Work Tactics: Finding a Job, Negotiating Comp, Managing Up, Getting Promoted and More

00:00:00.000 | I was teaching a course on Maven about product management, and I was interviewing coaches

00:00:05.360 | to help me with the course.

00:00:07.280 | And I had about 10 coaches.

00:00:08.280 | I was interviewing them with someone else that was helping me out with the course.

00:00:11.960 | And one of the coaches started her own sub-stack, subscribed me to it, and then just started

00:00:16.680 | writing posts about how she's the perfect fit to coach this course.

00:00:20.480 | And I was like, "Holy shit, we need to make sure that we talk to her for sure."

00:00:26.360 | And we did, and it didn't work out there because she wasn't quite the fit, but I found something

00:00:29.640 | else to do with her, and now she's a core part of my newsletter community, helps run

00:00:33.520 | a lot of the programs.

00:00:35.020 | The question is, how do you stand out?

00:00:36.020 | How do you stand out?

00:00:37.020 | You do something really remarkable that gets someone's attention.

00:00:39.880 | There's a lot of ways to do it.

00:00:40.880 | I do a lot of angel investing, and whenever I get a founder that makes a loom, "Hey, Lenny,

00:00:46.600 | I really wanted to talk to you about the startup I'm building.

00:00:49.240 | Here's why it's awesome."

00:00:50.560 | I watch them.

00:00:51.560 | Most of the time, I talk to them because they put in the effort and they do something unique.

00:00:56.280 | So I think it applies to investing too, pick the people you really want on your cap table

00:01:00.200 | and do some extra.

00:01:01.600 | Hello, and welcome to another episode of All The Hacks, a show about upgrading your life,

00:01:06.760 | money, and travel.

00:01:07.760 | Today, we're going to talk about the best strategies and tactics for your work.

00:01:12.240 | That means finding a job you love, interviewing, negotiating your comp, managing up, making

00:01:17.520 | an impact, getting promoted, and a lot more.

00:01:20.540 | And to do this, I'm joined by Lenny Ruchitsky, who sold his company to Airbnb in 2012 and

00:01:25.680 | spent seven years working in product across the company before leaving to start his newsletter

00:01:30.800 | and more recently podcast.

00:01:32.240 | Now, Lenny is well-known as one of the top minds in the world when it comes to building

00:01:36.760 | and growing software products, and his podcast, Lenny's Podcast, is the number one product

00:01:41.800 | podcast in the world.

00:01:43.440 | But product building isn't why he's here today.

00:01:46.000 | It's because he's written so many amazing newsletters about his professional work that

00:01:51.000 | I've found so valuable to my own career.

00:01:54.220 | So whether you're looking for a job right now, trying to have more impact in your current

00:01:58.240 | role, or thinking about what's next, I am sure you'll love this episode.

00:02:02.520 | So let's jump in.

00:02:03.520 | Lenny, thanks for being here.

00:02:10.960 | My pleasure, Chris.

00:02:12.840 | You have written a ton of content about product management and amongst product managers, which

00:02:17.680 | I formerly was, you are well-known in that space for being a thought leader.

00:02:24.420 | However, I found that a lot of your content is very, very applicable outside of product

00:02:30.060 | management to anyone who has a job.

00:02:32.380 | And now we're probably going to dig into a little bit more about the transition to creators.

00:02:35.540 | I just got to ask, are you aware of the breadth of applicability of your content and do you

00:02:41.180 | see a transition in the future to just more than product-related content and just really

00:02:46.780 | growing beyond that?

00:02:48.340 | I am aware the content is useful to a lot of people other than product managers, because

00:02:52.700 | I get emails from people and they're like, "Hey, our marketing team's finding this super

00:02:55.700 | useful."

00:02:56.700 | Or the funniest example is my mother-in-law, who is 75, I think, something like that.

00:03:04.100 | And she reads every post that I write and finds something in there that is applicable

00:03:08.340 | to her life.

00:03:10.420 | And that just shows me that there's all these little lessons that you can extract from things

00:03:14.280 | that are specifically meant for product managers and founders.

00:03:17.820 | But I will say I try very hard to stay focused on a PM, a founder, someone building product,

00:03:23.980 | because I think that's the reason it does well, is it's solving a very clear person's

00:03:27.740 | problem.

00:03:28.740 | And if I were to try to broaden it too wide, I think it would just lose the power and just

00:03:33.020 | become nothing amazing for any one person.

00:03:36.460 | So it is a balance, but it is cool that the second order effect becomes useful to a lot

00:03:40.980 | of other people.

00:03:41.980 | For anyone listening, Lenny has a newsletter, Lenny has a podcast.

00:03:44.720 | I have been a guest on his podcast that may or may not have come out before or after this

00:03:48.220 | comes out and highly recommend it, even if you're not in product, just like your mother-in-law

00:03:54.520 | said.

00:03:55.520 | However, we're not going to talk that much about product today.

00:03:58.500 | We're going to talk about some of those other things.

00:04:00.900 | And in fact, I thought as I went through a lot of your posts, that you have a really

00:04:05.380 | unique and great perspective on the process of someone going through their career, both

00:04:11.900 | getting a job, working at a company, starting on your own.

00:04:16.440 | And I've thought a lot about this too.

00:04:18.000 | So I thought we could just have a conversation to walk through that process.

00:04:21.860 | And you could share a lot of the lessons you've learned and shared and written about for anyone,

00:04:27.040 | whether they're trying to advance their career today, or they're looking for something new,

00:04:32.100 | or they're looking for something right now, because we're in an unfortunate situation

00:04:36.040 | where some people may have lost their jobs, and I would love to give them more tools to

00:04:40.400 | be successful in their search.

00:04:41.960 | So how's that sound?

00:04:43.720 | Sounds great with the caveat that I write these posts, and then the content leaves my

00:04:47.760 | brain and lives in the post.

00:04:49.780 | And part of the reason I write them is like, "Hey, go read this thing, because I forgot

00:04:52.360 | all the answers."

00:04:53.360 | So I'll do my best to extract what I can remember.

00:04:56.260 | And I did a little prep, but I won't have all of the answers in my head on demand necessarily.

00:05:01.520 | Well, fortunately for you, I try to do a really good job of putting resources in the show

00:05:05.840 | notes.

00:05:06.840 | And if there's one that we feel like your answer is lacking in comparison to what I've

00:05:11.560 | seen you write, I will make sure that we link that so people can follow up.

00:05:15.880 | But let's start with the process of finding the right kind of job.

00:05:20.400 | So there are so many types of companies out there.

00:05:23.680 | What advice do you have for people looking for something new, both in just how to narrow

00:05:28.400 | down the options and actually stand out to candidates to get that first interview?

00:05:34.200 | So just thinking that process.

00:05:35.680 | And for a side note, Lenny also runs a job board and a talent collective for people in

00:05:41.120 | the product space.

00:05:42.800 | So you've seen this both as a person in it and a person creating this thing.

00:05:46.760 | So just to recap, how do people narrow down what they want to do and find a company and

00:05:52.000 | then actually stand out to get in the door?

00:05:54.600 | Yeah, let me talk about the job board briefly because I think it's cool.

00:05:57.080 | It's a cool piece of context that shows kind of how much I spend thinking about people's

00:06:01.920 | profiles and companies and things like that.

00:06:04.220 | So it's called Lenny's Jobs.

00:06:05.880 | It runs on this platform called Palette, which is kind of like the substack for job boards.

00:06:09.680 | It's kind of this white labeled job platform.

00:06:12.760 | And the way it works, there's kind of two parts to it.

00:06:14.560 | There's a regular job board where people just post job openings.

00:06:17.520 | And then there's a reverse job board where candidates can sign up because they're interested

00:06:21.920 | in new opportunities.

00:06:22.920 | And they can just be like, "Hey, I'm open to a new opportunity.

00:06:25.400 | I'd love to hear from interesting companies."

00:06:27.600 | And it can be anonymous.

00:06:28.800 | You could hide yourself from companies that you don't want to see that you're looking

00:06:31.840 | for a job, and it's doing really well.

00:06:35.320 | It's become maybe the number one place to find product people.

00:06:38.840 | I don't know where else you go look for PMs better than this place.

00:06:42.440 | And fun fact, they make more income from just the job board than I made at Airbnb in salary.

00:06:50.080 | And so it turns into a really interesting business on the side and shows the power of

00:06:54.040 | an audience with the newsletter and the audience of that being funneled to the job board, creating

00:06:58.960 | a marketplace.

00:07:00.400 | It's really interesting.

00:07:01.800 | If you look at people that actually end up getting jobs from this, is it more from people

00:07:06.480 | finding the job from the employer or have things changed in the environment where the

00:07:12.080 | employee putting themselves out there is actually leading to more jobs?

00:07:15.840 | Yeah.

00:07:16.840 | So one thing I've learned from this is job boards do not work well.

00:07:19.800 | They're either, and job board meaning you post an opening on a job board.

00:07:25.400 | If it works for you, it's like the best ROI in the history of hiring, because it's like

00:07:31.200 | 50 bucks, 100 bucks, 200 bucks to post a job and you find someone for that and then you're

00:07:35.600 | done.

00:07:36.600 | But it almost never works is what I found.

00:07:38.800 | What actually worked is the reverse, the other piece where candidates that are awesome apply.

00:07:44.400 | I approve them and I only approve about 10% of people to keep the quality by really high.

00:07:49.200 | And that has led to so many companies finding PMs as a product, VPs a product.

00:07:54.440 | And so I think it's the model.

00:07:55.680 | I think that model is a lot more effective now before the economy changed.

00:08:01.160 | And so I'm leaning into that.

00:08:03.040 | I'm kind of moving away from the job board.

00:08:05.440 | And this site, you said pallet, does there, you might not know this, but is there a directory

00:08:10.360 | of all the different job boards they power for something like this?

00:08:13.200 | You know, if someone listening is like, I'm not a PM, but I would love to participate

00:08:16.880 | in this reverse job search process to put myself out there in front of companies.

00:08:20.620 | Are there other job boards or directory of them to go find places to post yourself?

00:08:24.700 | Yeah, they actually have a cool feature.

00:08:26.420 | I think it's called spotlight where you work with them and they give you access to a ton

00:08:30.820 | of different job boards for specific profiles.

00:08:34.300 | And so I get these applications for one company looking for like a designer and they can just

00:08:38.500 | only look at my designer candidates.

00:08:40.940 | So yeah, it's pretty cool what they're building, how, if you're building this profile, right,

00:08:45.020 | you're a candidate building a profile, setting aside that it's in product, but what are the

00:08:49.020 | things you think you've seen people do to one stand out, but also to identify what they're

00:08:54.580 | interested in?

00:08:55.580 | Cause I think there's a world of all kinds of companies you could work at.

