When Does “Strategic Fit” Actually Destroy Value?

One theme that stood out to me across this module is that strategic fit alone does not guarantee value creation—and in some cases, it may actually increase the risk of value destruction.

For example, the Air India–Indian Airlines merger had a strong strategic rationale on paper (scale, network integration, national carrier ambition), yet it failed due to cultural incompatibility, HR misalignment, and poor execution. Similarly, Polycom’s success with small, capability-driven acquisitions did not translate to larger, more complex deals, revealing limits to an otherwise sound acquisition strategy.

By contrast, transactions like Gallagher’s acquisition of AssuredPartners show how disciplined integration, decentralized operating models, and alignment with core capabilities can allow strategic fit to translate into real value—especially in regulated, relationship-driven industries.

My question for the group:
At what point does strategic fit become a red flag rather than a strength?

Are there warning signs that a “logical” deal is actually too complex to execute?

How should buyers adjust diligence and integration planning as deal size and complexity increase?

I’m curious how others weigh strategic logic versus execution risk when evaluating M&A opportunities.