I receive many messages from Product Managers and Product Owners who are close to going crazy because they constantly loop through the Planning Cycle of Madness with the accompanying Roadmap Circus that drains their energy.

Here’s what I see happening in many tech companies all over the world:

1. Once upon a quarter, the teams fail to meet their plans, roadmaps, and timelines.

2. The leadership teams and management are unhappy. They tell everyone to step up and do a better job at predicting and planning.

3. Everyone spends even more time debating, analyzing, predicting, and planning in meeting rooms. The roadmap planning circus runs full steam. All teams leave the meeting rooms with glorious plans polished to perfection. Management is pleased with the paper victory produced by the teams. After the planning sessions everybody feels great. Confidence is sky-high the teams will do a better job this time around.

4. Then as the teams begin their work, the confidence level drops. The plans that appear great on paper suck in reality. The teams encounter many obstacles and surprises. The teams struggle to deal with these surprises. All teams are locked into plans that drag everyone down, preventing collaboration, learning, and discovery. Subsequently, all teams fail to meet their plans, roadmaps, and timelines.

And then, all teams go back to step 1. The roadmap planning circus starts all over again. The company merrily goes for another loop of the planning cycle of madness.

Why Does This Roadmap Planning Circus Happen?

1. The managers in the company want to hit their targets, especially if they are tied to attractive individual bonuses.

1. By pushing teams to spend more time on planning, design, analysis, and coordination, managers try to increase the chance of the company hitting its targets. Managers believe by doing a better job at planning that we set ourselves up for success.

1. Managers optimize for teams with glorious plans: plans that look amazing on paper. Seeing a team presenting a planning home run gives managers the feeling a team really knows what they are doing.

2. Leaders and management want to have the feeling of control. Magnificent plans provide that timely shot of the illusion of control they need amidst intolerable uncertainty of whether the teams will hit their targets.

And what’s the end result of all these plans polished to perfection?

The teams don’t hit their targets because of a self-inflicted planning circus that clogs and obstructs the ability to deal with surprises and the unexpected. All that additional time spent planning works against the ability to deliver value and reduces our chances of making our plans succeed.

Plans that look simple on paper and appear lazy are the most realistic and have the best chance of succeeding. These plans consider how much we can’t know before starting the work.

But because the planning circus optimizes for providing the illusion of control, all these plans with a fighting chance are weeded out. All plans are reworked to appear glorious until they radiate the (unwarranted) confidence that our managers need to feel comfortable with what the teams will be doing.

What’s the alternative to producing paper victory plans?

Begin With Humble Planning

You have to accept the following:

1. You can only plan based on what you know, and we know this isn’t good enough to succeed. When you do complex work, it’s about what we don’t know. It’s about all the surprises and obstacles we can’t see coming before starting the work. We must start with humble plans that leave room for surprises and the unexpected. Those plans will appear lazy and like you don’t know exactly what you will be doing, but that’s precisely the point!

1. No matter what you do, your estimates will be wrong. The sooner you accept and embrace this fact instead of trying to fight it, the better.

2. When you plan at 100% of your capacity, you’re mega fucked. When you plan at 70%, you’re still absolutely screwed.

Leaders, please understand what this graph means for your plans:

What happens when the cashier at the supermarket is 100% busy? A queue will form and you’ll have to wait in line. We’re all familiar with that situation.

When you plan at 70% capacity, anything surprising or unexpected will make the waiting time for features shoot up. Once again, imagine yourself standing in line at the supermarket, not getting things as quickly as you want.

The more complex what we’re doing, the more surprises, and the less we can predict and plan. The more surprises, the more we should plan below 70% capacity. At least if we aim to deliver as much value as possible instead of keeping everybody as busy as possible.

The more complex what we’re doing, the bigger our natural response to try and reduce the uncertainty by spending more time on predicting and planning. The more uncertainty, risk, and things we don’t know before starting the work, the bigger our desire will be for glorious plans that, in fact, suck.

The more complex what you’re doing, the less you should plan before starting the work. Because by doing the work, you will discover what’s necessary to make your plans actually work.

What does it mean when we take all of this into account when we make our plans?

1. Start with humble plans. Only plan 40-50%. Give teams room to deal with the unexpected and collaborate as necessary when they find out what they couldn’t know before starting.

2. Pull in more work gradually as we discover how much we didn’t know before starting. Plan more as we find out how many surprises and obstacles we are up against.

3. When pulling in work, try to stay below 70% or more resource utilization. Waiting time of features shoots up quickly above 70% resource utilization. You’re creating a traffic jam that keeps everyone busy but doesn’t result in features going live any sooner.

Humble plans will require more collaboration and less coordination. It will be messy, and we don’t like it when things are messy. We can’t hide in our meeting rooms and planning sessions and then return to our desks to work in isolation.

When you need help, instead of waiting for a meeting, you immediately ask the other team for help. And because they planned at less than 70%, they will have time to help you out. You won’t end up in an argument because they are locked into the plans and promises that they’ve made at a point in time when they knew very little.

Leaders, please don’t fall for grandiose plans that keep up the illusion that it will somehow not be messy and, to some extent, unpredictable.

Deep down, we all know it’s going to be messy. Do you remember the time when all teams were able to deliver everything precisely on the roadmap as expected?

You don’t remember that time, because it doesn’t happen! At least not when you’re doing complex work.

Let’s stop trying to pretend otherwise. Let’s put an end to fooling ourselves and resist the urge to create the illusion of control through a planning circus that forces people to pretend they know more than they actually do.

Embracing that you can’t and don’t know everything before starting the work will always work better than sticking your head in the sand and trying to pretend you know everything there is to know.

Don’t be like this ostrich:

No matter how much we talk, design, analyze, or coordinate. We’ll never be in complete control.

Our ability to deal with surprises and the unexpected is what we should be worried about, not having perfect plans. Not knowing what will be doing isn’t the same as not knowing what we are doing.

Do you want to have plans that ooze the illusion of control or humble plans rooted in reality that allow you to make the most progress toward your goals?