Crucial Conversations:

How to Achieve

CIO-CEO Alignment

in the Era of

AI

Crucial Conversations:

How to Achieve

CIO-CEO Alignment

in the Era of

AI

Key Findings for CIOs

A positive CEO-CIO partnership can drive the enterprise forward, making it faster, smarter, and more competitive. A dysfunctional relationship that's rooted in misaligned thinking, however, will only result in inertia.

Misalignment at the top

31% of CIOs aren't confident they know what their CEO really wants and 34% don't feel empowered to make long-term strategic calls.

Modernization funding falling short

Only one in three CIOs (36%) think their business is investing enough in modernizing their IT infrastructure. Two-fifths (41%) say their business isn't investing enough (while 23% aren't sure).

Innovation disconnect

CEOs worry that their CIO is too eager to adopt emerging tech without fully weighing costs or disruption. But CEOs are giving CIOs a double-edged innovation mandate: Integrate AI to drive measurable business value, while also cutting costs and acting as gatekeepers against overspending.

CEO & CIO Perspective

The dynamic between CEOs and CIOs is crucial for organizations precisely because of tech's critical role at the heart of modern business.

The CIO commands a broad and wide-reaching view across a business's operations, while also being hyper-focused and in possession of in-depth insights. These combined perspectives are uniquely valuable to a CEO."

Kirk Ball - CIO, Worldpay

The more proactive, consistent, aligned and priority driven the CIO and their teams are, the less "air gap" between IT and the business."

Paola Arbour, EVP and CIO, Tenet Healthcare

So what's a CIO to do?

The answer, for those IT and digital leaders who want to deliver a modernization agenda that supports business growth, is to forge a more productive CEO relationship grounded in clearer communication and shared perspectives.

CIOs must crack the code in three key areas:

Better understand what CEOs really care about
Know which conversations it is critical to have with the CEO
Take the right approach to those discussions to drive optimal outcomes

Six Crucial Conversations

We've identified six crucial conversations that regularly take place between CEOs and CIOs—the places where, metaphorically speaking, the rubber hits the road.

[The CIO] was our BS meter. Somebody would come in and want to charge us the sun and moon. He'd go: 'Let's rewrite it this way, or give them a specific list of things.'"

CEO, U.S., Apparel/Fashion

Conversation one:
Cost

The CEOs we spoke to admitted to a degree of uncertainty when it came to scrutinizing and approving IT investment.

[The CIO] was our BS meter. Somebody would come in and want to charge us the sun and moon. He'd go: 'Let's rewrite it this way, or give them a specific list of things.'"

CEO, U.S., Apparel/Fashion

Conversation starter tip

Our current infrastructure limits our agility more than it enables it. I'd like to walk you through a modernization path that creates more flexibility, security, and cost control.

CEOs are typically focussed on the fundamentals. They can be disconnected from the tech—and don't always know the right questions to ask."

Jim Clark, Strategic Insights Director, Econsultancy

Conversation two:
Risk

CEOs want a "trusted lieutenant" in their CIO. Someone who makes sensible decisions, knows when to escalate and report emerging issues, and is aligned on shared goals.

Trust is currency. We must ensure our CEOs understand not just that we're secure, but how security supports resilience, reputation, and regulatory alignment."

Louise Leavey, CIO (financial services)

Innovations need to occur within the business's existing focus areas. It's the job of the CIO to enable a safe, sound and secure environment to experiment and innovate, but most importantly to also fail safely and capture learnings fast."

Pascal Boillat, former Group CIO, Commonwealth Bank and Deutsche Bank, and currently COO, LSEG

Effective innovation always starts with a use case, rather than a technology."

Ian Golding, Chief Digital and AI Officer, TC Group

Conversation three:
Innovation

For some CEOs, "innovation" can be viewed as another word for "complexity," which increases costs and raises risk levels.

Innovations need to occur within the business's existing focus areas. It's the job of the CIO to enable a safe, sound and secure environment to experiment and innovate, but most importantly to also fail safely and capture learnings fast."

Pascal Boillat, former Group CIO, Commonwealth Bank and Deutsche Bank, and currently COO, LSEG

Effective innovation always starts with a use case, rather than a technology."

Ian Golding, Chief Digital and AI Officer, TC Group

CIOs and CHROs can form a powerful partnership in co-owning how AI integrates into work, culture, and talent strategy. It's not just tech or people anymore; it's both, intertwined."

Joe Topinka, founder and CEO, CIO Mentor

Conversation four:
People

CEOs want their CIO to take the lead in evaluating opportunities with AI to understand where organizational efficiencies can be found that will materially impact the Human Capital Plan.

CIOs and CHROs can form a powerful partnership in co-owning how AI integrates into work, culture, and talent strategy. It's not just tech or people anymore; it's both, intertwined."

Joe Topinka, founder and CEO, CIO Mentor

Conversation starter tip

As AI scales, we'll need a clear plan for where it creates capacity, where it complements people, and where we need to reinvest in skills. Let's map that together.

You have to be aligned with business metrics, because your relationship with the CEO will be based on how relevant and impactful your function is."

David Smoley, former Global CIO, AstraZeneca and Flex

Conversation five:
Measurement

CEOs confess that their lack of technical knowledge makes measuring the performance of the technology strategy difficult. This situation is only getting more challenging with the pace of modern AI development.

You have to be aligned with business metrics, because your relationship with the CEO will be based on how relevant and impactful your function is."

David Smoley, former Global CIO, AstraZeneca and Flex

The CIO is responsible for aligning the IT team's objectives with the business objectives.

CEO, India, Pharma

At some point, aging systems pose unacceptable risks to the organization, and you must decide when to invest in modernization. Ideally, you introduce a new capability that also eliminates a legacy system."

Danyel Bischof-Forsyth, CIO, 7Brew

Bad news isn't like wine; it doesn't age well. The sooner we know, the sooner we can respond."

Mike Anderson, Chief Digital and Information Officer, Netskope

Conversation six:
The IT Estate

There's a sense among many CEOs that the IT function is a "black box" that they don't understand. Sometimes they feel their CIO doesn't enable or allow them to peer inside it, which can cause suspicion and frustration.

At some point, aging systems pose unacceptable risks to the organization, and you must decide when to invest in modernization. Ideally, you introduce a new capability that also eliminates a legacy system."

Danyel Bischof-Forsyth, CIO, 7Brew

Bad news isn't like wine; it doesn't age well. The sooner we know, the sooner we can respond."

Mike Anderson, Chief Digital and Information Officer, Netskope

The Last Word

Across the six crucial conversations, you will learn how to engage in a more effective and influential dialogue with your organization's leadership.

Speak the language of business value
De-risk and gatekeep innovation
Lead with credibility, clarity and candor
Drive transformation that's AI-powered and people-centric

The

last

word

Let's get started!

Crucial Conversations: How to Achieve CIO-CEO Alignment in the Era of AI was created to provide IT leaders with tangible and practical advice that will help structure more effective discussions with their CEO. Download the full report to level up your conversations and relationship with your CEO.

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Intro from Mike Anderson