The AI Leadership Insights That CIOs Bring to Your Board of Directors

In the first article in a two-part series, Tech Whisperers Podcast Host Dan Roberts shares insights about moving from the “messy middle” of stalled AI initiatives and skeptical stakeholders to driving value while managing risks and building profitable enterprises. Part two  of the series covers how CIOs and other IT leaders can gain traction to lead with clarity, confidence, and conviction in the AI era.

Rapid advancements in artificial intelligence mean many companies are struggling to push through what you might call the “messy middle” of their AI journey. On one end of the spectrum, enthusiastic adopters are rushing to experiment and innovate, but they lack business context, a strategic view, and appropriate guardrails. On the other end, compliance and risk teams may be halting progress with overly robust governance structure and constraints.

As with previous technological disruptions, those organizations that find the right balance will reshape the future of their industries. The laggards — if they survive — will be stuck playing catch-up.

“Enterprise cloud computing emerged almost 20 years ago with Amazon Web Services gaining momentum in 2010; yet in 2025, you can still find companies early in their journey to the cloud that have somehow managed to remain viable,” says former says former CIO Diana McKenzie, now a board member at agilon health, MetLife, Paradox AI, and Vertex Pharmaceuticals. “This is unlikely to be the case with AI. It’s been less than three years since ChatGPT ushered in the era of generative AI. To remain competitive, companies are being challenged to exponentially increase their pace of AI adoption to meet rising stakeholder expectations and that includes their board of directors.”

Why CIOs Belong in the Boardroom

Against this disruptive backdrop, companies are increasingly seeing the value of having technology executives serving on their boards. Chief information officers and other digital leaders can provide the strategic insight and depth of understanding needed to separate the hype from the reality and keep the board focused on business outcomes. This is also why more CIOs and tech-savvy board members are being called on to educate the board, not just advise.

Unlike other CxOs who are often siloed within their function, CIOs are expected to lead the enterprise AI narrative across functions, not just within IT. That means former CIOs bring a unique enterprise-wide view to a board. This is particularly valuable in the context of the AI journey, which needs to be in sync with the company’s broader strategy and objectives in order to drive meaningful business impact.

“The foundational elements required to drive successful digital transformation are similar to those needed to enable successful business-outcome driven AI adoption. As former CIOs, we can partner with the top tech person to help them prepare for their conversation with the board,” McKenzie says. “If you don’t have someone on the board who understands how complex and challenging these transformations really are, it’s just much more difficult for the board to fully appreciate, engage and support the ask of the tech leader.”

To better understand these dynamics, I spent some time talking McKenzie and two other CIOs-turned-board members: Julie Cullivan, board member at Axon Enterprise, Heartflow, Cobalt, and OPSWAT; and Wayne Shurts, who serves on the boards at Armstrong World Industries and Stater Bros. Markets. We discussed their experiences helping companies navigate these complex AI conversations and strategy decisions, as well as some of the key areas of focus for today’s boards.

As I spoke with each of these three leaders, it became clear that, more than navigating change, we’re now navigating compounded risk in uncharted waters. These conversations surfaced an urgent truth: C-suites and boards today have more access to data, tools, and dashboards than ever before, and yet, many feel less confident about what lies ahead. This is partly due to the dizzying pace of AI, but even more so the convergence of risk from every angle. What these CIOs-turned-board members offer is not just fluency in tech, but the pattern recognition, cross-functional mindset, and calm under pressure that boards desperately need to steer through this “messy middle.”

Board Fluency: Closing the Gap Between Hype and Reality

As C-suites muddle through the “messy middle” of the AI journey, they’re often finding themselves either pressured by over-the-top expectations from their board of directors or hampered by the board’s head-in-the-sand thinking. At the same time, many board members lack technical literacy around AI and feel unprepared to oversee AI strategy or risk. CIOs can act as interpreters to connect these strands of risk and opportunity – and encourage board members to acquire experience and education to help themselves. Board members who have served as CIOs, with experience implementing generations of IT strategy, have a built-in advantage in leading board-level AI discussions.

