The First 100 Days: A Comprehensive Roadmap for a New CEO

Stepping into the CEO role is like grabbing the keys to a supercar. You’re in the driver’s seat, ready to hit the accelerator, but you need to know the road ahead to avoid any wrong turns. The first 100 days? Think of them as your test drive — the time to get a feel for the controls, build confidence, and set your course.

This roadmap isn’t about reinventing the wheel; it’s about tuning up your leadership engine with the right tools and strategies. We’ll guide you through each phase — from gearing up on Day Zero to hitting top speed by Day 100. By combining cut through actions with powerful EOS (Entrepreneurial Operating System) tools, you’ll steer your organization toward success, build a culture of accountability, and maybe even have a little fun along the way. Buckle up!

Day 0: Pre-Start Preparation

• Prepare for the Role: Before officially starting, review all available information about the company, including financial statements, strategic plans, sales pipeline, customer lists, organizational structures, market reports, and any key challenges or opportunities. This preparation will help you hit the ground running.
• Schedule Key Meetings: Set up initial meetings with board members, key executives, major stakeholders, key customers, and suppliers. This will help to build relationships, establish rapport, and gather diverse perspectives on the company’s current state.
• Assess Organizational Strength: Have the leadership team complete an Organizational Check-Up to evaluate performance across the six key components of the business: Vision, People, Data, Issues, Process, and Traction. This will help identify strengths, weaknesses, and areas needing improvement.

Day 1 to Day 10: Conduct a Listening Tour and Establish Foundations

• Conduct a Listening Tour: Meet with key stakeholders, including board members, senior leaders, department heads, key customers, and suppliers. The goal is to understand the organization’s current state, challenges, and opportunities from multiple perspectives. This is crucial for building trust and setting the stage for change.
• Run an EOS Focus Day Workshop:
  1. Create the Accountability Chart: Develop an Accountability Chart to clarify roles, responsibilities, and accountabilities within the organization. This helps the leadership team understand both the current structure and the ideal future state.
  2. Set Quick Wins (60-Day Rocks): Establish 3-7 key priorities or “quick wins” for the leadership team to achieve within the next 60 days. These 60-day Rocks should focus on actions that can quickly demonstrate progress and build momentum.
  3. Introduce Level 10 Meetings: Train the leadership team on how to conduct effective weekly Level 10 Meetings to solve issues, track progress on Rocks, and ensure team alignment and accountability.
  4. Develop the Scorecard: Create an initial version of the Scorecard to track key measurables (metrics or KPIs) weekly. This helps maintain focus on the most important numbers.

Day 10 to Day 30: Implement Foundational EOS Tools

• Implement Level 10 Meetings: Start holding weekly Level 10 Meetings immediately. These meetings will help maintain alignment, track progress on Rocks and Scorecard metrics, and address any emerging issues.
• Evaluate Team Health: Use insights from the Listening Tour and initial meetings to evaluate the health and dynamics of the leadership team. This is also a good time to address any immediate issues or gaps identified in the Accountability Chart.
• Hold First Town Hall: Conduct a company-wide town hall meeting to introduce EOS, outline the first 60-day Rocks, and set expectations for the team. This is essential for ensuring everyone is on the same page.

Day 30 to Day 40: Vision Building Day One – Create Clarity and Alignment

• Vision Building Day One Workshop:
  1. Review Progress with EOS Tools: Assess how the team is performing with the tools introduced on Focus Day, including the Accountability Chart, Rocks, Scorecard, and Level 10 Meetings.
  2. Define Core Values: Conduct a discovery exercise to either review or establish the core values that define the organization’s culture. These core values should be authentic and unique, serving as a true reflection of the values that represent the best of your organization.
  3. Clarify Core Focus: Define the organization’s core focus, which represents its “sweet spot”—why the company exists and what it does best.
  4. Set Core Target (10-Year Target): Establish a long-term goal, also known as the Core Target, that sets a clear and inspiring direction. The timeframe is flexible, anywhere from 5 to 30 years.

