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Three Questions Executives Need to Answer

To persuade board members, executives, department heads, or shareholders, you must first have confidence in your answers.

Author

Todd Moses
July 30, 2025

As a 3x AI founder, I had to answer: "What are we building?", "Why are we the right people for the job?" and "Why is it the perfect time to do it?"

Why it matters: For leaders aiming to transform their company from a traditional, role-based workforce to a new skills-based organization through AI, they must address the same questions.

  • The problem is that these questions are complex.

  • Not hard to answer, but hard to believe the answer.

Between the lines: To persuade board members, executives, department heads, or shareholders, you must first have confidence in your answers.

  • This requires a significant amount of effort to ensure each question is thoroughly addressed.

  • The responses should be comprehensive and accepted by all members of your AI steering committee.

Yes, but: People often discover uncomfortable truths when answering these questions.

  • For instance, is what you're building truly what they need?

  • It's usually easier to face that reality than to admit you are not the right person for the job or that it is not the right time to pursue it.

Zoom in: It is essential to rehearse your answers to key questions with advisors, co-founders, and trusted staff members.

  • Sometimes the feedback you receive can be challenging to accept.

  • However, you shouldn't only share your answers with those who will tell you what you want to hear.

  • Instead, have the courage to seek out people who will offer honest feedback and have the expertise to provide valuable suggestions.

What's next: When you can confidently answer each of these questions accurately, you are ready to lead your organization toward a transformation into a skills-based future.

  • If you cannot answer them with confidence, it's time to dig deeper.

  • Consider conducting further research by discussing with your staff or seeking the input of another leader to drive the change.

Go deeper: Need help with your Enterprise AI transformation? Contact Todd Moses & Co for free resources, AI Literacy training, and guidance.