In a recent LinkedIn post, John Cutler discusses a common and costly form of organizational waste: senior leadership offsites that conclude without addressing the core issues, often referred to as “elephants in the room.” Cutler, a prominent voice in product management and organizational design, argues that the pressure to appear actionable can lead to superficial alignment and ultimately undermine durable planning.
The post details a scenario familiar to many in the corporate world. After intense discussions on the first day of an offsite, the group reconvenes on day two, eager to finalize a plan. However, Cutler suggests that this eagerness to become “actionable” often comes at the expense of truly grappling with uncertainty and divergence.
“One of the most costly forms of waste is when companies bring together senior leaders, at massive expense, and they walk away with the elephants still in the room.”
The Peril of Premature Actionability
Cutler highlights the common trap of moving towards action before foundational alignment is achieved. He describes how, after a day of diverging and converging ideas, a valid concern might be raised, leading to a “performative show of alignment” as the day ends, often fueled by informal discussions over dinner.
The real issue, according to Cutler, arises on the second day when the drive for action takes precedence. He posits that this push for immediate action, often driven by individual agendas or the need to produce documentation, leads to decisions based on “shaky foundations.”
“But someone thought it was time to be ‘actionable.’ Someone had an agenda. Someone had a doc to write.”
John Cutler argues that this premature move towards action initiates a detrimental cycle.
The Downward Spiral of Poor Alignment
As John Cutler explains, the consequences of acting on incomplete or unaddressed issues are severe. This leads to a “terrible cycle of poor alignment, back-channeling, and never really forging a durable plan that can withstand the inevitable shifts.” The focus shifts from strategic clarity to the mere completion of tasks, such as finalizing OKRs, rather than building a robust strategy.
The Illusion of Progress
Cutler points out the ironic outcome: “But oh boy, the OKRs are done! Back to work!” This signifies a superficial win – a plan or set of objectives is completed – but the underlying strategic challenges remain unresolved. Leaders then depart, only to revisit similar surface-level issues in future offsites, perpetuating the cycle.
In John Cutler’s view, the key takeaway is the importance of “staying in the uncertainty” and resisting the urge to force an actionable plan before the underlying complexities have been fully explored and understood. True progress, he suggests, requires patience and a willingness to confront the difficult conversations, rather than settling for the appearance of alignment.
📝 About This Content
This article is based on insights shared by John Cutler on LinkedIn.
📅 Originally posted on January 11, 2026 | View original post on LinkedIn →