Day 60 to Day 70: Vision Building Day Two – A Clear Plan to Achieve the Vision (Finalizing the VTO)

• Vision Building Day Two Workshop:
  1. Review and Refine Vision Elements: Revisit the core values, core focus, and core target established during Vision Building Day One. Make adjustments based on feedback and deeper discussions.
  2. Develop the Marketing Strategy: Define the company’s marketing strategy, including identifying key customers and markets that align with achieving the core target. This strategy outlines how the organization will attract and retain the right customers.
  3. Create the Three-Year Picture: Establish a three-year vision for the company, including high-level numbers like revenue, profit, and other key financial metrics. Describe what the company will look like in terms of culture, customer base, and key accomplishments.
  4. Set the One-Year Plan: Develop a detailed one-year business plan that includes top-line numbers (revenue, profit) and 3-7 specific goals. These goals will provide a clear roadmap for the next 12 months.
  5. Review and Set New Rocks: Evaluate the completion of the initial 60-day Rocks and establish new 90-day Rocks aligned with the one-year plan. This ensures continued focus and momentum.
  6. Identify and Prioritize Issues List: Create a comprehensive Issues List, identifying the key challenges that need to be addressed to support the organization’s vision and strategic priorities.
  7. Put All Information Together in the Company VTO: Compile the core values, core focus, core target, marketing strategy, three-year picture, one-year plan, and Rocks into the Vision/Traction Organizer (VTO).

Day 70 to Day 100: Get the Vision Shared by All

• Share the Vision with All-Hands Meeting: Hold an all-company meeting to share the company VTO. Communicate any structural or organizational changes, including the launch of the Accountability Chart, and outline new roles and responsibilities.
• Launch the Accountability Chart: Implement the newly defined Accountability Chart, which may involve redefining roles, changing responsibilities, or introducing a new structure. This is a critical step in ensuring that everyone understands their role and is aligned with the new direction.
• Monitor Team Engagement: Start monitoring how well the new structure and vision are being embraced across the organization. Use surveys or informal check-ins to gauge employee sentiment and address any concerns early on.

Day 90 to Day 100: Drive Execution, Build Engagement, and Develop Leadership Capability

• Continue Weekly Level 10 Meetings: Maintain the cadence of weekly Level 10 Meetings to review the Scorecard, assess progress on Rocks, identify issues, and solve them promptly. These meetings are essential for keeping the leadership team aligned and focused.
• Engage and Motivate Employees: Begin to Live the Core Values by recognizing and celebrating behaviors that align with the company’s core values. Consider implementing Culture Awards or similar initiatives to celebrate and reinforce the desired culture.
• Implement Regular Cadence Reviews: Set up a quarterly review cadence to assess progress against the one-year plan, reset Rocks, and adjust the vision and strategy as needed. Regular reviews help maintain focus and momentum throughout the year.
• Drive Financial Performance (Optional): If there is an immediate need to improve financial performance, use the Eight Cash Flow Drivers tool to identify opportunities for cost savings, cash flow optimization, and profitability enhancement.
• Assess Departmental Readiness for EOS Rollout: Begin evaluating the readiness of different departments to start rolling out EOS tools, such as Level 10 Meetings and Scorecards. Typically, start with larger departments to build traction and demonstrate the benefits of these tools.
• Develop Leadership and Management Capability Throughout the Organization:
  1. Read “How to Be a Great Boss”: As the CEO, read the book “How to Be a Great Boss” to understand the principles of effective leadership and management. This book provides practical advice on building a strong team and creating a culture of accountability.
  2. Distribute the Book to Leadership Team: Provide a copy of “How to Be a Great Boss” to each member of the leadership team and ask them to read it. Encourage discussion around the key takeaways and how they can be applied to build a high-performing team.
  3. Conduct a Leadership and Management Assessment: Utilize the tools from “How to Be a Great Boss” to conduct an assessment of leadership and management capabilities across all departmental leaders. This will help identify gaps and opportunities for development and ensure the company is building a strong leadership pipeline.

Plan for the Next Steps

• Plan for the Next Steps: After Day 100, focus on continuing the execution of the one-year plan and refining the longer-term strategies to ensure sustainable growth and success.

Conclusion

You’ve got the keys, the roadmap, and the tools — now it’s time to hit the open road. The first 100 days as CEO are your chance to rev up the engine, find your rhythm, and make some bold moves. With the right mix of strategy, communication, and EOS tools, you’ll turn your team into a high-performing pit crew, all working toward a shared vision.

Remember, great driving isn’t just about speed; it’s about control, direction, and keeping everyone on board. So, keep your hands on the wheel, eyes on the road, and don’t be afraid to enjoy the ride. After all, the journey is just getting started — and the road ahead is wide open.