What Could Possibly Go Wrong?

key players are in agreement. And I look for areas where there's not enough time to finish a component-or finish with desired quality. These questions help me identify natural areas of risk. I pull out a list of common software project risks to jog my thinking.

Then I start asking "What if" questions:

  • "What if we can't fill those three positions by week four of the project?"
  • "What if a competitor releases a new feature and Marketing wants to change our feature set?"
  • "What if we lose a key project team member?"
  • "What if our design won't carry the volume we think it will?"
  • "What if the vendor code is buggy?"

"What if" questions help me figure out the impact of potential problems and develop contingency plans that will help us meet project goals when something does go wrong.

I look around the organization: How have similar projects fared? What wisdom do other project managers, developers, and testers have to share about past efforts? What's the history of projects in the organization?

Finally, I ask someone else who has a fresh point of view or someone who has done something similar to poke holes in the plan. This isn't always fun. When I'm in the throes of enthusiasm over a new project, or think I've found an elegant solution, it's a drag to hear about what could go wrong. Sometimes I just want the other person to be as excited as I am about my neat design. In the long run, though, it helps me come up with an even better solution and develop a more resilient plan to help stay on track when something does go wrong (and it will).

Along with your other comments, why don't you share some of your best "What if" questions in the comment space below?

About the author

Esther Derby's picture
Esther Derby

A regular StickyMinds.com and Better Software magazine contributor, Esther Derby is one of the rare breed of consultants who blends the technical issues and managerial issues with the people-side issues. She is well known for helping teams grow to new levels of productivity. Project retrospectives and project assessments are two of Esther's key practices that serve as effective tools to start a team's transformation. Recognized as one of the world's leaders in retrospective facilitation, she often receives requests asking her to work with struggling teams. Esther is one of the founders of the AYE Conference. She co-author of Agile Retrospectives: Making Good Teams Great. She has presented at STAREAST, STARWEST and the Better Software Conference & EXPO. You can read more of Esther's musings on the wonderful world of software at www.estherderby.com and on her weblog at www.estherderby.com/weblog/blogger.html. Her email is derby@estherderby.com.