4. When You're Too Invested to See Clearly

Author:
Märt Ostra
Date:

September 5, 2026

There's a moment in almost every troubled transformation when the evidence becomes undeniable. The timelines are slipping badly. The costs are escalating in ways that weren't anticipated. The promised benefits aren't materializing. The team is exhausted. The business is getting restless. Anyone looking at the situation from the outside would say 'stop, reassess, change course.'

And yet the organization doublesdown. More resources. More time. More patience. Because they've already spent so much that stopping feels like admitting it was all a mistake.

How Sunk Cost Thinking Takes Hold

Sunk cost thinking is particularly powerful in high-visibility transformations because the personal stakes are so high. The executives who championed the initiative have their credibility tied to its success. The project team has worked evenings and weekends for months. The board has been briefed on the expected returns. Admitting that things are fundamentally off track requires an uncomfortable conversation with each of these audiences.

So instead, the problems get reframed. The delays become 'we're being thorough.' The cost overruns become 'we're investing in doing this right.' The missing benefits become 'we haven't fully activated the system yet.' Every piece of bad news gets a narrative wrapper that makes continuing seem more reasonable than stopping.

Warning Signs That You're in the Trap

- The official project status is green or amber when everyone on the project team knows it's red
- Key decisions that should have been made months ago keep getting deferred because there's no consensus on the right answer
- The business case has been revised multiple times to account for delays, but each revision assumes things will start going better from here
- People are afraid to surface problems because previous problem-raisers were seen as being 'not committed to the project'
- The original sponsor who championed the initiative is no longer actively engaged but also hasn't formally handed off accountability

What Breaking Out of It Requires

The single most important thing is creating a mechanism for honest assessment that isn't controlled by the people most invested in the outcome. This might be an independent project review. It might be a board-level conversation that goes beyond the usual status reporting. It might be bringing in an outside perspective specifically tasked with finding what isn't being said.

That assessment needs to answer a clear question: if we were deciding today, with everything we know, whether to start this initiative, would we? If the answer is no, or even a heavily qualified yes, that tells you something important about whether continuing is actually the rational choice.

Changing course takes courage. It requires leadership that can separate the decision from the identity, and that can communicate a change of direction without it being perceived as failure. Those things are hard. But they're far less damaging than years more of investment in something that was never going to deliver what was promised.

The best time to ask whether you're in the sunk cost trap was six months ago. The second best time is today.

New way for knowledge transfer

We have created an interactive newsletter experience where our experts share real-world insights, proven strategies, and hands-on tasks you can apply right away. Each month brings a new topic and focus, giving you practical knowledge and actionable takeaways - all in one powerful learning journey.

Our topic in July 2026 is Fundamentals First: Most transformations don't fail because the technology was wrong. They fail because the foundation underneath it was never solid. This category is about the unglamorous work that determines whether everything else succeeds - fixing broken processes before you automate them, understanding what readiness actually requires, getting your data into a state you can trust, and making sure your senior leaders are genuinely aligned, not just publicly supportive. None of it is exciting. All of it is necessary.

July 2026

Topic: Fundamentals First

We have created an interactive newsletter experience where our experts share real-world insights, proven strategies, and hands-on tasks you can apply right away. Each month brings a new topic and focus, giving you practical knowledge and actionable takeaways - all in one powerful learning journey.

Our topic in August 2026 is The Cost of Blind Trust: Optimism is useful until it becomes expensive. This category is about what happens when hope and faith replace rigorous scrutiny - in how you plan, in how you select vendors, and in how you evaluate whether an initiative is actually on track. Vendors are incentivized to keep you excited. Sunk costs are incentivized to keep you committed. Neither of those forces is working in your interest. Learning to ask harder questions, earlier, is what separates transformations that deliver from ones that just consume budget.

August 2026

Topic: The Cost of Blind Trust

We have created an interactive newsletter experience where our experts share real-world insights, proven strategies, and hands-on tasks you can apply right away. Each month brings a new topic and focus, giving you practical knowledge and actionable takeaways - all in one powerful learning journey.

Our topic in September 2026 is Know Your Scale: The most underestimated risk in any transformation isn't technical - it's scope. Organisations consistently underestimate how far the change actually reaches, what a successful pilot really predicts, and how long it takes people to genuinely adopt a new way of working. This category is about doing the honest math before you commit to a plan, mapping the full blast radius of the change, understanding what pilots do and don't tell you, and building an approach that's actually sized to the transformation you're undertaking, not the one you wished you were.

September 2026

Topic: Know Your Scale