30 Milestone Questions

Random Observation/Comment #550: Time-boxing commitments and projects creates the urgency for reaching milestones of change.


Why this List?

What a feeling it is to reach a big milestone! Milestones keep you honest on timing, but more importantly, give you something to celebrate. Do your happy dance. Done? The next step is crucial: review and learn from your milestone. Notice that this isn’t just a lessons learned of a full project or sprint, this is a retrospect of success. Notice that these do not just apply to career projects, but also with relationships of all types. Here are some questions I ask myself, the team, and the bigger community (bolded the important ones):

  1. What are our strengths?
  2. What’s working?
  3. What’s not working?
  4. What do we want?
  5. What do our clients/others want?
  6. What are we going to get when we get what we want?
  7. What tweaks do we want to make?
  8. Who should be involved?
  9. Should they be involved earlier?
  10. What’s the next milestone?
  11. What artifacts can you keep from your milestone?
  12. What artifacts can become templates?
  13. How can others learn from these successes?
  14. What could have gone wrong?
  15. How do we mitigate these risks going farther?
  16. What micro-goals can we create to encourage better collaboration?
  17. Is transparency and communication an issue?
  18. Operationally, are ideas brought up in a clear way?
  19. Does the group understand the long term strategy?
  20. Is your long term strategy still relevant given the results?
  21. Is there a gap in knowledge for your team that should be learned or shared?
  22. Do you need to hire a specific skill set to round out the group?
  23. What was the most difficult part?
  24. Are there more than one blockers that you need to address for long term?
  25. What was the most surprising part?
  26. Who should be recognized from the group?
  27. Can you present this success at a conference or meeting to recognize the participants?
  28. Can you summarize this success in an elevator pitch or deck slide for others to use?
  29. Has your team built a pattern of success?
  30. Is everyone in the team happy?

~See Lemons Reach Milestones