If you’ve ever sat through a strategic planning retreat thinking, “What a waste of time,” you’re not alone.

Your strategic plan will be wrong. Not because you’re doing it badly, but because the world is probabilistic. Markets shift. Customer preferences are fickle. Competitors are unpredictable. Your rockstar morning shift quits to become…actual rockstars.

And yet, not having a plan guarantees something worse: wasted time, wasted energy, and your team hustling in different directions under the illusion that they’re each working on the most important thing.

The real usefulness of strategic planning isn’t predicting the future. The value is in forming and pursuing a testable hypothesis: a best guess that aligns people long enough for organizational learning to occur.

Strategy Isn’t a Crystal Ball. It’s a Cohesive Response to a Challenge

In Good Strategy / Bad Strategy, Richard Rumelt notes that “Good strategy almost always looks…simple and obvious and does not take a thick deck of PowerPoint slides to explain.”[1] It focuses on the one or two critical issues and concentrates resources there.

Strategy is a coherent response to an important challenge. Not marketing puffery, not a list of disconnected initiatives, and not a set of KPIs. In other words: “increase revenue,” “improve throughput,” and “grow brand awareness” are not strategies. As Rumelt writes, “The kernel of a strategy contains three elements: a diagnosis, a guiding policy, and coherent action.”

Most bad strategies skip straight to goals. However, “A statement of desire is not a plan for overcoming obstacles.”

A real strategy starts with: What’s going on here?

And then: Given that, how will we respond?

By answering succinctly, you will:

Create constraint → make it easier to say no
Create conviction → motivate people around a shared direction
Create cohesion → ensure teams make aligned decisions

A good test: If you disappeared for 30 days, would your team still make the same decisions you would? If not, the strategy isn’t clear enough.

Treat Your Plan Like a Hypothesis. Revise When Needed

Strategy documents are tools to forge clarity out of chaos. People don’t need perfect assurance to move, but they do need to be reassured that they are moving in an endorsed direction. A good strategy distills messy inputs into a shared lens for decision-making. Think of your plan as a shared hypothesis: “We are doing X, because we think it is going to lead to Y.” This now creates a great frame of reference against which to compare reality as it unfolds — and to bend that reality towards your preferred outcome.

Rumelt says bad strategy often reflects “active avoidance of the hard work”. Because yes, it’s painful to choose. It’s scary to take a stand. And even good strategy decays as the realities of our competitor, customer, and supplier actions unfold.

Clarity has a half-life. That’s not failure — it’s a reason for maintenance.

A useful cadence:

Monthly: check progress, adjust activities
Quarterly: test whether the logic still holds, refine hypotheses as needed
Annually: go through the process again, because now you’re a lot smarter

You plan because alignment decays, not in spite of it.

How Strategy Helped One Client Pivot

A first-time strategic planning client experienced the benefits of having a strategy, and holding it loosely. In an effort to increase their credibility and leadership on technical capabilities, there were a number of different process technologies they wanted to explore; this guided their R&D and supplier partnering initiatives throughout the year. But when they discovered that a promising technology was misaligned with their core competencies, they dropped it and moved on to a different one that played off their existing strengths.

They were able to improve their product quality and processing efficiency in a way they can now market as superior, without having gone down a rabbit hole of additional processing agents and environmental hazards that would have increased the complexity of their operations. Without a clear hypothesis framing this work, they may have kept tinkering with the “bad” technology for far too long, mistaking the (wrong) solution for the outcome they were actually after.

Planning Saves Time

“That’s great,” you might be thinking, “but around here, we don’t have time to plan; we have real work to do!” Ironically, skipping strategy virtually guarantees you’ll have less time, because you’ll be working on too many things.

Rumelt writes that “Good strategy requires leaders who are willing and able to say no” and that strategy is “at least as much about what an organization does not do as it is about what it does.”

Strategic planning forces the essential conversations:

What are the real opportunities?
Which constraints matter?
How could we build new advantages?

Manufacturers face choices like improving line efficiency versus expanding distribution. Café operators choose between investing in the dine-in experience or chasing wholesale. You can’t do everything well. Strategy is the discipline of choosing. And choosing saves time.

Proximate Objectives: Because Your Crystal Ball Is Foggy

Rumelt emphasizes the need for “good proximate objectives” — goals close enough to be achievable. “The more uncertain and dynamic the situation, the more proximate a strategic objective must be.” While most organizations default to setting annual goals, perhaps quarterly goals are as far out as you can get in a turbulent situation.

That’s not small thinking; it’s respect for reality.

And it pairs quite nicely with a scientific approach to continuous improvement: establish a target condition, not a fantasy endpoint. You don’t need a perfect, detailed five-year vision, just a next step that tests your hypothesis.

If you're wrong? Great. You learn faster, and you can adjust your next step.

Strategy as an Operating System

Think of your plan as a temporary operating system for decision-making. It’s not “the truth.” It’s your best current version of what might be true, that holds long enough to guide action.

You’ll revise it. You’ll improve it. You’ll eventually rebuild it.
That’s the point.

Because without it, you get improvisation masquerading as strategy, and as Rumelt bluntly notes, “winging it…is not strategy.”

The Real Reason to Plan

Strategic planning isn’t about getting the future right. And it’s certainly not about creating a bunch of meaningless, flowery words on a page. It’s about getting your people aligned enough to move, learn, and adjust without thrashing.

It’s about diagnosing the situation, choosing a guiding policy, and taking coherent action. And in a world full of variability, that level of coherence is a competitive advantage all its own.

What if this leads to some ideas that don’t work? Good. You have new information about the world REALLY works. And because you had a hypothesis, you can understand how it was wrong.
You’ll know what you need to change.
You’ll know what you learned.

And you won’t have wasted a year learning it by accident.

[1] Rumelt, Richard P. Good Strategy/Bad Strategy: The Difference and Why It Matters. Crown Business, 2011.

Your Strategic Plan Will Be Wrong. You Still Need One.