“When we think about how AI is going to affect our future state of business, it shapes the strategy and potentially reshapes the strategy, may even recreate products, go-to-market experiences, re-envision retail, as Walmart's trying to do right now from a risk standpoint,” McKenzie says. There's an offensive component of, What are we doing to make ourselves more robust as we think about how we apply AI? But there's also the defensive component when we think about cybersecurity, for instance. And so that's a huge focus of boards and governance.”

It's not just CIOs, though. McKenzie encourages board members of all backgrounds to take advantage of the many options available to them to become educated on AI, from certification opportunities with the National Association of Corporate Directors to free courses offered by colleges and universities. She’s also adamant that “every board member should be using AI, not just learning about AI from a governance vantage point.”

Board members also need to bring their own experiences, perspectives, and learnings about AI to the table. As Cullivan notes, “Board members aren't just thinking about it as a technology problem. And because of their visibility into what other companies are doing, they often have a network of folks that could be really beneficial.”

Governance and Oversight

Traditional enterprise risk frameworks rarely address AI-specific concerns like model bias, hallucinations, intellectual property liability, model drift, or explainability. This leaves boards grappling with questions such as: Do we need a separate AI committee? Who owns AI risk?

“If you're using AI, you're using it in every function of the business, or trying to use it in every function of the business,” as Shurts says. “If you put it in audit, it's going to get a lot of risk and governance, and ‘don't do this, don't do that’ kind of attention. I think it needs that. But if you put it with the overall board, you'll also get, ‘here are the opportunities over in supply chain, over in sales.’ You'll get more of that innovation piece that comes into it.”

He adds, “In one of our boards, it’s the CIO who is talking about the framework, how they're approaching it, the governance, how he's trying to get it going in different spots. But then, fortunately, we have a lot of the business functional leaders in management talking about how they're looking to apply it, and where they're experimenting, whether that be our general counsel and legal, head of sales, or supply chain. And I think that's the healthiest way to approach it. You get the total engagement across the board from your functional leaders with a framework coming from the CIO, and the CIO always giving them the support and enablement they need to go get it done.”

These board members agreed that a lot of the structuring depends on the company, the industry, and the broader risk profile of the company. For example, some companies have formed dedicated AI committees, while many fold AI discussions into existing technology or risk committees. But McKenzie says, “What I have found to be true in all three boards where I serve, the fulsome conversation of the AI strategy, the risk element, and the talent element is still a board-level discussion. It's still too new, too disruptive and transformative for it to be embedded within any one community committee.”

Regardless of the board’s structure, Shurts emphasizes that balance between risk management and innovation is key: “Five years from now the early explorers are going to be in much better shape than the safe laggards. Put a proper framework and platform in place so that you can govern it properly and eliminate some of the risk. Be careful about where your data is going. But don't be turning off the spigot with governance and risk. The right governance and risk is finding out a safe way to let everybody go, explore, learn, and get into it.”

Ethics and Responsible Use

Boardrooms are being forced to rethink their playbooks on ethics, not because they want to but because they have to. The velocity of AI adoption and the volatility of today’s risk environment leave little room for “wait and see.” Former CIOs bring essential muscle memory here. They know what it’s like to implement new technologies under intense scrutiny, to weigh innovation against liability, and to stay grounded when compliance and reputational risk collide. At a time when leaders are placing massive bets with uncertain returns, their ability to anticipate ripple effects and ask the hard questions early is a boardroom superpower.

With pressure mounting from investors, regulators, and the public around transparency and explainability, boards are feeling an urgency to define ethical boundaries. Lawsuits about AI-infused systems are springing up, from allegations of bias to software being hacked and exposing employees’ personal information. Even when companies are using their own data sets to train AI, they may be inadvertently compounding bias issues if their own performance data is biased.

