination. Active procrastination is an intentional way of knowing the realistic time demands of a task, and delaying doing it, but only to a point that you can still finish before the deadline. This can induce the feeling of flow, with a reasonably low risk.

Passive procrastination, on the other hand, is unintentional and stems from the anxiety the task at hand causes. In this category, you might still pull it off, and you might still tell yourself that you procrastinate to experience the boost. Only you know the real answer, and it requires self-reflection.

Planning, or lack thereof, is a good indicator, though. Luckily, conference deadlines are usually (approximately) known in advance. A question I find useful is asking yourself—especially if you tend to leave things to the last minute:

What if you worked consistently beforehand, and the jolt of excitement only adds the cherry on top?

You might say that you work well under pressure, but if you have never tried out the alternative, how do you know?

Under stress and lack of sleep, it's more probable that you will get sick. Thus, there will be a sweet spot even for active procrastination.

Planning tools: pre-mortem and pre-victorem

There are two tools that can identify the critical steps of the project. Becoming aware of these will help set a more realistic timeframe and also identify the risk factors.

The pre-mortem³ assumes that the project failed and asks what caused the failure. The pre-victorem is similar, but it assumes that you succeeded. A few useful questions to ask:

• What caused the failure?

• Was the time plan appropriate?

• Was it clear who the owner of each task is?

• Was the communication unclear?

• Did we make a wrong decision?

• Did we make the right decision, it just did not play out?

Dig Deeper

1. As I wrote in How to Develop Great Ideas, the problem here is that finding an idea interesting does not make the responder have skin in the game. It is a statement about the abstract idea, not the execution

2. SMART goals are a good starting point, i.e., the steps should be concrete enough, should come with a responsible person and time allocation (i.e., put it on your calendar)

3. For crime lovers out there, this is like the post-mortem (where the medical examiner figures out the cause of death), but you do it beforehand