As I reach the halfway point of my digital MBA journey at CTO Academy, I’ve taken time to reflect on the content that’s resonated most deeply with me so far. One lecture in particular stood out: a focused and practical guide to navigating the first 90 days as a Chief Technology Officer (CTO). Whether stepping into a full-time executive role or taking on a fractional CTO assignment, the framework offered in this lecture provides a clear, actionable roadmap for building momentum and driving meaningful impact from day one.
Here’s a distilled version of the key areas that every new CTO should assess during those critical early days:
Business Plan and Objectives
Understanding the core of the business—its vision, mission, target audience, and strategy—is essential. A new CTO must assess whether the current technology initiatives genuinely support the business’s goals. Identifying gaps between the documented strategy and what’s actually happening on the ground is vital. From the start, tech decisions should be deliberately aligned with the broader business plan, ensuring technology acts as an enabler rather than a siloed function.
Senior Leadership Team (SLT) Relationships
Relationships matter. Early meetings with senior leadership are crucial for understanding strategic priorities and how aligned (or misaligned) the leadership team might be. These conversations serve a dual purpose: they help build rapport and uncover subtle tensions or misunderstandings that could hinder collaboration down the line. A CTO who invests in these relationships gains valuable insights and strengthens their position as a trusted advisor.
Team and Resources
Taking stock of the current team structure is another essential first step. This includes evaluating whether the org chart reflects business needs and whether roles are clearly defined. Understanding individual and collective strengths, as well as areas needing support, helps lay the groundwork for team development. It’s also critical to assess diversity, workload distribution, and fairness in compensation to ensure a balanced and motivated team.
Efficiency and Processes
Technology delivery must be efficient and high quality. The CTO should quickly evaluate whether existing processes and systems (such as CI/CD pipelines) are producing the desired results. When inefficiencies or outdated practices are identified, empowering team leads to champion process improvements ensures changes are embedded and sustainable.
Communication
Clear communication is the backbone of any successful tech organization. The CTO must verify that both internal team communication and cross-functional collaboration are effective. Encouraging structured documentation (like using ticketing systems for decision tracking) helps prevent knowledge silos. Simultaneously, it’s important to avoid tool overload—establishing and enforcing thoughtful usage policies can dramatically reduce noise and increase focus.
Budgets
A CTO must understand the financial landscape. This means assessing whether budgets are realistic and where risks of overspending or underuse might lie. Strategic investments should be made carefully, with a long-term view to avoiding budget cuts or constraints later on. Ultimately, budget oversight should align with broader initiatives that support growth and operational improvement.
Skeletons in the Closet
Every organization has its quirks, and a savvy CTO will dig deep to uncover any “skeletons in the closet.” Legacy systems, technical debt, or cultural resistance can all impact performance. By asking tough questions and investigating inconsistencies, a new leader can surface these issues early and develop short-, medium-, and long-term plans to address them.
This lecture has helped me crystallize how I would approach any new CTO role—whether full-time or fractional—with clarity and intentionality. As I continue through the second half of my digital MBA, I’m excited to apply this mindset to future engagements and leadership opportunities.
If you’ve had a similar experience onboarding into a new leadership role—or are thinking about stepping into one—I’d love to hear how your first 90 days went, please comment below.