AI recruiting: five questions to ask before hiring a strategist

Over the past 18 months, AI has shifted from an experimental tool to a core driver of enterprise value creation. Corporations, private equity firms and their portfolio companies are increasingly looking for leaders who can translate the promise of AI into measurable operational impact.

At our firm, we began building an AI strategy search practice focused on placing leaders who sit at the intersection of strategy, data science, technology and enterprise transformations.

As a result, we’ve had the opportunity to evaluate hundreds of candidates tasked with helping transform organizations with AI-enabled solutions. One insight has become clear: Not all AI leaders are built the same.

Some excel at building prototypes or playbooks, while others understand enterprise integration into existing business/industry processes. An even smaller subset can directly connect AI deployment to EBITDA impact and enterprise value creation.

To help distinguish between these profiles, we incorporate specific questions during our screening process to help determine where candidates succeed and where they may fall short.

These questions help to reveal whether a candidate can move beyond experimentation and drive true AI transformation:

How do you build and deploy AI solutions within an organization?

Many candidates can describe how they built proof of concept or MVP. Few understand what it takes to integrate AI across an enterprise. Deploying AI at scale requires more than understanding how to “vibe code” with an AI agent.

The leaders who stand out understand that AI implementation is an organizational challenge as much as a technical one. They can articulate how to bridge the gap between executive stakeholders, product teams and engineering organizations to move from experimentation to deployment.

This process requires an understanding of how to integrate solutions with existing technology infrastructure, manage data pipelines, adhere to governance frameworks, drive stakeholder alignment and ensure adoption across operating units.

If you think 12 months ahead, who will be the biggest winners and losers as AI adoption accelerates?

AI is evolving at an extraordinary pace. Leaders in this space must possess a strong degree of intellectual curiosity and market awareness. This question reveals how candidates think about the competitive landscape and technological trajectory.

Strong responses demonstrate a clear view of how AI could reshape specific industry economics, awareness of emerging platforms and thoughtful perspectives on where incumbents may struggle to adapt. The most compelling candidates anticipate how AI will reshape competitive dynamics across industries.

How do you measure the impact and ROI of the AI solutions you have deployed?

There is broad consensus that AI will unlock significant productivity gains and revenue opportunities. However, measuring the financial impact of AI initiatives can be surprisingly complex.

For private equity investors in particular, the ability to quantify value creation is critical. Leaders who understand how to connect AI initiatives directly to financial performance are far more effective partners to executive teams and boards.

Top candidates can clearly explain how they track revenue uplift from AI products as well as incremental EBITDA impact tied to AI deployments.

What are the most innovative applications of AI you have seen so far?

Today, nearly everyone is familiar with the basic applications of large language models: summarization, research, task assistance and workflow automation. But the real opportunity lies in applications that fundamentally reshape how businesses operate.

This question helps surface candidates who can think beyond conventional use cases. The strongest leaders demonstrate the ability to reimagine workflows using AI-native processes, combine multiple AI tools to unlock new capabilities and apply AI in ways that competitors have not yet considered.

What are your views on AI governance for an organization undergoing transformation?

AI adoption is accelerating faster than regulatory frameworks can keep pace. Organizations implementing AI today must navigate a landscape where legal, ethical and compliance considerations are still evolving.

Effective AI leaders recognize that governance is an essential foundation for scaling responsibly. We look for candidates who can thoughtfully address responsible AI usage, internal policy, data privacy, security, transparency and risk management.

Leaders who understand governance can design systems that allow companies to move quickly today while remaining adaptable to future regulations.

The future of AI leadership:

Execution will replace experimentation as the next era of AI strategy, and organizations that combine strong technological capabilities with leaders who can operationalize AI across the enterprise and translate innovation into measurable value creation will have the greatest impact.

Over the past 18 months, our AI strategy search team has focused on identifying exactly these types of individuals capable of bridging the worlds of strategy, technology and enterprise transformation.

As AI continues to reshape industries, the demand for this hybrid leadership profile will only accelerate. For companies looking to turn AI from a concept into a competitive advantage, asking the right questions is a good place to start.