
Asana’s Head of AI on the Profound Ways Work Is Changing | Paige Costello (Head of AI & Co-Head of Product Management at Asana)
05/28/24 • 31 min
Paige Costello is the the head of AI and co-head of product at Asana and on this episode of CRAFTED. we're exploring what it means to ship products with AI, how AI will change the way work gets done, and how to organize your teams for success in this brave new world.
We explore:
- How the future of work – and communicating about work – is changing
- Why Asana chose to create an “AI org” instead of a less centralized innovation approach
- How Asana ships — and measures the success of — AI-powered features, e.g. SmartStatus, that aim to take the drudgery out of work
- How product management is changing with the rise of AI
- Why running an A/B test is harder when a non-deterministic (i.e. unpredictable by design) GenAI tool is involved
- Why it’s so important to “get out of the building” and some of Paige’s favorite user research moments from doing so
- The latest with “PaigeBot” and what Paige hopes AI can do for her
***
CRAFTED. is brought to you in partnership with Docker, which helps developers build, share, run and verify applications anywhere – without environment confirmation or management. More than 20 million developers worldwide use Docker's suite of development tools, services and automations to accelerate the delivery of secure applications.
CRAFTED. is produced by Modern Product Minds, where Dan Blumberg and team advise companies on product, discovery, growth, and experimentation.
Subscribe to CRAFTED., follow the show, and sign up for the newsletter 👉 Crafted.fm
***
Key Moments:
[02:17] AI-generated status reports: How Asana summarizes a project – or many projects – using AI. And why it needs to do so carefully.
[05:00] How to organize for innovation: How Asana organizes its teams to integrate AI and the strategies they employ for effective AI implementation.
[09:06] How AI will change the role of product managers and why the stochastic nature of AI will be something we all have to get used to
[14:26] Challenges of prototyping and scaling AI
[16:07] How Asana uses AI internally and how it dogfoods its own products
[18:17] Profound implications of AI + the future of work
[22:20] Will AI really help product managers get out of the building more? Or do we just find new excuses not to? And what Paige finds so powerful about “being in someone’s space”
[25:32] An update on “PaigeBot” and what Paige wishes a bot would do for her
Paige Costello is the the head of AI and co-head of product at Asana and on this episode of CRAFTED. we're exploring what it means to ship products with AI, how AI will change the way work gets done, and how to organize your teams for success in this brave new world.
We explore:
- How the future of work – and communicating about work – is changing
- Why Asana chose to create an “AI org” instead of a less centralized innovation approach
- How Asana ships — and measures the success of — AI-powered features, e.g. SmartStatus, that aim to take the drudgery out of work
- How product management is changing with the rise of AI
- Why running an A/B test is harder when a non-deterministic (i.e. unpredictable by design) GenAI tool is involved
- Why it’s so important to “get out of the building” and some of Paige’s favorite user research moments from doing so
- The latest with “PaigeBot” and what Paige hopes AI can do for her
***
CRAFTED. is brought to you in partnership with Docker, which helps developers build, share, run and verify applications anywhere – without environment confirmation or management. More than 20 million developers worldwide use Docker's suite of development tools, services and automations to accelerate the delivery of secure applications.
CRAFTED. is produced by Modern Product Minds, where Dan Blumberg and team advise companies on product, discovery, growth, and experimentation.
Subscribe to CRAFTED., follow the show, and sign up for the newsletter 👉 Crafted.fm
***
Key Moments:
[02:17] AI-generated status reports: How Asana summarizes a project – or many projects – using AI. And why it needs to do so carefully.
[05:00] How to organize for innovation: How Asana organizes its teams to integrate AI and the strategies they employ for effective AI implementation.
[09:06] How AI will change the role of product managers and why the stochastic nature of AI will be something we all have to get used to
[14:26] Challenges of prototyping and scaling AI
[16:07] How Asana uses AI internally and how it dogfoods its own products
[18:17] Profound implications of AI + the future of work
[22:20] Will AI really help product managers get out of the building more? Or do we just find new excuses not to? And what Paige finds so powerful about “being in someone’s space”
[25:32] An update on “PaigeBot” and what Paige wishes a bot would do for her
Previous Episode

How to Grow Your Startup. Featuring “Growth Levers and How to Find Them” Author and Startup Advisor Matt Lerner (Founder & CEO, SYSTM)
“So if you take any great startup and look backwards, you'll see that 90 percent of their growth came from like 10 percent of the stuff that they tried. So how do you find that 10 percent as quickly as possible?”