“There has to be the right ethics framework, alignment, and oversight on these things — and even in what projects you decide to do, because not every idea will end up being a good idea. Not every idea, once you dig into the details and data, will end up being an ethical idea,” Cullivan says. “There's so much unknown, and with all good intentions, something could introduce risk to the organization.”

As for how to tackle it, she says, “I think every company is approaching it a little differently. In public board structures, it naturally feels like it needs to be in audit in some way. I think some companies recognize, you can continue to put emerging technology risks in audit, but will it get the focus that it needs there? So it’s about just making sure that there's recognition that the right attention and the right focus is given to make sure that something doesn't get missed.”

The key factor, Cullivan says, is strong board attention to responsible AI use, “so it’s making sure you have a high functioning board that is aware of those, that there's the opportunity to make sure things aren't getting missed, and that, regardless of the committee charters, the full board is engaged.”

Future-Ready Talent and Leadership

As is well documented, AI is reshaping entire organizations and demanding new skills sets, both technical and, especially, soft skills. As Cullivan puts it, “It's an opportunity to rethink just about every job in the organization from a perspective of, what we need today may not be what we need in the future.”

In today’s environment, workforce strategy is risk strategy, and this is where CIOs bring unmatched insight. According to a May 2025 Kyndryl  study , while most companies are investing in AI, 71% say their workforce isn’t ready, and 60% admit their culture isn’t either. These aren’t technical gaps, they’re leadership gaps. CIOs-turned-board members have lived through the messy middle of transformation, where trust is fragile, fear runs high, and change fatigue is real. They’ve led organizations through disruption with empathy, not just efficiency. Now, from the boardroom, they’re sounding the alarm: If you aren’t intentional about building trust, shifting mindsets, and preparing your people to operate at the speed of AI, no amount of AI spend will deliver impact. Emotional intelligence, communication, and cultural fluency aren’t soft skills; they’re the power skills for AI readiness.

McKenzie says boards need to make these workforce planning conversations a priority. “How many people will we need? What will the jobs look like? How will we keep our engagement scores high if employees are worried their jobs will be replaced by AI? How are we training and engaging them in the changes we are making? Those are big questions, and, as we all know, talent is everything. To remain relevant in the board room, board members regardless of their background are increasingly recognizing the importance of investing in continuous AI governance and literacy education.”

It's also important to bring together all the necessary leadership players. “This is a great time for the HR leaders in an organization to partner with their tech leaders, and then, collectively, have this ‘power couple’ help the business leaders understand what the potential is for rethinking their organization, and also make sure there are development and educational programs that help the employees modernize their own skill sets and get on board with using the capabilities of AI,” McKenzie says. “If that happens, there will be a strategic and proactive approach to the way the company's preparing itself for what it could look like in the future with AI. That is the level of leadership that needs to be demonstrated inside a company to get a handle on the talent.”

Cullivan believes leadership on this is critical: “Having the right technology leadership and open-mindedness is the key, because I do think this is one of the first times that you see purely technical roles being challenged with technology. Before it was, this improves my productivity, or it helps me do things more quickly. It wasn't, this is now potentially as smart as I am, if not smarter, and I need to embrace it and figure out how I get on board with it. This is about innovation and thinking about things totally differently than you ever thought about before. The more people are involved and informed upfront in the change process, the more they will feel engaged and that they have some opportunity to influence how their job might look going forward.”

AI Investment vs. Impact

While most companies are investing in AI, few are measuring ROI or scaling effectively. Boards are pushing for value-based outcomes, not just pilots and experiments.

In today’s boardrooms, a “Tale of Two Boards” is playing out. One side is panic spending, chasing AI without clear metrics or readiness, afraid to be left behind. The other is over-cautious, stalling innovation out of fear and risking irrelevance. The real challenge? Navigating that messy middle, where ambition outpaces execution, and hype drowns out strategy.

