In tech, we LOVE planning. We plan meetings to describe functions, which are the frameworks we use to plan user stories, which is a different framework we use to plan developer tasks and the acceptance criteria for testing user stories. We plan the crap out of stuff.

We need planning! It's really important to plan out what we're going to build, how we're going to build it, how it's going to serve the customer, and how we're going to know it works correctly. However, at some point along the way, we need to engage is something called Strategy. Strategy is great, it really help us to answer the why we're going to do something, and how all these plans we put into place are going to succeed.

However, at some point along the way, some MBA suits decided that planning and strategy as separate activities were too many steps and that we should smush both of those things together into a brand new activity, called Strategic Planning.

There's only one problem though. Strategy and planning aren't the same thing. Putting those two things together and giving it a catchy name doesn't help. It has nothing whatsoever to do with strategy.

Strategic Planning

When we talk about strategic planning, what we usually mean is describing a set of activities that we want to accomplish in order to achieve some out come.

• We're going to improve user experience
• We're going to market to a new type of user
• We're going to open west coast office

We make these plans because they all sound good and we can easily understand them. But they're not really going to get us where we want to go, because they're not a strategy.

What's a Strategy

The strategy definition that I like the best is defined as (I didn't come up with this, by the way, I'm not nearly clever enough):

An integrated set of choices that positions you on a playing field of your choice in a way that you win.

Strategy is a Theory

It's really nothing more than a theory. It's a set of educated assumptions about why this is the playing field we should be on, and not some other one, and how we're going to be better at playing the game than anyone else on the field.

The strategic theory must be coherent, and it must be doable. You have to be able to translate that strategy into actions for it to be a great strategy. Planning doesn't have to have any such coherence.

A plan is just the new set of features the sales team thinks they can sell, or what customer success wants to fulfil a client request, or what sort of new development environment engineering wants because it'll make some process faster, etc. It's an internal list of things that doesn't necessarily have any cohesiveness. What it's missing is some unifying mechanism that is going to help the company as a whole reach some goal.

Why Do Leaders Plan So Much?

We plan because planning is comfortable. It has a known value. Plans usually have to do with the resources you're going to spend. It's all on the costs side of the business. It's comfortable because I can control the cost side and I become the customer.

Strategy involves making a plan about some goal we wish to achieve, which involves customers wanting our product or services enough to pay for them. The tricky part is we don't control customers. We can't make them buy our product or service.

That puts us out there, it makes us uncomfortable. We're saying that we have some belief about an outcome. We can't prove it in advance and we can't guarantee it.

It's much easier to say, "I'll build this thing, I'll implement this policy, I'll hire these people", than it is to say, "I will have customers liking our product more than those of competitors".

The trouble with planning is that at least one competitor is out there trying to figure out how to win.

How to Avoid the Planning Trap

Accepting Angst

Recognize that strategy will have some angst associated with it. Just accept it. You can't prove that your strategy will work in advance, while you can prove the cost of your plans. It's difficult to go to your boss and say, "If our theory is right, and customers respond well to this, then we'll succeed". Accept the fact that you can't be sure about the outcome, and that's okay. That's what leadership is about.

Not knowing for sure isn't bad management, it's great leadership.

Lay Out The Logic

Lay out the logic of your strategy. What would have to be true about the playing field you're on in order for this strategy to work? What would have to be true about our customers, about our business model, our pricing model, the market environment, etc. in order for this to work?

With this in place you can watch your strategy unfold. Oftentimes our assumptions are not right, and we have to tweak the strategy. That's okay though! Strategy is a journey. We want to keep refining it to make it better and better as we go along.

K.I.S.S.

Don't make it overcomplicated. You strategy should be concise enough to fit on a sheet of paper, and simple enough to explain to one of your kids. I figure if my kids can get it, I'm not overcomplicating it!

It should lay out the basics: Here's where we're choosing to play, here's how we're going to win, here's the capabilities we need to have in place, and here's the management systems we need to succeed.

Having a strategy certainly won't guarantee that you'll win, but resorting to planning is a surefire way to guarantee you'll lose.

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