Unblock Your Team with Powerful Questions

Unblock Your Team with Powerful Questions

From Best Manager Ever by Annie Riley

May 13, 2026 · 53 min · Season 4 · Episode 9

About this episode

Annie Riley discusses the importance of asking powerful questions with Maayan Roth to enhance team performance.

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…

People in this episode

Host: Annie Riley

Guest: Maayan Roth

Topics covered

  • leadership
  • management
  • team dynamics
  • coaching
  • communication

Keywords

  • questions
  • leadership
  • coaching
  • teamwork
  • communication
  • curiosity
  • management

Mentioned in this episode

Organizations: Crux Climate

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