00:08:58.860 | The way I think about it, there's, there's a lot of personal things that are important

00:09:02.220 | to people like where they work, where they live and are they want to work and things

00:09:06.700 | like that.

00:09:07.700 | But I'd say if you just, if I think of four things that are really important, I think

00:09:10.900 | of the people at the company, the stage of the company, the mission of the company, and

00:09:15.700 | then just the quality of the business.

00:09:18.100 | So just to go through them briefly.

00:09:20.100 | So with people, what I look for and what I think you should look for is where the smartest

00:09:24.140 | people, you know, going to go work, trying to go work or already working.

00:09:29.620 | And there's kind of a few reasons why that's really powerful.

00:09:32.620 | One is it's more likely that they'll build an awesome product and awesome business that'll

00:09:36.340 | do really well.

00:09:37.340 | So the smartest people working in a company more likely to succeed to you'll learn a lot

00:09:43.300 | more from that group.

00:09:44.420 | If you're just working with the smartest people, you can find, you're going to learn a lot

00:09:47.460 | more.

00:09:48.460 | And then three, which is a little bit underappreciated.

00:09:50.400 | I think the alumni network that you build from a company that you work at ends up being

00:09:54.900 | a really huge asset.

00:09:56.180 | If you work at a company that ends up succeeding and doing well and growing.

00:09:59.940 | And so there's a lot of benefit to working in a place where you can build this really

00:10:04.100 | smart, successful, growing alumni network.

00:10:08.860 | As an example, a friend and I started the Airbnb alumni investing syndicate called Air

00:10:13.940 | Angels.

00:10:14.940 | We invest in companies as a group, there's about 500 of us in the syndicate.

00:10:19.060 | And basically we find companies to invest in, we invest using an SPV and look for ways

00:10:24.460 | to be helpful.

00:10:25.460 | And it ends up being a really awesome, fun experience we all learn together.

00:10:29.100 | That's one, find the place where the smartest people you know are going to.

00:10:34.060 | I think a lot of people under appreciate the importance of stage of company.

00:10:37.980 | There's such a different experience working in a startup versus a big company.

00:10:41.740 | And so I think it's really important to think about what's the stage that you want to focus

00:10:44.540 | on.

00:10:45.540 | I find there's like a really nice middle ground where you look for a series B or a series

00:10:50.380 | C company where it's not so early that it's likely to go out of business or it's going

00:10:55.780 | to be like so stressful all the time, but it's not like a meta or Google.

00:11:01.420 | And so that's kind of interesting middle ground where it's still like a lot of upside, still

00:11:04.300 | really fast moving.

00:11:06.300 | And there's a lot of opportunity, but not boring and slow and big company.

00:11:09.900 | So stage, I would think about the mission of the company.

00:11:12.980 | If you like, look back on your life, you're going to be like, okay, look, I spent three

00:11:16.780 | years at this company.

00:11:17.780 | I moved this metric 5%.

00:11:19.260 | And so like, you're not going to be that excited about that unless the mission is something

00:11:23.980 | that you really care about.

00:11:25.740 | And moving that metric 5% leads to something that matters in the world.

00:11:29.460 | As an example, Airbnb, they basically help people travel and go on better trips.

00:11:33.620 | And if you ask people, what would you do?

00:11:35.300 | And this applies to your podcast a little bit.

00:11:37.180 | Like what would you do if you had all the money in the world?

00:11:39.700 | Everyone says I travel and how cool is it to let people go on better trips, more trips,

00:11:44.540 | have better experiences.

00:11:45.860 | So there's a really meaningful mission there.

00:11:48.620 | So and then the fourth is you just want to pay attention to the quality of the business.

00:11:52.860 | Like is it going to work out?

00:11:53.860 | Is it going to grow?

00:11:54.860 | Is it going to, do they have to keep raising money forever?

00:11:56.900 | Are they going to be profitable?

00:11:58.740 | Especially important in today's climate.

00:12:01.580 | And this is especially important because one of the, and we'll talk about how to stand

00:12:05.460 | out, one of the most powerful things you can do to give yourself a chance to get a better

00:12:09.980 | job is to have a logo or two from a company people recognize and respect, because that

00:12:15.900 | kind of pre-validates that you're solid.

00:12:18.460 | Somebody else has interviewed you that you really trust.

00:12:20.660 | And they've said, Chris is great.

00:12:22.340 | We hired him.

00:12:23.340 | He worked here two years.

00:12:24.340 | That like says a lot.

00:12:25.340 | They may not necessarily be amazing, but at least it's some level that gives you a quick

00:12:29.060 | like, okay, I'll talk to this person.

00:12:31.020 | So you want to work at a company that ends up being like, oh, wow, they worked that.

00:12:34.660 | Now we were going to talk to them.

00:12:36.700 | So those are the four.

00:12:37.700 | I had an idea around that when I first wanted to get a job at a startup, I was like, I'm

00:12:41.500 | going to pick a startup.

00:12:42.500 | That's really popular.

00:12:43.500 | People will remember.

00:12:45.100 | And I was like, oh, what company just raised a bunch of money?

00:12:47.540 | What's kind of in the zeitgeist.

00:12:49.700 | It turns out I was wrong.

00:12:50.700 | And that company ended up like not actually going on to raise any further funding.

00:12:54.060 | But that was a hypothesis I had actually played out because five years later, even though

00:12:58.140 | that company was out of business, people were like, oh, I remember that company.

00:13:01.340 | And so just the fact that I worked at this company that was a hot company at the time,

00:13:05.020 | even though it went out of business within a small niche of people was, was valuable.

00:13:08.900 | I'll add on a couple thoughts to what you said, which is when you talk about stage and

00:13:15.300 | for people listening that aren't in tech, forget whether it's series a series B or something,

00:13:19.780 | it's just a small company, big company.

00:13:22.440 | I think another way to think about that, those stages is kind of the speed at which you will

00:13:27.460 | learn and the type of learning you will do.

00:13:30.160 | If you want to really hone your craft in a specific vertical, a later stage company is

00:13:36.180 | often going to be a place where you can really focus on one thing and really hone that, that

00:13:41.580 | skill, whether it's a set of managerial skills or, um, you know, anything at an early stage

00:13:46.820 | company, you're going to accelerate the speed at which you learn, but it might not be as,

00:13:52.060 | as kind of focused on craft, or at least so I've found because there's so many opportunities.

00:13:56.820 | You might think you're doing one role in product, but you might also be doing a role in marketing.

00:14:00.140 | And you might also be, you know, being the janitor sometimes, you know, I think I've

00:14:03.660 | had every role at a company except engineer at times.

00:14:07.100 | And um, that, that happens at a smaller company.

00:14:09.740 | So while you might trade off stability, you might learn a ton and a lot faster and be

00:14:15.020 | able to make transitions easier.

00:14:17.040 | You know, if you're trying to jump into a new career, it's going to be a lot easier

00:14:20.660 | at a small company to say, Hey, I've never done this thing, but can I jump in and try

00:14:24.620 | it?

00:14:25.620 | And at a small company, someone's like, Oh, Lenny's really good at this thing.

00:14:28.840 | Let's let Lenny do that.

00:14:30.020 | And then you can kind of move, move across very, very easily.

00:14:33.220 | Yeah.

00:14:34.220 | That reminds me real quick story of when we sold our company to Airbnb, that's how I joined

00:14:39.100 | Airbnb.

00:14:40.100 | I went from being the CEO of the startup to a PM at Airbnb, and I felt such relief not

00:14:46.420 | having to think about all the things at the company and just focus on the one problem

00:14:50.860 | that we had to solve at Airbnb.

00:14:53.020 | Like you would think that's painful, but it was so nice.

00:14:55.060 | And I have to think about fundraising and I have to think about paying people salaries

00:14:58.800 | every month.

00:15:00.260 | It was just like, cool.

00:15:01.260 | You can solve this problem.

00:15:02.260 | Life's going to be so much easier.

00:15:03.920 | And so sometimes you want that.

00:15:05.700 | Sometimes you don't.

00:15:06.700 | Yeah.

00:15:07.700 | And my wife was the chief of staff at Lyft for a bunch of years.

00:15:10.980 | She joined when the company was very small and she had, you know, the opposite experience,

00:15:15.100 | which is she got to see everything.

00:15:17.580 | And it was an amazing opportunity because the company was growing and she had all these

00:15:20.640 | different war, every hat there was.

00:15:23.180 | And finally she was like, Oh, I'm spinning up a team to work on insurance.

00:15:26.420 | I don't love that.

00:15:27.420 | I'm spinning up a team to work on BD.

00:15:29.080 | Oh, I'm like really interested in this.

00:15:31.460 | Let's go do that.

00:15:32.580 | And then she built a career in BD and loves doing BD and partnership stuff, but she never

00:15:37.500 | would have found that if she hadn't joined a company small enough to be able to do lots

00:15:41.300 | of stuff.

00:15:43.100 | And then this is a little bit out of the way, because it's really hard.

00:15:45.980 | It's not necessarily hard, but it's difficult to find these people.

00:15:49.960 | But I think about trying to think about who you want to work for also.

00:15:54.480 | So in any industry, there are people that are well known in their industry for, you

00:15:59.400 | know, you could look at like any conference for an industry, like who are the people speaking?

00:16:02.740 | Who are the people that are writing, who are the people you respect?

00:16:06.600 | And sometimes there might be a good opportunity to go learn from that person.

00:16:11.020 | And it might not be the mission that you love, but it might be the best mentor you can find.

00:16:15.880 | And so that's another thing that I think you could focus on when you're trying to figure

00:16:21.360 | out where to go, what's important to you.

00:16:23.240 | It's like, do I care about the mission and will that fulfill me?

00:16:25.700 | Or do I care about the learning?

00:16:26.860 | Will that fulfill me?

00:16:27.860 | Or do I care about the resume boost?

00:16:29.740 | Will that fulfill me?

00:16:31.380 | All of those are options.

00:16:33.980 | And so you just have to process them all.

00:16:35.540 | Yeah, it reminds me of a quote that I don't know if I believe, but a lot of people believe

00:16:39.460 | it that you don't quit a job, you quit a manager.

00:16:42.660 | And so to your point, finding a manager that you're really excited about and think you

00:16:46.100 | can learn from and want to work from, and that will champion you is really important.

00:16:50.580 | And I think super underappreciated in my career, the biggest trajectory inflection was just

00:16:56.020 | one manager I had that just taught me a ton and just pushed me to do better.

00:17:00.540 | And to your point, there's so much power and value in finding that person.

00:17:03.780 | Yeah.

00:17:04.780 | And if you can find, you know, the Japanese phrase, Ikigai, if you're familiar, if you

00:17:08.900 | can find that, obviously it's like the dream, right?

