Embarking on a new journey as a CTO is sure to be exhilarating. It’s also heckin’ daunting! The first 100 days are critical for setting the tone, establishing your credibility, and laying the foundation for future success. Because this role is so pivotal for success in modern businesses, your performance in these first 100 days will be heavily scrutinized and harshly evaluated. No pressure!
This guide provides one example roadmap for new CTOs to navigate their initial days in the role, covering essential tasks like assessing the current tech infrastructure, setting priorities, building relationships with stakeholders, and establishing your strategic vision. It’s not one-size-fits-all, and it might not suit your organization, but it should give you a framework for crafting your own first 100 days in a CTO role.
Day 1-30: Lay the groundwork
Assess the infrastructure and offerings
Your first task as a new CTO is to understand what’s good, what needs improvement, and what might need to go. Conduct an overall audit of the existing technology stack, processes, and team structure. This includes:
- Determine your purview; you should audit more than just engineering, e.g. support, QA, or customer relations.
- Review the current systems and software in use.
- Evaluate the current technical debt (support debt, etc.) and potential risks.
- Check out the backlog, ongoing projects, and development roadmap.
- Assess the offerings and weigh them against competitors.
- Measure your first impression of strengths, weaknesses, or areas for improvement.
Meet your stakeholders
Building strong relationships with your peers and stakeholders is crucial. You want to get their perspectives on those first impressions: do they have their own ideas of strengths, weaknesses, or areas for improvement? Schedule one-on-one meetings with:
- CEO and executives: Understand their vision, expectations, and ✨business goals✨.
- Department heads: Learn about their needs, challenges, and how technology can support their objectives.
- Tech team members: Get to know your team, their roles, and their opinions on current processes and tools.
Quick Wins
Identify a few quick wins to demonstrate your value early in your tenure. These could be small improvements or optimizations that can be implemented quickly to show immediate impact. Processes are a good place to start, as are impactful bugs. Consider the infrastructure and offerings in light of the business goals. Evaluate the weaknesses and areas for improvement using a decision matrix, as described in our previous post on the Eisenhower Matrix.
Day 31-60: Setting Priorities and Building Momentum
Develop a Strategic Vision
Based on your initial assessment and discussions, start formulating a strategic vision for the technology function across all teams within your purview. This vision should align with the overall business objectives and provide a clear direction for your team.
Set Clear Goals
Break down your strategic vision into specific, actionable goals. Ensure these goals are SMART (Specific, Measurable, Achievable, Relevant, and Time-bound). Key areas to focus on might include:
- Enhancing system performance, scalability, and reliability
- Refining, replacing, or introducing new processes to the team
- Reducing technical debt
- Improving security and compliance
- Opening new markets
- Better serving existing markets
- Driving innovation through new technologies
Establish a Roadmap
Create a detailed roadmap outlining the steps needed to achieve your strategic goals. This roadmap should include:
- Short-term, medium-term, and long-term plans
- Key milestones and deliverables
- Estimated timelines and resource requirements
You might have your own personal roadmap comprised of personal goals, “soft skill” changes, and subjective goals that aren’t easily measured or tracked. Mark them down, revisit them weekly, and denote your progress.
Communicate the Vision
Communicate your strategic vision and roadmap to your team and stakeholders. Ensure everyone understands the direction and their roles in achieving these goals. Foster a sense of excitement and buy-in around the vision. Depending on the shape and size of your organization, this might require a simple document, a few meetings, or an extensive slide deck and company-wide presentation. You may wish to recruit resources from design or marketing to infuse this communication with greater impact. However you spread the message, you want to ensure your vision reaches everyone in your purview and all the stakeholders it might involve. Expect more detail on building excitement for your vision in future posts.
Day 61-100: Driving Execution and Measuring Progress
Build and Empower Your Team
By now, you should have a clear understanding of your team’s strengths and areas for improvement. Use this knowledge to:
- Address Skill Gaps: Whether through hiring, training, or reassigning roles, ensure that your team has the right mix of skills to execute your strategy.
- Foster a Collaborative Culture: Encourage cross-functional collaboration and create an environment where innovation thrives. Empower your team to take ownership of their work and contribute ideas.
- Provide Resources and Tools: Make sure your team has access to the necessary tools, software, and resources to do their jobs effectively. Remove any obstacles that could hinder their productivity.
Implement Key Initiatives
Now that your roadmap is in place, it’s time to start executing the most critical initiatives. To ensure smooth implementation:
- Set Clear Expectations: Clearly communicate the goals, timelines, and deliverables for each project. Ensure everyone understands their responsibilities and how their work contributes to the overall strategy.
- Monitor Progress Regularly: Establish regular check-ins, such as weekly or bi-weekly status meetings, to assess progress. Use these meetings to address roadblocks, adjust timelines, and keep the momentum going.
- Stay Flexible: While it’s important to stick to your plan, remain open to adapting based on new information or changing circumstances. If an initiative isn’t yielding the expected results, don’t hesitate to pivot and try a different approach.
Establish Key Performance Indicators (KPIs)
To measure the success of your initiatives, define and track KPIs that align with your business goals. These metrics will provide insight into whether you’re on the right path or need to make adjustments. Examples of KPIs for a CTO might include:
- System Uptime and Reliability: Measure the stability of your infrastructure and the frequency of outages or downtime.
- Deployment Frequency: Track how often your team is releasing updates or new features, indicating the efficiency of your development process.
- Incident Response Time: Monitor how quickly your team resolves critical issues or security incidents.
- Customer Satisfaction Scores: Use feedback from users or customers to gauge the impact of your technology initiatives on the overall experience.
By regularly reviewing these KPIs, you can make data-driven decisions to refine your strategy and ensure that your efforts are driving the desired business outcomes.
Create Feedback Loops
Continuous improvement is key! Establish feedback loops that allow you to gather input from your team, stakeholders, and customers. This can be done through:
- Regular Team Retrospectives: After completing key milestones, hold retrospectives to discuss what went well, what didn’t, and how processes can be improved moving forward.
- Stakeholder Updates: Keep executives and other stakeholders informed about progress. Use their feedback to ensure that your initiatives remain aligned with broader business goals.
- Customer Feedback: Don’t forget to involve the end-users of your technology. Collect and analyze customer feedback to identify areas where improvements can be made.
Communicate Successes and Learnings
As your team achieves key milestones, take the time to celebrate and communicate successes. Recognize the hard work and contributions of your team members, and use these moments to reinforce the positive impact your initiatives are having on the company.
At the same time, be transparent about any challenges or setbacks, and use them as learning opportunities. This balanced approach will help build trust and keep your team motivated.
Plan for Continuous Improvement
The end of your first 100 days isn’t a finish line; it’s a checkpoint. As you wrap up this initial phase, take time to reflect on what has been accomplished and what still needs to be done. Begin planning for the next phase of your strategy, focusing on continuous improvement and long-term success.
In future posts, we’ll dive deeper into strategies for assessing teams and technology, working with stakeholders, developing and communicating vision, building and maintaining momentum beyond the first 100 days, KPI definition and measurement, and much more.
Conclusion
The first 100 days as a CTO are a critical period for establishing your leadership, setting the direction, and building momentum. By focusing on assessing the current state, building relationships, setting a strategic vision, and driving execution, you can make a significant impact and set the stage for long-term success. Remember, your journey as a CTO is a marathon, not a sprint. Stay adaptable, keep learning, and lead with confidence.