Enthusiasm is the tiebreaker

One thing that you can control is your enthusiasm. I think about it like going to see your favorite musician perform. They’re playing the same songs that they play every night, but you wouldn’t know that by how they show up and perform for you, because you’re hearing it for the first time. Well, guess what? It’s the same thing when you’re answering questions in an interview.

Thank you. Glad to be here.

I have most of them, I think, actually.

Absolutely. So I mean, my career hasn’t exactly been a straight line. I do this presentation whenever I join a team, and it’s like a line that starts and then it’s like a whole bunch of squiggle lines, and lines to the other end. And that’s how I actually think about my career. I think when you’re young in career, you want to map everything out. Yeah, I did that. It’s nothing what I thought it was going to be. And I have zero regrets.

So I began my career actually as a self-taught engineer. So when I was young, my parents did not buy me a gaming system. I had no Nintendo. I was terrible at Super Mario Bros. when I went over to a friend’s house. But they bought me a computer, and I started taking it apart and I’d put it back together, and sometimes it would work when I put it back together, other times it didn’t, and it taught me to try different things and explore. And then when the internet came out, I did the same thing. I started clicking around, looking at different websites, looking at the source code, trying to duplicate it. Sometimes it worked, sometimes it didn’t. And that’s how I started.

And so I began my career as an engineer. It was my first job out of college. And then I moved to New York about 18 years ago, and I joined Google as a designer. And in between, I had started switching from just implementing. In my 20-year-old nothing engineering brain, I thought of engineers as doing someone else’s vision. Just not right, but that’s how I kind of approached it. And I wanted to help create the vision, and I saw design as the way to do that. So then I started exploring design. I got a job at Google, which was amazing, I was there for about five years. And then I joined Etsy as a product manager. And so I’ve been an engineer, a designer and a product manager.

Funny story about Etsy is, it was probably about 100 people at the time when I started talking to them, and it started as an informal conversation. I got introduced to someone, talk to this person, talk to that person, before I know it I had an offer. But the recruiter said, we’d like to offer you an offer to be a PM at Etsy. And I didn’t know I was interviewing for a PM role, I thought I was interviewing for a designer role. So literally on the phone to the recruiter, I said, do you think I’m a shitty designer? I don’t recommend it, but it’s like, you know, again, young, dumb. He’s like, no, no, no, no. He’s like, at Etsy we’re going to win if we have a really great experience, right? Because we’re a marketplace, our tech is relatively simple, we’re going to win if we have great experience. And so we want our PMs to have a background in design. And I was like, oh, that’s kind of interesting. And I was like, sure.

And so I did two things. I accepted, and then I emailed all the PMs I ever worked with in my career and I was like, I need to get on the right side of karma now, because now I’m going to be a PM and I feel bad for how I treated you at times. But yeah, so I was a product manager at Etsy. That’s where I started managing people and building teams. And since then, a little more than a decade, had my own startup, led teams, design teams, PM teams, engineering teams, public companies, private companies. But my journey up to this point has really been mostly in product, working closely with those two roles that I did early in my career, engineering and design.

Not planned. You know, like it sounds cliche, but I just really love solving problems and working with others, and I think as a PM you get to do that. Also, to be fair, I wasn’t the best engineer, I wasn’t the best designer, which actually means you could be a pretty good PM as it turns out. Because you kind of need that breadth of background, it helps.

When I hire PMs, I look for PMs that have one to two hard execution skills, because I think of product management as a leadership discipline, and the best leaders flex to the needs of their team. So the deeper, harder skills you have is more of an opportunity to flex to what your team needs. It’s very much an experience driven role, right? The idea that you could be a PM having not executed in any capacity, it’s possible, but it wasn’t my path.

Oh yeah. Fair enough. Fair enough. So I joined Google when I moved to New York as a designer. I was at Etsy, I was at Betterment, I was at Casper pre-IPO, I worked at InVision, I most recently worked at Slack. So yeah, a good mix. I’ve been very lucky. It’s a good mix of public companies and scaleups. So it’s been fun.

