This post is part 5 of 5 in the series Startup questions.


What is the project’s purpose? (What are you trying to do?)
What are the problems you are trying to solve? What is it that you are hoping to achieve from this project?
What specifically is driving this project?

  • What are the compelling reasons for devoting energy to this effort?
  • What’s happening that needs to be changed?
  • What’s the opportunity to be pursued?

How do you know there is a problem? What are the symptoms? Why is this a problem?
What other concerns do you have that you would like to see addressed in the progress of this project?

Outcomes and benefits

What will it look like when this project is completed successfully? How do you want it to be?
If you solved this problem, what would be the benefits to your department and the overall organization?
What are the implications of not solving this problem? What is the negative consequence of not doing this project or not completing it successfully?

Process and milestones

What do you imagine are likely steps in the solution?
How do you imagine this project happening? What are your expectations today?
What are the critical points in time for this project? Milestones could be hand-off points; completion of deliverables; pre-determined progress points; evaluation points; and/or celebration points.
Have you already defined some components of the solution?
What has already been decided?
What are some critical assumptions that may impact the project?
What challenges do you anticipate in solving the problem?
What are some known constraints that will impact the project?
How do you see this project coordinating with other activities?


Who will lead/coordinate the project from your organization? Who else will be involved? board? task force? steering committee? committees?
List name, contact info and availability


Who will be impacted by this project?
What organizations units will be involved in this project?
What other challenges is the organization facing during this project?
What are the non-negotiable givens? Givens are defined as decisions or factors that only you or a higher authority can define and that, at the moment, are non-negotiable.

Decision process

How will decisions be made?
How does the organization usually make decisions?
What are the decision steps?
Who is involved?

Project progress

What project progress information do you want?
When or how often do you want it?
How do you want this information delivered?
Who else should get this information?
How should this information be delivered to them?

Results evaluation

What criteria will indicate success?
How will you know the project was successful?
What existing tools, reports or indicators could be used to evaluate success?
Are there new tools, reports or indicators that should be developed?


What specific deliverables are you expecting? Deliverables could be products, services, information and changed/improved relationships.


Have funds and resources been allocated for the project? How much has been budgeted?
What resources are now available? How does it work today? How many people are involved?
What information is available about your current customers?

  • % with email addresses
  • zip analysis of current buyers
  • results of past audience surveys
  • % of multi-event attendees
  • # of new households yearly
  • % of audience connected to performers

What information is available about the current condition of the organization?

  • last 5 years of financials
  • current and past sales and fundraising plans and results — What is the overall scope of the activity? What is included? What is specifically excluded?
  • current budget; projected budget

Success working together

Why go outside the organization for help?
What are your hopes for our work together?
What conditions bring out the best in you? Which conditions help you shift your thinking?
What do you want to learn?
When we’re done with our work together, what will success look like? When and how will we know we’re there?
What role would you like us to play?
What concerns do you have about our ability to meet this role?
Based on our conversation today, what do you find hopeful about our collaboration?

Next steps

What are our next steps?
What questions do you now have?
What are the next steps in moving forward?

Plus/Delta for today’s meeting

Plus — what worked?
Delta — what would we do differently next time?