Best Manager Ever

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 scratch05:27 – Why asking better questions is a leadership superpower06:16 – Open vs. closed questions 08:28 – The “Socratic trap” and fake curiosity10:09 – Letting go of having the answer12:03 – Why leaders should speak last14:17 – Go-to questions to unblock your team18:58 – How to know if you’re asking the right questions23:39 – Common traps: not listening, fake coaching, dead ends31:23 – When coaching doesn’t work (and switching styles)32:20 – What coaching actually means as a manager39:31 – Growth should feel uncomfortable43:46 – Hard lesson: stop doing everything so your team can step up47:07 – There’s no “easy mode” in leadership + finding your peopleJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Maayan RothNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

Amit Shah is the COO of Virta Health, where he’s built the company from ~30 team members to over 800 colleagues working to reverse obesity and diabetes. Amit has 10+ years of experience in building and scaling entrepreneurial and high-growth healthcare organizations, with a focus on delivering financial and operational results while aligning on mission and values.Amit’s direct reports praise his ability to balance the needs of Virta’s members, business, and staff, describing him as incredibly kind, caring, driven, and a fierce protector of his team. He is celebrated for his passion, structured thinking, dedication to his own growth and development, and continuous improvement in leadership.In this episode, show creator and Fort Light founder Annie Riley sits down with Amit,and they cover:How to build a gratitude practice that supports your team – and yourselfThe importance of emotional awareness and regulation in leadership Energy management habits and practices   A process to take charge of feedback, learning, and growth The relationship between execution and strategy in startups If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Amit Shah Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Sophie Ruddock brings deep expertise in scaling mission-driven tech companies, and is now the COO at Empathy. Sophie was an early employee at Multiverse, where she grew with the company and ultimately became their global COO leading through rapid growth and market expansion. Sophie’s direct reports praise her empowering leadership style, her commitment to their development, and her unwavering advocacy. She hires people for their unique expertise and encourages them to bring their full selves to work, and reminds them of their value even in moments of self-doubt.In this episode, show creator and Fort Light founder Annie Riley sits down with Sophie, and they discuss:What a “founder mindset” really means for employees How to earn the right to dissent How to lead when someone on the team has an unexpected crisis The mindset shift that enabled Sophie to go from managing 3 to 600+ people If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.comJoin us on Substack Connect with Sophie RuddockConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

​​In this special Halloween episode of Best Manager Ever, host Annie Riley recounts the top worst manager moments of her career. Tune in to hear scary manager stories, from tales of micromanagement to vague (and unsettling!) feedback… and even Annie’s own manager missteps. There’s value in learning from the best, and ALSO from the worst! You’ll finish this episode feeling less alone, and even with some actionable lessons to help you avoid the same manager mistakes. If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Adam Fishman is a product and growth advisor with 20+ years of experience building and leading startup teams. Adam was on the early team at Lyft, where he served as Head of Growth. He then went on to lead Product & Growth at Patreon and Imperfect Foods, before launching his portfolio career. Adam has been an advisor and fractional leader at ResortPass, Mozilla, HelpScout, Peerspace and more. He is also the creator of FishmanAF newsletter and the host of the Startup Dad podcast. Adam’s direct reports praise him for his exceptional support, trust, and empowerment, as is recognized as a catalyst who brings people together across teams, fostering high trust and commitment. His team members appreciate his transparency, proactive communication, and the way he sets clear mutual expectations. In this episode, show creator and Fort Light founder Annie Riley sits down with Adam, and they discuss:How to build trust quickly as a new leader or fractional executive, and why starting from a place of trust matters.How to get more honest feedback from your direct reportsThe best way to manage defensiveness when receiving feedback– and how Adam learned it the hard way Predictions for how AI will impact product leadership roles Why distributing credit and advocating for your team’s growth leads to higher performance and engagement.If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Adam FishmanConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Charlie Coglianese is the Chief Technology Officer at Paloma Learning, a VC-backed edtech startup using AI to improve student learning outcomes. Charlie started his career in finance, before making the leap into startups. He was the Founder & CEO of a startup called Schoolrunner, which was acquired by SchoolMint. Charlie served as the CTO at SchoolMint post-acquisition before returning to early-stage building in his current roleCharlie's direct reports describe him as a leader who invests deeply in the growth of his team. He’s recognized for his ability to spot potential, provide the right level of challenge, and create an environment where people feel trusted to take ownership, try new things, and grow. The most common theme in their feedback is that Charlie empowers his team—he’s known for his intellectual honesty, willingness to jump in alongside his team, and his focus on building trust and clarity.In this episode, show creator and Fort Light founder Annie Riley sits down with Charlie, and they discuss:How to spot talent through trajectory, instead of outcomesThe concept of “productive struggle” and how to balance challenge and supportAdvice for working with founders and navigating the founder-executive relationshipStrategies for retaining top performers and keeping them engagedThe importance of clear goals and mission in motivating teamsIf you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Charlie CoglianeseConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Darius Contractor is the Chief Growth Officer at Otter AI. Darius has had a long and impactful career in the startup and tech worlds. Prior to Otter AI, he led engineering, growth and product teams at Vendr, Airtable, Facebook, Dropbox, Bebo and more. He is also an investor and advisor in multiple companies and funds. Darius’s direct reports describe him as a master of frameworks and analogies, someone who balances detail orientation with a big-picture vision, and a manager who pushes boundaries with unconventional but memorable approaches.In this episode, show creator and Fort Light founder Annie Riley sits down with Darius,and they discuss:How to support your team’s career path in a fast-paced, high-growth environment The SEEN framework for career development Designing jobs like dinner plates How frameworks and analogies make concepts more memorable If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Darius ContratorConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.