Kickoff Questions Every Leader Should Ask

10 questions to uncover blind spots and hidden risk before your project even begins.

Guy at a kick-off wearing a VelocityHero helmet.

The success of a project is often determined before the work even starts. Poor alignment, unspoken assumptions, and vague goals are all seeds of future chaos. That’s why great leaders use the kickoff not just to “start,” but to surface risks, stress-test plans, and build true clarity.

Here are 10 questions every leader should ask before the team begins:

1. What does success actually look like — in business terms?

2. Who will make the hard calls when trade-offs come?

3. Where might this project clash with other initiatives?

4. What decisions are still pending?

5. Do we have the right roles — or just people filling gaps?

6. How aligned are stakeholders really (not just on paper)?

7. What would cause this project to stall?

8. What’s our warning system if something drifts?

9. Are we tracking output or outcomes?

10. What happens if the scope grows — who decides and how?

Ask these before kickoff — and you’ll catch what most teams only discover when it’s too late.