What to Ask in Week 1 as a CEO & Co-Founder

Stepping into the CEO & Co-Founder role is like inheriting a complex machine mid-operation. The pressure is on to deliver, but diving in without understanding the landscape can be disastrous. This isn’t about asking generic “get to know you” questions; it’s about gathering critical intel that shapes your strategy and ensures early wins. This article will give you the exact questions to ask, the metrics to track, and the artifacts to demand within your first week to set yourself up for success. This is not a generic onboarding guide; it’s a CEO & Co-Founder-specific action plan.

The Week 1 CEO & Co-Founder Icebreaker: Intel Gathering, Not Chit-Chat

By the end of this read, you’ll have: (1) a prioritized list of questions to ask key stakeholders, (2) a checklist for assessing the current state of critical projects, and (3) a script for your initial all-hands meeting that sets the tone for your leadership. These will help you make informed decisions faster and prioritize actions that protect revenue and drive growth—all within your first week.

• A prioritized question list for key stakeholders: Know what to ask the CFO, CTO, and other leaders.
• A project assessment checklist: Quickly evaluate the health of ongoing projects and identify potential risks.
• An all-hands meeting script: Set the tone for your leadership and communicate your vision clearly.
• A risk assessment framework: Identify and prioritize potential threats to the business.
• A communication cadence plan: Establish a regular communication schedule with key stakeholders.
• A decision-making rubric: Guide your prioritization and resource allocation.

What a hiring manager scans for in 15 seconds

Hiring managers want to see that you can quickly assess a situation and identify key areas for improvement. They look for signals that you understand the complexities of running a company and can prioritize effectively. Here’s what they scan for:

• Strategic focus: Do you understand the company’s mission and how your role contributes to it?
• Financial acumen: Can you analyze financial data and make sound business decisions?
• Operational efficiency: Can you identify and improve inefficient processes?
• Team leadership: Can you motivate and guide a team to achieve its goals?
• Risk management: Can you identify and mitigate potential risks to the business?
• Communication skills: Can you communicate your vision clearly and effectively?

Initial Questions for Key Stakeholders

Your first week is about listening, not dictating. These questions are designed to extract crucial information from key stakeholders:

Questions for the CFO

Focus on understanding the financial health of the company. Ask about key performance indicators (KPIs), cash flow, and budget variances.

• What are the top 3 revenue drivers, and how are they trending?
• What are the biggest cost centers, and what initiatives are underway to reduce expenses?
• What is the current cash runway, and what are the key assumptions driving the forecast?

Questions for the CTO

Understand the technology roadmap and any potential bottlenecks. Focus on scalability, security, and innovation.

• What are the key technology priorities for the next 6-12 months?
• What are the biggest technical risks, and what are the mitigation plans?
• How is the technology team structured, and what are the key skill gaps?

Questions for the Head of Sales

Assess the sales pipeline and identify opportunities for growth. Focus on customer acquisition, retention, and revenue generation.

• What is the current sales pipeline, and what is the conversion rate?
• What are the biggest challenges facing the sales team, and what support do they need?
• What are the key customer segments, and what are their needs?

The mistake that quietly kills candidates

Failing to ask insightful questions and instead presenting a pre-packaged solution is a critical mistake. It signals arrogance and a lack of understanding of the specific challenges facing the company. The fix? Prioritize listening and asking questions over presenting solutions in the first week. Show you’re there to learn and collaborate.

Use this in your first meeting with the leadership team:

“My priority this week is to understand the current state of the business. I want to hear your perspectives on the biggest opportunities and challenges we face. I’ll be asking a lot of questions, and I appreciate your candor and insights.”

Project Assessment Checklist

Quickly evaluate the health of ongoing projects. Use this checklist to identify potential risks and areas for improvement.

• Project Scope: Is the scope clearly defined and agreed upon?
• Project Timeline: Is the timeline realistic and achievable?
• Project Budget: Is the budget sufficient to complete the project?
• Project Resources: Are the necessary resources available and allocated?
• Project Risks: Are the potential risks identified and mitigated?
• Project Communication: Is there a clear communication plan in place?
• Project Metrics: Are there clear metrics to measure project success?

All-Hands Meeting Script

Set the tone for your leadership. Communicate your vision clearly and inspire confidence in the team.

Use this to open your first all-hands meeting:

“Hello everyone, I’m [Your Name], and I’m excited to join you as your CEO & Co-Founder. My first priority is to understand our strengths and opportunities. I believe in transparency, collaboration, and a focus on delivering value to our customers. Over the next few weeks, I’ll be meeting with many of you to learn more about your roles and perspectives. I’m confident that together, we can achieve great things.”

Prioritization Framework: What to Focus on First

Not everything is equally important. Use this framework to prioritize your actions and focus on the most critical areas.

• Revenue-Generating Activities: Focus on activities that directly contribute to revenue growth.
• Cost-Saving Initiatives: Identify and implement initiatives that reduce expenses.
• Risk Mitigation: Address potential risks that could negatively impact the business.
• Team Alignment: Ensure that the team is aligned on the company’s goals and priorities.

Setting Up a Communication Cadence

Establish a regular communication schedule with key stakeholders. This ensures that everyone is informed and aligned.

