Avoiding Costly Strategic Mistakes
Organizations that thrive on innovation can often end up funding the wrong ideas for too long. When this happens, leaders are left with a flurry of deep dives, hotwashes, and after-action reports to identify why the initiative didn’t land as expected. VPs find themselves counting the zeros of money lost and explaining costly missteps to the CEO. No organization is immune to these unfortunate miscalculations.
A recent example in the private sector is CNN+. The media giant launched a streaming service platform with high expectations and significant investment, only to shut it down within weeks. On the surface, this looks like a failed product launch. But deeper analysis reveals a more important question: Was there sufficient evidence that customers actually wanted a paid news streaming service at that scale?
From a decision standpoint, this highlights breakdowns that should have been identified much earlier. At the front end, questions around problem significance and strategic alignment should have been clearly validated. And during deeper evaluation, the demand environment and stakeholder need should have been tested with stronger evidence before moving forward.
A similar pattern can be seen in the public sector. During the COVID-19 pandemic, California’s unemployment system experienced widespread fraud and operational breakdowns, resulting in billions of dollars in losses. While driven by extraordinary circumstances, it exposed deeper issues and begs the question: Were the risks, system limitations, and scale requirements fully understood before the system was relied upon at that level?
Here again, execution was likely not the core challenge. This situation reflects gaps in early-stage evaluation, where evidence strength and risk considerations were not fully accounted for, and where the operational environment was not adequately stress-tested.
Whether in the private sector or government, the pattern is the same. Decisions to execute are made. Resources are committed, teams are formed, and expectations are set. At this point, the organization is far past evaluating the initiative. It’s now defending it.
This is where most initiatives go wrong. Organizations often have the talent and vision but fail to determine whether an initiative should move forward before it becomes real—when millions, or sometimes billions, are already invested.
In my experience, I’ve seen good initiatives fail because of how decisions are made under uncertainty. The cycle usually goes like this:
Initiatives quickly gain momentum.
They sound promising in a meeting.
They align loosely with strategic goals.
They are backed by stakeholders who feel confident in success.
And before long, the organization moves forward on the initiative, while uncertainty remains.
The repeated pattern of issues I’ve witnessed are:
Initiatives or ideas are framed too broadly, making them difficult to challenge.
Assumptions are treated as facts, backed by anecdotal evidence and not systematic evaluation.
Alignment takes place because the idea sounds like the right move but hasn’t been objectively tested.
And most importantly, there is rarely a clear definition of what success actually looks like.
Once an initiative enters motion, costs begin to compound. We often focus only on financial costs, but organizational costs are just as significant:
Time.
Attention.
Leadership bandwidth.
Opportunity cost.
Every hour spent advancing the wrong initiative is an hour not spent advancing the right one.
So where does this leave us?
If you zoom out, the real issue becomes clear. Organizations have a growing queue of ideas and initiatives competing for attention. The race toward AI adoption and implementation is only accelerating this challenge, increasing the risk of overwhelmed decision pipelines.
Now, more than ever, organizations need discipline at the front end—before execution begins.
Before any initiative is funded, there should be a moment of pause. A structured, deliberate effort must take place to answer a few critical questions:
Is the initiative addressing a problem worth solving?
Do we clearly understand the problem or opportunity?
Who is actually impacted?
What evidence supports this being real and tangible?
What value would be created if we get this right?
Most organizations believe they are answering these questions. In reality, they are often moving too quickly to execution without a systematic approach to validate their answers. This is because speed is rewarded, action is visible, and early skepticism is uncomfortable.
At Strategic Futures Initiative, I’m building a system to help organizations navigate this challenge. Now is the time for organizations to make better decisions in environments defined by uncertainty, complexity, and rapid change.
Today, the cost of poor decisions is increasing. The ability to make high-quality decisions is quickly becoming a competitive advantage. The organizations that will outperform in the coming years will be those that are most disciplined in deciding which initiatives deserve to move forward.
This discipline requires a shift.
Leaders must place equal emphasis on encouraging ideas and evaluating them rigorously. Speed should be rewarded but it must be matched with clarity. A critical shift from assuming value to proving value early must become a standard practice.
Risk cannot be eliminated, but it can be better managed. The goal is to identify weak initiatives before costs compound and to move forward with confidence on those that show real promise.
Consider what happens without a disciplined approach:
Initiatives are funded.
Teams are staffed.
A strategic commitment is born.
At that point, the decision to execute has already been made, whether the organization realizes it or not. Momentum has taken over.
But what if you could apply the brakes early, before momentum makes stopping nearly impossible and becomes costly?
If you could, you would stop funding bad ideas and start scaling the right ones.