How to Be a Better Leader in a Startup

Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber.

In today's episode, we discuss:

• Best-practice product management
• How to achieve alignment at scale
• The importance of cross-functional performance
• Anique's unique approach to finding top organizational talent
• How to hire for roles outside your area of expertise
• Common fail cases with internal and external recruitment
• Tactics for effective interviews

Referenced:

• Loom: https://www.loom.com/
• Navan (formerly TripActions): https://navan.com/
• Teach for America: https://www.teachforamerica.org/
• Uber: https://www.uber.com/

Where to find Anique Drumright:

Twitter: https://twitter.com/aniqued

LinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1a

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/

Timestamps:

[00:03:00] The similarities and differences between PM and executive leadership roles

[00:06:53] How Loom uses storytelling when launching a product

[00:10:01] Managing cross-functional scope and performance

[00:13:41] Goal-setting with functional leads

[00:16:59] The importance and difficulty of organizational alignment

[00:20:40] How Uber achieved alignment at scale

[00:24:06] Rituals for staying aligned

[00:25:23] Loom's winning one-on-one format

[00:27:49] When and how to help functional leads

[00:29:13] Hiring for roles outside your area of expertise

[00:32:55] Go-to interview questions for prospective leaders

[00:33:55] Changing the hiring process for roles outside your area of expertise

[00:36:09] Common patterns of failed external hires

[00:37:40] Common patterns of failed internal hires

[00:39:05] Avoiding over-promotion in your organization

[00:40:51] What inspires people in a company

[00:45:40] Tactics for getting honest answers in interviews

[00:47:12] Asking the right questions during reference checks

[00:51:29] A month in the life of a COO

[00:52:52] The importance of employee energy levels

[00:54:53] Loom's leadership dynamics and why it works

[00:57:30] People who had an outsized impact on Anique's career