“Mayday!  Mayday!  We are stuck on Waterfall Island!  Please send help immediately!”  If you received this alert, how might you respond to the citizens of Waterfall Island?

At the Scrum Gathering in Phoenix, Peter Stevens from Switzerland offered this provocative list of questions to consider when thinking about how to help people move from the old way of doing things (Waterfall Island) to a more Agile approach.

1. Do you want me to be here?  Often times people claim they want to start doing Scrum or Agile, but in reality they are not interested in making any significant changes in their behavior or the organization.  Or they are willing for other people to change just as long as their world does not change.  Another pitfall to watch out for is when the Team declares their expertise in an Agile process, but in reality has (sub)optimized their Agile process around their particular organizational dysfunctions.
2. What are you trying to to achieve?  In the rush to get a new project started, this question often gets overlooked.  More importantly, how does Scrum and Agile supports the business objective the organization is hoping to realize.  I would also add that if the Stakeholders cannot describe their Vision for a better organization, is poorly articulated or not alignment with what the Teams have in mind for a better organization, then whatever gets implemented with respect to Scrum and Agile will be shallow and temporary.
3. What is your biggest impediment?  Something is happening (or not happening) in the organization that prompted the business to start this process of inquiry into adopting an Agile process.  I recommend asking Stakeholders how this impediment affects their future growth, revenue targets, product innovation, quality and\or customer satisfaction.  If the impediment does not move one of those five factors, it is not the real impediment.
4. What was your best project?  Ask people about their experiences of being a member of a successful project in the organization.  Investigate what were the factors that enabled that project to be succeed.  Was it the work?  The people?  Management involvement?  Customer involvement?  Something about the technology?  Put these items on a list and make sure you have these items before starting.  Refer to the list as the change initiative takes flight to confirm these factors remain present.
5. What has worked in the past?  Most every organization knows how to succeed otherwise they would go out of business.  IMO, one of the driving factors why many companies are interested in Scrum and Agile is they have forgotten how to deliver, i.e. get a win.  With this question, the job is to unearth what the business already knows how to do well and then find ways to leverage that experience in the new way of working together.
6. Who wants this to be the best project?  This question may seem completely obvious, but take a moment to ask the participants if they want to make this project the best project ever.  This simple question has multiple goals.  One, it sets the standard of success very high.  No one wants to deliver something mediocre.  Two, the question encourages the participants to commit early to being active participants in culture change.  Three, this question unearths the obstacles that will prevent this project from being the best project ever.  If what the participants say are a lot of obstacles, I recommend playing  Fearless Journey to help the participants see that change possible and real.
7. Who is the Product Owner?  Without a Product Owner, Scrum will not work.  Do not start Scrum unless you have a Product Owner who is empowered, engaged and available.  In almost all cases the Product Owner must come from the business.  I really don’t like technical Product Owners.  If the business does not see the benefit of  close collaboration with the technical team, i.e. does not assign a Product Owner full-time to the Team, don’t do Scrum.
8. Where does it hurt?  So what is really so bad about Waterfall Island?  Again, another evident question, but the goal is to gather information from every part of the organization about what hurts.  Remain empathetic while capturing what people tell you and make sure to point out any pains they have grown accustomed to.  Ask them to rank these pains from extreme to moderate.
9. What is the Definition of Done?  If the organization is new to Scrum and Agile, take a moment to create the Definition of Done (DOD).  If the participants are experienced, review their current DOD and update it.  I guarantee that it is out-of-date.  DOD is an important concept and vital to restoring trust between the Team and the business.  As more and more Teams work on the same product and code base, the DOD will have to converge so everyone has the same expectations on what defines a quality product.