After 8 ventures, I unveil the pitfalls and provide 16 smart questions for sales leaders interviewing at VC-backed companies to dodge the perils of working for a leader with Founder Syndrome.

Founder Syndrome is more common in VC-backed tech startups than you might think. It stems from inexperienced leaders, lack of proper training, and the echo chamber of 'yes-men' around them. Let's dive into this phenomenon and equip sales leaders with the tools to identify and avoid it.

Understanding Founder Syndrome

What is Founder Syndrome?

Founder Syndrome is a set of behavioral traits exhibited by a company's founder, often negatively impacting the organization's growth and success. It arises when founders struggle to adapt as their startup evolves, hindering effective leadership.

Signs of Founder's Syndrome

1. Resistance to Delegation: Founders may find it challenging to delegate tasks, clinging to a hands-on approach that becomes unsustainable as the company grows.

2. Avoidance of Feedback: A founder under the influence of Founder Syndrome may resist constructive criticism, shielding themselves from diverse perspectives that could aid growth.

3. Centralized Decision-Making: Decisions often become centralized around the founder, limiting collaboration and stifling innovation.

Dangers of Founder's Syndrome

1. High Turnover: Employees may leave due to frustration with an autocratic leadership style, leading to high turnover rates.

2. Stifled Innovation: A founder resistant to change may impede the company's ability to innovate and adapt to evolving market dynamics.

3. Poor Company Culture: The negative traits of a founder can permeate the company culture, impacting morale and hindering collaboration.

16 Smart Questions to Ask the Founder/CEO

1. What is your leadership philosophy, and how has it evolved as the company has grown?

2. Can you share instances where you've actively sought and implemented feedback from your team?

3. How do you empower your team through delegation while ensuring accountability?

4. Describe a situation where you faced failure and how you handled it, both personally and as a leader.

5. In what ways do you encourage a culture of continuous learning and adaptation within the organization?

6. Can you provide examples of decisions where you sought input from diverse perspectives within the team?

7. How do you handle disagreements or conflicts within the leadership team?

8. What steps do you take to ensure a healthy work-life balance for yourself and your team?

9. Describe your approach to talent acquisition and how you foster a diverse and inclusive work environment.

10. In what ways do you encourage creativity and innovation within the organization?

11. Can you share instances where you've recognized and addressed your own shortcomings as a leader?

12. How do you prioritize and set long-term goals for the company, and how do you ensure alignment throughout the organization?

13. What mechanisms do you have in place for gathering and acting upon employee feedback?

14. How do you handle periods of rapid growth or unexpected challenges within the company?

15. Describe your strategy for building a collaborative and cohesive leadership team.

16. How do you plan to evolve your leadership style as the company continues to grow and change?

Conclusion: Steering Clear of Founder Syndrome

Sales leaders, particularly in the dynamic world of tech startups, must be vigilant during interviews to discern signs of Founder Syndrome. Armed with these 16 questions, you're equipped to gauge a founder's leadership style and make an informed decision about joining their team.

If you're a sales leader interviewing at a VC-backed company, download my comprehensive guide on 16 other smart questions to ask during interviews here. It might help you avoid working for a crazy founder who will make your life miserable.