TEAM-5 Tech Due Diligence

Tech Due Diligence TEAM-5: CTO and Technical Leadership Assessment

What This Control Requires

The assessor evaluates the technical leadership, including the CTO's technical depth, strategic vision, people management capabilities, and whether the leadership is appropriate for the company's current stage and growth trajectory.

In Plain Language

The CTO and senior engineering leaders set the direction, culture, and standards for the entire engineering organisation. Whether that leadership is the right fit for where the company is today - and where it is heading - is one of the most consequential questions in any DD review.

We assess the CTO across several dimensions: technical depth (do they genuinely understand the stack, the architecture, and the engineering challenges?), strategic vision (can they connect technology decisions to business outcomes?), people management (can they build, grow, and retain a team?), communication (can they explain technical topics to non-technical stakeholders?), and scalability (is the CTO's role appropriate for the company's growth trajectory?).

One of the most common patterns we see is the founder CTO who built the initial product as a hands-on engineer but now needs to lead a larger team. We assess whether that transition is happening successfully, whether there is support in place (coaching, management training), or whether the CTO is becoming a bottleneck as the organisation scales.

How to Implement

Start by defining the CTO role clearly for your current stage. Early-stage means primarily hands-on technical contribution with some hiring and architecture responsibility. Growth-stage shifts to architecture, team building, and technical strategy with decreasing hands-on coding. At scale-up, the role becomes predominantly leadership, vendor management, compliance, and strategic technology decisions.

Make sure the CTO has a documented technology strategy that the team can rally around. It should cover technology choices and their alignment with business objectives, architecture evolution, team growth and skill development, technical risk management, and investment priorities for the engineering organisation.

Invest in leadership development for the CTO, especially during the transition from hands-on to strategic. Executive coaching focused on delegation, strategic thinking, and communication is valuable. Management training for people leadership skills, peer networking with CTOs at similar-stage companies, and advisory relationships that provide strategic guidance all help.

Build a technical leadership layer beneath the CTO. As the engineering organisation grows, the CTO should not be making every technical decision. Develop senior engineers, architects, or engineering managers who share decision-making authority and can operate independently.

Ensure the CTO is connected to the business. They should participate in business discussions, understand the commercial strategy, and translate business needs into technical priorities. A CTO who is purely technology-focused without business context risks making decisions that are technically interesting but commercially off-target.

Plan for CTO succession, even at early stage. Document critical decisions, share knowledge broadly, and develop potential successors within the technical leadership team. Understanding what happens if the CTO is unavailable is a question DD reviewers will always ask.

Evidence Your Auditor Will Request

Technology strategy document authored or approved by the CTO
CTO role definition appropriate for the company stage
Technical leadership team structure below the CTO
Evidence of CTO participation in business strategy discussions
Leadership development or coaching activities for the CTO

Common Mistakes

CTO is still the primary coder; cannot delegate and is a bottleneck
No documented technology strategy; direction exists only in the CTO's head
CTO disconnected from business context; makes technically elegant but commercially poor decisions
No technical leadership layer below CTO; single point of failure for all technical decisions
CTO has not developed people management skills; team morale and retention suffer

Related Controls Across Frameworks

Framework	Control ID	Relationship
ISO 27001	A.5.1	Related

Frequently Asked Questions

Is it a problem if the CTO still writes code?

It depends on the stage. With a team of 5-10, significant CTO coding contribution is expected and healthy. At 20+ engineers, the CTO should be spending most of their time on architecture, team building, and strategy. If they are still heavily coding at that scale, it usually means they are struggling to delegate and may be becoming a bottleneck.

What if the CTO assessment reveals a capability gap?

This is more common than you might think, and it is not automatically a dealbreaker. We evaluate whether the gap can be addressed through coaching, training, or hiring complementary roles like a VP of Engineering. What matters most is that the gap is recognised and there is a credible plan to close it.

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