00:17:11.700 | It's, which is the intersection of what you love, what you're good at, what the world

00:17:15.660 | needs and what you could get paid for.

00:17:17.340 | Like, you know, that's the dream.

00:17:19.140 | It's like, you know, I'm learning as fast as I want at a company with the mission I

00:17:22.700 | want.

00:17:23.700 | But I will say in my career, it's been very hard to find all of those things all the time.

00:17:28.120 | And so you've got to prioritize and sometimes they morph into that, but you know, I wouldn't

00:17:34.060 | necessarily hold out for, for finding something that ticks every box.

00:17:38.460 | I think one way to think about as long as you're getting closer to that, because you

00:17:41.460 | like your wife, you said she like, didn't know she wanted BD and the more experiences

00:17:46.620 | you have, the more you kind of narrow in on, okay, here's the thing I really want.

00:17:51.600 | The other way to think about it is I realized this is my fourth career.

00:17:55.260 | First I was a engineer.

00:17:56.260 | Then I was a founder.

00:17:57.260 | Then I was a PM and I'm whatever I am now, I was a newsletter.

00:18:02.100 | And so there's always options to go change and go in different directions as you learn

00:18:06.180 | more about what you're excited about.

00:18:07.620 | Like you're not stuck in the path that you chose.

00:18:10.780 | Yep.

00:18:11.780 | And you, I don't know about you, but I went through investment banker, management consultant,

00:18:16.260 | founder, uh, or employee PM BD, I did BD then founder, then, uh, went to Google and

00:18:25.180 | was a venture capitalist.

00:18:26.180 | And then I was, you know, I went through a lot of, and now I'm a creator.

00:18:29.460 | Um, I never knew half of those things more than three months before, you know, like some

00:18:34.260 | of them, I was like, I never knew I would be VC.

00:18:36.060 | And then that opportunity arose.

00:18:37.180 | I never thought I'd be a creator.

00:18:39.220 | And then I started a podcast.

00:18:40.840 | And so I think you don't need to know the future.

00:18:43.820 | I love this idea of where do you want to be with your life in 10 years?

00:18:48.100 | And if you, if you're in a career where that exercise is helpful, great, but I can tell

00:18:52.340 | you that where would my career be in 10 years, 10 years ago would be so wildly off from where

00:18:59.060 | it ended up that, you know, maybe it would have been a fun exercise, but it certainly

00:19:03.100 | wouldn't have been anywhere close to accurate.

00:19:05.300 | Yeah.

00:19:06.300 | I think to that point, there's so much value in a variety of experiences, like just doing

00:19:10.460 | a lot of different stuff later on ends up being really valuable to whatever you end

00:19:15.580 | up doing later.

00:19:16.580 | I was just interviewing a newsletter guy who was like the number one tech newsletter on

00:19:20.900 | Substack.

00:19:21.900 | And he's like, yeah, I launched a newsletter.

00:19:23.100 | I got a thousand subscribers really quickly.

00:19:24.780 | It just started working.

00:19:25.780 | But in reality, I spent six years writing a book on engineering and then working at these

00:19:30.660 | jobs, learning a bunch of stuff.

00:19:32.540 | So the thing you end up doing later ends up being built on the experiences you have.

00:19:37.300 | And a lot of people don't understand the value of just trying a bunch of different stuff

00:19:40.940 | and not feeling like they have to be stuck.

00:19:42.980 | Here's the thing I'm going to do for 10 years.

00:19:44.540 | You found a handful of jobs.

00:19:46.020 | My personal belief is that in today's world, you're much better off trying to narrow it

00:19:51.080 | down to three or four companies that you're really excited about and double down on your

00:19:55.860 | efforts to get in front of them.

00:19:57.860 | And things I've done in the past are find every person that I can that knows them.

00:20:02.140 | I've tried creating a presentation and sending it to them.

00:20:06.260 | You could create a video about how excited you are, lots of things like that.

00:20:10.460 | I've had this work for me, and I think it's underappreciated.

00:20:14.660 | But as a founder, someone emailed me and said, I am so excited about your company.

00:20:19.660 | Here's my ideas.

00:20:20.660 | And I was like, I have to interview this person.

00:20:23.040 | Anyone who would take more than an hour to put something creative together about my company

00:20:28.700 | is someone I will want to talk to.

00:20:31.620 | And the bigger the company, the more it's like, well, they actually have to fit a role

00:20:34.700 | we're hiring for.

00:20:36.220 | But I've interviewed people who I was like, I don't even have a role for you, but I just

00:20:39.180 | want to understand who you are, so I know where to slot you in later.

00:20:42.340 | And so you can't scale that if you're interviewing, if you have a thousand companies you're excited

00:20:46.860 | about.

00:20:47.860 | But if you have three, I'm like, go all in on those three before you try to find three

00:20:51.160 | more because I think that you can easily stand out by doing those things.

00:20:57.940 | There's an episode I did with Sunil Gupta, who wrote a book called Backable.

00:21:01.660 | And one time he just did customer research for the company and sent it to me.

00:21:05.940 | He was like, hey, I interviewed your customers, here's what I learned.

00:21:09.300 | If you were in sales, you could go close a customer and be like, hey, I just convinced

00:21:13.460 | a customer to sign up for you.

00:21:15.020 | I just wanted to let you know.

00:21:17.580 | Who doesn't want to interview a person who's closing deals before they even work there?

00:21:20.740 | So I think if you can go through the hard exercise of figuring out what you want, that's

00:21:25.140 | it.

00:21:26.140 | So those are my tactics of standing out.

00:21:27.140 | I'm curious at what you've seen to try to have candidates either who've applied to you

00:21:30.620 | or you've done yourself, kind of put yourself out there in different ways.

00:21:33.900 | I think that's awesome advice.

00:21:35.580 | It reminds me, I was teaching a course on Maven about product management and I was interviewing

00:21:41.380 | coaches to help me with the course.

00:21:44.100 | And I had about 10 coaches.

00:21:45.100 | I was interviewing them with someone else that was helping me out with the course.

00:21:48.780 | And one of the coaches started her own sub stack, subscribed me to it, and then just

00:21:53.300 | started writing posts about how she's the perfect fit to coach this course.

00:21:57.260 | And I was like, holy shit, we need to make sure that we talk to her for sure.

00:22:03.180 | And we did, and it didn't work out there because she wasn't quite the fit, but I found something

00:22:06.460 | else to do with her.

00:22:07.460 | And now she's a core part of my newsletter community, helps run a lot of the programs.

00:22:12.700 | So yeah, I love that advice.

00:22:14.820 | I think that's awesome advice.

00:22:16.900 | I think generally the question is how do you stand out?

00:22:19.060 | How do you stand out?

00:22:20.060 | You do something really remarkable that gets someone's attention.

00:22:22.860 | There's a lot of ways to do it.

00:22:23.860 | I do a lot of angel investing and whenever I get a founder that makes a loom, "Hey Lenny,

00:22:29.620 | I really wanted to talk to you about the startup I'm building.

00:22:32.260 | Here's why it's awesome."

00:22:33.540 | Like I watch them.

00:22:35.300 | Most of the time I talk to them because they put in the effort and they do something unique.

00:22:39.340 | So I think it applies to investing too, pick like the people you really want on your cap

00:22:42.840 | table and do some extra.

00:22:44.460 | I think broadly, like if you don't do anything like this, the things you need, because I'm

00:22:49.860 | with the job board, I review, I probably reviewed 3000 profiles of people that applied to join

00:22:54.180 | the job board or the collective.

00:22:56.100 | And so the things like if you think about from the perspective of hiring manager, like

00:23:00.180 | what are they looking when they're scanning resumes?

00:23:02.380 | They're looking for logos that they recognize from companies that have pre-vetted that person

00:23:07.420 | in some form versus like a bunch of random companies they've never heard of.

00:23:11.100 | So like you're not going to be able to do a lot about this, but this is what hiring

00:23:14.260 | managers look for.

00:23:15.660 | Companies that they respect, that have kind of done one pass at this person and they're

00:23:19.940 | probably solid.

00:23:21.980 | And then I think you mentioned this is just like impact, show some kind of impact that

00:23:26.100 | you've driven.

00:23:27.100 | So they're hiring you to have impact.

00:23:29.260 | What impact have you had in your career?

00:23:31.660 | And so the more you can highlight those things, the better.

00:23:33.940 | But if you don't have those things, your advice is, is great.

00:23:37.380 | Do something, do something remarkable.

00:23:39.580 | I love the idea of like a loom resume.

00:23:41.180 | I wonder if you just like, you're, you know, send in your resume, but it's like, if you'd

00:23:44.540 | rather not look at another, I can imagine getting an email, if you'd rather not look

00:23:48.180 | at another 50th resume of the day, here's a five minute video of me walking through

00:23:53.220 | the highlights.

00:23:54.220 | And by the way, you can put it on two X, if you want to get through it in two and a half.

00:23:57.380 | I bet if I got an email that was like a little bit snarky, a little bit funny, but a little

00:24:00.780 | bit informative, that would be great.

00:24:02.740 | And if you don't have those logos, it might be exactly what you need to get through that.

00:24:06.660 | Yeah.

00:24:07.660 | And then you could track that.

00:24:08.660 | They watch the video too, which is cool.

00:24:09.660 | You get an email.

00:24:10.660 | What about interviewing?

00:24:11.660 | Have you thought a lot about, you know, both on both sides of it, what people should be

00:24:15.420 | focused on versus not like, I don't know if I'm going to give you anything that you haven't

00:24:19.900 | heard before, other than just spent a lot of time preparing like a lot of interview

00:24:23.380 | questions or stuff you'll hear from a lot of different people.

00:24:26.740 | So I think that's probably 90% of it.

00:24:29.180 | Just spend a bunch of time preparing.

00:24:31.940 | If you're interviewing at a big company, my sister was interviewing.

00:24:35.180 | There's just like videos of all the interview questions they ask you online.

00:24:37.780 | It's pretty crazy.

00:24:38.780 | There's like courses you could take, like how to interview at Google.

00:24:41.620 | And it's like all the questions they ask you, it's like you can go through all of them.

00:24:45.660 | There's like a pool basically.

00:24:47.500 | So there's like a lot of answers out there if you put in the time.

00:24:53.420 | Another piece is, I guess, get good at telling your story and why you want to do this job,

00:24:59.380 | what you've done in your career, highlight the things that have had impact.

00:25:03.220 | I think it's just like get good at pitching yourself and then you want to ask good questions

00:25:10.380 | of the interviewee, like stuff you hear all the time.

00:25:13.180 | So I don't think there's anything dramatically new, but yeah, people want you to ask them

00:25:17.820 | questions because they want you to, they want to feel like you care about the company.

