Nickey Skarstad

A 'calendar energy audit' is a powerful tool for determining if a role or company is the right long-term fit.

"I actually went through my calendar and I changed the colors of all of the meetings on my calendar to red, yellow, and green after I had the meeting. And I looked. And basically if it was yellow, I wa..."

Strategy fails without collaborative buy-in; people must feel they had a hand in crafting the direction to support it.

"I've seen a lot of director level people through my career who will try to work on strategy in a vacuum alone. They'll write a document and they'll be like, 'Okay, team. Here's what we're doing. Here'..."

Using asynchronous video tools like Loom keeps feedback loops tight and ensures the team feels informed about leadership decisions immediately.

"I used Loom, which is another one of my favorite products... And so I just recapped, 'All right, here's what I presented to leadership. Here are the feedback that we got. Here's the strategic feedback..."

A structured three-stage review process (Principles, Approach, Readiness) ensures quality without micromanagement.

"Ideally in a perfect world, there's three check-in moments. There is the first principles check-in. What are you trying to build... What is the most important thing?... Once you've aligned on that, th..."

Early-stage PMs must bridge the gap between 'existential thinking' and practical market validation to find product-market fit.

"I joined that team when the product had just launched. So they had done sort of their early thinking, the existential thinking. Had a brand new product in market, and then I joined the team. And so I..."

Distinguishing between reversible and irreversible decisions allows teams to maintain high velocity while protecting long-term strategy.

"I love the concept of one way versus two way door decision making... If your team is making a really critical long-term decision that's going to be limiting to a lot of the future things that you coul..."

Aligning on first principles at the start of a project prevents fundamental disagreements during the later design or technical phases.

"If you can get teams to align on first principles early on, it saves you a lot of heartache later because you've got people to align way early days before you even got into the design process, or befo..."

Remote collaboration requires intentional use of lightweight, asynchronous, and audio-only tools to replace 'water cooler' moments.

"Slack has this really great feature called huddles where you can just quickly get on. It's just audio. So there's no video. And you can just have a 30 second conversation. It's good for standups and t..."

The guest emphasizes 'second-order thinking' and 'thinking in systems' as a critical skill for PMs to understand how current decisions impact future constraints and ecosystem dynamics.

"Basically what second order thinking is is you being able to think beyond the decisions that you're making today."

Starting in community roles provides a deep, foundational understanding of the customer that can transition effectively into product management.

"I actually joined them on their community team. So I worked as a forums moderator, and then as a seller education specialist. Yeah. Spent a couple years doing that. And then through that process becam..."

Engaging a passionate community early through 'building in public' and beta testing ensures product launches land successfully.

"Etsy was out there building in public... because they had such a passionate, involved, engaged early community that they could not just ship things and have them land well if they did not involve thei..."

A quality-based North Star metric, like review rate, can effectively balance and guide growth metrics in early-stage products.

"One of the things Airbnb did for experiences is we had this balancing metric, which was basically using the review rate as sort our end all, be all top line goal... we were obsessed with making sure e..."

The Vision-Mission-Strategy-Objectives pyramid provides a clear hierarchy for translating long-term aspirations into daily work.

"I really like the vision mission strategy pyramid... At the top is vision. Below it is mission and strategy, and then objectives. And this is a very simple framework... where do you need to go long te..."

Effective visioning sessions require pre-structured environments that explicitly permit 'existential' thinking away from daily constraints.

"I would pre-fill out the Miro beforehand... create them as headers in the Miro document... give everyone the space and the freedom to think existential and to frame it that way, 'we are going to be th..."

OKRs serve as the bridge between abstract strategy and concrete feature-level execution.

"Good OKRs to me are just clear articulations of your strategy, whatever it is that are important to you, and it boils it down into the next three months, here's what we're working on. And I think that..."

The specific framework (OKRs vs. others) matters less than having a shared, cross-functional language for goals.

"You should have some sort of goal framework that is shared across functions is useful no matter the size or the scale of your business... because again, it takes your strategy and it brings it down in..."