Artificial intelligence is dominating conversations in boardrooms across the country. CEOs often see it as a transformative tool capable of reshaping businesses, creating efficiencies, and opening new opportunities.
Meanwhile, IT leaders – those responsible for bringing such visions to life – frequently approach AI with caution, aware of the complexities involved in integration, security and scaling.
Dominic Ball is Managing Director at Thinc.
In mid-market companies, where leadership teams are smaller and more tightly connected, one might assume alignment would come naturally. Yet differences in perspective can still stall progress before it begins. CEOs often focus on ambition and opportunity, while IT leaders focus on practicality and feasibility.
Without a shared approach, AI initiatives risk remaining aspirational rather than impactful.
Understanding the evolving IT landscape
The role of IT has fundamentally changed. Once, CIOs held specialized expertise that set them apart. Today, technology is central to almost every aspect of business and leaders at all levels recognize its importance.
At the same time, technology is increasingly familiar to everyone, from smartphones to AI-powered tools, which raises expectations and lowers tolerance for slow or inflexible systems.
In mid-market teams, where skills often overlap and people wear multiple hats, this creates both opportunity and tension. CEOs may have experience with business systems or even basic coding, while IT leaders may have operational experience beyond technology.
But their roles will often mean they get their information and advice from very different places. Without clear alignment, these overlapping perspectives can blur responsibilities and create misaligned expectations.
Building a shared language
Bridging the gap begins with creating a shared language for discussing AI. Leaders need to move beyond abstract notions of “transformation” and focus on specific outcomes that matter to the business.
Framing AI in terms of tangible goals – efficiency gains, improved customer experiences, or enhanced decision-making – helps everyone understand both the ambition and the constraints.
Equally important is transparency around risk and readiness. By openly discussing infrastructure limitations, integration challenges, and workforce capabilities, boards can set realistic expectations without dampening enthusiasm.
IT leaders can play a critical role in translating technical constraints into business terms, while executives can clarify strategic priorities, ensuring everyone is focused on the same objectives.
Creating a practical AI roadmap
A successful AI plan is both aspirational and actionable. Mid-market boards can adopt a phased approach: identifying high-impact opportunities, piloting projects in manageable scope and scaling gradually based on measurable results.
Clear milestones, KPIs and accountability ensure initiatives do not stall, and regular review cycles allow strategies to evolve alongside business needs.
To support adoption, boards can encourage cross-functional collaboration. Bringing finance, operations, marketing, and IT together ensures that AI initiatives are practical, achievable, and aligned with overall business strategy.
Small, cross-disciplinary teams can surface issues early, avoid duplication, and ensure that pilots are designed for success before broader rollouts.
Encouraging cultural alignment
Technology adoption is as much about people as it is about systems. Boards need to foster a culture where experimentation is safe, learning is continuous, and failure is seen as an opportunity to iterate. Leaders can encourage this by championing small wins, celebrating early successes and sharing learnings openly across teams.
When the executive team models curiosity and openness to AI, it sets the tone for the wider organization.
Mid-market companies can also invest in upskilling staff, helping both technical and non-technical team members understand the possibilities and limitations of AI. This shared understanding reduces friction, empowers decision-making and ensures that AI is used effectively across departments rather than siloed within IT.
Turning alignment into impact
The gap between CEOs and IT leaders is real, but it is not insurmountable. Boards that create a shared understanding, define tangible goals, and build phased, measurable plans will see AI move from a buzzword to a practical business lever.
Mid-market organizations, with their lean teams and agility, are uniquely positioned to adopt AI rapidly and scale it efficiently, delivering outcomes that truly matter.
Bridging the divide requires commitment, communication and clarity. It requires executives to appreciate technical realities and IT leaders to think strategically about business impact.
The reward is clear: a board that speaks the same language can turn AI from ambition into action, potential into performance, and ideas into measurable results.
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