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Career Arc and Selling His First Business
- Please walk us through the chronology of your career
- After your first exit, how did you make the decision to become a CEO again?
- After you sold your first company, you stayed on to help with the integration process. What was most difficult or surprising about this period of your career?
- How should exiting CEOs think about the length of transition periods and what appears to be a positive correlation with exit proceeds?
- When you purchased Predictive Index it was largely a service business, and it’s now largely a software company. What were the most challenging or surprising aspects of navigating the company through this transition?
- How did you think about when to begin executing on such fundamental changes within a newly acquired business?
Personality Profiling Tools
- How well do these tools translate into “blue collar”, “old economy” types of businesses?
- How useful are these types of tools when making hiring decisions for roles that are largely performed individually, not as part of a team?
- Based on your own Predictive Index results, what within your profile is suggestive of your success as an entrepreneur and CEO?
- If an acquisition entrepreneur approached you to invest in them, what would you look for in their personality profile? Are there profiles that are more predictive of success than others?
- How might we use tools like Predictive Index, if at all, in our personal relationships?
- Do people’s personality profiles change over time?
Lessons Learned as a CEO
- Explain your “head, heart, and briefcase” framework for evaluating talent, and tell us where within that framework do most hiring mistakes tend to take place?
- What are some of the hiring mistakes that you’ve made recently, and what generalizable lessons did you extract from those mistakes?
- How do you modify yourself as a leader when communicating with employees with very different personality profiles? How do you maintain your authentic leadership style but modify your style simultaneously?
- What should leaders do when managing somebody with a personality profile that tends to clash or conflict with their own?
- If you could buy a business all over again, knowing what you know now, what would you do differently with respect to talent evaluation during the due diligence process?
Working with a Partner
- What have you learned about the merits and risks of pursuing any entrepreneurial endeavor with a partner versus doing so on your own?
- For prospective entrepreneurs wrestling with the question of whether or not to work with a partner: Are there any introspection exercises, questions, exercises, or frameworks that they should utilize or think through?
- What are some of the best practices that you’ve used over the years to maintain a healthy and functioning partnership for as long as you have?
- If you were to evaluate the respective personality profiles of yourself and your partner, what about these profiles might suggest such an enduring, healthy partnership?
- A few years ago, you decided to take your family on a one-year trip to the Caribbean. What prompted that decision, and what did you learn from that experience?
- What are some of the practices or rituals or tools that you’ve put into place to ensure that your work does not take precedence over your life?
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