This chapter examines whether you can see and act on the technology and digital trends that matter most for your business, rather than being swept up in hype. Boards expect CEOs to be conversant enough in technology to ask sharp questions, see strategic implications, and choose where to lean in—and where not to. The skills here assess whether you’ve already used digital, data, and technology to reshape customer experience, operations, and business models, working effectively with your CIO/CTO/CDO. In short, this chapter helps you gauge whether you can lead a technology-enabled enterprise, even if you did not grow up as a technologist.
9.1 Understanding technology and digital trends relevant to the business
What the Board is looking for
When Boards evaluate a candidate’s understanding of technology and digital trends relevant to the business, they are not looking for a hands-on engineer but for a strategically literate, curious, and informed leader. They want evidence that the candidate has identified which technologies and digital shifts genuinely matter in their industry—and which are noise—and has translated that into concrete choices and actions. They also look for a track record of engaging deeply enough with tech and digital leaders to challenge, refine, and ultimately sponsor initiatives with real business impact. Ultimately, they want someone who can connect technology trends to strategy, risk, and value creation, not just talk about them at a superficial buzzword level.
Open-ended question
“Tell us about specific technology or digital trends that you judged as strategically important for your business in the last several years—what you saw, how you educated yourself, what decisions or initiatives you sponsored as a result, and what measurable impact those had on customers, operations, or financial performance.”
Rubric – 9.1 Understanding technology and digital trends relevant to the business
Nascent
- Has limited exposure to or engagement with technology and digital trends beyond high-level articles, conferences, or vendor pitches.
- Few examples where they personally identified a relevant tech trend and drove any follow-on exploration or business response.
- Has largely relied on CIO/CTO or vendors to define what matters technologically, with little challenge or strategic framing.
- Past strategies and plans show minimal reference to technology or digital themes as core enablers or threats.
Developing
- Has taken steps to educate themselves on key technologies affecting their sector (e.g., data/analytics, cloud, automation, AI, digital channels).
- Can point to at least one initiative where a specific tech or digital trend informed a business decision or pilot.
- Engages periodically with technology and digital leaders to discuss implications, though conversations can still be somewhat tactical or reactive.
- Demonstrates growing ability to distinguish between hype and plausible, relevant trends, but application is still selective and uneven.
CEO-Ready
- Has consistently incorporated technology and digital trends into strategic thinking and planning for a significant business or enterprise.
- Can demonstrate multiple cases where anticipating or responding to a tech/digital trend led to concrete initiatives with measurable impact (e.g., growth, efficiency, risk reduction).
- Regularly engages with internal and external experts (CIO/CTO/CDO, vendors, startups, ecosystem partners) to stress-test their view and refine priorities.
- Is recognized by peers and tech leaders as someone who “gets” the key technology issues for the business and uses that understanding to make better strategic and investment decisions.
Distinctive
- Has repeatedly spotted and acted early on critical technology or digital shifts that later proved pivotal for the business or industry.
- Can point to strategic moves (e.g., platform bets, digital business launches, significant tech-enabled operating model changes) that were driven by superior understanding of tech trends.
- Has shaped a clear enterprise narrative about where technology and digital create advantage, influencing Board, investors, and employees.
- Across roles or organizations, is known for being ahead of the curve on relevant technology trends and for turning insight into durable competitive advantage.
9.2 Setting digital and data strategy (customer-facing and internal)
What the Board is looking for
When Boards evaluate a candidate’s ability to set digital and data strategy (customer-facing and internal), they are looking for evidence that this person has turned “digital” and “data” from buzzwords into a coherent, prioritized agenda. They want to see that the candidate has made explicit choices about where digital will transform customer experience and growth, and where data and analytics will reshape decision-making, operations, and risk. They also look for a track record of focusing scarce resources on a few high-impact digital/data bets, rather than a scatter of pilots, and of tying those bets to measurable business outcomes. Ultimately, they want someone who can connect digital and data strategy tightly to overall business strategy and then drive execution with appropriate ambition and realism.
Open-ended question
“Describe the digital and data strategy you have set or significantly shaped for a business—how you defined the priorities across customer-facing and internal use cases, what you chose to invest in (and not invest in), how you organized and governed the work, and what tangible impact it had on customer experience, efficiency, growth, or risk management.”
Rubric – 9.2 Setting digital and data strategy (customer-facing and internal)
Nascent
- Has had limited involvement in defining digital or data strategy; most initiatives were owned by IT, digital, or analytics teams with minimal strategic framing.
- Digital projects and data efforts under their remit were largely opportunistic or reactive (e.g., tools, apps, dashboards) without a clear, integrated roadmap.
- Cannot point to a documented set of digital/data priorities linked explicitly to business strategy and value drivers.
- Outcomes of digital and data activities are hard to trace to meaningful business impact beyond localized efficiencies or features.
Developing
- Has participated in shaping digital or data priorities for a function or business unit, often focused on a handful of use cases.
- Can point to several initiatives (e.g., new digital customer journeys, analytics tools, automation projects) with some measurable benefits.
- Has begun to articulate a digital/data direction, but scope is narrow, and there is still fragmentation across teams and platforms.