This is where CIOs-turned-board-members step in as Goldilocks leaders, not too hot, not too cold, but calibrated to get it just right. They’ve lived through digital transformations, cloud migrations, and cybersecurity upheavals. They know how to pace investments, pressure-test assumptions, and align tech bets to business outcomes.

The magic happens when these leaders help boards move from confusion to clarity, from the messy middle to what I call the magic middle—the sweet spot where innovation and governance are in sync, pilots scale with purpose, and AI delivers real enterprise value. In a world full of extremes, CIOs have a golden opportunity to guide the way toward balanced, bold, and measurable progress.

When it comes to making smart investments, Shurts recommends distinguishing between generic AI tools and proprietary, business-specific innovations: “Don’t go invent your own AI for those kinds of [generic] things. Use the tools that are out there. But then there are the really transformational, important, specific to your strategy and your business uses of AI. That’s where you want to invest your own IP.”

Principles are principles, though, and from an ROI standpoint, McKenzie argues that the way we measure AI investment and impact is no different than the way we’ve always measured ROI, with “evangelization from the CEO down and a support structure in place to ensure the change management and incentive systems allow for the thoughtful risk-taking and learning that is associated with these initiatives,”

She adds, “The teams that are going to be good at this are the ones that have already shifted to an agile, product-focused way of working collectively between tech and the business and can clearly define how outcomes will be measured. Within the first few weeks following the initial deployment they should be able to assess, adjust, and iterate where necessary to ensure they are progressing toward achieving the desired outcome.”

Getting the Board’s Culture Right

AI has ushered in a new and accelerated disrupt-or-be-disrupted era, but the fundamentals remain the same. Like any successful technological transformation, the journey hinges on your people — from the boardroom to the front lines.

Culture is the ultimate risk amplifier or risk mitigator. In this era of AI-fueled disruption, boards need members who understand how technology, trust, and transformation interact. That’s where seasoned CIOs come in. They’ve guided organizations through digital upheaval and resistance. They know how to shift mindsets without breaking morale. As boards confront the rising tide of uncertainty, these leaders bring not just tech fluency but the cultural EQ to help organizations adapt without losing their people, their minds, or their soul.

“When I think about it in terms of the change management, it’s really assessing whether you have the right people in the broad organization,” Cullivan says. “I'm not talking about IT. I'm not talking about engineering. I'm talking about the broad organization, making sure you have the right executive and leadership team. They don't have to be experts in AI, because, frankly, there aren't that many out there, but they need to be open to rethinking everything now.”

As experienced CIOs understand, being comfortable with change — being open to rethinking everything — is not a new directive. It’s a way of life. And in these still-early days of AI adoption, these CIOs-turned-board-members are seeing this as a once-in-a-generation opportunity for IT leaders like themselves to make a difference in the boardroom.

“I think it is a tremendous opportunity for CIOs to really show themselves as businesspeople and the value they add,” says Shurts. “We used to complain about not having a seat at the table. Well, this is the perfect opportunity to have that seat and help your organization understand AI, where to use it, and how to govern it, and to facilitate that across the organization. I would encourage CIOs not to want to control it. You want to facilitate it and let it get legs within the business.”

Here’s the uncomfortable truth: Boards today aren’t just wrestling with their AI journeys. They’re also facing compounded risk, from cyber threats and regulatory uncertainty to workforce transformation, governance gaps, brand trust, and ethical landmines. And even though leaders have more dashboards, data, and decision support tools than ever before, many feel less prepared than ever to anticipate what’s next or steer confidently through it.

Those realities and these conversations underscore the value of having CIOs in the boardroom, and not just for their technical expertise. Their cross-functional view, pattern recognition, and change leadership instincts make them uniquely suited to help boards navigate this moment of unprecedented complexity. Directors who’ve lived in the messy middle, who’ve had to balance innovation with accountability, speed with safety, and vision with execution are no longer a nice-to-have. They’re a boardroom imperative.