Introduction

Why Strategy Is Hard

Even with a clear mission and vision, most organizations struggle to turn intent into impact. The root cause is what many strategists call the messy middle problem — the gulf between work and outcomes.

Teams can see the goals at the top and the tasks at the bottom, but what happens in between often feels like a black box. The factors that matter most to long-term success — customer retention, profit, engagement, growth — are lagging indicators. They move slowly, are influenced by countless hidden factors, and can’t be directly controlled.

As a result:

Teams drown in dashboards but can’t act on what they see.
Roadmaps become power struggles.
OKRs turn into glorified to-do lists.
Employees lose confidence in direction.
Work multiplies while impact plateaus.

This “strategy execution gap” isn’t a failure of effort or talent — it’s a failure of shared understanding. Every team has a slightly different mental model of how the organization works. Those models rarely align, and often, they’re never made explicit at all.

As Itamar Gilad and John Cutler have written, this leads to the feature factory problem — where teams optimize for shipping output instead of learning what truly drives outcomes.

When organizations don’t understand how actions create impact, they can do a lot without getting anywhere — like running faster on a hamster wheel.

The way forward is to make the system visible.

Map Your Impact Drivers

Every organization is a network of causes and effects. Behind every outcome you care about lies a chain of impact drivers — factors that influence one another over time.

The first step to solving the messy middle is to make that chain explicit. Mapping your impact drivers turns individual mental models into a shared understanding of how the system works.

Start by asking:

What are the measurable factors that lead to the outcomes we want?
How do they influence each other?
Which relationships are we most confident in — and which are uncertain hypotheses?

You can approach this from two directions:

Work backward from your ultimate impact
- Start from the outcome you want to achieve — informed by mission, values, and goals.
- Then trace backward to the drivers that shape it.
- This approach helps you reason from first principles.
Work forward from the work already in motion
- Begin by mapping how your current projects or initiatives are intended to create impact.
- Then connect them to the metrics or signals they’re expected to influence.
- This approach helps you quickly visualize your current strategic model.

As you map, keep in mind: this is not just a list of metrics — it’s a model of how change happens in your system.

As Donella Meadows wrote in Thinking in Systems,

“You can only understand the system if you see the relationships, not just the parts.”

Map Bets to Your Impact Drivers

When you’re introducing new work, you rarely know its true impact. You can hypothesize — but not guarantee. That’s why we call them bets.

Each bet represents a belief about leverage:

“If we do this, it should move that.”

By connecting bets to your impact drivers, you make those beliefs explicit and testable. You can visualize which parts of the system each bet touches — and how strongly you expect it to influence key outcomes.

Over time, this builds a living model of your strategy:

Past bets reveal what has worked (or not).
Current bets show where the organization is focusing now.
Future bets highlight potential opportunities or hypotheses to test.

This practice transforms strategy from a static plan into a system of learning — where every initiative refines the organization’s understanding of how impact is actually created.

Choose Indicators of Impact

Once you’ve mapped your drivers and bets, you need to measure the health of the system.

Choose indicators that help you see whether your drivers are changing as expected. These indicators can be quantitative (metrics, analytics, conversions) or qualitative (user interviews, stakeholder feedback, surveys).

A few principles help guide good indicator selection:

Use input metrics to measure early signals (e.g., activation, usage, engagement).
Use output metrics to measure lagging results (e.g., retention, revenue, satisfaction).
Choose metrics that reflect meaningful progress, not vanity performance.
Collect just enough data to learn — don’t let perfect become the enemy of progress.

To ensure clarity, define:

What success looks like for each indicator.
Where the data comes from.
How frequently you’ll review it.

As you instrument your drivers, you’re effectively wiring up the nervous system of your organization — creating feedback loops that allow learning and adaptation.

Learn What’s Working and Refine Your Strategy

Once your model is mapped and measured, the real work begins: learning.

Use your indicators to evaluate how well your bets are influencing your drivers. Did the expected changes occur? Were there unintended effects? Did a driver behave differently than assumed?

When something doesn’t work, it’s not a failure — it’s a data point that refines your understanding of the system.

You can then:

Adjust your model to reflect what you’ve learned.
Refine your next set of bets.
Update or replace indicators that aren’t predictive.

This process turns strategic planning into a continuous learning loop — a rhythm of hypothesis, action, and insight.

As John Cutler describes, it’s about moving from quarterly strategy cycles to continuous roadmapping — keeping the organization adaptive as reality changes.

Strategy as a Living System

The most resilient organizations don’t treat strategy as a plan to be executed; they treat it as a system to be understood and improved.

Each impact driver, bet, and indicator is a piece of that system. As you connect them, you make your organization’s logic visible — turning tacit assumptions into testable structure.

Over time, this system becomes the foundation for:

Clearer prioritization.
Stronger cross-team alignment.
Smarter resource allocation.
Faster organizational learning.

Strategy stops being something you revisit once a quarter — it becomes something you continuously evolve.

As Donella Meadows reminds us:

“The goal is not to predict the system, but to dance with it.”