00:25:21.680 | I've interviewed people who I'm like, why do you want to work here?

00:25:23.660 | And they're like, well, when I had a financial planning startup and they're like, I just

00:25:26.340 | love personal finance.

00:25:27.340 | I'm like, that's why you want to work in the industry.

00:25:28.980 | That's not why you want to work here.

00:25:30.820 | So I would say, especially the smaller the company, but it probably works at any scale.

00:25:35.880 | If you don't have a really solid answer for why you want to work at this company, I think

00:25:41.740 | that is tough for the other person to hear if they ask you.

00:25:47.000 | And even if they don't, I'd try to slot it in because I think that's great.

00:25:50.620 | And I would also try to come up with a personal question that I know this sounds like a lot

00:25:55.880 | of work, but try to come up with the best question you can ask someone.

00:25:58.820 | Because whenever anyone asks me a really hard question, I remember that person.

00:26:03.980 | That person really thought hard about this.

00:26:08.100 | Or they transferred from interview to interview, they're like, oh, this person told me this

00:26:11.060 | is your biggest problem, uh, your company's facing.

00:26:13.620 | And in the next one, they'd come in and say, Hey, I talked to the head of marketing and

00:26:17.340 | they said, this is the biggest challenge you're facing, you know, from a product standpoint,

00:26:22.560 | what are you guys doing to help the marketing team solve this?

00:26:24.980 | And it's like, wow, now you get to learn a lot of stuff, but it actually shows that you're

00:26:28.580 | actually trying to solve problems.

00:26:30.300 | You're trying to be, you know, get more out of it.

00:26:32.340 | So I just try to say, as the candidate, don't forget, you can ask questions and don't assume

00:26:37.320 | that the questions you ask are purely selfish.

00:26:40.220 | I think that they can often leave people with a better impression of you and not just be

00:26:44.900 | information gathering.

00:26:45.900 | It reminds me, one of the most interesting, so I have a TikTok account for my podcast.

00:26:51.100 | It's called Lenny's podcast on TikTok.

00:26:53.180 | And I think it's like, my name is the actual handle.

00:26:55.860 | And the most popular content is guests talking about their favorite interview question.

00:27:01.020 | I ask that often at the end of my podcast episodes.

00:27:04.300 | And so if you're looking for more questions to practice on, if you go to Lenny's podcast

00:27:09.660 | on TikTok, you'll sort, I think by views, you could probably see a bunch of really fun

00:27:13.700 | interview questions.

00:27:15.740 | I will link to that show notes so people can find it.

00:27:19.220 | Now let's say you get the job and this is something I know you've written about.

00:27:22.940 | And I know it was actually a guest post, but I'm hoping you have some of the takeaways

00:27:26.340 | because they were fantastic about salary negotiation.

00:27:31.060 | You know, I think it's something that people spend far less time on than they should.

00:27:35.100 | And you highlighted a lot of that in the post you put out in your newsletter.

00:27:38.460 | This post ended up being the most popular post of my newsletter of all time, partly

00:27:42.380 | because it got on Hacker News and got a ton of views and some recruiters did not like

00:27:47.260 | it.

00:27:48.260 | And so I kind of, it's, it's good and bad, but I learned a ton from it.

00:27:52.420 | And the reason I asked, so the author's Nia Drugova.

00:27:56.920 | And the reason I asked her to write this is because I'm really bad at negotiation.

00:28:00.420 | I don't even know if I've ever negotiated a salary.

00:28:04.000 | And so I wanted to learn how to do this well.

00:28:06.220 | And she, her full-time job basically is helping candidates negotiate their offers and help

00:28:12.340 | them find jobs.

00:28:13.380 | So she's done this a ton.

00:28:15.700 | And I'm not going to share, go through everything.

00:28:18.300 | There's 10 kind of steps that she shares.

00:28:20.340 | I'll share a few highlights, things that I thought were most interesting.

00:28:24.060 | One is she super recommends you never give a number of what you think your salary should

00:28:29.440 | be or the range you're thinking about.

00:28:31.540 | Her advice is just ask them, like, here's the question she suggests you ask.

00:28:35.980 | Can you tell me the salary band for this level?

00:28:39.180 | I'm happy to let you know if it's within my range and we can discuss the specific number

00:28:43.980 | later once I've met the team.

00:28:46.580 | That's her advice.

00:28:47.980 | And that range ends up being really useful later when you start to negotiate.

00:28:52.380 | That's tip one.

00:28:53.900 | Tip two is to mine for Intel from your hiring manager and the recruiter into what they're

00:29:00.460 | looking for from this role.

00:29:02.380 | Like what's the number one priority of the team right now?

00:29:05.140 | Why why is this role open?

00:29:07.820 | What's the biggest challenge for someone getting into this role?

00:29:10.740 | And the reason that's important is then you can mirror that back when you're pitching

00:29:14.140 | yourself.

00:29:15.140 | Once you've got an offering, you want to counter, you can highlight, hey, here's what I'm going

00:29:18.940 | to help you with.

00:29:20.300 | Here's what I'm going to do in this role.

00:29:22.700 | Here's the challenges I'm going to tackle immediately.

00:29:25.380 | And people are going to be like, holy moly, that's exactly what we need to know.

00:29:29.260 | So the tip there is just mine, like ask these questions so that you have notes when you're

00:29:32.780 | actually pitching yourself later.

00:29:35.420 | And then the third tip that I love is once you get an offer, her advice is don't counter

00:29:41.100 | it immediately and don't come back with, no, I think this is a better, more fair number.

00:29:45.860 | Instead, you want to win the hearts and minds of the decision makers.

00:29:50.160 | You want them to feel like, oh, my God, we need Chris in this company.

00:29:53.820 | We got to pay him whatever he wants.

00:29:55.940 | And the way you do that in her advice is after you get the offer schedule, try to get a meeting

00:30:00.340 | with a decision maker, like a director or VP or something.

00:30:03.820 | Just like, hey, I just want to chat about this role.

00:30:06.020 | And then in the discussion, ask questions about how they would want you to create meaningful

00:30:11.620 | impact.

00:30:12.620 | Share some ideas maybe you've had about what you're going to do there.

00:30:16.020 | And then maybe share obstacles that you have in accepting the offer and taking on the role.

00:30:21.620 | And generally just get them, try to get them excited about you joining the company.

00:30:25.180 | And with that, then you can come back with like, okay, here, I've talked to everyone.

00:30:28.740 | I understand the role better.

00:30:30.380 | Here's where I think the offer should be.

00:30:32.500 | And in theory, if you got them really excited to be like, oh, yes, yes, yes, let's do whatever

00:30:35.800 | we need to do.

00:30:37.300 | I love that third tip because, uh, it's almost like, you know, come up with a plan.

00:30:42.060 | You could even talk to the person that would be your manager and be like, Hey, you know,

00:30:45.820 | I know we're talking about salary negotiation already, but I just want to figure out like,

00:30:49.180 | what's the 90 day plan.

00:30:50.340 | What can I hit the ground running on?

00:30:51.660 | And you get them to like, buy into this is what this person's going to do.

00:30:55.420 | And they're like, gosh, we already, we've already decided where first project, like,

00:30:58.660 | can we get going?

00:30:59.660 | Right.

00:31:00.660 | Like get them in the hell.

00:31:01.660 | Let's get going.

00:31:02.660 | What are we doing?

00:31:03.660 | Negotiate?

00:31:04.660 | My, my, my other piece of advice to people is the salary is a component of your compensation,

00:31:09.620 | but there's often a lot of flexibility in other places.

00:31:12.500 | So it's not the only place to focus on some companies, uh, you know, things like vacation

00:31:18.260 | days are flexible.

00:31:19.380 | Some they're just based on tenure or everyone gets the same.

00:31:22.340 | Um, some educational reimbursement is one that you can focus on.

00:31:26.180 | Um, others, I've found companies that say, you know, we're not really willing to flex

00:31:30.380 | on the salary and then, but I've heard from, you know, after I've worked there that they

00:31:34.760 | are willing to flex on a signup, a signing bonus, um, you know, they are willing to flex

00:31:39.400 | on various other aspects of compensation, like what your estimated bonuses, uh, I helped

00:31:44.440 | a friend negotiate.

00:31:45.440 | He said, you know, sometimes it's like, Oh, well now I know the band for the level, but

00:31:49.740 | why could I be at the next level?

00:31:51.980 | Like I'm not trying to tell you how much to pay me.

00:31:53.940 | I'm trying to tell you that I'm at the next level.

00:31:55.740 | And they said, well, we're, we're not confident you're at that level.

00:31:58.900 | And he said, great.

00:31:59.900 | How about we have a check-in in six months and you tell me what I need to demonstrate.

00:32:04.760 | I will demonstrate that.

00:32:06.060 | And if I will, would you retroactively update my compensation?

00:32:10.020 | As if I came in at that level, you're not willing to believe I'm there now, let me prove

00:32:13.640 | it to you.

00:32:15.100 | And he set out a series of things that they needed to demonstrate three months in.

00:32:19.780 | He checked in with them and said, am I on track to demonstrate these things, which by

00:32:23.060 | the way, genius move, uh, for this person, because it's so much easier for your manager

00:32:27.960 | to say you're on track for something than actually getting your promotion put through

00:32:32.500 | or getting your, you know, compensation adjusted.

00:32:35.180 | But then when you check in six months later and you say three months ago, you said I was

00:32:38.500 | on track.

00:32:39.500 | Like we haven't had any conversation to the contrary.

00:32:41.940 | So like, if I'm not getting this, then what, why were you telling me that?

00:32:45.980 | So you're kind of similar to how you said, getting the buy-in before you negotiate, you're

00:32:49.340 | getting the buy-in that you're already going to get approved for this change.

00:32:52.780 | So I just think there's a lot of wiggle room about things, um, other than your salary.

00:32:58.540 | And so if, if a company's not willing to flex there, go down all the other paths, it's still

00:33:03.060 | so hard to do.

00:33:04.060 | It's a negotiation thing.

00:33:05.860 | I worked with Andy Ratcliffe for a while.

00:33:07.220 | He was the CEO of wealth threat.

00:33:08.220 | His advice was to always just put the decision in someone else's hand and say, what, what

00:33:13.380 | do you think is fair?

00:33:14.900 | And he said 90% of the time, uh, they do what's fair and 10% of the time they don't.

00:33:19.780 | And you know, that they're trying to kind of screw you over and maybe that's just not

00:33:22.620 | the right fit.

00:33:23.620 | Um, I I'm trying to think, you know, I, I always like sharing negotiation advice, even

00:33:27.500 | if it's not relevant to salary.

00:33:29.180 | Um, but you could basically say, here's all the data I've collected about what this role

00:33:33.660 | should be compensated.