- Governance, talent, and technology choices are partially aligned, but there are overlaps, gaps, or duplicated efforts.
CEO-Ready
- Has led or co-led a coherent digital and data strategy for a substantial business or enterprise, covering both customer-facing and internal use cases.
- Can demonstrate multiple high-impact initiatives (e.g., digital channels, data-driven pricing, predictive maintenance, personalization) that delivered clear financial and/or customer outcomes.
- Has made explicit choices about platforms, data foundations, talent, and governance to support the strategy and avoid “pilot purgatory.”
- Is recognized by technology, digital, and business leaders as someone who sets clear priorities, funds them appropriately, and holds teams accountable for value, not just delivery.
Distinctive
- Has used digital and data strategy to materially reposition a business—e.g., creating new digital businesses, radically changing cost-to-serve, or reshaping customer engagement models.
- Can point to a multi-year roadmap that was executed with discipline, resulting in a step-change in digital revenue mix, data-driven decision quality, or automation-driven productivity.
- Has built durable digital and data capabilities (platforms, teams, operating model) that continue to generate new use cases and value beyond the initial strategy cycle.
- Across roles or organizations, is known for turning digital and data from a set of projects into a core strategic engine of transformation and competitive advantage.
9.3 Prioritizing and governing major IT and digital investments
What the Board is looking for
When Boards evaluate a candidate’s ability to prioritize and govern major IT and digital investments, they are looking for evidence that this person can separate “must-have, value-creating” from “nice-to-have, shiny” and then follow through. They want to see a track record of setting clear investment criteria, making tough trade-offs across competing initiatives, and insisting on robust business cases—not just technical justification. They also look for proof that the candidate has put governance in place to track benefits, manage risks, and stop or reshape projects that are underperforming. Ultimately, they want someone who treats IT and digital investment as part of capital allocation, with the same rigor applied to factories, M&A, or new product lines.
Open-ended question
“Describe how you have prioritized and governed major IT or digital investments—how you decided what to fund or stop, what criteria and processes you used, how you stayed close to delivery and value realization, and where you had to make difficult calls to redirect or halt significant spend.”
Rubric – 9.3 Prioritizing and governing major IT and digital investments
Nascent
- Has had limited responsibility for approving or prioritizing large IT or digital investments; most decisions were made by IT/digital leaders or above them.
- Past involvement focused mainly on accepting standard budget proposals or reacting to urgent needs, rather than shaping a portfolio of initiatives.
- Few examples where they challenged business cases, asked for alternatives, or stopped underperforming IT/digital projects.
- Benefits, risks, and interdependencies of IT/digital investments under their remit were not tracked in a structured way.
Developing
- Has participated in prioritizing some IT or digital initiatives at functional or business-unit level, using basic criteria (e.g., cost, urgency, compliance).
- Can point to at least one case where they delayed, reshaped, or canceled a project after reviewing value, risk, or readiness.
- Has begun to use more structured portfolio views (e.g., roadmaps, value vs. risk maps) and governance forums to discuss IT/digital investments.
- Tracking of value realization and risk is improving, but still uneven across projects and over time.
CEO-Ready
- Has led or co-led the prioritization and governance of a substantial portfolio of IT and digital investments for a business or enterprise.
- Can demonstrate clear links between prioritized initiatives and strategic objectives, with disciplined choices about what not to fund.
- Has established governance mechanisms (e.g., steering committees, stage gates, benefits tracking, risk reviews) that are used to manage scope, timing, and value.
- Can point to multiple examples where projects were accelerated, reshaped, or stopped based on performance, freeing resources for higher-value initiatives.
Distinctive
- Has materially improved the overall return on IT and digital spend by reshaping the portfolio and governance model—reducing waste and increasing impact.
- Can point to major investment themes (e.g., core platform modernization, data foundations, key digital journeys) that were prioritized and executed with strong value realization.
- Governance disciplines they put in place are still used as the standard way of managing technology and digital investments after their tenure.
- Across roles or organizations, is seen by CIOs, Boards, and investors as a leader who brings true capital allocation rigor to IT and digital, consistently delivering more value for each dollar spent.
9.4 Working effectively with CIO/CTO/CDO and challenging their plans
What the Board is looking for
When Boards evaluate a candidate’s ability to work effectively with the CIO/CTO/CDO and challenge their plans, they are looking for a relationship that combines mutual respect with real challenge and accountability. They want to see that the candidate does not simply defer to technology leaders, but tests their assumptions, prioritization, and value logic—while still backing them publicly and enabling their success. They also look for evidence that this partnership has produced better outcomes: clearer roadmaps, sharper trade-offs, stronger delivery, and tighter linkage between tech/digital and business priorities. Ultimately, they want someone who can be the senior executive counterpart that top technology and data leaders both trust and take seriously.
Open-ended question
“Tell us about how you have worked with your CIO/CTO/CDO or equivalent technology/data leader—describe specific situations where you constructively challenged their plans or priorities, how you handled disagreement, what decisions or changes resulted, and how this affected the impact and credibility of technology and digital initiatives in the business.”
