Unblock Your Team with Powerful Questions

Better questions create better teams. Annie Riley sits down with Maayan Roth, Head of Engineering at Crux Climate, to unpack the skill most managers overlook: asking questions that actually move things forward. Maayan shares how to use curiosity to uncover what’s really going on and guide conversations without controlling them. Plus: the traps new managers fall into, the difference between coaching and interrogating, and the simple question that turns hesitation into action.

TimeStamps:

00:00 – Meet Maayan Roth

02:53 – Startup leadership: building everything from scratch

05:27 – Why asking better questions is a leadership superpower

06:16 – Open vs. closed questions

08:28 – The “Socratic trap” and fake curiosity

10:09 – Letting go of having the answer

12:03 – Why leaders should speak last

14:17 – Go-to questions to unblock your team

18:58 – How to know if you’re asking the right questions

23:39 – Common traps: not listening, fake coaching, dead ends

31:23 – When coaching doesn’t work (and switching styles)

32:20 – What coaching actually means as a manager

39:31 – Growth should feel uncomfortable

43:46 – Hard lesson: stop doing everything so your team can step up

47:07 – There’s no “easy mode” in leadership + finding your people

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