Paige Costello

For rapidly evolving technologies like LLMs, bypass standard heavy processes in favor of rapid prototyping to discover technical possibilities quickly.

"When it came to the massive leap forward in LLMs recently, we staffed a team to really prototype quickly, and discover what was possible, and just apply hypotheses outside of the typical norms of how..."

The strongest promotion case is built on high-quality outcomes and solving problems that make others advocate for you organically.

"If you're present in your job, and you actually have fun with it and solve the problems, people will come out of the woodwork, say, 'You're great, and tell your boss you should be promoted.' You don't..."

Assess career moves based on three criteria: the steepness of the learning curve, the quality of the environment/team, and the inherent interest of the problem.

"I evaluate whether I'm in a healthy role and in a good setup by asking myself about my learning curve... thinking about whether the environment is positively impacting your ability to grow your career..."

When communicating with leadership, address the strategic context or the 'better' question rather than just providing a literal answer to build trust and show strategic thinking.

"Always answer the question that they should have asked... there's actually another altitude, another point of strategy when you've- in a meeting or in a conversation to make sure that you're covering..."

Capping meeting attendance and prioritizing high-quality decision notes increases organizational pace and clarity.

"If a meeting has more than 10 people on it, we ask the person hosting the meeting to kick out the other people and write better decision notes."

Use task management tools to formalize pre-reads and action items, ensuring meetings are focused on discussion rather than information sharing.

"I use Asana to run all my meetings and assign pre-reads. So I use the multi-assign feature in subtasks all the time where I make a task with a due date that says, 'Read this thing by this date,' and t..."

Map design reviews and critiques to specific inflection points in the product development lifecycle to ensure timely feedback.

"The inflection points are the kickoff... design concept review. Then, the products spec. Then, the full experience review or design crit of the end-to-end experience and launch."

Use behavioral questions about failure to assess a candidate's mindset, self-awareness, and problem-solving approach under pressure.

"I like to ask, 'Tell me about a time something went wrong. What was it? What did you do about it? Yada, yada.'... evaluating people's mindset, and the way they talk about it, and the way they relate t..."

The Situation-Behavior-Impact (SBI) framework makes feedback objective and actionable by focusing on observed behaviors and their personal impact.

"Convey this feedback as situation, behavior, impact. The situation is on Tuesday in that meeting at 3:00. Behavior, you interrupted me while I was saying this thing. Impact, made me feel like you were..."

Leaders should practice restraint in meetings to allow their team to step up and find answers themselves, fostering agency and growth.

"I would go to my meetings with a stack of Post-Its, and I would write what I wish I was saying on Post-Its and see if someone else would say it first... you've got to police yourself because no one el..."

Avoid 'daisy chains' of approvals by designating a single person responsible for the final decision to maintain momentum.

"We actually don't care. We don't want a daisy chain of approvals. We just want one person with whom the buck can stop with them, and they can be responsible for how the work moves forward."

A rolling 12-month planning cycle revisited every six months balances long-term strategic confidence with the agility to pivot.

"Before, we planned annually primarily. Now, we plan every six months, but for a rolling 12 months. So we have higher confidence in the immediate half, lower confidence in the following half, but we ju..."

Use a nested metric structure (R&D -> Pillar -> Area -> Team) to align high-level product strategy with specific team-level execution.

"We have an R&D set of metrics, we have pillar metrics, we have area metrics, and then at the team level, there's often one or two that they're really driving forward. So you can think of it as a neste..."

To build trust with more experienced stakeholders, bring deep insights about the market and competitors rather than relying on functional expertise.

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

The Double Diamond framework prevents opinion-driven decisions by forcing teams to systematically explore and then narrow down the target customer and problem space.

"The Double Diamond Process... forces people to get out of their opinion-driven lens... You go broad when you ask like, 'What customer should I solve for?' and then you pick one... Then, you go broad,..."

Explicitly build the option to pivot or cut features into the product process to avoid the 'sunk cost' fallacy of roadmaps.

"We added into our product process a notion that we might pivot or cut from stuff that we put on our roadmap because it felt like once it was on the roadmap, it had to be done, and that's just not smar..."

Direct observation of customers is the fastest way to build credibility and understand real-world product usage versus internal assumptions.

"Become best friends with a researcher, and spend time watching customers use the product firsthand because what they maybe report on or are trying to do a study about might be very different from what..."