Matt Lerner has advised hundreds of startups on how to grow. Now, the CEO of SYSTM has written a book called Growth Levers and How to Find Them where he shares his approach. This episode of CRAFTED. is full of actionable advice on how you can grow your products and companies. Matt will tell us about the mindset shift founders need to make from thinking about their products to thinking about their customers needs. We'll talk about jobs-to-be-done (JTBD) style interviewing and why it's such a powerful approach, but also why at first Matt was put off by some of the overly academic language that often goes with jobs. And we'll talk about how you can get new customers to that aha moment as quickly as possible, so they stick with your product. Plus, lots of real talk about founders and the mistakes they make.
Welcome to CRAFTED., a show about great products and the people who make them. CRAFTED. brings you stories of founders, makers, and innovators that reveal how they've built game changing products and how you can too.
—
Key Moments:
- [0:00] Intro
- [2:20] 90 percent of growth comes 10 percent of the stuff you try
- [3:53] Over-thinkers, under-thinkers, and delegators: the 3 types of founders and the mistakes they make
- [7:40] Why the pace of learning is so important
- [9:51] Great examples of companies that learn quickly
- [10:52] The “locksmith moment” and why you need to find yours
- [12:45] Jobs-to-be-Done style interviewing and why it’s so effective
- [14:07] How to do a JTBD interview
- [16:05] The mindset shift founders need to make from thinking about their product to thinking about the customers’ needs – and why it’s so hard for them to do so
- [21:24] Growth Sprints and how to set them up for success
- [25:07] Retention and customer activation: still (!) overlooked by most and why it’s so critical
- [29:00] Matt writes a blog post on the spot about how working at an oil refinery taught him about startups
- [31:36] Writing a book is not an agile process! And the fantastic reception for Growth Levers
—
More on Matt Lerner:
- His company: SYSTM
- The book: Growth Levers and How to Find Them
—
CRAFTED. is produced by Modern Product Minds, where host Dan Blumberg also advises companies on product discovery, growth, and experimentation. Learn more and sign up for the CRAFTED. newsletter at modernproductminds.com
Next Episode

Making Music With AI – And Doing So Ethically | Diaa El All, Founder & CEO of Soundful
Diaa El All is the founder and CEO of Soundful, which enables anyone to create brand new music in just a few seconds with AI. And on this episode of CRAFTED., we are literally making music.
We’re also talking about the ethics of using AI to make music. Diaa has been very outspoken about what he sees as the misguided practices of other AI+music companies that train their models by just scraping the web. At Soundful, they’ve taken a different approach: they are painstakingly building their own proprietary data by recording musicians playing one note at a time and then layering the notes to create music that sounds better than if you’d just sampled songs.
“We've done it. There is a way where technological advancement and working with the rights-holders and protecting them can co-exist together.”
We discuss:
Why Diaa stands with the music industry against what he sees as other companies' move fast & break things approach to AI
Diaa’s background as a classical musician, DJ, ghost producer, and founder
How Soundful built its data and how it layers sounds together to make music
Soundful’s origin story and how it emerged from Diaa’s work with AI and marketing automation
Why humans are so important when making music
Why music theory rules are important to follow – except when they’re not!
What to expect next... and how incredible AI voice cloning has become
***
CRAFTED. is brought to you in partnership with Docker, which helps developers build, share, run and verify applications anywhere – without environment confirmation or management. More than 20 million developers worldwide use Docker's suite of development tools, services and automations to accelerate the delivery of secure applications.
CRAFTED. is produced by Modern Product Minds, where Dan Blumberg and team advise companies on product, discovery, growth, and experimentation.
Subscribe to CRAFTED., follow the show, and sign up for the newsletter 👉 Crafted.fm
***
Key Moments:
[02:01] Ethical AI in Music Creation: How Soundful builds its AI ethically, avoiding training on copyrighted materials and using proprietary data.
[05:00] Diaa’s journey from Cairo to the Royal Academy of London, and his various roles in the music industry before founding Soundful
[07:02] Soundful’s origin story
[10:10] Soundful's music creation process, including the use of music theory rules and proprietary data sets to generate tracks
[12:08] How Soundful manages the non-deterministic nature of AI to ensure unique, high-quality music outputs for users.
[14:36] How Soundful levels people up and why he’s so excited to level up that great singer who is not yet a great producer
[17:00] The hardest part of building Soundful - working with the music industry and winning their acceptance
[21:55] Predictions for the future, including advancements in voice cloning and the potential for democratizing creative opportunities.
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