'How to Make Sense of Any Mess' Questions

The following are helpful questions I try to answer whenever approaching a new project. Not all of the questions are applicable every time.

These questions were taken from Abby Covert's incredible book, 'How to Make Sense of Any Mess'. Thank you Abby. ✌️


  • who are your intended users?
  • what do you know about them?
  • how can you get to know them better?
  • how might they describe this mess?


  • who are your stakeholders?
  • what are their expectations?
  • what are their thoughts about this mess?
  • how might they describe it?


  • what interpretations are you dealing with?
  • what information is being created through a lack of data or content?

current state:

  • are you dealing with too much information?
  • not enough information?
  • not the right information?
  • or a combination of these?

who matters:

  • who is the most important to get agreement from?
  • who is the most important to serve?
  • what words might make them defensive?
  • what words might put them at ease?
  • how open are they to change?
  • how will this affect their lives?
  • how does the current state of things look to them? Is that good or bad?


  • why does this work need to be done?
  • why is change needed?
  • why do these changes matter?
  • why should other people care?
  • why hasn't this been tackled correctly in the past?
  • why will this time be different?


  • what are we trying to change?
  • what is your vision of the future?
  • what is within our abilities?
  • what do you know about the quality of what exists today?
  • what further research will help you understand it?
  • what has been doe before?
  • what can you learn from those experiences?
  • what is the market competition like?
  • has anyone succeeded or failed at this in the past?


  • how much time and effort will this take?
  • how could this solution look and feel?
  • how will this be produced?
  • how will this be maintained?
  • how will this be measured?
  • how will we know if we've succeeded?
  • how could we communicate our message?