Technology leaders share honest insights about stepping into CTO roles and what really lies beneath the title
The Chief Technology Officer role remains one of the most sought-after positions in technology leadership, yet also one of the most misunderstood. La Fosse recently brought together seasoned CTOs and CPTOs to cut through the romanticised perceptions and share the unvarnished truth about what it really means to step into these senior technology roles.
The reality check: it’s not what you expect
The conversation opened with a sobering reality that few CTO roles match initial expectations. The technical playground that many engineers envision simply doesn’t exist at the CTO level. The role demands far less hands-on technical work than anticipated, with significantly more organisational responsibilities that many don’t expect.
The common thread across all CTO experiences is that there’s no one above you who can answer technical questions. Yet this technical authority comes with responsibilities that extend far beyond technology itself.
The great title confusion: no two CTO roles are the same
Perhaps the most crucial insight shared was the massive variation in what CTO roles actually entail across different organisations. The title itself can be almost meaningless without understanding the specific organisational context and structure.
This variation creates a critical challenge for anyone considering the transition. Due diligence becomes essential when exploring CTO opportunities. Understanding the full technology leadership structure, including whether there are CIOs, CPTOs, and other C-level technology roles, can make the difference between success and stepping on colleagues’ toes.
Different organisational structures dramatically affect the role’s scope and effectiveness, with some companies having multiple C-level technology roles that can create confusion and conflict.
The courage to seize the moment
Despite the challenges, timing and courage are crucial when CTO opportunities arise. Many successful transitions happen when individuals find themselves already performing CTO-like responsibilities and have the courage to formalise the role.
The advice from experienced leaders is clear: when the opportunity presents itself, you must be prepared to act decisively. These positions don’t follow linear career paths, and opportunities may not present themselves again if missed.
The difficult conversations nobody talks about
The discussion revealed the darker aspects of CTO responsibilities that many don’t anticipate. People management challenges, particularly around restructuring and redundancies, often fall squarely on the CTO’s shoulders.
This responsibility creates a fundamental conflict for those transitioning from engineering management roles. As a VP of Engineering, your primary concern is the engineering team. As a CTO, your allegiance shifts to the executive team, creating difficult decisions that can feel conflicting.
The guidance for managing this tension focuses on authentic decision-making. Following your heart and doing what you genuinely believe is right for the business becomes essential, even when those decisions are difficult for teams you care about.
The enterprise architecture blind spot
An unexpected theme emerged around the critical importance of enterprise architecture in certain organisations for CTO success. Many of these organisations lack proper enterprise architecture functions, which can create a significant blind spot for CTOs.
In these companies, this gap can impact strategic technology decisions and organisational alignment, highlighting how
enterprise architecture skills become increasingly important as AI and data initiatives require
strong foundational structures.
In smaller, or less regulated companies, this is less of a concern and often is picked up by senior developers in conjunction with the CTO.
What makes the role worthwhile
Despite the challenges, the unique opportunities that CTO roles provide consistently emerge as the primary draw. The breadth of impact extends well beyond technology, offering input into commercial vision and organisational strategy.
Technology leaders are no longer confined to back-room roles. There’s a growing recognition that tech should have a voice at the top table, though this requires fighting for that position in many organisations.
The networking and learning opportunities, combined with involvement across multiple business areas, create a stimulating environment for those ready to embrace the broader responsibilities.
The not-so-one-way door
One encouraging insight is that CTO roles aren’t necessarily permanent commitments. Internal promotions in particular can offer flexibility, allowing individuals to step back if they discover the role isn’t suitable.
This flexibility provides reassurance for those hesitant about making the transition, though it’s more feasible with internal moves than external CTO appointments.
The challenges: time, politics, and technical distance
When examining what leaders dislike most about CTO roles, several consistent themes emerge. Limited personal time, including challenges taking adequate holiday, represents a practical concern that impacts work-life balance.
More significantly, the political aspects of senior leadership prove challenging for many technically-minded individuals. The energy required to navigate organisational politics can be draining for those who prefer direct, solution-focused approaches.
The distance from hands-on technical work represents perhaps the biggest adjustment. The excitement of exploring new technologies and solving technical problems becomes limited, replaced by higher-level strategic considerations.
The workforce evolution: AI’s impact on roles
Looking forward, the traditional boundaries between CTO and CPTO roles are blurring, particularly with AI enabling product managers to create prototypes and demos independently. This technological shift is driving role evolution and potentially consolidating responsibilities.
Economic pressures are also forcing organisations to reconsider multiple C-level technology roles, with many companies finding such structures duplicative and expensive.
Making the decision: honest self-assessment
The final consideration centres on honest self-assessment. Before pursuing CTO roles, individuals must genuinely examine whether they’re prepared to leave behind hands-on technical work.
Many talented engineers discover they prefer remaining close to technology rather than moving into the broader organisational responsibilities that CTO roles demand. This preference is perfectly valid and important to recognise before making the transition.
Managing change and communication
Successful CTOs must excel at change management, requiring clear communication about end states and extensive effort in explaining changes to diverse stakeholders. The ability to modify messages for different audiences becomes crucial, whether speaking to technical teams or broader business stakeholders.
Starting with why becomes essential. People need to understand the reasoning behind changes, even if the specific destination isn’t completely defined.
Remote leadership considerations
The modern CTO role increasingly involves remote team management across multiple locations and time zones. Success requires dedicated effort in communication, including regular town halls and structured updates that maintain connection across distributed teams.
While fully remote CTO roles are possible, they demand additional investment in communication structures and relationship-building to maintain effectiveness.
The path forward
The conversation revealed that successful CTO transitions require more than technical expertise. They demand political acumen, people management skills, strategic thinking, and perhaps most importantly, a genuine desire to operate at the intersection of technology and business.
For those considering the step up, the guidance is clear: understand exactly what the role entails in your specific organisation, be honest about what you’re willing to give up, and when the opportunity arises, have the courage to seize it.
The technology landscape continues evolving, and with it, the nature of senior technology leadership roles. Understanding these realities helps ensure that career transitions align with personal goals and organisational needs.
La Fosse continues to facilitate these crucial conversations, providing technology leaders with the insights needed to make informed career decisions and navigate the complexities of senior technology roles.