Going to just jot down some questions I've enjoyed asking new founders of teams under ten;

For the First Design Hire

1. Role of Design
   Q: What role does design play today, and how will this hire change that?
   W: Understand current processes and the vision for design.

   
   

2. Impact of Design
   Q: What struggles will a designer help your team overcome?
   W: Clarify their thesis for hiring a designer.

   
   

3. Internal vs. Contract
   Q: Why hire a full-time designer instead of using contractors?
   W: Gauge their commitment, risk tolerance, and prior experience with design.

   
   

4. Customer Expectations
   Q: What are your customers' expectations of their software?
   W: Reveals the team’s quality standards and shipping comfort level.

   
   

5. Business Risks
   Q: What are the major risks to your business today?
   W: Assess how they handle uncertainty and their realism about challenges.

   
   

6. Your Fit
   Q: How does my experience align with what you're building?
   W: Ensure their expectations match your expertise and career goals.

For the Second/X Design Hire

1. Cultural Design Practices
   Q: What are the company’s design practices?
   W: Understand the team’s structure (crits, reviews, tools).

   
   

2. Decision-Making
   Q: How are decisions made?
   W: Learn if the culture prioritizes consensus, autonomy, or hierarchy.

   
   

3. Team Skills
   Q: What skills does the team have today, and what are they hiring for?
   W: Identify opportunities for growth and collaboration.

General Questions

1. Values
   Q: What are your values as a company and as individuals?
   W: Check alignment with your own values and decision-making framework.

   
   

2. Business Model
   Q: How does the business make money, and what’s the opportunity?
   W: Understand their approach to scaling, sustainability, or exit strategy.