• Weekly Leadership Team Meeting: Discuss key performance indicators, project updates, and strategic initiatives.
• Monthly All-Hands Meeting: Communicate company updates, celebrate successes, and address employee concerns.
• One-on-One Meetings: Meet with key team members to discuss their progress, challenges, and goals.

Key Performance Indicators (KPIs) to Track

Monitor key performance indicators to track progress and identify areas for improvement. Here are some essential KPIs for a CEO & Co-Founder:

• Revenue Growth: Track revenue growth to assess the company’s overall performance.
• Customer Acquisition Cost (CAC): Monitor CAC to ensure that customer acquisition is cost-effective.
• Customer Retention Rate: Track customer retention rate to measure customer loyalty.
• Gross Margin: Monitor gross margin to assess the profitability of the company’s products or services.
• Cash Runway: Track cash runway to ensure that the company has sufficient funds to operate.

Potential Failure Modes and Mitigation Strategies

Identify potential failure modes and develop mitigation strategies. This helps to prevent problems before they occur.

• Lack of Communication: Implement a clear communication plan to ensure that everyone is informed.
• Misalignment of Goals: Align the team on the company’s goals and priorities.
• Inadequate Resources: Ensure that the necessary resources are available and allocated.
• Poor Execution: Implement project management best practices to ensure that projects are executed effectively.

Language Bank: Phrases That Signal Competence

Use these phrases to communicate your competence and leadership. Sound like you’ve been in the room before.

• “Let’s focus on the key drivers of revenue growth.”
• “We need to improve our customer acquisition cost.”
• “I want to ensure that we have a clear communication plan in place.”
• “We need to align the team on our goals and priorities.”
• “Let’s identify and mitigate the potential risks to the business.”

Quiet Red Flags: Subtle Signs of Trouble

Pay attention to these subtle signs of trouble. They can indicate deeper problems within the organization.

• Lack of Data-Driven Decision Making: Decisions are based on gut feeling rather than data.
• Resistance to Change: Employees are resistant to new ideas and initiatives.
• Blame Culture: Employees are quick to blame others for mistakes.
• Lack of Accountability: Employees are not held accountable for their actions.

What a strong CEO & Co-Founder does vs. a weak one

• Weak: Makes sweeping changes without understanding the current state. Strong: Asks questions, listens, and gathers data before making decisions.
• Weak: Focuses on short-term gains at the expense of long-term sustainability. Strong: Balances short-term needs with long-term strategic goals.
• Weak: Micromanages the team and stifles creativity. Strong: Empowers the team and fosters a culture of innovation.

FAQ

What are the most important things to focus on in the first week as a CEO & Co-Founder?

The most important things to focus on in the first week are gathering information, building relationships, and setting the tone for your leadership. Ask questions, listen to your team, and communicate your vision clearly.

How do I build trust with my team in the first week?

Building trust requires transparency, empathy, and a willingness to listen. Be open and honest with your team, show that you care about their concerns, and be receptive to their ideas.

What should I do if I identify a major problem in my first week?

If you identify a major problem, don’t panic. Take a step back, gather more information, and develop a plan to address it. Communicate the problem to your team and solicit their input.

How do I prioritize my actions in the first week?

Prioritize your actions based on their impact on revenue, cost, and risk. Focus on activities that will have the biggest positive impact on the business and address the most critical risks.

What are the common mistakes that new CEO & Co-Founders make?

Common mistakes include making sweeping changes without understanding the current state, focusing on short-term gains at the expense of long-term sustainability, and micromanaging the team.

How do I set expectations for my team in the first week?

Set clear expectations for your team by communicating your vision, goals, and priorities. Be specific about what you expect from them and provide them with the resources and support they need to succeed.

What should I do if I disagree with a decision that was made before I joined the company?

If you disagree with a decision, don’t immediately overturn it. Take the time to understand the rationale behind the decision and consider the potential consequences of changing it. If you still disagree, discuss your concerns with the relevant stakeholders and propose an alternative solution.

How do I handle difficult stakeholders in my first week?

Handling difficult stakeholders requires patience, diplomacy, and a willingness to listen. Try to understand their perspective and find common ground. Communicate your goals clearly and be prepared to compromise.

How do I balance the need for quick wins with the need for long-term planning?

Balancing quick wins with long-term planning requires careful prioritization. Focus on activities that will deliver immediate results while also laying the foundation for future success. For example, you might implement a cost-saving initiative that generates immediate savings while also developing a long-term strategic plan.

What are the key metrics that I should be tracking in the first week?

Key metrics include revenue growth, customer acquisition cost, customer retention rate, gross margin, and cash runway. Track these metrics to assess the company’s overall performance and identify areas for improvement. For example, if revenue growth is slowing, you might focus on initiatives to increase sales or improve customer retention.

How do I build relationships with key customers in my first week?

Building relationships with key customers requires a personal touch. Reach out to them, introduce yourself, and ask for their feedback. Show that you value their business and are committed to their success. For example, you might schedule a call to discuss their needs and challenges or invite them to an exclusive event.

What should I do if I feel overwhelmed in my first week?

If you feel overwhelmed, take a step back and prioritize your tasks. Focus on the most important things and delegate the rest. Don’t be afraid to ask for help from your team or other colleagues.

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