00:33:34.980 | I, I, I I'd like to be compensated fairly with this data.

00:33:39.540 | Here's the data.

00:33:40.540 | Let me know what you think.

00:33:41.540 | And like force it on them to make a fair decision.

00:33:43.860 | I feel like, you know, that that's maybe depending on the circumstance, uh, a good last tactic

00:33:48.660 | or a starting point, but I like, and have used many times the tactic of letting someone

00:33:53.260 | else decide what's fair and not have to throw out the number first.

00:33:56.740 | I like it.

00:33:57.740 | Okay.

00:33:58.740 | So we've gotten hired.

00:33:59.740 | We're now at a company.

00:34:01.500 | And I want to focus on something that applies to everyone actually working at the company

00:34:05.820 | they're at.

00:34:06.820 | Um, there is a lot we could cover here.

00:34:09.220 | I don't want to go through every possible thing, but there are a few things that I think

00:34:12.940 | you might have, you know, outsized impact on the conversation about.

00:34:17.660 | And the first one is actually about having impact in an organization, uh, and hopefully

00:34:22.780 | a little bit about how to get promoted on the way.

00:34:25.060 | But I know you kind of believe those two things are both similar and very different.

00:34:29.340 | So what do you, what do you think people should be optimizing for when they're working at

00:34:33.120 | any company?

00:34:34.380 | If I had to pick one thing, I would say have impact on the company in their bottom line.

00:34:38.820 | I think if you think about it, like, why the hell are they paying you a salary?

00:34:41.780 | It's to have impact on their business, to help them grow faster.

00:34:46.660 | And so if there's any one thing that you can just always come back to, if you deliver more

00:34:51.340 | impact, you will do better.

00:34:53.540 | I think that's like 90% of your success at a company.

00:34:56.820 | And there's like, people need to know about your impact.

00:34:58.740 | You need to be working on things that matter.

00:35:00.900 | Like you could have an impact on like a leaf at the end of the tree of the business, or

00:35:05.500 | you could have impact on the core number one goal.

00:35:08.140 | And that's a big difference, but I'd say if you had to pick anything, it's just, how can

00:35:12.460 | I deliver more impact?

00:35:13.460 | And it's especially important for PMs who are basically marshaling the resources of

00:35:18.300 | their team.

00:35:19.780 | And the more you focus on how can our team have more impact, the better everyone on the

00:35:23.660 | team does.

00:35:24.660 | Let's pretend you just started a new company and you're like, how do you find the way you

00:35:28.260 | can have that impact?

00:35:29.700 | Well, there's one way I think about it.

00:35:32.060 | I kind of think about Lord of the Rings and the Eye of Sauron.

00:35:36.660 | If you think about like, what's the most important project to the CEO right now, I think about

00:35:41.500 | that as the Eye of Sauron.

00:35:42.500 | He's looking at that, or she's looking at that, and that's going to be like so stressful

00:35:46.820 | and difficult.

00:35:47.820 | They're like right on you, on your butt.

00:35:50.300 | And then the alternative is you could be working in a shire where nobody cares what's going

00:35:54.460 | on.

00:35:55.460 | Like you could have the most amazing product and everyone's like, that's nice, good job.

00:35:59.500 | I would say generally you want to optimize like on average to be like, not in the Eye

00:36:04.940 | of Sauron, but right off to the side.

00:36:07.060 | Work on something that's really important, but not like the most important thing to the

00:36:10.340 | company, at least for a long time, because you just get burnt out being in that thing

00:36:13.860 | that's like the number one most important product.

00:36:16.580 | So that's just like a general piece of advice.

00:36:18.420 | Work on something really important, but maybe not the most important thing.

00:36:21.620 | Just a tip there.

00:36:23.260 | Impacts the most important thing.

00:36:24.340 | I've seen you write about how to get promoted effectively and that impact matters.

00:36:30.100 | So any comments on that?

00:36:32.140 | If you're like, why am I not getting promoted?

00:36:34.620 | It usually means that you're not delivering enough impact or people don't have confidence

00:36:38.900 | that you will deliver the impact that you need to at a higher level.

00:36:42.900 | So if you think about working backwards from a hiring manager or the company, thinking

00:36:47.380 | about show you promote Chris, basically you need to give them confidence that you can

00:36:51.940 | handle more scope, more responsibility, more, more impact.

00:36:56.360 | So how do you show that one deliver more impact?

00:37:00.300 | Find ways to hit more ambitious goals, maybe lead a really important project, work on something

00:37:06.420 | closer to the eye of Sauron, something higher visibility and more important, maybe help

00:37:10.620 | the company save money or run more efficiently.

00:37:13.640 | Just like find ways where you can show that you've done things that are really important

00:37:17.420 | to the company.

00:37:18.420 | Now two is part of the idea of a promotion is people are going to give you more scope,

00:37:24.980 | more responsibility, and again, they have to have confidence that you can handle it.

00:37:28.460 | How do you do that?

00:37:29.460 | You take on more scope, more responsibility before you are promoted to show people, look

00:37:33.580 | at me, I can handle this.

00:37:35.060 | So you want to find ways to take on work, maybe your manager's doing and knock it out,

00:37:40.500 | take on a project that someone else is doing while they're out and do it for them.

00:37:44.140 | Pick a really ambitious project that's just going to take a year or two.

00:37:47.800 | It's going to be really important to the company.

00:37:50.760 | Take the reins on like a visioning exercise and just like, look at me, I did this thing.

00:37:55.100 | This is awesome.

00:37:56.100 | So, and I think what's important here is a lot of people only get promoted after they've

00:38:00.740 | shown they can handle this additional scope.

00:38:03.580 | And so you've got to look for things, you've got to find opportunities to take on more

00:38:06.600 | scope.

00:38:07.600 | Those are two, there's five more in this post that I wrote, so let me just run through them

00:38:13.060 | pretty quick.

00:38:14.060 | Three is part of the reason you get promoted is there's this gap that your manager has

00:38:19.960 | identified.

00:38:20.960 | Like Chris needs to work on a better deadline setting or, or, uh, hiring.

00:38:27.120 | There's usually like a gap that keeps you from the next level.

00:38:30.560 | And it's really important that you and your manager are aligned.

00:38:33.440 | Here's the gaps that keep you from the next level.

00:38:35.640 | Like you shared this story about your friend, am I on track for this next level?

00:38:38.920 | There's usually like a set of things that your manager gives you feedback on, usually

00:38:42.120 | in your performance review, a tip that I would suggest that I found really powerful, um,

00:38:48.120 | either as a manager or as a report is when you have a performance review, align with

00:38:54.480 | your manager on like a spreadsheet of things that you plan to do in the next, say six months

00:38:59.760 | until the next performance review, um, create basically a roadmap.

00:39:03.840 | Like I'm going to work on becoming a better public speaker.

00:39:06.600 | I am going to get deadlines 90% of the time.

00:39:09.640 | I'm going to update our JIRA, uh, to be up to date by the end of Fridays, make a list

00:39:15.440 | of the things that are the biggest, uh, things you can actually do that'll bring you to the

00:39:20.240 | next level.

00:39:21.480 | And then meet with your manager slash report every month and review the status of each

00:39:25.680 | of those things.

00:39:26.680 | And it becomes this little roadmap where you're aligned on here's the things say Chris is

00:39:31.160 | working on and how they're going.

00:39:33.000 | So that by the time you get to the performance review, you, uh, you don't, you're unsurprised

00:39:38.800 | like here, we did five of these things.

00:39:40.440 | We didn't get to these things.

00:39:42.240 | So that's where you're at.

00:39:44.240 | So demonstrate you've addressed the gap for finding someone that can champion you.

00:39:49.740 | That's often really powerful at a company, get someone really excited about you and can

00:39:53.800 | champion you inside of these calibration sessions.

00:39:56.600 | That's really powerful.

00:39:57.600 | Um, five is you want to pay attention to what gets promoted at the company.

00:40:02.560 | A lot of companies have these like gray area things that matter a lot that you may not

00:40:06.920 | be aware of.

00:40:07.920 | So just look at people who are getting promoted and just understand, look for things that

00:40:12.360 | they're doing.

00:40:13.360 | Maybe that you're not doing.

00:40:14.360 | Maybe you have to be friends with the CEO.

00:40:15.360 | I don't know.

00:40:16.360 | Maybe you have to be really good at communication that really matters at the company.

00:40:20.480 | And then two more, um, something that's way underappreciated is you just need to ask to

00:40:24.680 | get promoted.

00:40:25.680 | Sometimes, sometimes managers don't know you want to be promoted.

00:40:28.900 | So simplest thing you could do is just like, Hey, I would love to be promoted to the next

00:40:32.840 | level.

00:40:33.840 | What do I need to do to get there and what are my gaps?

00:40:36.480 | And that often leads to the biggest impact on getting promoted.

00:40:40.080 | And then the last idea and tip is just sometimes you need to leave and work somewhere else.

00:40:44.240 | Sometimes you're just like stuck in a rut and you just have, I don't know, certain reputation.

00:40:48.880 | Your manager is just not good at championing you.

00:40:51.340 | So sometimes you're not going to get promoted and it's time to try some other place where

00:40:56.000 | you kind of start with a clean slate.

00:40:57.320 | I remember it was so depressing, but, uh, when I was a venture capitalist, the role

00:41:02.280 | of like, I guess, non general partner, we were told it was like, this is a terminal

00:41:07.300 | position.

00:41:08.300 | Like they were just very transparent.

00:41:10.240 | They're like the expectation for this job is not that you will get promoted to be a

00:41:14.440 | general partner of the fund.

00:41:16.080 | That is just how it works.

00:41:17.520 | Uh, and we just want you to know that.

00:41:19.680 | So you don't have those expectations.

00:41:20.680 | And it was like very clearly set.

00:41:22.760 | I think it was a little depressing at times because the word terminal position just sounds

00:41:25.920 | like, you know, going nowhere, but I appreciate the honesty.

00:41:29.200 | I appreciate the transparency.

00:41:30.960 | The one thing that I learned and you, you reminded me in what you said was a lot of

00:41:35.600 | times in order to get promoted, you don't need to meet the expectations of your role.

00:41:40.020 | You need to demonstrate that you can handle the next role.

00:41:42.840 | And I think I'd always thought, you know, as someone who hasn't studied this or been

00:41:46.560 | a prolific manager at any point in time, I always thought, Oh, when someone could do

00:41:50.360 | their job really well, you move to the next level.

00:41:52.800 | But it's actually in a lot of companies, it's when someone could demonstrate that they can

00:41:56.280 | do the job that they want to get promoted to is when that happens.

00:42:00.760 | And so it's really important to understand what do I need to, if I'm a level five manager

00:42:05.220 | and I want to be a level six director, it's like, what do I need to demonstrate to be

00:42:09.080 | a director?

