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First 100 Days

"The beginning is the most important part of the work." - Plato


As a CTO, mastering the first 100 days in your role is crucial for laying the foundation of your tenure and ensuring long-term success. These initial days are a unique opportunity to establish credibility, build trust, and set a clear vision for the future.

In this chapter, we will explore the significance of these first 100 days and guide you through the challenges and strategies to prioritize and navigate this critical period. By focusing on building meaningful connections, understanding the company culture, and aligning your technology strategy with business objectives, you can position yourself for continued growth and make a lasting impact on the organization.

Your First 100 Days

During the first 100 days in your new role, it is crucial to establish a solid and positive foundation that will set the tone for long-term success and lay the groundwork for future growth and achievement. This initial period presents an exceptional opportunity to make a lasting impact by implementing strategic initiatives and proactively seeking out and seizing new opportunities for improvement and innovation.

Start building strong and meaningful relationships with key stakeholders, as these connections will enhance collaboration and contribute to a deeper understanding of the organization's culture and goals. By dedicating ample time and effort to navigate this critical phase, you will not only position yourself for continued growth and achievement but also contribute to the overall success and prosperity of the organization.

"The first hundred days are not just about getting things done, but also about setting the tone for the rest of your tenure." - Michael D. Watkins


Openness: During the transition period, it is crucial to have an open dialogue with the outgoing CTO. Schedule a meeting to understand the technologies, opportunities, and challenges faced. This approach will help you build trust with the other team members and avoid negatively affecting the existing workplace culture. Understanding the previous CTO's work style, successes, failures, and vision will improve your transition and success.

Observe: Ask open-ended questions to gain insights and perspectives from the ground up. Take your time with solutions or assurances at this stage. Just listen, absorb, and build a picture of the current landscape. Then, make informed decisions moving forward. Avoid making too many changes quickly when taking over from an existing CTO. Take the time to learn about the environment and build bridges within the organization. Most things don't need immediate attention, so carefully assess the situation and plan the company's future.

Culture: Understanding the company's culture is essential. It allows you to adapt and thrive in your new environment while bringing fresh ideas and changes. To understand the culture, start by observing how people interact. Pay attention to the unwritten rules and norms that govern behavior. Ask questions and listen carefully to the answers. And most importantly, be patient. Building relationships takes time, but it's worth the effort.

Leadership: You need a defined leadership style that makes it easy for subordinates to understand you. Defining your leadership style early on sets the tone for how you will lead the team and the adoption of your technological vision in the company. During your honeymoon period, seek to establish yourself as the CTO and showcase the leadership skills you bring in.


The success of a CTO is attributed to establishing quality relationships in and outside the organization. During the transition period, work on building critical relationships to understand the company culture, business requirements, and technical needs. Take time to understand team members' preferences and what they need to excel at. By doing this, you will create a collaborative environment, and it will also lead to the establishment of a positive work environment.

Meeting with key stakeholders is a critical step in any technology initiative. These stakeholders include other executives, department heads, and team members. By meeting with these individuals, you can build relationships and establish trust, which will be crucial to the success of your project. During these meetings, listening carefully to their concerns and ideas is essential. You want to make sure that everyone feels heard and valued. Be transparent about your goals and plans for the project.

Identify the different stakeholders and their communication needs to establish effective communication channels. This may include team members, managers, executives, clients, and vendors. Once these stakeholders have been identified, it is essential to determine the most appropriate communication channels for each group. This may include email, instant messaging, video conferencing, or in-person meetings. Establish your guidance in situational communication style.

"Courage starts with showing up and letting ourselves be seen." - Brené Brown


You are assessing your current technology platform in terms of its stack, programming languages, and frameworks used. By evaluating your existing systems, you can identify areas for improvement and modernization, leading to increased productivity, cost savings, and improved customer experiences.

Inventory your company's software and hardware to assess your technology stack. Evaluate each system's functionality, security, and compatibility with other systems. Identify any redundancies or inefficiencies that could be eliminated through consolidation or upgrades. Prioritize the changes most significantly impacting your business and develop an implementation plan.


