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Why Do Good CTOs Fail?

Updated: Nov 1

The role of Chief Technology Officer is crucial and highly coveted in the modern business world. However, the real question is whether CTOs are genuinely positioned for success within organizations today. At RedCorner, our founder and principal FCTO, Oshri Cohen, has delved into the factors impacting leaders in our field — exploring why even the most skilled and courageous CTOs might face premature challenges or failures.

On average, CTOs hold their positions for less than four years but on average, two years, which is shorter than other senior management roles. Despite the role's increasing prestige — as technology shifts from being viewed as a cost center to a value creator — it's often a role filled with little thanks and much isolation.

But what causes good CTOs to fail or leave their positions out of frustration and disappointment? Here are several common reasons identified by our CTO clients, colleagues, and friends:

The Constant Pressure: CTOs often grapple with daily stress and high expectations. Waking up to a dashboard filled with issues is a challenging start. This is usually due to a need for more experience in leadership and delegation.

RedCorner's Tips:

  • Delegate and empower team leaders.

  • Limit 'always on' periods to critical times of the year.

Rapid Technological Change: The pace of technological change is relentless, and keeping up can seem impossible, even for the most adept teams.

RedCorner's Tips:

  • Assign market segments to team members for research and regular updates.

  • Encourage succinct, relevant reporting on these insights.

  • There is no need to research new technologies continuously; there is little to no value in ripping and replacing tech because the value added is minimal at best.

Overambitious Transformation Projects: Large-scale transformation projects are often costly, lengthy, and risky, potentially failing and leaving the CTO to deal with the aftermath.

RedCorner's Tips:

  • Implement changes using the strangler pattern; it takes more time, but value can be realized much quicker.

  • Divide large programs into manageable segments.

Tech-Unsavvy Boards: A CTO surrounded by a non-technical board faces significant challenges.

RedCorner's Tips:

  • Advocate for technology as a top business priority.

  • Ensure at least one board member is tech-savvy.

  • Hire RedCorner to coach the board and executive team on all matters of technology if the CTO doesn't have the capacity to do so.

Legacy Obligations: While leading digital initiatives, CTOs also manage fundamental IT tasks, which can be overlooked or undervalued.

RedCorner's Tips:

  • Please focus on the most significant cost drivers in terms of time and money and offload them to a contractor or hire individuals to manage them properly until a plan can be drafted to reduce this liability.

  • Focus discussions on value creation rather than service delivery.

Vendor Overload: Being a CTO means being inundated with calls, offers, and pitches from eager suppliers.

RedCorner's Tips:

  • Set clear boundaries with suppliers.

  • Dedicate specific times for supplier engagement.

  • Create a process for vendors to follow with a minimum set of criteria that must be met.

Responsibility Without Recognition: CTOs often face criticism during failures and go unnoticed during successes.

RedCorner's Tips:

  • Maintain transparency and celebrate successes openly.

  • Encourage team engagement through demonstrations and follow-ups.

  • Generally, improved and more frequent communication and communication training; we have seen this in first-time CTOs.

Diminishing Control: As the role of the CTO evolves, there's often a tug-of-war between central oversight and decentralized innovation.

RedCorner's Tips:

  • Establish clear, understandable standards.

  • Foster good relationships with independently-minded business units.

  • The CTO should not be in the middle of it all, and their team should be empowered to make decisions on their own. Any CTO who holds on to all decision-making power is not a good fit for the role.

Strategic Ambiguity: The challenge for CTOs is aligning technology strategy with overall business goals, especially when there's pressure to turn every organization into a "tech company."

RedCorner's Tips:

  • Understand the role of technology in your business's strategy.

  • Balance in-house development with strategic outsourcing based on global market realities.

Understanding these challenges and implementing strategic, effective solutions is key for any CTO to not only survive but thrive in their role.

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