The Self-Assessment

I have been working on these questions as a useful (but non-exhaustive) tool for leaders who are in the process of closing down their company, organization, or project. I recommend you work through them with a trusted partner, I think one section per session is enough. Give yourself some emotional space!

The idea is that they will help you think through the messy/more emotional stuff but also identify critical TODOs. Write out your answers but keep a separate notepad space for reminders that pop up as you think this through.

(If you aren’t sure whether you are at a closing point yet, I suggest you first work through the excellent Sensing An Ending toolkit from my friends at Stewarding Loss.)

Self-Assessment Questions

History of [ORG] and you!

  • What brought you to (create) [ORG]?
  • What kept you at [ORG]?
  • What role does [ORG] play in your day to day life? How long has it played that role?
  • What did you do try to keep [ORG] alive longer?
  • Do you feel there were any social structures that unfairly contributed to this end? Are there any larger hardships you felt you and/or [ORG] faced?
  • What were you able to accomplish through working with/at [ORG]?

You and Loss

  • What is your history of grief and loss?
  • What rituals, practices, and our cultural traditions do you already have?
  • How are they working? How have they worked?

Wreckage of the Past

  • What do you wish you had done differently during your time at ORG?
  • What do you wish ORG had been able to do/accomplish?
  • What do you wish ORG had never done? Any other regrets?

Wreckage of the Future

  • What do you feel like you will you lose when ORG closes?
  • Who do you feel like/worry you will be when ORG closes?
  • How do you think that you will you structure your days when ORG closes? What changes?

The Present

  • Who needs to know that ORG has closed?
  • Who will tell them?
  • What thing/things from ORG hold meaning to you? Can you keep them? Why or why not?
  • What thing/things from ORG could be useful to others? Can you give those things to them? Why or why not?
  • What else feels unclear?
  • What else feels unspoken?
  • What else needs attention?
    • Is there anything you still want to do in the time you have left and what help do you need?
    • Is there anything you still want to make right in the time you have left?

The Team

  • Do people need to be let go? 
  • How to communicate that? 
  • How to soften the blow? 
  • Can/should they be brought into this process? 
  • Emotional and tangible resources? 
  • What mark do they still want to leave?