00:42:10.680 | Not what do I need to do as a manager?

00:42:13.120 | Because sometimes you need to do the next level's job to get the promotion.

00:42:16.240 | Yeah.

00:42:17.240 | And that's how it works in calibration.

00:42:18.240 | When you're looking at someone's level, there's like a lot of big companies have these ladders

00:42:22.540 | and they tell you what each level needs to achieve.

00:42:25.640 | And so if someone's going to be promoted to say L seven, there's like, here's what L seven

00:42:29.680 | has to be good at, at each of these things.

00:42:31.880 | And that's a manager.

00:42:32.880 | Look at is Chris ready for all these things in L seven.

00:42:35.880 | Makes sense.

00:42:36.880 | Like your job is going to now be that you want to be confident that they can handle

00:42:40.120 | that.

00:42:41.120 | And if that ladder is not public, ask for it.

00:42:43.560 | There are some companies that might not publish it on any internal doc, but you could say,

00:42:46.680 | Hey, my boss, could you please show me the career ladder for my role or could the requirements

00:42:51.560 | of the next level of my role?

00:42:53.120 | And hopefully you can get that and understand it so you can work towards it.

00:42:57.200 | Yeah, I've actually, I've actually collected the career ladders at 20 something companies.

00:43:02.640 | And I have this doc that we'll link to in the show notes that has all their level names

00:43:05.800 | and then the attributes that they live for product managers specifically that they look

00:43:09.920 | for to promote people.

00:43:11.160 | We'll link to that in the show notes.

00:43:13.480 | One of the things I tell people is they think that to be promoted, that that strategy is

00:43:18.600 | to always kind of do whatever your boss wants and never push back.

00:43:22.600 | And you know, I am someone who probably has never adhered to that, maybe to my own demise

00:43:26.720 | and kind of pushed back too much.

00:43:29.700 | What do you think is the right balance of, you know, saying no?

00:43:33.720 | And what's the value of saying no, as opposed to kind of always being willing to do what

00:43:38.120 | other people want?

00:43:39.560 | As a PM and just as a leader in general, like you're the person that needs to say no, because

00:43:45.080 | you're kind of responsible.

00:43:46.080 | And I'm thinking from a PM perspective, product manager perspective, you're kind of responsible

00:43:50.560 | for what a whole team of people does.

00:43:53.240 | And so part of your like, you could almost say your job is to say no so that you can

00:43:57.200 | say yes to the stuff that is really important.

00:43:58.880 | So it's really important to say no to push back.

00:44:02.080 | It's still very hard, especially if your manager is like, hey, we need to do these things.

00:44:07.080 | So I wrote this post with, I think, five ways you can say no that and many of them are you

00:44:13.320 | say yes to say no.

00:44:15.240 | So I'll share some of these quotes that you can steal.

00:44:18.760 | And they're also in this post.

00:44:20.620 | So the first two is someone asked you to do something.

00:44:23.560 | You could say yes, but here's what's going to have to change.

00:44:27.680 | If we do that, should we move forward?

00:44:30.680 | And oftentimes they're like, yes, let's go ahead.

00:44:32.360 | Or otherwise they're like, no, shoot, I don't want to, I don't want to deprioritize that.

00:44:36.640 | Forget that.

00:44:37.640 | So that's one trick.

00:44:39.640 | Two is you could say yes, but not right now because we got to stay focused on X because

00:44:44.640 | of X, Y, Z.

00:44:45.840 | Do you agree with that?

00:44:46.960 | Or do you think we should deprioritize that?

00:44:49.860 | So that often works really well because it basically communicates, again, here's like

00:44:53.800 | a very clear trade off and why it's important.

00:44:57.440 | Another way you could say no is no, but how about we do X, Y, Z instead of that?

00:45:03.960 | And it's going to achieve a similar outcome.

00:45:05.560 | Basically, this is when you have a better idea, but you want to communicate here's something

00:45:10.600 | we could basically do exactly what you want, but here's a better approach to doing that.

00:45:14.680 | Another way you could say no is no, but there's something there.

00:45:18.680 | There's like something to this idea.

00:45:20.640 | How about we explore this a little bit further?

00:45:22.840 | And here's the next step that I suggest.

00:45:26.280 | And then the fifth way you could approach is just like, no, I don't think this is a

00:45:30.320 | good idea.

00:45:31.560 | Here's why.

00:45:32.940 | Would you agree?

00:45:33.940 | Or is there something I'm missing?

00:45:35.420 | So first off, I wish I had read this post earlier in my career because I was like, no,

00:45:39.680 | that's so crazy.

00:45:40.680 | Why would we do that?

00:45:41.680 | I could have used this.

00:45:42.920 | I was never good at, you know, politics is the wrong word, but I was never good at a

00:45:47.840 | lot of this stuff.

00:45:50.200 | And one of the tactics I shared when we spoke on your show was that like, I was so confrontational

00:45:55.840 | about things because I was so used to working at a company that I started where everyone

00:46:01.400 | always knew that obviously I was always optimizing for the company because like it didn't matter.

00:46:07.180 | And then I joined a company where I wasn't in charge and, and you know, it turns out

00:46:11.320 | that in big companies, there are a lot of people who are optimizing for themselves way

00:46:14.440 | more than the company.

00:46:15.760 | I didn't really realize that.

00:46:16.760 | I was like, everyone's got it optimized for the company.

00:46:19.040 | That's the most important thing.

00:46:20.320 | That's how I lived in my last companies that I've run.

00:46:23.200 | And so a tactic that helped me when I was pushing back on people, colleagues, bosses,

00:46:28.600 | is just always making sure that I told people, Hey, I'm thinking about this from the perspective

00:46:34.600 | of trying to maximize the impact from the company.

00:46:38.600 | And because sometimes I'd say, Oh, well that we shouldn't do that.

00:46:41.200 | That's not a good idea.

00:46:42.200 | And people would be like, Oh, well you just don't want to do more work or you want to

00:46:44.360 | focus on this thing you're more excited about.

00:46:46.280 | And that wasn't true, but the more I just transparently said, here's how I'm thinking

00:46:51.160 | about this.

00:46:52.160 | Here's what I'm focused on.

00:46:53.160 | It just helped so much.

00:46:54.160 | And so just stating your intent before you push back.

00:46:57.440 | So people know where you're coming from.

00:46:59.960 | It was very helpful for me and hopefully helpful for some others.

00:47:03.200 | Yeah.

00:47:04.200 | I think we all fall into this.

00:47:05.200 | Like people are going to read our mind and know exactly why we think no, or why we're

00:47:08.700 | saying this.

00:47:10.000 | And it turns out people cannot read your mind real quick before we, we talk about what happens

00:47:15.400 | when you move on from a job, you know, part of getting things done as being productive.

00:47:19.440 | I've talked a lot about time management.

00:47:21.280 | I'm a nerd.

00:47:22.280 | We don't have to go super deep because I've done a few episodes, but any few tactics you

00:47:26.080 | want to pull out on how you manage your time and get a lot done and be effective with your

00:47:30.480 | output so that you do have impact.

00:47:32.320 | Yeah.

00:47:33.320 | And it's especially important in this world of writing and podcasting full time.

00:47:37.520 | I'll share a few things that worked really well when I was working full time and I don't

00:47:41.760 | think anything will be revolutionary, but, but these things really work for me at least.

00:47:45.960 | One is I blocked three hours on Monday, Wednesdays and Fridays on my calendar.

00:47:51.640 | And I had, I called the meeting, do not book or I will slap you.

00:47:56.740 | And it made people laugh, but it really worked really well.

00:47:59.080 | People did not book over these slots.

00:48:00.680 | They were like, okay, I get it.

00:48:03.320 | And so find some like funny way to have a block where people know, okay, I see he's

00:48:07.640 | like really serious about this time.

00:48:09.240 | Let me leave him alone because I'm sure you've talked about deep work and the importance

00:48:13.000 | of focus and all that.

00:48:14.720 | But I find that that's so important for creative work.

00:48:18.660 | In my new life of newsletter or podcast person, I, uh, I have no meetings until 3:00 PM.

00:48:24.040 | That's my rule.

00:48:25.040 | And only at three, I have meetings and things like this.

00:48:27.280 | So that helps them too is just what's like an app or something that keeps you focused

00:48:32.840 | when you're working.

00:48:33.840 | I use this app called centered dot app.

00:48:36.160 | That's kind of like brain FM, which is this like binaural beat music meets a to do list

00:48:41.360 | meets like a playlist.

00:48:42.880 | So once you're ready to work, click play and music starts and it's like Lenny, you're starting

00:48:47.880 | with your newsletter posts and then you can knock them off as you're working through them.

00:48:52.160 | And it works really well for me.

00:48:54.480 | Something I'm trying right now that works well is picking one highlight of the day.

00:48:58.640 | One top goal for the day.

00:49:00.440 | There's this book I'm reading right now called make time.

00:49:02.120 | Oh yeah.

00:49:03.120 | It's called make time.

00:49:04.120 | Yeah.

00:49:05.120 | Sprint guys.

00:49:06.120 | And they're, that's one of their key things.

00:49:09.200 | Just like pick a highlight.

00:49:10.200 | What's going to be like a highlight of your day that you look back on that I did this

00:49:13.320 | thing.

00:49:14.320 | You'll feel good no matter what else happened.

00:49:15.320 | So I'm trying to do that.

00:49:16.320 | And that's been working really well.

00:49:18.480 | Another tip is to have a, a waiting for list.

00:49:21.200 | It's very like getting things done, David Allen style, where I have all these open threads

00:49:25.820 | of people doing stuff.

00:49:27.640 | And I keep a list of who am I waiting for on these things so that the to do, even though

00:49:32.080 | it's on someone else's plate, I don't lose track of.

00:49:34.600 | And the way I do it as in my to do list, I just have W for Chris and then it's like record

00:49:39.640 | podcast or whatever.

00:49:41.140 | So that ends up being really helpful.

00:49:42.920 | The other interesting thing I find is procrastination.

00:49:45.880 | Like it has a bad rap.

00:49:47.320 | I find that sometimes I procrastinate on a hard thing, but I get a lot of other smaller

00:49:51.360 | things done.

00:49:52.360 | So I like work through this list of stuff that isn't important, but I get them done

00:49:57.160 | and there's value to just procrastinating off the thing that's like really hard because

00:50:01.480 | you still get other stuff done.

00:50:02.480 | So I try to channel my procrastination and get stuff done that, uh, I need to get that

00:50:08.240 | anyway.

00:50:09.240 | I think about there's deep work and I don't know if you could say flow state and deeper

00:50:12.800 | or the same thing, but I think that sometimes it just takes a little bit of momentum to

00:50:17.360 | get into that flow state.

