The sport of golf is a mathematician’s dream. Players succeed by getting ever closer to the objective. First, you hit the ball from the tee to some point partway down the course. Then you get a little closer with a second shot. Once on the green, you putt the ball towards the hole, getting still closer. And finally you complete the hole by sinking a final putt.

Applying this iterative approach to making progress should be natural in leadership, but terms like analysis paralysis are common in corporate vernacular. Why?

First, can you imagine how daunting golf would be if you stood 400 yards from the hole and took a swing with the mindset that the ball had to find the cup on the first shot? On most holes, it’s actually impossible to do. Oddly enough, it’s the fact that it’s impossible that makes that first swing doable in the first place. Without the pressure of trying to sink every shot, you can be less precise so long as you are directionally correct.

Most good golfers move up and down the course with this mindset. Each shot is an attempt to get closer to the hole. You identify some target range, and then you aim for that. Success is not measured by pure precision; you gauge success by whether you land within your next closest target area. The better a golfer you are, the more narrow these targets (an amateur might be satisfied with getting on the green, whereas a professional might aim to be within 15 feet of the hole).

Now think about how companies manage long-range planning.

For most companies, budget planning is a months-long exercise. Based on strategic and market input, the company arrives at a set of desirable projects. These projects are then prioritized and distributed to the supporting development teams. Over the months of planning, teams scope these projects to arrive at a bottom-up view of the resources and budget required to execute. When all these projections are added up, leaders can draw cut lines and determine what is above and below the funding line.

Never mind for a moment that the scoping for some projects is wildly inaccurate. What you end up with at the conclusion of this exercise is a projection of resources down to the individual head and likely the closest thousand in terms of cost. If an organization has only 400 heads, being within 4 would mean an accuracy of 99%. If the budget is $30M, trying to get within $300k would be 99% accurate.

Doing that for the full year considering that not all conditions are controllable (macro economic climate, customer buying patterns, and so on) already borders on ridiculous. Now extend that planning process out 3 or 5 years.

This is basically the same as standing on a tee 400 yards from the hole, gripping the club, and taking a swing with the expectation of finding the bottom of the hole. It’s just not realistic.

But so what? Who cares if the projection is way off?

Everyone ought to care. The whole planning exercise becomes needlessly difficult. In our pursuit of precision, we end up wasting an awful lot of time. The scoping efforts, the project planning, the headcount projections… it all adds up. And to make things worse, you go through all this work to exit the year with a workable plan, and then as soon as Q1 comes, you end up predictably revisiting the plan when you get better visibility into the economy, the customers, sales, and whatever else.

Worse than that, we end up fooling ourselves into thinking that our planning is accurate. Because of the precision with which we document the plan, we start to think that our plans are solid. This project will consume 36 Full-Time Equivalents or Employees (FTEs). Any subsequent discussion is now about whether the right number is 36 or 35 or maybe 37. And if we can steal one head from each of our 15 projects, maybe we can staff an all-new project!

Of course, once we get to the first project milestone, we realize that the actual headcount required is 44. But we can’t even adjust now because we staffed that other project with 15 FTEs. And by the way, that project really needed 22, so we have two under-staffed projects, neither of which is complete. Great for the business, right?

Some of you might be thinking: Sure, but I don’t even participate in budget planning! This dynamic plays itself out in virtually every project. A large product initiative might go through quarters of planning. The aforementioned budget process produces a cost envelope (the budget into which the project must fit). So after the initial planning, you are asked to Sharpen your pencils! You start to shave off estimated work over a 2.5-year schedule so that you can fit within the budget constraints.

When we do this, we are in essence aiming for the hole from the tee. Sure, some projects are small enough where we can take a good swing, but what about the projects that aren’t?

The point here is that planning with this kind of precision is counterproductive. Because we think our planning is flawless, we don’t start until we have everything planned out (analysis paralysis). And then when life introduces variability (as it invariably will), we have to revisit our plans anyway. So how do we counteract that? We just randomly overestimate everything by a factor of 2 to account for unknowns. Why? Because if we are over schedule or over budget, we are told our planning was poor.

This is nuts. Because we are planning too precisely, we randomly add a fudge factor to our estimates!

You might be thinking: Ok, but I am not a project lead! That might be true, but this dynamic plays out in our own individual tasks. Have you ever been assigned a project (or a term paper) that you didn’t know immediately how to complete? The sheer enormity of the assignment stresses you out, so maybe you end up watching television or playing video games or reading Reddit. Everyone does this by the way. This is why analysis paralysis is such a common term. We all feel it.

So when do you actually make progress? At some point, you realize that you are mere hours away from the deadline. When the panic sets in, the plan is less important than the keystrokes, and you just start typing. Miraculously, you finish just before the deadline. But how did you do it?

Those first few keystrokes might not have been part of a plan, but they were directionally correct. You teed up the ball and hit it somewhere towards the hole. From there, you looked at what had to be done next. You grabbed a club and put the ball somewhere up near the green. Then you lofted the ball onto the green and finished up with a couple of putts for bogey. Sure, the plan was 4 strokes (a par 4), but most of the time, a 5 is actually pretty darn good.

Understanding that this is the way people operate for the most part, leaders need to change how they manage teams and projects:

  • The objective ought not be to get the forecast within 13 decimal points. We need to be directionally correct. Identify the objective (get the ball in the hole, or deliver some product, or whatever), and then make sure you know where the first shot needs to land.
  • Understand that planning is not an event so much as an ongoing task. The goal is to iteratively get closer. Work ongoing planning into the operating model.
  • As soon as you hit the first shot, you are already thinking about the second shot. Do some basic scenario planning so you have an idea what comes after each subsequent shot. The key here is not the precision of the future planning but rather how you will identify which scenario you are in. What are the key indicators? And what will you do differently based on these (staff up the project? move resources around? drop parts of the project?)?
  • Reward progress, not precision. Teams will deliver what their leaders demand. Start demanding progress. Stop scrutinizing over the 13th decimal place 3 years out. And don’t harass teams over failure to plan when life inserts variability.
  • Take time to understand what your target area is. Are you content hitting the ball on the green? Or do you need to be within 15 feet of the pin? You need to understand how good a golfer you are and set your target range to your abilities. If, as a leader, you have a mismatch here, you are setting your team up for frustration.
  • When we have unrealistic expectations of precision, even the completion of a project can be a frustrating moment. But when we approach projects more iteratively, we have a real opportunity to relish in the objective. And nothing makes the drive for improvement more powerful than enjoying the process.
[Today’s fun fact: The elephant is the only animal with four knees.]