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Lenny's Podcast / episode intelligence

The one question that saves product careers | Matt LeMay

14 Aug 2025 22 published claims 2 attributable people
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Speakers in the public record

Matt LeMayLenny Rachitsky

Claim mix

belief 8evaluation 4observation 2uncertainty 2commitment 2preference 2recommendation 1prediction 1

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Claim ledger

The useful parts, with receipts.

22 published records

01 / recommendation

Recommends Radical Focus. Recommends The Wisdom of Insecurity.

“Radical Focus, by Christina Wodtke, is obviously, I cite it a lot in my book, I think it's the best book about OKRs. I love her style of writing. I love the way she tells stories. I love the focus on focus, this idea that again, the way you do it is less important than the result of the way of doing it. I just find that so inspiring, always. The other book, this is a bit of a curveball, is by Alan Watts, the Buddhist philosopher. It's called The Wisdom of Insecurity. And a lot of the way I talk about control, and giving up control, comes from that book. It also has a concept. It opens with a concept called the law of reverse effort, which is that sometimes, the harder you try, the worse you make things. When it comes to setting goals, doing OKRs, doing strategy, I think about this a lot, that there is a tendency sometimes to put effort towards the overcomplication of things, which in turn makes those things less effective, what they're ultimately intended to achieve. So, highly recommend that book. It helped me a lot through some dark times, mentally. There's an idea in the book. He talks about how trying to keep yourself perpetually safe in an imagined future is effectively killing yourself to the present. And ooh, that hit hard. That hit me really, really, really hard. So, highly recommend that book. If the things we've talked about today make you even a fraction of, as anxious and fearful as they make me when I navigate them in my work, then I highly recommend The Wisdom of Insecurity, by Alan Watts.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

05 / belief

I think an important part of this is just, if you believe what you're building is not helping the business grow and succeed, either, they'll let you go someday, because you're not doing something that matters.

“I think an important part of this is just, if you believe what you're building is not helping the business grow and succeed, either, they'll let you go someday, because you're not doing something that matters.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

06 / belief

How can we understand this?" So I think the challenge, when things are going well, is to keep that curiosity going, and to keep celebrating the things, not just that your team is doing, but that everyone is doing, and to take that time, where you have a little bit more leeway, where there's less pressure on you in the moment, to build those connections with other parts of the organization, to see where that really good work is happening.

“How can we understand this?" So I think the challenge, when things are going well, is to keep that curiosity going, and to keep celebrating the things, not just that your team is doing, but that everyone is doing, and to take that time, where you have a little bit more leeway, where there's less pressure on you in the moment, to build those connections with other parts of the organization, to see where that really good work is happening.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

08 / belief

If your team is not a good investment for the business or you don't really know if your team is a good investment for the business, but you figure you're showing up, so probably it's fine, you guess, then that puts you in a really tenuous position, and a position that I think we've all seen not work out terribly well for everybody in recent history.

“If your team is not a good investment for the business or you don't really know if your team is a good investment for the business, but you figure you're showing up, so probably it's fine, you guess, then that puts you in a really tenuous position, and a position that I think we've all seen not work out terribly well for everybody in recent history.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

10 / belief

I think that there are certainly situations where revenue goals would be too broad or not exactly what the business needs, but at the end of the day, money is how the impact of most teams is going to be measured.

“I think that there are certainly situations where revenue goals would be too broad or not exactly what the business needs, but at the end of the day, money is how the impact of most teams is going to be measured.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

13 / commitment

I think especially given that we are no longer in a zero interest rate environment, given that hiring and retaining employees is expensive, given that companies are looking at cost savings, I think we are in a moment where it is really incumbent upon each product team and each member of each product team to be able to understand, articulate, and work towards the top line business impact of their own work.

“I think especially given that we are no longer in a zero interest rate environment, given that hiring and retaining employees is expensive, given that companies are looking at cost savings, I think we are in a moment where it is really incumbent upon each product team and each member of each product team to be able to understand, articulate, and work towards the top line business impact of their own work.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

15 / preference

" And I think I needed to hear that from her because I think there is a tendency, especially for those of us who do really thrive in that collaborative environment, who our nature is to not want to take credit for work that could only exist via the contributions of many people with diverse experiences and perspectives. It's really hard to say, "Well, I did this and I contributed to that," but that's part of why I wrote this book at the team level, because I think for folks, like myself, who really enjoy and thrive in that team environment, if you can look at the product team as the foundational unit of impact and say, "We delivered this.

“" And I think I needed to hear that from her because I think there is a tendency, especially for those of us who do really thrive in that collaborative environment, who our nature is to not want to take credit for work that could only exist via the contributions of many people with diverse experiences and perspectives. It's really hard to say, "Well, I did this and I contributed to that," but that's part of why I wrote this book at the team level, because I think for folks, like myself, who really enjoy and thrive in that team environment, if you can look at the product team as the foundational unit of impact and say, "We delivered this.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

16 / evaluation

We will have a successful business. But honestly, most of the companies and teams I work with, if I ask them how their lowest-level goals add up to their highest-level goals, they look at me like I just asked them the most impossible question in the world.

“We will have a successful business. But honestly, most of the companies and teams I work with, if I ask them how their lowest-level goals add up to their highest-level goals, they look at me like I just asked them the most impossible question in the world.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

17 / prediction

The problem is if you have 10 teams adding rhinestones to a car, eventually the hood of the car is going to be so heavy that you can't lift it to get to the engine anymore, and that's exactly what happens in most product organizations.

“The problem is if you have 10 teams adding rhinestones to a car, eventually the hood of the car is going to be so heavy that you can't lift it to get to the engine anymore, and that's exactly what happens in most product organizations.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

18 / observation

I've been in a lot of rooms having workshops and sessions with teams I work with, where they're pulling up the last town hall meeting to look for slides from their CEO because they're so busy, they have so many day-to-day things to deal with, that for them that town hall day is, like, "Okay, finally I can just not have to deal with people emailing me every 10 seconds.

“I've been in a lot of rooms having workshops and sessions with teams I work with, where they're pulling up the last town hall meeting to look for slides from their CEO because they're so busy, they have so many day-to-day things to deal with, that for them that town hall day is, like, "Okay, finally I can just not have to deal with people emailing me every 10 seconds.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

19 / uncertainty

I can't say, if you do these things, then you will be looked upon favorably by the people who manage you because I don't know those people, and maybe they're not going to react well.

“I can't say, if you do these things, then you will be looked upon favorably by the people who manage you because I don't know those people, and maybe they're not going to react well.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast

20 / evaluation

You're going to feel less like you lost a battle or that you were overridden by an unjust tyrant, and it's going to be more like, "Okay, I made sure they had all the information I would want to have if I were making that decision.

“You're going to feel less like you lost a battle or that you were overridden by an unjust tyrant, and it's going to be more like, "Okay, I made sure they had all the information I would want to have if I were making that decision.”
Speaker
Matt LeMay
Publisher
Lenny's Podcast
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