Digital Economy Dispatch #251 - Using AI as a Critical Friend: Redefining Strategic Leadership

Just last week, a senior manager confided something to me that would have been unthinkable a few months ago. He had cancelled an expensive consulting contract. His replacement is a combination of ChatGPT, Perplexity, and Claude.

“I get better strategic conversations with AI than I ever got from those consultants.”

He’s not an outlier. Across my various conversations I am hearing of more leaders who are quietly but decisively shifting how they approach their biggest strategic challenges. Instead of relying solely on human advisors, they are finding in AI an unexpected ally: the AI critical friend.

The Rise of the AI Strategic Advisor

From boardrooms to business-unit meetings, executives are increasingly turning to generative AI as a sounding board. They are using it to design strategic plans, stress-test assumptions, explore restructuring options, and model potential business innovations before taking them to stakeholders.

These aren’t one-off experiments. A pharma executive told me she spent an evening “debating” with Claude about whether to pursue a vertical integration strategy. An events and conference leader described how ChatGPT helped him think through the financial implications of entering a new market. An EdTech founder I know has been using AI for months to analyse investment options and anticipate competitor plays as he decides on his next entrepreneurial venture.

The appeal is easy to see. AI is available 24/7. It doesn’t have competing client interests. It processes vast amounts of context quickly and can draw on diverse case studies and business frameworks. Most importantly, it can challenge assumptions without the political sensitivities or hidden agendas that often shape conversations with human advisors.

The “Critical Friend” Concept

The term “critical friend” comes from education and organizational development. As Costa and Kallick put it in their classic 1993 work, “a critical friend is a trusted person who asks provocative questions, provides data to be examined through another lens, and offers critiques as a friend. A critical friend fully understands the context and advocates for the success of the work.” No reason why that “person” can’t be a GenAI tool!

In practice, this use case for AI means the “critical friend” will challenge your thinking without undermining your competence, offer alternative perspectives while respecting your context, and create an environment of intellectual rigour with emotional safety. That combination enables leaders to explore ideas, test assumptions, and admit uncertainties without fear of judgment.

This is exactly the role AI can fill. Unlike consultants, it doesn’t worry about preserving future revenue streams. It doesn’t avoid uncomfortable truths. It doesn’t leak information or use your insights to position against you later. The AI critical friend offers the intellectual challenge of an experienced advisor combined with the psychological safety of a private, judgment-free partner.

The Power and the Risk

The benefits of AI as a critical friend are compelling. Leaders describe how it helps them break through cognitive biases, avoid groupthink, and maintain a clear line of analysis even when the topics are emotionally charged. The iterative nature of the interaction for testing ideas, refining them, then looping back with new data makes it possible to build strategies gradually and flexibly in a way that is often cost-prohibitive with human advisors.

For smaller organizations, the impact is even more significant. Leaders who previously lacked access to top-tier advisory resources suddenly have powerful tools at their fingertips. The result is a democratization of strategic thinking, enabling more diverse leaders to operate with the rigor once reserved for large enterprises.

But risks remain. Strategy is not only about analysis; it is also about people. AI does not know what it feels like to deliver a layoff notice, lose a client relationship, or lead a team through cultural upheaval. As Inc. Magazine warns, “AI can’t apply business judgment” or replicate the human aspects of strategic problem-solving. Leaders who over-rely on AI risk creating strategies that are analytically sound but emotionally tone-deaf.

There is also the danger of homogenization. If every leader uses similar AI frameworks, the diversity of approaches that drives innovation could shrink. Strategy could become standardized at the very moment when differentiation matters most.

Disrupting Traditional Consulting

This shift is reshaping the consulting industry. Strategic work that once demanded weeks of research and six-figure fees can now be handled through iterative AI conversations. Generative AI is transforming consulting by streamlining tasks that once required massive amounts of time and effort for research, analysis, and slide decks. Some have gone so far as to question whether major strategic consulting companies can survive in the age of AI.

This doesn’t make human advisors obsolete, but it does change the nature of their value. AI is increasingly able to take care of the heavy lifting: building initial frameworks, conducting assessments, and mapping scenarios. Human consultants will need to emphasize what machines cannot: the wisdom that comes from industry experience, the power of networks, the craft of implementation, and the delicate skill of navigating organizational politics.

Leading firms are already repositioning themselves. Rather than selling analysis, they are offering facilitation, context, and execution support. As McKinsey research shows, AI “democratizes access to knowledge” and makes sophisticated tools available to organizations that could never afford them before.

The economics are stark. An annual AI subscription costs less than a single day of senior consultant time, yet for many leaders, the quality of insight is remarkably close, especially if they have learned to frame effective prompts.

The Path Forward

AI as a critical friend is not a passing experiment; it is a structural change in how to approach strategic leadership. The leaders who thrive will be those who blend AI’s analytical power with human judgment and empathy. As Stanford research suggests, the most effective executives will be those who apply AI insights while keeping their focus on human-centred outcomes and customer experience.

The future of leadership will not be about choosing between data-driven machines and human wisdom. It will be about combining them, drawing on AI for rigour and perspective, while relying on human insight for empathy and judgment. That balance will define strategic excellence in the years ahead.

As a leader, I encourage you to ask whether you’re using AI in its most effective way and to embrace AI as a critical friend in defining and reviewing your strategy. But as you do so, always remember one thing: leadership itself remains fundamentally, irreplaceably human.