Bring the Insight: How a Young Product Leader Earns Trust at Asana

Costello leads the product organization responsible for Asana's desktop, web and mobile apps, covering goals, portfolios, projects, tasks and reporting. The aim is to answer the question at work of "who is doing what by when, and why." She has been at the company for about four years, and describes a nested structure in which R&D is split into pillars, pillars into areas, and areas into working teams.

Each area has a specific target customer and problem space, and metrics are nested too, from R&D to pillar to area to team. When she joined, teams were organized around projects and locations; the shift to durable, problem-focused areas means roadmaps are about what is most meaningful for the business rather than features. An example area is Coordinate, which cares about paying-organization weekly active users and healthy project use as a guardrail against driving one metric at the expense of real value.

Planning used to be annual; now Asana plans every six months for a rolling twelve. Confidence is higher in the first half and lower in the second, and the cadence helps align go-to-market and product planning while reducing churn when something changes. Costello says teams know roughly when work will happen, but asking for dates by quarter or week leads to odd scope choices, so the process now openly allows items to be pivoted or cut from the roadmap.

Costello describes the Double Diamond as a repeated pattern of going broad and then narrow: first on which customer to solve for, then on the customer's problems, then on possible solutions. She says it does not take long but it "breaks the frame" and pushes people to be curious, quantitatively and qualitatively, rather than argue from opinion. It also defines success, because if the metric is simply that people use a feature, you are teaching to the test.

Asana maps its review artifacts onto the inflection points of the diamond. These include a kickoff, customer and direction selection, a design concept review, the product spec, a full-experience design crit, and a launch review. By launch, the product has often been dogfooded for a while, so that review is mostly a check on metrics and readiness. Reviews are a mix of in-person crits and asynchronous spec reviews, depending on complexity.

Asana is in the office Monday, Tuesday and Thursday and mostly works from home on Wednesday and Friday. Costello says the company decided on this office-centric hybrid from the beginning rather than debating remote versus office. Even so, people had to relearn habits such as standing up during standups and using whiteboards, and she says the office felt more vibrant as of June 2023.

She sees real value for mental health and for impromptu strategy conversations, such as a lunch chat with her head of data science about evaluating experiments and the return on learning. She also finds that the remote days are now more impactful because people are better at them. Her personal tip is to know your chronotype: as a morning person she avoids meetings before 10:00 and does her hardest task then.

Costello is often the youngest person in the room. Her advice is to bring the insight: be the person who has watched customers use the product and who has a confident point of view on the market, competitors and numbers. You do not need the expertise of other functions, and you should not pretend to more experience than you have; ask great questions and be curious.

She cites a First Round article by Asana's Anne Raimondi on the trust equation: credibility plus reliability plus authenticity, divided by the perception of self-interest. Insight builds credibility, reliability is your say-do ratio, and authenticity is vulnerability. To build insight, she recommends befriending a researcher when taking a new role and watching customers firsthand, especially in dogfooding-heavy cultures where teams may mistake themselves for the customer.

On confidence, she says to be brave in small moments, say things before you feel ready, and be willing to say "I don't know what you mean." Vulnerability earns more trust than armor. Be fully present in meetings, scan faces for questions, and close by asking whether anything was missed, which she says conveys confidence more than constant assertiveness.

Costello says she leads by example because people learn through repetition. She likes the three Es framework of experience, exposure and education, and stresses exposure: being in the car even when you are not driving, and learning from what you observe. She runs meetings the way she wants to attend them, with a clear agenda, quick pace and room for debate.

Her most memorable piece of advice came after a high-stakes review at Intuit, when the business unit leader told her to always answer the question they should have asked. That points to another altitude of strategy beyond answering one-to-one. Her own recurring advice is not to self-select out of opportunities and to think big and ship small.

She also credits Asana's Conscious Leadership training, including the idea of being above the line (learning, curious) versus below it (committed to winning and being right). The question "How might the opposite be true?" helped her when she felt she had to cancel either a strategy brief or the podcast; reframing showed she could do both. She notes that she shared a 70% draft of the brief and said openly what was missing.

Costello says it is an exciting time to be a product leader given the pace of LLM development. Asana already had an ML team for prioritization models, but for the recent leap in LLMs it staffed a team to prototype quickly outside the normal process. They skipped the Double Diamond and went straight to prototypes, which showed some ideas were far better than expected while others sounded good only in theory.

The prototype work is then handed to the teams with the most expertise in the relevant customer problems, such as status and progress reporting, along with a starting hypothesis and what has been learned. She also reflects on Intuit's APM and manager training, which emphasized customer centricity rooted in the story of Scott Cook watching his wife balance a checkbook. The most useful part, she says, was feedback framed as situation, behavior and impact, which presents a subjective observation that opens a conversation about next steps.

Costello says the illusion that you must be all-knowing sets new PMs up for advocacy rather than inquiry. They do discovery and specs in a "little dark room" and then announce the answer, and she calls out performative collaboration where the reviews are held but the feedback is not really wanted. Her advice is to be curious, ask the question behind the question, and ask whether feedback is something you must, should or could consider. She also tells ambitious PMs not to let the sound of their own wheels drive them crazy, since outcomes speak for themselves.

On her own mistakes, she describes moving from individual contributor to manager and learning to guide without micromanaging. She would write what she wanted to say on Post-Its and see whether someone else said it first. She also learned that her natural optimism made her team think she was not being authentic about problems, so she now says plainly what is incomplete.

For career decisions she focuses on skills and experiences rather than roles. She assesses her learning curve, her environment and whether the problem is interesting, believing that "passions are made, not found."

In the lightning round, Costello recommends Marty Cagan's *Inspired*, and says her favorite interview question asks candidates to describe a time something went wrong. She has been playing with Poe.com to learn about LLM capabilities, including making a bot of herself.

The small process change with the biggest impact was getting strict about who reviews and approves work. Asana wanted one person who can stop the buck rather than a daisy chain of approvals, and set limits: no more than three reviewers on a piece of work, with only one blocking. If a meeting has more than ten people, the host is asked to remove some attendees and write better decision notes. Her Asana tip is to run meetings in tasks, assigning pre-reads with multi-assign subtasks and converting live notes into subtasks.