00:50:18.520 | So it's like, ah, I got this really big, hard thing.

00:50:20.800 | Do I want to sit down and do all this research and you know, or do I want to knock off a

00:50:26.440 | few quick things?

00:50:27.440 | And then I'm like, oh yeah, I'm making progress.

00:50:29.000 | I just cleaned up this, this set of my emails.

00:50:31.640 | I just, you know, got this one thing done and now I'm feeling really productive and

00:50:34.760 | at least for me, once I start feeling productive, it's just so much easier to be more productive,

00:50:40.040 | get more done.

00:50:41.040 | Then I find myself like, oh, I just wish I could work longer.

00:50:43.320 | I've got so much.

00:50:44.320 | So, um, I love making momentum in that.

00:50:47.000 | So those are some really great tips.

00:50:48.760 | I won't share too many of mine because I've done an episode with Ali Abdaal on productivity

00:50:52.560 | on with Cal Newport on deep work and, uh, with Laura Vanderkam on time management.

00:50:57.440 | So if you're new here, there's a lot in the archives to go check out.

00:51:01.480 | So go check those out, but let's talk about moving on because, you know, you said, uh,

00:51:06.000 | you've left here.

00:51:07.000 | You're no longer a full time employee with a company you're doing on your own.

00:51:10.760 | How did you make that decision to move on?

00:51:13.000 | How did you create space for it?

00:51:14.960 | Um, and, and did you ever think about ways to test out, uh, going out on your own before

00:51:22.000 | before that?

00:51:23.000 | That's a lot.

00:51:24.000 | So, uh, maybe, maybe start with, uh, how did you even kind of decide maybe I should move

00:51:28.760 | on.

00:51:29.760 | I'm ready for a big change.

00:51:30.760 | If you look at my resume, I'm like a serial monogamist of career.

00:51:34.640 | I worked at my first company for nine years, then at a startup, that was the short stint

00:51:39.400 | year and a half, and then worked at Airbnb for seven years.

00:51:43.120 | And uh, I, like, I never thought I'd stay there that long.

00:51:46.360 | They bought our startup and I'm like, oh, I'm going to be out of here in three years

00:51:49.520 | when I'm going to start another company.

00:51:51.880 | And then seven years later, here I am.

00:51:54.400 | And along the way, I thought about leaving, but it never felt like it was time.

00:51:57.720 | It was always interesting.

00:51:58.720 | There's always reasons to keep working there and try new stuff.

00:52:03.000 | Um, and the way that it happened that I left is I took a sabbatical, uh, they gave me a

00:52:08.920 | sabbatical.

00:52:09.920 | So I took three months off, uh, right around when I was reaching seven years and about

00:52:14.900 | halfway through, I remember just opening my email for the first time.

00:52:19.240 | So a month and a half in the work email, just to see what was going on.

00:52:23.440 | And I just had this like, heart sinking feeling where I'm like, I don't care about this at

00:52:28.480 | all anymore.

00:52:29.480 | What the heck is, what is going on here?

00:52:31.880 | And I just, I don't want to think about any of this ever again.

00:52:35.680 | And so that was kind of an important moment where I was like, wow, maybe, maybe I'm not

00:52:39.000 | excited about this work anymore.

00:52:41.560 | I still came back to Airbnb after that and kind of wanted to feel out, am I ready for

00:52:47.480 | some new, like, am I, am I, is there like a new team?

00:52:52.520 | Maybe I could work on a new project that would get me excited.

00:52:55.520 | But basically the way it felt as I got there and I immediately felt like my heart was done

00:53:00.180 | with that work, but my brain wasn't ready to move on.

00:53:02.800 | It was like, maybe there's something more interesting.

00:53:04.360 | Maybe there's a new manager.

00:53:05.360 | Maybe there's something else I could work on.

00:53:06.360 | So it took a month basically to think about and talk to people about other roles, other

00:53:10.400 | teams, other opportunities.

00:53:12.520 | But I'd say at the end of the month, it was like, nope, nothing that gets me very excited.

00:53:17.400 | It's time to do some new.

00:53:19.480 | And we'll say it's rare.

00:53:20.480 | It's like very fortunate to be able to have that feeling of like, I can leave and things

00:53:24.760 | aren't going to, I'm not going to go bankrupt and live on the street.

00:53:27.760 | So it's a really, I'm grateful that I have the opportunity to even have thought that,

00:53:33.600 | but I did.

00:53:34.840 | And so what I decided to do is I'm going to leave Airbnb and I'm going to give myself

00:53:38.160 | six months to think about what I want to do next.

00:53:41.240 | And something that really helped there.

00:53:42.240 | And here's a tip.

00:53:43.240 | When you're thinking about something like this is to figure out a personal runway of

00:53:47.240 | like how much it's going to cost you to take six months off and just budget that like it's

00:53:51.080 | going to be $30,000, take six months off to pay all the things I'm paying.

00:53:56.840 | And just knowing that number ahead of time gives you so much less stress knowing I'm

00:54:01.400 | like burning through money as I'm not working, but I've already accounted for that.

00:54:04.760 | And it's like maybe sitting in a bank account somewhere and that gives you more freedom

00:54:08.480 | to just explore and not have to worry about, oh my God, I need to find something as soon

00:54:12.040 | as possible.

00:54:13.040 | And I'll just highlight the importance of actually putting it in an account.

00:54:17.240 | It's one thing to be like, well, I know I have enough savings to take time off.

00:54:20.560 | And this is something that I'm actively thinking about now that I'm grading this business on

00:54:25.000 | my own.

00:54:26.000 | Just like you did it.

00:54:27.240 | It's like actually putting it somewhere.

00:54:30.520 | It takes it one step further.

00:54:31.600 | I think it has even more it because a lot of it's emotional.

00:54:35.040 | It's not always rational.

00:54:37.080 | It's like, gosh, I don't have a salary coming in.

00:54:39.640 | I almost went as far as to take the salary, put it in a bank account and automate the

00:54:44.480 | transfers.

00:54:45.480 | So it like simulated as if I was getting my paycheck so that I felt like it was not as

00:54:50.220 | scary to not have that stability.

00:54:53.140 | The other thing that I found really powerful during this time, in addition to the personal

00:54:57.480 | runway is there's so little structure when you aren't working.

00:55:01.340 | Like I worked for, I think 19 years in our, since like, you know, 18 years old and I never

00:55:07.640 | take a break and it's so weird to not have structure in your life.

00:55:11.100 | That's like, there's deadlines, there's no deadlines.

00:55:13.920 | There's no like, I need to achieve this thing by then.

00:55:16.400 | Like you could work all day.

00:55:17.960 | You could not work at all.

00:55:18.960 | Nobody's going to say anything.

00:55:20.120 | And it's hard to work without that.

00:55:21.880 | Like it feels like it shouldn't be, but it really is.

00:55:24.200 | So what I created structure for myself and the way I did that is I created these little

00:55:28.320 | sprints where every two weeks I wrote down, here's the three goals I have for the next

00:55:35.120 | two weeks that are work goals and three personal goals.

00:55:38.080 | And I emailed that to three friends that became kind of this like personal board of directors

00:55:42.840 | kind of group.

00:55:44.280 | And I had no expectation they'd reply.

00:55:45.800 | I didn't need them to reply.

00:55:47.000 | I just found that just emailing them, here's what I'm trying to accomplish.

00:55:51.880 | And then circling back in two weeks and sharing, here's how I did, created so much accountability

00:55:56.360 | and gave me some focus for these two weeks.

00:55:59.760 | And I ended up doing that for a year straight.

00:56:01.320 | Every two weeks I did a little check-in in one weekend, just to like, here's how it's

00:56:05.280 | going so far per sprint.

00:56:07.760 | And that was so powerful and important to where I ended up just creating a little bit

00:56:11.920 | of structure.

00:56:13.200 | And that email list ended up being like 30 people eventually, just because it became

00:56:16.260 | a cool way to update my friends on what I was up to.

00:56:18.480 | And just like, Hey, you want to join this list I'm doing.

00:56:21.320 | And so that's a tip in your, if you don't have enough structure around your, your free

00:56:25.200 | time.

00:56:26.600 | I think one thing interesting that I've thought a lot about recently is, you know, as a creator,

00:56:30.640 | which you, you know, you left and you started, I think the first thing out of, out of Airbnb

00:56:34.240 | was a newsletter.

00:56:35.240 | I think a lot of people are kind of scared.

00:56:36.880 | I don't know what my thing is, but I love the idea of experimenting with creation.

00:56:41.760 | And I think depending on the company you work at, you might be able to kind of experiment

00:56:45.880 | before you leave.

00:56:47.080 | I would encourage everyone to, you know, get it cleared to make sure that, you know, your

00:56:50.960 | company isn't going to own whatever you're working on, you know, clear that don't do

00:56:54.920 | it on your work computer, do it on your personal computer and all those good things.

00:56:59.080 | But how did you start to think about, because I think, I think one thing for me that was

00:57:03.400 | strange was I had all this knowledge about optimization, like, but I, it didn't really

00:57:07.320 | click that it could actually be a thing that I do.

00:57:10.760 | That could be a business that could be how I, you know, spend my days.

00:57:14.560 | Do you have any advice for someone who hasn't quite figured that out?

00:57:17.920 | And they're like, I would love to do that, but I don't know what my thing is, or I don't

00:57:20.680 | know how I could test if it really is a thing.

00:57:23.360 | I think there's two things I'll cover there.

00:57:24.880 | One is, can you start something while you're at a company?

00:57:28.400 | My experience is, I, it's so hard.

00:57:31.480 | I found that like, I'm done at the end of the day, working at a full-time job, like

00:57:35.640 | Airbnb, I'm just like, I have no brain energy left to experiment with writing awesome posts

00:57:40.960 | or a podcast or anything like that.

00:57:43.080 | It's like very, very hard.

00:57:45.200 | And I think the advantage folks like you and I have that are doing this full-time is there's,

00:57:49.600 | I find there's a strong correlation between quality and, and how well it does.

00:57:54.120 | And so we just, and time, sorry, quality and time, there's a strong correlation between

00:57:58.840 | how much time you put into something and the quality of that work.

00:58:01.840 | And people that have a full-time job are not going to have as much time as someone like

00:58:04.920 | you and I that are doing this full-time.

00:58:07.840 | And so I think it's just really hard to try something like this for real when you have

00:58:12.680 | a full-time job.

00:58:13.840 | So don't feel weird if like, oh my God, everyone's writing all these side projects and writing

00:58:17.120 | things and starting podcasts, like very, very hard.

00:58:20.280 | When I started writing, like I hadn't really written anything public in my life before

00:58:25.740 | I started this newsletter, just experiment with it.

