31 Questions I ever wanted to ask a Chief Learning Officer

Leaders of past knew the right answers, Future Leaders will know how to ask the right questions.
Managers ask How, Leaders ask what and why ?
Peter Drucker

here is my list of favorite questions that i always wanted to get answers from L&D Leaders.


1. Is there someone in your team who manages informal ( social) learning formally ?
2.Do you have a Leadership Development Program which is tied to Succession Planning ? Who designed that program ? Who delivers that program ?
3. What do you value more if the focus is to develop say Collaborate Globally competency , heavy content loaded deck with case studies which is just sufficient to last for a 2 day workshop or 1 hour session which focuses on lab training to learn new tools usage of which percolates new behaviors amongst target audience .
4. Share an example of one of a good design you have seen in recent times for an LD Program.
5. What are the present tools, resources, process which support Leaders Learning from Leaders in your organization ?
6. Where is the focus on LD in your organization ? On Formal classroom training sessions or informal social learning ?
7. What are the tools & platforms which support knowledge , best practices sharing ?
Does a training calendar gets published on recurrent basis for LD Programs ?
8. How many LD sessions got cancelled last month due to less enrollments ?
9. What is the average duration of a LD workshop in your organization ?
10. Do you leverage assessment center for assessing Leadership competencies ?
11. Would you rather prefer a short duration sessions at regular intervals for Leadership Development or one several months long intervention ?
12. How is the response to Blended Learning from senior leaders in your organization ?
13.What is the ususal response from Leaders in your company to a Leadership development program ? Do they consider it gyaan or fun ?
14. What makes Leaders take interest and be curious about a program that has been designed to address specific business challenge ?
15. What is the most pressing People / Leadership problem that you face in your organization ?
16. What keeps you wake at night ?
17. What when someone performed brilliantly well on your team last time ?
18. What was your response when one of your team member had a perfect recipe for disaster ? or actually had done a blunder ?
19. How often you spend time with your team members ? formally & informally
20. Do you like to coach ?
21. Do you have Executive Coaches capabilities developed in house ? Do you plan to invest in developing these capabilities in your team for organizational success ?
22. When was the last time you had much fun on a project at work ? Describe how did it feel like ?
23. Did you enjoy going through the above questionnaire ? then , go through some more...;-)
24. Is the focus on quality of LD program or operational efficiency or something else ?
25. What gets measured for your team performance ?
26. How does a typical scorecard for your team looks like ?
27. How many dollars were wasted due to non- participation by Senior Leaders in LD programs that were designed to solve business problems.
28. Are workshops conducted in house or at outside location ?
29. Which is that one book that you like going back to often ?
30. What does success look like for your team ?
31. Do you write , tweet , share yourself online ?