Yeah. So I opened my own independent coaching practice about seven to eight months ago. And looking at my career, every five years or so I kind of mix it up. I was an engineer for about five years, I was a designer for about five years, I was a product manager, and then I started managing other people and then leaders. So every five years I’m mixing it up, and for the last several years I felt like I was overdue to kind of mix it up.

And I was craving, I have an addictive personality. Like whenever I discover a new hobby or a passion, I go deep. Like I go really deep. And I just love that beginner’s mind. And I love also feeling growth, right? And when you’re early on it’s easy to feel growth, because you know nothing and then you know more than nothing, and so on and so forth, so you really feel it. And so I felt like I was overdue to shake things up.

So I left Slack about a year ago. I took the summer to kind of go on my own vision quest, if you will. And I thought a lot about, what is it that I really enjoy doing? And a lot of people will say, again cliche, but when you really think about what are the things that give you energy, not take things away but give you energy. I started to think a lot about that. And I emerged from that vision quest with two things that really felt like they gave me energy. One is working directly one-on-one with people that want to grow, and the other is writing more code, which is where I began my career. Right, clicking, looking at the source, figuring out what worked and didn’t work, putting the computer back together. I missed doing that. And so I’ve started doing that kind of full-time.

And I love coaching because I love helping others in their hero journey, to be quite honest, right? To help them kind of get out of their own way a little bit and grow and try new things and be comfortable with the messy parts of growth. I find it incredibly rewarding. And it’s a little different than managing. With a coach, if you think about it like an athletic pursuit or something, you kind of raise your hand and you’re like, I want you to push me. I know I will probably hate you at times, I know I might even yell at you at times, but I want you to push me. No one’s yelled at me yet. But yet. But it’s different than managing someone. When you manage someone, they didn’t always pick you, they don’t always necessarily want to grow. Maybe it’s not a time for them where they can, maybe they have too much going on in their personal life. So I love coaching because people are seeking it out, they’re craving that. And so that’s what I started doing.

It’s a good question. I don’t know if I have a great answer there. I think it was more of a feeling, quite honestly.

Yeah, maybe. Maybe. I don’t know. It just felt like what would give me energy, right? I have two young kids, I’ve had a pretty big career, and so at this point I’m not focused on climbing a career ladder. It’s like, how do I, what gives me energy? That’s what I want to do, right? And I try not to think, is this what I want to do forever or not? Maybe it is, I don’t know. But it’s definitely what I want to do right now.

So I thought about, how do I get started in coaching? To your point, I’ve had a coach in my career, so I reached out to former coaches, talked to them, they introduced me to other people, I talked to them. I thought about taking some certifications, I took some classes. But really I had two big questions. And one was, would I enjoy it? I think I would, right? But I didn’t know if it would just be a novelty. Like maybe I think I would just enjoy it because it’s so different than what I’ve done, and playing into that beginner’s mind. And the second is, could I make it a business, right?

And so to answer the first question, what I did, I distinctly remember it was like a Wednesday, I went on to LinkedIn. I know, cringe, social media, I know. I went on to LinkedIn and I wrote up a note, and it was something like, Q4, winter is coming for the job market. If you’re in market and you want to land something before the end of the year, or if you’re frustrated, or if you’re thinking about next steps, you just want to talk to someone, former hiring manager, executive, someone you just want to vent to, whatever. Here’s my link to my calendar, book time, happy to chat with you, totally free.

But it was also valuable to me, because for me to understand if I would want to do this, I need to start doing it. I need to get out of my head. Not abstract, not thinking, not business plans. Like, do the work. Talk to people, right? Talk to people you don’t know. How does that feel, right? I don’t know, let’s see it. And so I typed that up, I hit send, I closed my laptop, I did something else. Next morning I woke up and my calendar was completely wrecked. I had 50 meetings booked over the next several weeks, and 80% of the people I’d never met in my life before. Don’t know how they found me. All over the world, India, Berlin, Spain, Portugal, Indianapolis. It was random. And I was like, oh, okay, we’re doing this.

There’s a market here. Or, I think it really tells you how bad the job market was, quite honestly. I mean, I was thinking about this, like would I do that? I don’t know, a meeting with a random person, I don’t think I would do that. I think I had like two no-shows. And one of them had emergency dental surgery or something like that, you know. I was like, okay, I’ll give you a pass on that. So it’s really only one actually. And I think we ended up rescheduling it.

