In a recent LinkedIn post, Greg Head discusses a crucial shift he observed in evaluating candidates for COO positions, highlighting how traditional management skills are becoming more valuable than pure technical implementation, especially in the context of AI deployment.
Greg Head presented a scenario involving two COO candidates with similar backgrounds. The first candidate focused heavily on the AI tools they had deployed, naming specific vendors and the technologies used. This approach, according to Head, emphasized implementation skill but missed a more critical aspect of leadership.
“The first walked through the AI tools deployed at their last company. There were six of them and the candidate named the vendors.”
In contrast, the second candidate offered a different, more impactful narrative. This individual detailed the implementation of a forecasting model, critically including its failures, the associated costs, and, importantly, the lessons learned. They explained how they identified the errors, corrected them, and refined the review process before customer delivery.
“The second described a forecasting model they had put in, and what it did to the numbers. Then the three times it was wrong and what each one cost. They went on to describe how they caught each one and what they changed about who reviewed the output before anything went to a customer.”
This distinction, as Greg Head points out, is where the real value lies. The second candidate demonstrated a deeper understanding of management’s core responsibilities: evaluating work not personally produced, deciding when to delegate, and knowing when to intervene or override decisions.
The Shift from Implementation to Management Acumen
Greg Head argues that this ability to manage and de-risk is the truly scarce competency in today’s business environment. While the technical skills to implement AI tools are becoming more widespread, the capacity for strategic oversight, critical evaluation, and adaptive problem-solving remains paramount.
“None of that is a new competency. It is the oldest thing in management. What changed is that it’s now the scarce one while pure implementation skill is not.”
This is particularly relevant in the private equity (PE) world, which often seeks operators who can effectively manage risk and accelerate growth. As Head notes, the second candidate implicitly answered the core PE question before it was even asked.
De-risking Investments and Accelerating Exit Velocity
The post emphasizes that effective leadership isn’t just about adopting new technologies; it’s about understanding their impact, anticipating potential failures, and building robust processes to mitigate risks. The second candidate’s detailed account of errors and corrections showcased their ability to learn and adapt, thereby demonstrating a clear path to de-risking the investment and improving the company’s trajectory.
Greg Head’s analysis suggests that while a familiarity with AI tools is becoming standard, true leadership in operations—especially at the COO level—is defined by the ability to manage complex processes, learn from mistakes, and make sound decisions under pressure. This core management skill, honed over decades, is what truly sets candidates apart and signals their potential to drive significant business impact.
📝 About This Content
This article is based on insights shared by Greg Head on LinkedIn.
📅 Originally posted on September 30, 2026 | View original post on LinkedIn →