Credit: Kris Besley Caption: Kris Besley
In the high-stakes arena of enterprise change, where billions in capital and countless careers hinge on the outcome, failure is a familiar specter. Conventional wisdom points to flawed execution as the primary culprit. Yet, according to strategic advisor Kris Besley, this diagnosis misses the mark. The true fracture point, he argues, occurs long before the first initiative is launched. It occurs in the often overlooked, deeply human realm of readiness.
That belief is deeply personal. When Besley left his previous role just over a year ago, it followed nearly three decades immersed in the startup world. Since the mid-1990s, he has operated almost nonstop inside high-growth, high-pressure environments. Sixteen-hour days were routine. Sleep was fragmented and negotiated around meetings. For years, intensity was not the exception; it was the operating model.
Throughout his career, Besley has been a builder by instinct. He architects, executes, and thrives in complexity. Maintenance, he jokes, has never been the work that energizes him. Instead, he gravitates toward chaos, the unresolved problems, the pressure points, the moments where systems strain. That same instinct, sharpened by decades of frontline experience, ultimately led him to challenge one of enterprise transformation’s most persistent assumptions.
Besley, founder of the Akahai Group, has built his career navigating the turbulent waters of complex organizational transformation. His experience has led him to a singular, compelling conclusion: most change does not fail in execution it fails in readiness. This readiness, however, is not merely a function of meticulous planning and Gantt charts. It is, fundamentally, about people. It is the cultivated confidence to make hard decisions when data is incomplete, the forged alignment that allows a team to move as one entity under pressure, and the clarifying vision that guides leadership through inevitable uncertainty.
This philosophy forms the bedrock of Akahai Group, which Besley describes as a strategic navigation partner. The firm operates on the premise that while market shifts, technological disruption, and competitive pressures are inevitable, an organization’s preparedness to meet them is a deliberate choice. Akahai’s methodology is designed to architect this choice, helping clients traverse periods of intense pressure and complex transformation with what Besley terms “structure that holds, clarity that connects, and leadership that feels human.”
The distinction Besley draws is critical. Many consultancies provide a rigid structure a framework of steps and stages. Akahai seeks to build an adaptive structure, one robust enough to provide stability yet flexible enough to withstand the human and operational tremors that accompany real change. The “clarity that connects” speaks to moving beyond communicating a plan to embedding a shared purpose, ensuring every layer of the organization understands not just what they are doing, but why it matters within a larger narrative.
Perhaps most resonant in today’s climate is the concept of “leadership that feels human.” In an age of remote work, digital fatigue, and societal flux, the traditional, stoic command and control model often fractures. Besley advocates for a model where leaders are equipped to acknowledge complexity, demonstrate vulnerability where appropriate, and connect with their teams on a level that transcends quarterly targets. This human centric approach is not about softness; it is about building the psychological safety and trust that fuel resilience, innovation, and decisive action when it matters most.
Besley’s services, encompassing business and management consulting, pricing strategy, and non profit guidance, are unified by this readiness principle. For a commercial entity facing a pricing model overhaul, readiness might involve aligning sales, finance, and product teams around a value-based narrative before a single calculator is touched. For a non profit embarking on a digital transformation, it might mean first ensuring board and stakeholder alignment on the core mission imperatives the technology will serve, thereby preventing the initiative from devolving into a mere IT project.
The implication of Besley’s work is a subtle but powerful reframing of leadership responsibility. It suggests that the primary task of a leader steering change is not to be the first to see the future, but to be the most diligent in preparing their people to journey toward it. It shifts the investment from solely external analysis to internal capacity building, from a focus on the destination to a mastery of the collective mindset required for the voyage.
In a business landscape characterized by perpetual volatility, the quest for a sustainable competitive advantage continues. Kris Besley posits that this advantage may increasingly be found not in the agility to pivot, but in the profound readiness to do so effectively. It is the difference between being reactive and being resilient, between merely announcing change and truly embodying the readiness to embrace it.
Because as Besley succinctly frames it, change is inevitable. Readiness is a choice. And in that space between inevitability and choice, he believes, lies the ultimate determinant of an organization’s fate.