There was a lot of similarities. You know, I think about getting a job as two distinct funnels. One funnel is getting that initial call back, and the other funnel is getting an offer. And I think about the tasks, I think about it like a product, I think the tasks on those funnels are just different, right? And a lot of people were stuck with getting the call back. Because in this market, every job you apply to probably has six, eight times the resumes it got before. And there’s less recruiters at companies than there’s ever been before. So that means every recruiter is overworked, getting more resumes, probably spends less time per role on evaluating candidates, right? It’s very tough to break through.

And so that’s where most of the conversations were. There were some other stuff, I’m like, I thought I had a good conversation but I didn’t land an offer, what happened? You know, people are usually very critical of themselves. They try to guess what went wrong. And in this market a lot is like, you didn’t do anything wrong. It’s like, the company’s looking for one person. They’re just looking for one person, right? And you were one of three that they really liked. So a lot of it also was taking a step back and reminding people not to be quite so hard on themselves.

It’s very low. It’s very low. I mean, you don’t get a lot of positive feedback. You don’t get any feedback, actually, or not at all. And when you do get feedback, some of it is BS feedback. They feel bad they don’t give you any feedback, so they give you feedback, and then you shouldn’t action on it, you know. So it’s really tough.

I mean, I remember when I was peak hiring for people during boom times. I would sit down with the recruiter ahead of time and I would say, this is what I’m looking for in this role, right? Because they don’t know the role. I mean, they’re supporting half a dozen different people in the company. And this is what I’m looking for in this role here, profiles that look like this, profiles that don’t look like that, I’d give them some different kind of lookalikes to match against, right? And so they would go through the first set of resumes that would come in, and then they would give me a curated batch. But the curated batch would be like 30 resumes, and I would look at those 30 resumes between meetings, right? So it’s like 30 seconds. What else can you do?

Pass/fail, is this person, the question I ask myself is, is this person interesting enough that I want to talk to them? Not, can they do the job. Is this interesting enough? And so I also try to remind people of that, is like, how do you show that you’re interesting? What’s unique about you? What’s unique about what you’ve done? In boom times, where it was an employer market, recruiters might try to connect the dots and try to see how every individual candidate could fit into a role. They’re not doing that now.

Who has time for that, right? So it’s like you have to connect the dots for them. You might need to come up with multiple resumes. You need to network like crazy, because one way to go from one of a thousand to one of a hundred or 50 is through a referral.

And I know JobQuest allows you to have multiple versions of your resume and tweak your own job. I mean, yeah, you really got to do that now. Because every recruiter is just looking for a reason not to talk to you. Not because they’re mean, but because they just have so many. They’re trying to get to a manageable stack.

And that’s only through that funnel, to be clear.

Yeah. It’s a lower bound.

That’s insane. Nobody can look at all of those.

Trying to narrow down. And one of the folks I talked to said that they only look at jobs that have been posted in the last 6 hours now, because they felt like after that it was saturated. And I was like, oh, that’s interesting. Again, somewhat depressing, but interesting.

Yeah. Well, there’s very low friction to apply for jobs, right?

Yeah, I mean, look. Yeah, for sure. One click. And even if that, I think there are some tools that will even apply for you, which is a whole other thing.

Yeah. So I think, again, this is my definition, a lot of people use them kind of interchangeably. I think about mentoring and advising as, I’m sharing with you things that I’ve learned in my career, or maybe I’ve worked on a project just like this and I’m telling you, this should be our pricing strategy, or this is how you have to work with the sales team, or something like that. So I’m kind of like, here are my battle scars, you know, I’ve already done the work, take it. I’m showing you the answer, so to speak.

Coaching is, I’m not showing you an answer, I’m helping you come up with your own answer. And again, let’s go back to a sports metaphor of coaching. Like if you have a running coach, they’re not running a race for you. They’re looking at your technique. They’re, think about this, think about that, right? But you’re still putting in the work. They’re there to support you in that process, and understand what your goals are, and how maybe you should train to reach those goals, right? Advising is different. I can do both, I enjoy doing both.

