Make a Great Plan in 4 Steps

If there is one thing I have learned from leading teams, it’s that the small insights carry the most power. And the best way to get those insights is through good old fashioned planning.

Planning is the machine that converts ambiguity into action and action into success.

No matter the undertaking, teams I lead have success in proportion to the quality of our planning. There are only a few simple steps to follow that always work, provided I trust my instincts and remain open minded.


Context matters. A useful backdrop can be gleaned from considering what is happening in the world, in an industry, and in a particular organization. That’s why I often begin a planning exercise by getting a sense of the big picture. It helps me to start to build a framework for thinking.

Data, perspectives, and ideas are scattered about. So I go looking for them and try to dig up as much as possible. I collect snippets and links along the way, placing them all into a single working document.

Great stuff is sometimes hiding in plain sight—in news articles and industry journals. Other times I find useful things buried down a chain of links I happen to follow. Serendipity is key.

I never know where something provocative will be found, though I often aim for conflicting points of view. I love the opportunity to wander around in a set of ideas for a while. It has a way of priming my own thinking in interesting ways.

Once I’ve gathered some good background information, I also examine the stuff right under my nose. I review any reports, presentations, or meeting minutes on the topic. Much of this didn’t get thorough consideration the first time around. I also try to recall hallway conversations, read through my notes, and dig through my email conversations, all the while adding snippets and thoughts to the collection in my working document.


The framework that starts to emerge from these highlights helps to shape more productive thinking. I try to assess and organize everything I’ve gathered, figuring out what is important and what can be set aside.

From all the points of view gathered so far, I wonder what they are trying to tell me. How are they looking at the situation? What is important to them? Why are they focused on what they are focused on? What do they fear? What are they hoping for?

Themes emerge as some ideas line up. Issues arise as some ideas clash. Attempting to mesh this together helps give my own thinking some cohesion.

I start to see turning points in various arguments. Important levers become apparent. Some of my own thinking is validated, and some of it is challenged.

At the heart of this planning machine is exactly this critical thinking that shapes an initial approach. The foundation of a plan starts to take shape.

That plan needs to consider the specific situation, so I start to think in terms of the capabilities and limitations of the team and the organization. To consider the personalities and the politics. And what it might really be feasible. Things won’t move forward if the plan is unrealistic.


In order to give it shape, I will organize the document into an outline and start to put the pieces in some kind of order. This is where things get organized into a logical flow.

I organize my thinking and I start to talk it out by writing in full sentences and organizing those into paragraphs. I find prose more powerful than bullet points for planning because it forces me to put my thoughts forth more completely. Can I explain this in a way that someone could read it without my being there to explain and expound? If I can do that, I am on my way to a good plan.


Next, I share my work with the team and ask for feedback and input. What have I missed? Which parts are not clear? Does it make sense to you? How would you adjust it?

Having written prose makes this part easier. Not only is my thinking clearer than it would be from a simpler sketch, but the working document is now something that can start to stand on its own. Team members can look at it independently. It also makes it easier for them to offer very specific feedback.

If I can make it as easy as possible for others to weigh in, I will get better participation. Greater participation makes the plan better. It also builds team ownership of the plan.

This is my favorite part because it is where I learn the most. Not only about my blindspots, misjudgements, and inaccurate assessments. But also about specific details. I learn nuances from people with specialized knowledge and experience, nuances that strengthen my understanding and often become crucial to shaping my broader view.

At the same time, it gives me an opportunity to teach. I can help to share context that might not be immediately apparent. Often this amounts to explaining why the goals are important and the realities of how the plan needs to fit into the dynamics of the situation at hand.

All the research, organizing, analyzing, and discussions and debates with the team leads to a good plan. And a good plan is what leads to success, even if that plan needs to change along the way—especially if that plan needs to change along the way.

Because the secret isn’t the plan, it’s the planning. Planning is leadership in action.