So many leaders or teams quickly move too quickly (or skip entirely) the early parts of a new project/initiative, failing to invest real time in wrestling with questions like:

• Should we do this project? (This question is skipped way too often — think about investing in exercises like a business case or a project charter to ensure everyone is clear on the value/ROI)
• Who are all the stakeholders/users (not just the primary one(s)) who are affected or will be affected by this project? What do they really want/need?  What are their pain points?  What are their issues they don’t even know they have?  (Note: The whole field of User Experience (UX) and User Centered Design (UCD) has many, many tools and techniques to help navigate this area)
• Do we really understand why we’re doing this project? (What is the business problem?  What value will the ‘business’ receive at the end of the project?
• Do we understand the different ways we could break down the value we’re going to deliver, to understand the trade-offs in different ways to approach the project (e.g. could we deliver value earlier and get validation (reduce risk) by starting to focus on a specific Minimal Viable Product instead of running in the direction we think is ‘most efficient’ for the final product (which almost certainly isn’t the most efficient way, because there’s so much we don’t know at this point) (See The Startup Way by Eric Ries)

After we get through those phases, we should avoid the desire to jump into execution by taking a breath and asking ourselves:

• Conduct a Premortem (see HBR Premortem article):  Get the team together and ask everyone to imagine this project has failed spectacularly — start writing down, independently, all the ways it failed, and then have the group discuss (Heard about this from Seth Godin)

Clayton Christensen, in his book How Will Your Measure Your Life? encourages people to ask a great question early on in a new project/initiative:

What assumptions must prove true for this plan to work?