How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana)

You're often the youngest person in the room. What have you learned about how to garner trust and win over skeptics?

The thing I would say is bring the insight. Know thy customer, know thy market, know thy competitors, know thy numbers, know thy product.

I'm curious what you find most holds back new PMs.

Your brain is so accustomed to having a scarcity mindset, as opposed to, like, creating alternative options or seeing a different path. Effectively, there's this notion of how might the opposite be true? And the moment I challenged myself and said, "How might the opposite be true?" my shoulders dropped. (laughs) I felt more relaxed. I was like, "Oh. Yeah, I can do both. It'll be fine."

(intro music plays) Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Paige Costello. Paige is a product lead at Asana, overseeing teams responsible for the core product experience of Asana. Before Asana, she was director of product at Intercom. And prior to that, she was a group product manager at Intuit, where she spent five and a half years. In our wide-ranging conversation, we dig into strategies for building trust with people who are more experienced than you or older than you. We talk about coaching product managers, including why leading by example is often the most effective strategy. We talk about Asana's product development process and how it's evolved over the years as the company has scaled, plus some of Paige's product and career missteps and what she's learned from those moments. To prep for this interview, I got input from some of Paige's colleagues and former colleagues, and everyone I talked to loved Paige. You'll soon see why. Enjoy this episode with Paige Costello after a short word from our sponsors. Today's episode is brought to you by Brave Search and their newest product, the Brave Search API, an independent global search index you can use to power your search or AI apps. If your work involves AI, then you know how important new data is to train your LLMs and to power your AI applications. You might be building an incredible AI product, but if you're using the same datasets as your competitors to train your models, you don't have much of an advantage. Brave Search is the fastest growing search engine since Bing, and it's 100% independent from the big tech companies. Its index features billions of pages of high-quality data from real humans, and it's constantly updated thanks to being the default search engine in the Brave browser. If you're building products with search capabilities, you're probably experiencing soaring API costs or lack of viable global alternatives to Bing or Google. It's only gonna become harder to afford these challenges. The Brave Search API gives you access to its novel web-scale data with competitive features, intuitive structuring, and affordable costs. AI devs will particularly benefit from data containing thorough coverage of recent events. Lenny's Podcast listeners can get started testing the API for free at brave.com/lenny. That's brave.com/lenny. This episode is brought to you by Attio, a new type of CRM that's powerful, flexible, and built around your data. Traditional CRMs were built for a different era, with totally different speed, scale, and data demands. Attio is different. It allows you to quickly build a CRM that matches your unique workflows and data structures. Within minutes of connecting your email and calendar, you'll have a CRM that's already set up, complete with customer profiles and automatic data enrichment. You'll also have real-time dynamic reporting at your fingertips. No more slow deployments, outdated user experiences, or tedious manual data input. With Attio, you can build and adapt your CRM on the fly, no matter your business model or company stage. Attio is the CRM for fast-growing startups. Get started today and get 15% off your first year at attio.com/lenny. That's A-T-T-I-o.com/lenny. Paige, welcome to the podcast.