A few things that I found is that most people, by the time I talk with them, they’ll start off and they’ll say something like, I don’t know what to do. And I’ll be like, okay, well, tell me where your head’s at. Like, what does that even mean, right? And they’ll start talking about something and it’ll become clear. Most, not always, they actually know what they want to do. They don’t know how to do that. They don’t need a mentor. They need to somehow give themselves permission, or try to understand what is blocking them from feeling confident about taking that step. But they know what they want to do. So it’s different. I do both, I like doing both. Look, if I can save you some pain of what I’ve learned in my career, I love to do that.

Yeah. So I was doing a lot of this coaching, and I would always end a coaching call with something that goes like, I would say, I’m old, so that means I know a lot of people. So before you apply for your next job, let’s connect on LinkedIn and look to see if I know someone at that company. If so, I’m happy to introduce you. I can’t vouch for you because I’ve never worked with you, but I’m happy to promote you, raise your visibility to someone at the company, and maybe that gives you a little bit of an edge to go from applicant 900 to applicant 120, right? And super happy to do that. I’ve benefited from others’ generosity and always happy to do that.

And so I say that, and then about half the people I never heard from again. It’s okay, not insulted. And the other half of the people, every day they would LinkedIn message me, do you know someone here? Do you know someone here? Do you know someone here? And it was a drain on me. But I’m also like, they’re doing what I asked them to do. It’s just not efficient.

So what I did was, I built a product that does a couple different things, but it’s called Jobasaurus, and I’ll give you the link and maybe you can share it around. But it aggregates from 500 companies in tech every morning. It pulls in the jobs from their career pages. So they’re real jobs that are being hired, they’re not paid listings. And then it also takes my LinkedIn connections, or your LinkedIn connections, and it overlays them on top. So you can see where I have a first-degree connection with who’s hiring. And so when people were like, do you know somebody here, I was like, go just check that. Just use this tool. If the answer is yes, I will do it. You don’t have to ask for permission, just send me an email and I will take care of it. And so that helped me help more people, and just made their process more efficient.

And so I built that. And then that led to the next challenge that I had, which was now people started reaching out saying, hey, can you introduce me to this person or that person? And I’d be like, well, can you just send me a note that I can easily forward on? Like, you need to make this as easy as possible for me.

So then yeah, so then I built a tool. I wish I had that. So I built a tool where they upload their resume. And I always give people the guidance that when you write your resume, you need to write about why the work you did was important to the company and the impact of that work, not just the activities, right? Like, why did it matter that it was done, and why did it matter that you did that work?

Okay, so you write a resume, you have that content in there, so you upload that to me, and then you give me a link to the job you want to post to. And then what my program does is, it looks at that job description, it takes out what the most important qualifications are, it then looks at your resume and it looks for opportunities where there’s synergy. And then it writes a little quick email with some bullets, couple sentences on either side, short and sweet. They can copy that and put it in an email to me, and then I hit forward and write a little bit on top. And so I was like, okay, you don’t know who I know, here’s this tool. You can’t write about yourself, here’s this tool. Just make it as easy as possible. So I’ve started building some software that helps me with my process so I can help more people.

Yeah, no, they are. I mean, my goal wasn’t for thousands of people, right? But yeah, no, it feels good. Look, it feels good to help. And they’ve been using it, and they seem to value it.

Well, it’s an employer market, right? And in an employer-driven market, employers have a luxury of talent to pick from. And every hire, even in boom times, every hire is a risk. Because think about it, maybe you spend seven hours interviewing a candidate before you give them an offer. Well, guess what? They work eight hours on their first day. And so every hire is a risk. And one way you might mitigate risk is you look for people that have done the work before, not could. Have they done it before? And so that makes it difficult for people that want to change roles in their career, or change industries in their career. Or a lot of people that have less than three years of experience, or even five in some ways, can be squeezed out in this market because they’re competing with people that have more experience. That’s another way to mitigate risk, right? And that’s not something you can control, it’s just something to be aware of.