Developing a budget and resource plan is your most crucial delivery within the first 100 days. With a clear financial and resource allocation plan, you can ensure that your company's resources are used effectively and efficiently. This will help you identify areas where you may need to cut costs or invest more resources.

To develop a budget and resource plan, identify your company's priorities and goals. This will help you determine which business areas require the most resources. Once these priorities have been identified, allocate resources accordingly. You may need to reallocate resources from less essential business areas to more critical ones. You may also need to seek additional funding or help from external sources.

Outgoing CTO

When assuming the role of an outgoing CTO, it is essential to consider the dynamics within the team. If the previous CTO had a long tenure and personally hired all team members, a loyalty issue might need to be addressed.

To navigate this situation, taking advantage of the honeymoon period can be beneficial by asking basic questions that do not raise eyebrows. This will allow you to get to know the team members and build relationships with other peer executives.

Acknowledging that the team may initially perceive you as an enemy who has ousted their beloved leader is crucial. To overcome this perception, it is advisable to make subtle changes while still honoring the work and contributions of the previous CTO. By doing so, you can gradually win the trust and support of the team, fostering a positive and collaborative environment.



Understanding the company culture is crucial for your success as a CTO. By observing how people interact and asking questions, you can adapt and thrive in your new environment while bringing fresh ideas and changes. Building relationships and patiently listening to gain insights into the unwritten rules and norms will help you navigate the team dynamics. By honoring the previous leadership and making subtle changes, you can win the trust and support of the group, fostering a positive and collaborative environment.

Assessing your current technology stack is another crucial aspect of your role. You can identify areas for improvement, modernization, and increased productivity by evaluating existing systems. Prioritize changes that will have the most significant impact on your business and develop a clear implementation plan. This will ensure that your technology aligns with your business goals, keeping you ahead of the competition.

Establishing effective communication channels with stakeholders is crucial for the success of your technology initiatives. Identify the stakeholders' communication needs and determine the most appropriate channels for each group. Being transparent and listening carefully to concerns and ideas can build relationships, establish trust, and ensure everyone is working towards the same objectives.

Identifying key challenges and opportunities is critical. Prioritize these factors and develop an action plan to address them effectively. Turn challenges such as operational inefficiencies, outdated technology, or a lack of innovation into opportunities for growth. You can lead your team towards a successful future by staying ahead of the curve and driving growth.

Embrace the first 100 days as a chance to set the tone and lay the foundation for your tenure. Be courageous by showing up, letting yourself be seen, and making informed decisions. With a clear vision, effective communication, and a focus on continuous improvement, you can navigate challenges, seize opportunities, and lead your team toward a successful future.


As a CTO ask yourself the following:

  1. How can you ensure that your technology strategy is aligned with your business objectives and stays ahead of the competition?

  2. What steps can you take to establish a successful technology strategy, including assessing your technology stack, identifying challenges and opportunities, and developing a technology roadmap?

  3. How can you turn challenges such as operational inefficiencies, outdated technology, or a lack of innovation into opportunities for growth?


Your takeaways from this chapter:

  1. Understanding the company culture is crucial for success as a CTO. Adapt and thrive in the new environment while bringing fresh ideas and changes.

  2. Assess your current technology stack to identify areas for improvement, modernization, and increased productivity.

  3. Establish effective communication channels with stakeholders to ensure the success of technology initiatives.

  4. Identify critical challenges and opportunities to drive growth and innovation.

  5. Embrace the first 100 days as an opportunity to set the tone and lay the foundation for your tenure.

  6. Be courageous in showing up, being seen, and making informed decisions.

  7. Ensure your technology strategy aligns with business objectives and stays ahead of the competition.

  8. Develop a clear plan for technology development, considering potential challenges and constraints.

  9. Turn challenges into opportunities for growth and improvement.

  10. Continuously assess and improve your technology stack, communication channels, and stakeholder relationships.


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