Today’s article is about the role of modern CTOs and the challenges they face when it comes to digital transformation. We love the modern CTO because they believe that technology is the business and the business is the technology. In other words, they understand the essence of digital transformation – where tech is being leveraged in every area of the organization – but they also understand that the road to get there can be bumpy if they don’t have the commitment of other leaders on the journey.

The Modern CTO: How Gen X Leaders Are Pioneering Digital Change

At Tuckpoint, we work side-by-side with CTOs as they try to move their organizations into the future. This emerging class of tech leaders has pride in their part of the organization and knows the potential their teams hold.

They know in their bones that Marty Cagan is right when he says: “If you’re only using engineers for coding, you’re leaving half their value on the table.”

Modern CTOs also understand that organizational and cultural change will be necessary to sustain transformation – it isn’t just IT’s job to make transformation happen, it’s the responsibility of the entire org.

These CTOs usually arrive in their role with knowledge and experience on delivering value in faster, better ways. But, historically, their role has been one of execution, not strategy.  That makes it pretty damn hard to drive organizational change.

Understanding CTO Challenges: Common Organizational Obstacles

CTOs encounter a lot of challenges that can impede progress and hinder the realization of digital objectives. Here are some of the most common obstacles that stand in their way: 

Contextual & Cultural Challenges CTOs face: 

• The organization utilizes a passive command/control leadership style

• Technology teams are being treated as order takers and estimators rather than strategic partners

• There are extensive regulatory/compliance requirements that deter progress

• Fragmented/competing priorities make it difficult to get things done

• Change fatigue and/or resistance is a major barrier 

• Talent strategies are failing in competition for top talent, both in engineering and in business

• There’s a failure among leadership to understand that the company is competing on experience, regardless of industry 

Structural & Systemic Challenges CTOs face:

• Bi-Modal funding (annual/project-based, limites team/capacity based)

• Aging technology stack and outdated Build-vs-Buy approach

• Slow, inconsistent patterns of execution

• Abundance of “coordinating” roles vs owners

• Swarm/Execute/Redeploy resource

• Separation of Build, Run, and Fix responsibilities

Anything on this list feel familiar? You’re not alone. Many CTOs looking to lead their organizations into a more digitally-fuelled future are facing one or more (or many!) of the above. We formed this list at Tuckpoint because our clients were consistently surfacing these as the biggest barriers to their success, and the driving factors to seeking outside support for navigating these issues. 

If you’re a CTO reading this list and nodding your head in frustration, just know you’re not alone and we’re here to help.

Want more resources related to this topic? Check these out:

• The Key to Digital Transformation? CTO and C-suite Alignment

• Keep the Rest of the C-Suite Committed To Transformation with This 2-Step Guide

• The 2 Things Leaders Can Do Right Now To Prep Teams for Transformation