Lenny Distilled

How to ask the right questions, project confidence, and win over skeptics

July 09, 2023

Featuring: Paige Costello (Head of Core Product, Asana)

13 quotes · 11 insights

Watch Full Episode

Excellence in execution earns you strategic opportunities

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 need to ask for a promotion. Your outcomes should speak for themselves.
Paige CostelloHead of Core Product, Asana 00:48:17

Vulnerability and authenticity build stronger influence than authority

Real confidence is often conveyed by being willing to ask the question or to say, 'I don't know what you mean by that. Can you say that again?'
Paige CostelloHead of Core Product, Asana 00:26:36

Clear ownership beats consensus for execution speed

No more than three reviews on a given piece of work where people are blocking one approver. 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.
Paige CostelloHead of Core Product, Asana 01:00:31
We got really aggressive about, functionally, who is in charge and at what level for a given review, and pushed to say to actually have limits on the number of people per meeting, on the number of sub-task reviews for a given body of work. What this did is it created a lot more agency and pace within given working teams.
Paige CostelloHead of Core Product, Asana 00:59:18

Relentless curiosity trumps knowing all the answers

I would say this illusion that you have to be all-knowing and super confident sets you up to be in a place of advocacy instead of inquiry.
Paige CostelloHead of Core Product, Asana 00:46:11

Ask specific questions to get real feedback

Trust is built through deep knowledge and consistent delivery, not tenure

The thing I would say is bring the insight. Know thy customer. Know thy market. Know thy competitors. Know thy numbers. Know thy product.
Paige CostelloHead of Core Product, Asana 00:00:07
Trust is equal to credibility plus reliability, plus authenticity, divided by or over perception of self-interest.
Paige CostelloHead of Core Product, Asana 00:23:34

Live in your customer's world, not your conference room

When you take a new role, 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 you observe.
Paige CostelloHead of Core Product, Asana 00:24:59

Ask better questions to get better answers

Your brain is so accustomed to having a scarcity mindset as opposed to creating alternative options or seeing a different path. Effectively, there's this notion of, 'How might the opposite be true?' The moment I challenged myself and said, 'How might the opposite be true?' my shoulders dropped. I felt more relaxed. I was like, 'Oh, yeah, I can do both. It will be fine.'
Paige CostelloHead of Core Product, Asana 00:00:19

Great work doesn't speak for itself - tell the story

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 need to ask for a promotion. Your outcomes should speak for themselves.
Paige CostelloHead of Core Product, Asana 00:48:17

Don't self-reject - let others say no

Don't self-select because I think it's really easy to say, 'I don't have the experience,' or, 'I'm not X, Y, Z enough,' and not apply.
Paige CostelloHead of Core Product, Asana 00:33:59

Timeline roadmaps create false commitments

If you ask too much for a particular quarter, a particular week, or date, you will make strange choices about scope.
Paige CostelloHead of Core Product, Asana 00:10:38

The Missing Stamp

Every episode of Lenny's Podcast, distilled into the insights that matter and the quotes that make them stick.

LENNY WAS HERE__STAMP_DATE__

Lenny, if you're reading this, the stamp's ready when you are. 🧡🔥