The Power of a “What If We Get Stuck?” List

20 key questions to ask... before it's too late.

Most projects start with optimism:

“We’ve got a problem… We’ve found a solution! Let’s get started today!”

And often… we dive in too fast.

The reality?

Every project has contingencies.

What if things take longer? What if costs creep up? What if the team can’t get aligned? What if the tool doesn’t work like we expected?

Asking “what if we get stuck?” upfront doesn’t kill momentum. It prevents derailment.

Of course… this takes time.

And it can feel like dampening the mood.

But it’s one of the best investments you can make.

Here are 20 questions to consider for your next “What If We Get Stuck” list:

20 Questions to Ask BEFORE Your Next Project

1. What if the scope keeps expanding?
   Scope creep kills projects. Decide now how new requests will be handled.

2. What if we go over budget?
   Agree on how to prioritize spend before the dollars run out.

3. What if we go over time?
   Every extra week has a cost. Clarify who decides what’s worth extending.

4. What if we can’t get stakeholder buy-in?
   No buy-in, no adoption. Plan for who needs to be convinced, and how.

5. What if our vendor drops the ball?
   Have a backup plan. Know your exit options. Can you cancel the contract and get a partial refund?

6. What if the technology doesn’t integrate?
   Integration is where projects stall. Ask for proof-of-concept early. Otherwise your project risks requiring a bunch of APIs duct-taped together in a way that may slow progress.

7. What if the team can’t agree?
   Conflict slows everything. Decide now how you’ll resolve disagreements.

8. What if we lose a key team member mid-project?
   People leave. Figure out how you’ll document processes so knowledge doesn’t walk out the door.

9. What if compliance slows us down?
   Regulations can’t be ignored. Plan reviews early so they don’t stall launch.

10. What if data migration fails?
    Moving data is messy. Have rollback plans to avoid being stuck halfway.

11. What if leadership priorities change?
    Figure out how you’ll respond if leadership changes their tune on the project.

12. What if the cost of downtime is higher than we think?
    Every hour offline has a price… Know that number so decisions are grounded in facts.

13. What if our assumptions about users are wrong?
    Build in checkpoints to validate real user behavior before launch.

14. What if communication breaks down?
    Silence breeds delays. Agree on cadence and channels upfront. And stick to the plan.

15. What if testing reveals major flaws?
    Testing isn’t failure. It’s feedback. Plan for enough cycles (hint: it’s usually more than we first estimate).

16. What if adoption lags after go-live?
    Launch is step one. Have training and support ready to boost usage.

17. What if the ROI isn’t clear?
    Define success metrics before kickoff so you can measure real value.

18. What if competitors beat us to market?
    Speed matters. Balance thoroughness with urgency. Better to be on-time with something that’s minimum viable than so late someone else beats you to the punch.

19. What if we burn out the team?
    Overwork leads to mistakes. Monitor workloads and morale.

20. What if this project just doesn’t work?
    Sometimes projects fail. Decide the exit criteria so you don’t waste more than you should.

Final Thought

Optimism fuels projects. But contingencies protect them.

A “What If We Get Stuck?” list won’t slow you down. It will make sure you finish strong.