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?