The Art of Not Killing a Project: Navigating the Fine Line Between Risk and Reward

Killing a project is easy. There’s a laundry list of reasons why something “shouldn’t move forward”: it’s too expensive, not aligned with strategy, lacks clear ROI, or simply isn’t the “right time.” Most organizations are primed to find these flaws—whether it’s a risk-averse culture, overly legalistic thinking, or a fear of failure.

But what about spotting the hidden gems, the black swans no one else notices? What about that underappreciated asset that, with the right approach, could become a game-changer? How do you acquire it at a reasonable price and make it work, especially when resources are tight, timelines are short, and uncertainty reigns?

The Culture of Saying No

Let’s start with the reality: it’s far easier to justify killing a project than pushing one forward. Decision-making committees are often filled with people whose job it is to find faults—lawyers looking for risks, finance folks looking for cost overruns, strategists looking for misalignment. These concerns are valid, of course, but they also create an environment where saying “no” feels safer than saying “yes.”

Even in forward-thinking organizations, there’s often an unspoken culture of analysis paralysis. Teams screen dozens, if not hundreds, of opportunities to hit an arbitrary KPI (“we evaluated X number of assets this quarter!”). The result? Overworked junior colleagues drowning in spreadsheets and due diligence reports, deals that never make it past the starting line, and a lot of talent walking out the door, burned out by the grind.

The Challenge of Spotting the Black Swans

Here’s the paradox: the assets that change the game are often the ones that don’t fit neatly into the usual frameworks. They’re the risky, unconventional, or undervalued opportunities that most people overlook.

But how do you spot a black swan when most processes are designed to flag risks, not opportunities?

• Look for the Outliers: The asset that doesn’t quite fit the mold might be worth a second look. Why isn’t anyone else seeing its potential?
• Challenge the Assumptions: What if the reasons to kill the project aren’t as fatal as they seem? Could new technology, partnerships, or market conditions turn the tide?
• Keep an Open Mind: This is easier said than done, especially when you’re under pressure to meet set targets. But sometimes, the key is being willing to embrace uncertainty.

I once had dinner with a senior executive who shared an excellent example of this. She was asked how she justified attending certain conferences or meetings and how she measured success. Her cheeky (but spot-on) reply? “I can tell you once a deal goes through whether that meeting was successful.”

She’s absolutely right. You can’t always predict which connections, conversations, or seemingly insignificant insights will lead to something meaningful. Staying open-minded is crucial—but it’s hard to quantify, and even harder to defend in a results-driven environment.

The Art of Decision-Making

At the heart of all this is the fundamental challenge of decision-making. There’s never a perfect moment to commit. The data will always be incomplete. The risks will always be real. The confidence intervals will always have gaps.

So how do you move forward when there’s no guarantee of success?

1. Develop Better Tools: It’s not about evaluating more projects; it’s about evaluating them better. Use tools that help prioritize what’s possible and weigh risks against potential rewards in a meaningful way.
2. Accept Uncertainty: Especially in early-stage assets, you’ll never have all the answers. The key is to make the best decision with the information available—and be prepared to adapt.
3. Focus on Strategic Fit: Not every asset is a black swan, and not every deal needs to happen. The art lies in identifying what aligns with long-term goals, even if the short-term metrics are fuzzy.

Balancing Targets with Open-Mindedness

The tension becomes especially acute when you’re operating under set targets. You need to deploy capital, find assets, and close deals—yet maintaining an open mind is critical to finding the right opportunities.

The answer? It’s complicated. And frustrating. But perhaps the best approach lies in balancing discipline with flexibility:

• Discipline to focus on what matters, prioritize effectively, and avoid chasing every shiny object.
• Flexibility to embrace serendipity, adapt to changing circumstances, and pursue the unconventional when it feels right.

Courage in Complexity

The art of spotting—and not killing—a promising project is as much about courage as it is about analysis. It’s about being willing to take calculated risks, challenge the status quo, and make decisions in the face of uncertainty.

Yes, there will always be reasons to say no. But there will also be those rare, transformative opportunities that only reveal their value to those who dare to look beyond the obvious. And sometimes, just sometimes, saying “yes” to the right opportunity is what makes all the difference.