Every strategic plan starts with ambition and vision, yet most of them fail or fall short. In fact, it is estimated that 90% of strategies are not successfully executed, and only a fraction of transformations hit the mark.
We are in the early days of a technology revolution that will exceed the transformative impact of electricity, the automobile and the internet. With both traditional insurance players and tech-savvy upstarts already investing billions into modernizing the industry in recent years, the rapid pace of AI development adds additional opportunities but also creates more complexity and, for some, strategic uncertainty.
Given this environment, in a highly competitive industry with compressed margins and a bumpy track record on growth, strategic missteps in the next few years could create devastating setbacks for businesses. Now, perhaps more than at any other time in a generation, it's critical that strategies and transformative projects are thoughtfully planned and brilliantly executed.
See also: How to Respond at Inflection Points
Common Reasons for Strategic Failures
The times may be changing, but the biggest reasons for failure are evergreen. We'll break down the top six reasons, but at the heart is poor execution.
1. Lack of Clear Vision and Objectives; Misalignment With Mission
Many strategic plans and initiatives fail due to the lack of a clear, actionable vision or poorly defined objectives that do not align with the company's core competencies or market reality. For example, "We must invest in and embrace AI" is not a strategy—it is a tactic. Yet many leaders are chasing the technology, without a clear objective.
2. Underestimating and Misunderstanding Disruptive Technologies
Predicting the future isn't easy, and it shows. Most business leaders tend to overestimate the impact of technology in the short term and underestimate it over the long term. Leaders often expect new technology to fix a range of problems, but unless they plan carefully and set realistic expectations, they are just digitizing many of their problems and sometimes even amplifying them. Over the longer term, technology often disrupts even the most unlikely and insulated of businesses.
Being too quick to adopt can lead to costly disappointment, while being too slow can put you at a competitive disadvantage.
3. Resistance to Change; Poor Change Management
This frustrating obstacle appears in multiple industries and environments. There are two distinct, though closely related, issues here:
First, there is likely a segment of your company who absolutely does not want your strategy or transformative project to succeed. This may manifest simply as indifference, but there are often one or more people actively working to undermine your plans. This is usually due to either (a) fear for their job or (b) fear of or unwillingness to change.
Second, companies often undervalue the impact of good change management and simply don't do enough of it, failing not only to combat the first problem but actually compounding it. When stakeholders do not clearly understand what the plan is, why it is important, how they will be affected, and other key details, the likelihood of failure skyrockets, confusion takes hold, and morale deteriorates.
4. Misalignment of Resources
If you like delays, errors, unexpected expenses, and poor morale, misaligning resources may be one of the best ways to unintentionally sabotage your plans. This comes in a variety of flavors, including not having enough people or budget allocated, having the wrong people or skills involved, bringing resources in at the wrong time, spending money in the wrong places, doing too much at once, and not prioritizing projects and resources for maximum alignment with strategy.
Having been through many strategic plans and transformational projects, I can assure you improper resourcing will always result in a greater cost and negative impact to the company.
5. Lack of Agile Development and Inability (or Unwillingness) to Pivot
Executing a significant strategy shift or transformational project often takes years, not months. Given the fierce competition for market share and the lightning-fast pace of innovation, your strategic plans may be outdated before you've even finished launching.
Leaders who refuse to embrace agile execution will almost certainly find themselves at a competitive disadvantage and at high risk for delays, rework, or completely missing the market opportunity. Leaders must be willing and able to adjust course and adapt during the process of executing their strategy.
6. Lack of Follow-Through and Continuing Improvement
Strategic execution is rarely a one-and-done effort. Failure to complete "day two" items, monitor results, and make continuing improvements has been the death of countless "successful" projects. Too often, senior leaders are eager to move on to the next big thing or bring a premature end to the project funding in an attempt to harvest the savings. Clients don't receive the full benefits promised, shareholders don't see the profits expected, and employees bear the brunt of systems and processes that "almost" do what was intended.
See also: 5 Key Mistakes in Long-Term Planning
Case Studies
1. Early in a career, one might participate in a "paperless transition" project. It could be a significant effort involving new teams, systems, and processes. Imagine the surprise when some teams were using just as much paper as before—and some even more! The capabilities of the new imaging system were not well understood, and some users resorted to printing documents to review, highlight, and annotate. Others were simply uncomfortable or struggled with visibility on their screens.
The problem? Key stakeholders on the front lines weren't properly engaged, and the change management and training were poorly executed. The solution? Additional training and the introduction of portrait-oriented monitors. Only then did paper usage begin to drop, as the mistakes were addressed, and lessons were learned for the future.
2, During the implementation phase, a groundbreaking project delivered a smooth launch of the desired capabilities despite inadequate resourcing. However, despite millions of dollars and years of effort into the project, the resulting sales were well below expectations, and as a result, the platform's costs were unsustainable.
The problem? The original objectives weren't aligned with the mission, and the strategy had been developed in an echo chamber without sufficient input from broader stakeholders. The solution? Because key elements weren't aligned to the core mission, they were repurposed and successfully implemented elsewhere in the organization, and the initiative was closed down.
Turning Strategy Into Results
The ability to make an honest assessment of both your past results and your current situation is the first step to improving your odds of success. Based on statistics about strategic failures, it's almost certain that your organization—no matter how capable—needs improvement in one or more areas. An assessment requires more than a report from the project manager; the C-suite should actively engage with stakeholders at all levels, particularly those on the front lines, along with customers and key partners, to gain an unfiltered, well-rounded perspective.
You may not like what you find—but that's how you learn and adjust.
The challenges of strategic execution are significant, but they are not insurmountable. By addressing common pitfalls—such as misaligned objectives, resistance to change, and inadequate resourcing—you can dramatically improve your chances of success. It begins with a clear vision and actionable objectives, continues with thoughtful planning and agile execution, and demands relentless follow-through and a commitment to continuous improvement.
In a world where technological disruption is rewriting the rules, businesses must rise to the occasion. Strategies that balance ambition with adaptability, supported by strong leaders and engaged teams, can drive transformation and deliver results. The road from vision to victory is rarely straightforward, but with focus, resilience, and the right execution, it is absolutely achievable.
