Home Podcasts Best Manager Ever
Best Manager Ever

Best Manager Ever

Annie Riley 60 episodes Latest May 27, 2026

Best Manager Ever reveals the secrets of successful management and empowers leaders to build winning teams. Join a community dedicated to sharing insights and stories from the most successful and beloved leaders in the startup world. All guests have been nominated as the “best manager ever” by a recent direct report. Before each interview, we go behind the guest’s back to collect feedback and stories from their team about what they’re *actually* like to work for. Then we sit down with the guest to unpack that feedback and to dig into their leadership playbook and lessons learned.

Episodes

Self-Compassion Break for High Performers Jun 10, 2026 55:32 The voice pushing you forward is also holding you back, and your inner critic is costing you more than you think. Annie Riley talks with clinical psychologist and self-compassion teacher Dr. Michael Klein to explore the psychology behind ambition, achievement, and the never-ending pursuit of "more." They discuss why success doesn't automatically lead to happiness, how striving and self-criticism c
Speed to Signal with JZ - Laurel CPO Jun 3, 2026 48:08 JZ has built product teams at Airbnb, Webflow, Dropbox (and now Laurel), and in this episode she shares her honest leadership playbook and lessons learned. JZ covers why conviction is really about speed to signal, how to move fast without creating chaos, and why great leaders should share uncertainty instead of performing conviction. JZ also shares hot takes about 1:1 meetings, asking for help, an
How "Temporary Permanent" Drives Progress May 27, 2026 50:41 Don’t let perfectionist fantasies kill progress. Annie Riley sits down with Anna Randall, Director of Enterprise Sales at Curri and former VP of Sales at TigerEye, Autodesk, and PlanGrid, to explore the power of “temporary permanent” thinking. They break down why the best teams prioritize momentum over precision, normalize imperfect solutions, and keep moving when the path changes. Plus: why the t
 Ex-Pinterest & Canva Exec: Curiosity As A Muscle May 20, 2026 47:37 Work is not like school– there are no right answers, and if you’re looking to be “right” then you will always fall behind. Annie Riley sits down with Silvia Oviedo Lopez, Founder & CEO of Blomma AI and former Canva and Pinterest leader, to unpack how the best leaders train curiosity, learn in real time, and see hard questions as a gift.Time Stamps: 00:00 — Meet Silvia Oviedo Lopez03:48 —
Unblock Your Team with Powerful Questions May 13, 2026 52:56 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 coachin
Top CEO Coach On The Difficulty of Empathizing Up May 6, 2026 49:59 Leadership is lonely. Most leaders don’t get enough support or positive feedback. And that includes our own boss too. Annie Riley and top executive coach Ed Batista break down why it’s so hard to empathize up— and how simple shifts like checking in or offering genuine positive feedback can change the dynamic, because sometimes the most powerful move is truly seeing the person behind the role.Time
“Smart Rats”: Belief Boosts Performance Apr 29, 2026 52:13 You don’t become a great manager by regurgitating frameworks. Management is a craft and a skillset that gets built over time.  Annie Riley sits down with Maura Church, VP of Product & Engineering at Two Chairs, to talk about how a manager’s mindset impacts team performance. From the “Smart Rats” theory to balancing tough feedback with real belief, Maura breaks down how to coach growth, bu
Be Champagne, Not Flat Soda Apr 22, 2026 36:36 Building a strong network is a skill. Annie Riley sits down with Whitnie Narcisse, former First Round Capital Partner, to unpack how she has built one of the best networks in Silicon Valley. Whitnie breaks down how to be memorable and build connections that last using her FACE framework (Factual, Authentic, Credible, and Engaging). Plus: why most networking advice falls flat, how to design rooms p
Get Yourself Some “Boast Bitches” Apr 15, 2026 47:18 “Polite silence” is a silent killer on teams. Annie Riley sits down with Dorothy Kilroy, Chief Commercial Officer at Oura Ring and former Airbnb to talk about how to invite productive disagreement while fostering psychological safety and how to give direct feedback without making it personal. Plus: the career-changing power of building your own “Boast Bitches”—a trusted circle that advocates for y
Time Kills Follow-Up: Share Context Now Apr 8, 2026 47:04 Speed beats perfection every time. Annie Riley dives in with Junan Pang, VP of Customer Success at Intercom, to unpack how he gives direct reports the context they need to act independently. He talks through why most leaders under-share, and how quick, imperfect updates unlock better decisions– without drowning the team in meetings or messages.Timestamps:00:00 Meet Junan Pang01:58 Learning as a mi
Bad Meetings Are Disrespectful Apr 1, 2026 49:29 Meetings can be a real problem when they’re not run well or have the wrong people in them. Julia Bernstein, COO at Brightside Health joins Annie Riley to break down how she audits, redesigns, and even “dress rehearses” meetings to make them actually useful. From cutting unnecessary attendees to auditing recurring meetings regularly, Julia shares her no-BS approach to protecting time and driving re
A Manager’s Word Has To Mean Something Mar 25, 2026 54:59 What if the secret to great leadership is actually learning to say no? Annie Riley sits down with Gautam Prabhu, VP of Engineering at Scribe AI and longtime startup operator, to unpack his lessons from 25+ years of building teams at PagerDuty, Zendesk, and Opentrons. Gautam talks through why leaders should treat every “yes” as a promise, how winning teams are built through systems (not heroics), w

Recommended

Playing