What to do when your strategy is not working

Admitting a strategyglossary×StrategyStrategy is a high-level plan that defines long-term goals and the approach to achieving them.Open glossary term→ isn't working is uncomfortable. A lot has usually already been invested by that point: time, budget, stakeholder alignmentglossary×Stakeholder AlignmentStakeholder alignment is the process of ensuring all stakeholders share a common understanding of goals, priorities, and direction.Open glossary term→, internal momentum. The strategy has likely been presented, agreed, and socialised across the organisation. Walking that back can feel like failure, so the natural instinct is to push forward, refine execution, and hope the results start to improve. Sometimes they do. Often they don't.

What tends to happen instead is that more effort is applied to the same direction. Teams double down on deliveryglossary×DeliveryDelivery is the process of building, testing, and releasing a product or feature.Open glossary term→, more featuresglossary×FeatureA feature is a specific piece of functionality within a product that delivers value to users. It represents something users can do or experience as part of the overall product.Open glossary term→ are added, more iterationsglossary×IterationIteration is the process of repeatedly improving a product through cycles of testing, feedback, and refinement.Open glossary term→ are made. The assumption is that the problem sits in how the work is being executed, rather than questioning whether the direction itself is correct. This is where strategies begin to quietly break down, because execution can only take you so far if the underlying thinking is wrong.

The sunk cost is rarely just financial, which is what makes it so hard to move past. Somebody has stood up in front of the organisation and committed to this direction. Reopening it is not only a change of plan, it is a public revision of something they were confident about, and that cost is felt personally.

The first thing that needs to happen when a strategyglossary×StrategyStrategy is a high-level plan that defines long-term goals and the approach to achieving them.Open glossary term→ isn't delivering isn't more work. It's a pause. Not a full stop, but a deliberate step back to understand what's actually happening. Without that pause, decisions continue to be made based on assumptions that may no longer hold true. The focus needs to shift from deliveryglossary×DeliveryDelivery is the process of building, testing, and releasing a product or feature.Open glossary term→ to understanding.

A pause is easier to get agreement on than a change of direction, which is part of its value. Two weeks to establish what is actually happening is a small ask compared with abandoning a roadmapglossary×RoadmapA roadmap is a strategic plan that outlines the direction, priorities, and timeline for a product or initiative. It communicates what will be delivered and why, rather than just listing features.Open glossary term→, and it produces the evidence that any subsequent decision will need anyway.

It also needs to be genuinely protected. A pause where deliveryglossary×DeliveryDelivery is the process of building, testing, and releasing a product or feature.Open glossary term→ quietly continues is not a pause, it is a review running alongside the thing it is meant to be reviewing, and its findings will arrive too late to change what was already being built.

Start by looking at the evidence properly. What's actually happening in the dataglossary×DataData is raw, uninterpreted information collected and stored so it can be analysed, processed, or used to inform decisions. On its own it carries no meaning; context and interpretation are what make it useful.Open glossary term→? Where are users dropping off? Which parts of the experience are being used, and which are being ignored? What feedbackglossary×FeedbackFeedback is the system response that informs users about the result of their actions. It helps users understand what has happened and what to do next.Open glossary term→ is coming through? Look at this objectively, without trying to justify the existing direction.

In some cases, the strategyglossary×StrategyStrategy is a high-level plan that defines long-term goals and the approach to achieving them.Open glossary term→ itself is sound but the execution hasn't aligned with it: featuresglossary×FeatureA feature is a specific piece of functionality within a product that delivers value to users. It represents something users can do or experience as part of the overall product.Open glossary term→ may have been delivered in a way that doesn't fully address the problem, or key parts of the experience may have been overlooked. In those situations, the answer is refinementglossary×RefinementRefinement is the ongoing work of clarifying, breaking down, and sizing backlog items before they enter development. It is where ambiguity gets resolved while resolving it is still cheap.Open glossary term→. But in other cases, the issue is deeper. The assumptions that shaped the strategy may be wrong. Perhaps the problem was misdiagnosed, or user behaviour was misunderstood. When that happens, no amount of iteration on the current path will produce the right outcome.

One question separates the two more reliably than most analysis. If everything on the plan had shipped exactly as intended and on time, would the outcome be what you needed? Where the honest answer is no, the problem is the direction, and improving deliveryglossary×DeliveryDelivery is the process of building, testing, and releasing a product or feature.Open glossary term→ will not reach it.

At that point, the strategyglossary×StrategyStrategy is a high-level plan that defines long-term goals and the approach to achieving them.Open glossary term→ needs to be revisited, not patched. That doesn't mean starting from scratch, but it does mean being willing to challenge the original thinking. A failing strategy doesn't mean everything within it is wrong. There are often elements that still have value, insightsglossary×InsightAn insight is a meaningful understanding that explains why something is happening and what it means.Open glossary term→ that remain relevant, and progress that can be built upon. The key is to separate those from the parts that aren't working, and to be deliberate about how the direction is adjusted.

One of the reasons strategiesglossary×StrategyStrategy is a high-level plan that defines long-term goals and the approach to achieving them.Open glossary term→ are allowed to drift is because people are hesitant to surface issues early. Being transparent about what isn't working is what allows the strategy to improve. Strategies don't fail all at once. They drift. They move slightly off course, then a little further, and over time the gap between intention and outcome becomes too large to ignore. Recognising that early is what separates strategies that recover from those that continue to underperform. A strategy not working isn't the problem. Not recognising it is.

Salvaging the parts that still hold is what makes the conversation possible at all. Framing it as a correction based on what has been learned, rather than as a reversal, is both more accurate and considerably easier for the people who backed the original direction to accept.