Retailers Plan in Years. Then They Had to Learn to Plan in Days.

Published 2014-09-18 · Updated 2026-06-23 · By Alan Wizemann

Topics: Retail, Digital Transformation, Product Strategy & Development, Team Building & Culture

I like to open my talks with a comparison that always gets a knowing laugh from anyone who has spent real time inside a big retailer, which is that large retailers are farmers, and I mean that with genuine respect rather than as a dig. Farming is a discipline built on stable ground. You read the seasons, you plan months ahead, you think in years, and then you commit to the plan and execute against it. A great retailer has historically run exactly the same way. The assortment for next fall is decided long before next fall ever arrives, and the store layout, the buys, the promotional calendar, and the supply chain to support all of it are planned far in advance and then executed against with enormous skill. It worked for over a hundred years because the ground really was stable, and the seasons came when they were supposed to come.

Then, somewhere along the way, the ground stopped holding still. Digital did not just add a new sales channel to the mix – it changed the entire environment the business operates inside, which is a much harder thing to absorb. Customers started moving faster than any planning cycle could track, a trend could form and crest inside a single quarter, and a competitor could change pricing across the whole country in a single afternoon. The annual plan, the farmer's plan, was still being executed beautifully while the world it quietly assumed was dissolving underneath it, and that is a strange and disorienting thing to watch happen in real time.

What the moment demanded was a completely different skill, and the way I came to describe it was that the farmer had to learn to fish. Fishing is the opposite discipline. You do not plant in spring and harvest in fall; you go out into an environment you do not control, you read what is actually happening right now in front of you, and you adjust constantly as you go. Plans are made daily and results are immediate, and you find out within hours whether the thing you tried is working, which means you change course based on what you can see rather than on what you projected six months ago. It is a faster, twitchier, more uncertain way to operate, and for an organization built around an annual cadence it feels deeply unnatural, almost like a betrayal of the craft that made the company good in the first place.

The hard part of this transition, I came to believe, is almost never the technology. It is the cadence, the operating rhythm. You can buy the tools (the tools are the easy part, and everyone is selling them to you), but what you cannot buy is an organization's operating rhythm, and rhythm is exactly what has to change. A company that has spent a century rewarding careful long-range planning has built every one of its habits, its incentives, and its meetings around that planning, and telling those teams to "move faster" accomplishes almost nothing, because speed is not actually the ask – the real ask is to change how often you decide.

That reframe was the one I found most useful, because the shift from farming to fishing is not about working harder or caring more – it is about moving the decision point itself. A farmer decides once, up front, and then executes against that decision for a season. A fisher decides continuously, in small increments, with fresh information each time the line goes out. Most of the friction in a digital transformation comes from teams trying to operate in a fisher's environment while keeping a farmer's decision cadence, committing to one big plan and then white-knuckling it as reality diverges, because the structure they live inside gives them no permission to decide again. You do not fix that with a motivational speech, you fix it structurally. You give teams something current to react to, which means real-time data instead of a monthly report, and you shrink the size of each decision so that changing course is cheap instead of catastrophic. You stop rewarding adherence to the original plan and you start rewarding responsiveness to what is actually happening, and you make it genuinely safe for someone to say "what we committed to in January no longer fits, so here is what we are doing instead," because in a fishing environment that sentence is a sign of health and not a confession of failure.

None of this means the farmer was ever wrong, and this is the part people miss when they get excited about speed. Long-range planning is a real and hard-won strength, and the discipline behind it is valuable in a way that does not go out of style. There are still parts of a retail business, the physical supply chain, the store fleet, the seasonal buys, that genuinely require thinking in years, and pretending otherwise just breaks things in expensive ways. The goal was never to turn the whole company into a startup. It was to build a second muscle alongside the first one: to keep the farmer's discipline wherever the ground is still stable, and to develop the fisher's reflexes everywhere it is not.

The companies struggling most, in my experience, are the ones picking a side. Some cling to the annual plan and get steadily out-maneuvered by faster competitors who decide every week, while others throw out planning entirely in the name of agility and lose the long-range discipline that made them formidable in the first place. The ones that will come through this are learning to do both at once, and, harder still, learning to know which situation calls for which. I think the farmer-and-fisher framing is the most honest way I have found to describe what this shift is really asking of big retail, because it is not a demand to abandon what you are already good at; it is a demand to learn an entirely second way of operating, in an environment that no longer rewards the first one on its own, and to hold both of them in your hands at the same time. The ground is not going back to stable, and the retailers who truly get this will not just plant more carefully. They will learn to fish.