00:58:28.920 | And to segue to the second question is like, how did I discover this path?

00:58:32.580 | I just had like stuff I wanted to get out of my head when I left Airbnb, just to make

00:58:36.280 | sure I don't forget it in case I start another company.

00:58:39.120 | And so I just started, I wrote a Medium post, it did shockingly well.

00:58:41.920 | I wrote a few more posts, they did well.

00:58:44.440 | And then just kind of in the sprint goal thing that I talked about, I just had like every

00:58:48.440 | sprint just like write one more post, see how that goes.

00:58:50.800 | So I just kept along that path and the whole time I was like, why am I doing this?

00:58:54.920 | I thought I was going to start a company, like why am I spending time writing?

00:58:58.520 | This is such a not going to go anywhere.

00:59:01.960 | Time invested, my wife's like, what are you doing writing?

00:59:04.080 | You're not a writer, I thought you wanted to start a company, why don't you spending

00:59:08.480 | time on that?

00:59:09.960 | And I had this really important conversation with a friend who pointed out, okay, you really

00:59:14.840 | enjoy this thing, people seem to value it, that's like very rare, you found like some

00:59:19.160 | kind of product market fit.

00:59:20.960 | Maybe this goes somewhere if you keep at it.

00:59:23.640 | And even if there's no way you could ever make money with it, maybe just double down

00:59:27.680 | on that.

00:59:28.680 | And forget the startup stuff for now and just see where it goes.

00:59:31.200 | And that's exactly what I did.

00:59:32.200 | I just started writing every week, launched a newsletter just to create a little time

00:59:35.640 | pressure to post something once a week, and did that for nine months every week.

00:59:40.160 | And then at that point, I'm like, huh, this is still going great, growing fast.

00:59:44.080 | Maybe I could charge for this.

00:59:45.080 | I launched a paid plan that went well.

00:59:47.600 | And I just kept following that path.

00:59:48.800 | And so it was very one step at a time without any master plan.

00:59:53.280 | And you say it just kind of grew.

00:59:54.960 | How big is the newsletter now?

00:59:56.880 | It's about to hit 300,000 subscribers.

00:59:58.640 | Yeah, it's a number one newsletter and massive number one business newsletter on Substack.

01:00:04.880 | And growing fast.

01:00:06.200 | I love it.

01:00:07.280 | It's kind of the core of my, my work and then the podcast kind of spun out of that.

01:00:11.120 | Well, I've enjoyed it thoroughly.

01:00:12.880 | In fact, in preparation for this interview, I was a little stressed out because I was

01:00:17.240 | thinking, gosh, I'm leaving my job, but I really do love building products.

01:00:20.800 | And I was like, scrolling through trying to like, look at all the posts you've written.

01:00:24.040 | And I was like, gosh, wow, I really want to build this impactful project.

01:00:27.520 | Like, I really want to make another roadmap.

01:00:29.280 | So you know, now I'm like, I've got to channel that energy.

01:00:33.920 | And for everyone listening, now I'm focused on what kinds of products and experiences

01:00:37.840 | and communities and all of the things that I build around what I've done with all the

01:00:41.520 | hacks.

01:00:42.520 | It's hard to come there, but it's been it was very helpful.

01:00:45.760 | So thank you for that.

01:00:47.680 | Anything we missed in this process, we went through, you know, finding a job standing

01:00:50.960 | out, running through, you know, working and having impact and moving on.

01:00:55.720 | I know you've written so many great newsletters.

01:00:57.280 | So I want to make sure we hit on something that you've thought about.

01:01:00.400 | There's something that I thought would be good to share, which is around managing up.

01:01:04.760 | I find that whenever I tweet about managing up, it's like the most popular tweets ever.

01:01:09.560 | Really people really want to learn how to manage up better.

01:01:12.520 | And there's one thing that I'll share that I found really effective, which is around

01:01:16.180 | how to keep your manager aware of what you're up to.

01:01:19.520 | There's a lot of value in your manager knowing what's on your mind, what's important to you

01:01:23.480 | right now, what can they help with.

01:01:25.280 | So something that I found to be really powerful is an email that I call the state of me email.

01:01:31.080 | So it'd be like the state of Lenny email, I call it the subject line state of Lenny

01:01:35.640 | and in the email and I email this to my manager every Monday or every Friday, once a week,

01:01:40.640 | I write out, here's blockers that I need your help with 1, 2, 3.

01:01:45.560 | Here are my current priorities, 1, 2, 3.

01:01:48.280 | And then here's what's on my mind in general, 1, 2, 3, 4, 5.

01:01:52.440 | And then at the end, just like, let me know if there's anything that I can clarify if

01:01:55.360 | you have any questions about anything.

01:01:56.600 | And I found that one email created so much value because my manager knew what I was up

01:02:02.200 | to.

01:02:03.200 | They could tell me, Hey, why are you working on that?

01:02:05.080 | They can, they can unblock stuff that I'm blocked by, which a lot of times I don't know

01:02:09.360 | that you're blocked by some.

01:02:10.360 | And then generally there's stuff on your mind, like, Hey, I'm thinking about this project,

01:02:13.960 | this person's thinking about leaving this competitors doing this thing.

01:02:18.240 | So just that one email can make a huge dent and really simple, just like blockers, priorities,

01:02:23.400 | what's on your mind, send your manager that once a week and honestly great things are

01:02:27.680 | going to happen.

01:02:28.680 | Yeah.

01:02:29.680 | I mean, I said earlier, you don't want to be always saying yes to your manager, but

01:02:32.280 | making your manager's life easier is certainly something that is a very valued attribute

01:02:38.800 | of an employee.

01:02:39.800 | So making it, making it easier for them to understand everything you're working on, making

01:02:43.160 | it easier for them to say, I love this email idea.

01:02:46.320 | It's like, Oh no, actually work on this, that will let you have more impact.

01:02:49.640 | So love it.

01:02:50.960 | And this has been so helpful.

01:02:52.520 | I, you know, I wish that some of these things I had taken before, but like I said, you know,

01:02:58.000 | I didn't know where I'd be now, who knows where I'll be in 10 years.

01:03:01.240 | And certainly many people listening will hopefully get a lot of value out of this and out of

01:03:05.320 | the newsletter before we go, I do want to ask you, is there a place that you feel like

01:03:10.680 | you could give some recommendations to people who might find themselves there on whether

01:03:14.880 | it's eating activities, drinks, something to do?

01:03:17.720 | Sure.

01:03:18.720 | I'm not, I'm not like the guy people go to for advice on what to do in a place, but yeah,

01:03:22.920 | you gave me a heads up on this question.

01:03:24.400 | And so here's what I got for you.

01:03:26.120 | I live in Marin, California, which is North of San Francisco.

01:03:30.080 | And so here's a little, there's a little agenda.

01:03:32.200 | If you can want to come to Marin, I'd say stay at this hotel called Cavallo Point Lodge.

01:03:37.760 | It's going to blow your mind.

01:03:40.320 | Then go take a little walk around Sausalito along the water.

01:03:43.280 | There's this boardwalk that goes along the water.

01:03:45.960 | Then just grab lunch at a restaurant there.

01:03:48.120 | There's like these piers with these beautiful seafood restaurants.

01:03:51.680 | Then take a drive to San Francisco across the Yule game bridge.

01:03:55.600 | There's this art piece called the wood line in the Presidio that is this like curvy piece

01:04:00.040 | of wood that you could walk along amongst these huge eucalyptus trees.

01:04:03.440 | And that's right across the bridge.

01:04:05.600 | Then you can go to say Fillmore Street or Chestnut in the Marina and get a coffee, buy

01:04:13.600 | some nice fancy things in some of the nice stores.

01:04:17.080 | Then I'd say drive back to Marin and maybe to Fairfax, which is further North, rent a

01:04:22.080 | mountain bike, find some trails.

01:04:24.720 | Mountain biking was invented in Fairfax and there's this huge mountain, Mount Ham, there's

01:04:29.440 | like a thousand trails you could go on.

01:04:31.580 | So maybe spend a few hours hiking around Mount Ham, sorry, biking around Mount Ham.

01:04:36.080 | Then have dinner in Fairfax or there's another cute little town, San Anselmo, and then head

01:04:41.720 | home to your little, your cute little hotel in Sausalito.

01:04:44.240 | If you're in Sausalito, I'll throw out a recommendation for a place called Fish, which

01:04:49.320 | is just like a seafood restaurant on the water.

01:04:51.440 | Sweet.

01:04:52.440 | There's your lunch spot.

01:04:53.440 | It meets the requirement of being Bay Area expensive, but also delicious.

01:04:58.520 | I love that.

01:05:00.280 | I don't know if you've been to the Mill Valley Lumber Yard.

01:05:03.680 | Oh yeah.

01:05:04.680 | The cutest little complex.

01:05:07.000 | Someone was like, "Can we meet at this bakery in Mill Valley?"

01:05:09.200 | I showed up and I was like, "This is literally like this quintessential cute little shops

01:05:14.660 | and a little flower store and a bakery and a little creperie."

01:05:18.560 | If you need a place to just relax for an hour and a half or two, I highly recommend that

01:05:23.560 | as a stop in Mill Valley.

01:05:24.720 | I have not spent much time in Marin, but that place was just an awesome spot.

01:05:29.440 | Yeah.

01:05:30.440 | It's like very unknown, but so cute.

01:05:31.960 | The bakery is called Flower Craft and it's gluten-free, all gluten-free.

01:05:35.000 | My wife's got celiac and so it's her favorite place.

01:05:38.920 | Well, before we wrap, where can people go find all of these great newsletters, all the

01:05:43.560 | conversations you're having with people, myself included, which depending on whether this

01:05:48.600 | comes out at the same time, we had a great conversation over there.

01:05:52.280 | The hub of all things I do is lennysnewsletter.com.

01:05:55.300 | That's where my newsletter is, my podcast.

01:05:57.760 | It's designed for anyone that's building product, growing product, mostly product managers,

01:06:02.840 | founders, designers, engineers, anyone basically working on software.

01:06:07.720 | Lennysnewsletter.com.

01:06:08.720 | Just check out lennyspodcast.com, the newer thing, but doing super well and I'm really

01:06:13.960 | proud of it.

01:06:14.960 | So check that out.

01:06:15.960 | And I'm @LennySan on Twitter.

01:06:19.480 | What's the story behind the San?

01:06:20.640 | One of my friends when I was in high school, just called me Lenny San for some unknown

01:06:24.560 | reason and I stuck with it.

01:06:26.400 | I didn't know I was going to be stuck with that username for the rest of my life, but

01:06:29.280 | here we are.

01:06:30.280 | Awesome.

01:06:31.280 | All right.

01:06:32.280 | Thank you so much for being here.