So what I do coach people on is, one thing that you can control is your enthusiasm. And I wrote a piece about this a month or so ago. But I think about it like going to see your favorite musician perform, and they’re playing the same songs that they play every night, right? But you wouldn’t know that by how they show up and perform for you, because you’re hearing it for the first time. Well, guess what? It’s the same thing when you’re answering questions in an interview, right? You’re answering the same question that everyone, tell me about a time in which you ran into challenges with launching this, or tell me about a time where you didn’t have enough resources, sure, right?

But you have to show up, you have to have energy, you have to give an answer that feels authentic. And when someone asks why you want to work here, you need to give an answer that’s unique to that company, not just an answer that could be for any place. And it’s so hard, because you’re doing so many interviews back to back. But as a hiring manager it matters so much, because it breaks the tie. I want someone that has done the work before slash can do the work, and I want someone that wants to be here, because that means they share the same values that I have.

Yeah, I mean, it’s tough. So I think intros are great, right? And figuring out a way to leverage your network, my tool or someone else’s tool, I think is really important now. Like, we have bad memories as humans, right? You remember who you worked with in your last job, but three jobs ago you don’t remember who you worked with all the time. And you sure as hell don’t remember where they are now. So chances are you have people that you’re not yet tapping in your network. So that’s really important.

I think the other ways are thinking about how you can highlight your passion or your interest or something that’s unique and different about yourself, right? So one thing I tell candidates that are in between jobs is, they have a luxury right now. It doesn’t feel like it, but they have a luxury right now to go really deep in AI, where people that have full-time jobs don’t. So I’m like, go deep in AI. Learn some things. Talk about what you’re learning. Create a Substack, or post about it, or create some simple automation for yourself, or think about how it might change your process in the future. That’s where the industry is going. Spend some time doing that. Write about it. You’ll learn things about yourself, you’ll learn things about this tool, and you’ll have something else to talk about with employers, and who knows, maybe it helps raise your visibility. So you should do that.

Also just think about other creative ways you can tell your story. I remember early in my career I read about, and this was probably like 20 years ago, but I read about someone that wanted to work for an agency in New York. So what this person did was they bought Google AdWords in search results for executives at that ad agency, because one thing that everyone does is they search for themselves on Google. And so when those executives searched for themselves, they would see an ad, you should hire me, here’s why. And he had dedicated landing pages.

Last week, I don’t know if you saw this, last week a woman created a video because she wanted to be Shopify’s first marketing intern. So she created this video about her work and how she built connection, community, and storytelling. The whole video was storytelling. It was amazing. And tagged Shopify, hey Shopify, do you have room for one more? Less than 24 hours, she had a job. Incredible, right? Thinking about ways that you can get noticed that also align with your passion, right? Because for every story where someone does that, someone might have tried three things, they didn’t get noticed, but they learned something along the way, right?

Totally. Yeah, no, you have to, again, I think about it like building products, right? Like, how do you hedge your bet on a strategy? You try multiple tactics. Same thing here, right? It’s not just one. You should tweak your resume, but if that’s all you’re doing, no. You should apply for jobs, but if you’re spending eight hours a day applying for jobs, I don’t know if that’s the best use of your time. I’m pretty sure it’s not, right? So it’s like, what are all the tactics to go past that first hurdle of getting noticed?

I mean, it goes a little bit back to kind of owning your story. But I think that there’s so many different ways to craft that. Look, I’m an AI optimist, okay? And I think that you can write your story and you can ask AI for feedback to help strengthen it, or look where you have gaps. You can record yourself. You can have AI dictate it back to you. You can hear how it sounds. Spending time there has such a lasting impression, because while you’re doing a lot of these interviews back-to-back, the hiring manager is doing the same thing, right? And so to plant a seed and to have something unique kind of shine through, both on getting discovered as well as in conversation, I think is so important. So really focus on your story, and what it is, where you’ve been, how that is going to get you where you want to go.

Right. So it’s a little vision questy, but yeah.

100%. And I would say, as PMs, one of the most important skills for PMs to have, which is usually underdeveloped, is storytelling. Designers constantly are doing storytelling, maybe engineering a little less so, but it is such an effective way to communicate and rally and inspire people, that it’s a great way to also invest in yourself in that journey.

Of course. Thanks for having me on.