Rubric – 9.4 Working effectively with CIO/CTO/CDO and challenging their plans
Nascent
- Has had limited direct engagement with CIO/CTO/CDO or equivalent leaders beyond formal updates or steering meetings.
- Typically accepted technology and data roadmaps as presented, with minimal challenge on value, risk, or prioritization.
- Rarely initiated joint problem-solving or strategic discussions with technology leadership; interactions were largely transactional.
- Technology and digital agendas under their remit often felt disconnected from business priorities or were perceived as “IT projects.”
Developing
- Has built a basic working relationship with technology/data leaders and occasionally challenged assumptions or scope.
- Can point to one or two instances where they influenced the reprioritization, rescoping, or timing of key tech/digital initiatives.
- Still tends to engage more heavily at late stages (e.g., funding approval, issue escalation) rather than early in shaping the agenda.
- Is developing confidence and skill in asking probing questions about architecture, delivery risk, and value without overstepping into micromanagement.
CEO-Ready
- Has an established pattern of partnering closely with CIO/CTO/CDO or equivalents to co-shape the technology and digital agenda.
- Can demonstrate multiple cases where robust challenge and dialogue with technology leaders improved focus, sequencing, or design of major initiatives.
- Regularly convenes or participates in governance forums where business and technology leaders jointly make decisions on priorities, investments, and trade-offs.
- Is regarded by technology leaders as a demanding but fair partner who both raises the bar and provides the sponsorship needed to succeed.
Distinctive
- Has elevated the stature and effectiveness of the CIO/CTO/CDO role(s) in the organization, turning them into true enterprise value creators, not just service providers.
- Can point to transformative technology or digital programs whose success depended on a strong, trust-based, high-challenge partnership between them and the technology leadership.
- Has helped reshape how technology and data interact with the rest of the business (e.g., product teams, agile structures, joint ownership), leaving a more integrated model behind.
- Across roles or organizations, is known by Boards and tech leaders as an exceptional “bridge” between business and technology, consistently getting more impact from tech than peers.
9.5 Managing cyber, data, and tech-related risks at Board/CEO level
What the Board is looking for
When Boards evaluate a candidate’s ability to manage cyber, data, and tech-related risks at Board/CEO level, they are looking for evidence that this person understands these as enterprise risks, not just IT issues. They want to see a track record of engaging on cyber and data risk in a structured way—understanding key vulnerabilities, threat scenarios, regulatory exposure, and business impacts—and ensuring appropriate controls, governance, and response plans are in place. They also look for proof that the candidate has led through at least some real incidents or near misses, communicating effectively with Boards, regulators, customers, and employees. Ultimately, they want someone who will neither underreact (“it’s an IT problem”) nor overreact (“shut everything down”), but will manage tech risk with the same judgment and transparency as financial or operational risk.
Open-ended question
“Describe how you have overseen and managed cyber, data, or technology-related risks in your recent roles—include any incidents, audits, or major risk assessments you were involved in, what governance and controls you put in place or strengthened, how you engaged with the Board and other stakeholders, and what changed in the organization’s risk posture as a result.”
Rubric – 9.5 Managing cyber, data, and tech-related risks at Board/CEO level
Nascent
- Has had limited exposure to cyber, data, or tech risk discussions beyond occasional updates from IT, security, or compliance.
- Tended to treat cyber and data issues as technical matters for specialists, with minimal direct involvement in governance or prioritization.
- Few examples where they engaged with the Board, regulators, or customers on tech-related risk topics.
- No clear record of leading responses to cyber incidents, data breaches, or significant IT outages beyond delegating to technical teams.
Developing
- Has participated in some structured cyber or data risk reviews, often as part of broader risk or compliance processes.
- Can point to at least one situation where they supported improvements in controls, policies, or investments after a risk assessment or incident.
- Has begun to include cyber and tech risk in leadership discussions and risk registers, though cadence and depth are still evolving.
- Communication with Boards or senior stakeholders on tech risk has occurred, but mainly in a supporting role or focused on reporting, not framing.
CEO-Ready
- Has overseen a defined governance approach for cyber, data, and tech risk, including regular reporting, ownership, and escalation paths.
- Can demonstrate instances where they led or co-led the response to significant tech-related risk events (e.g., cyber incidents, outages, data issues), including external communication and remediation.
- Has ensured that investment and prioritization decisions (e.g., security, resilience, data protection) are made with a clear view of risk appetite and business impact.
- Is regarded by Boards and senior leaders as someone who can explain tech risks in business terms and who ensures they are managed as part of enterprise risk, not in isolation.
Distinctive
- Has led organizations through major cyber, data, or tech-risk challenges (e.g., serious attacks, regulatory investigations, systemic outages) in ways that ultimately strengthened resilience and trust.
- Can point to significant upgrades in security posture, resilience, or data governance (e.g., zero-trust models, major architecture changes, comprehensive data programs) that were driven by their leadership.
- Has embedded tech risk into broader risk and strategy discussions so that it is routinely considered in M&A, new products, partnerships, and transformations.
- Across roles or companies, is known for being ahead of the curve on cyber and tech risk, with Boards and stakeholders explicitly crediting their leadership for preventing or mitigating major exposures.
