Surviving the Job Search While Staying True to Your Values (LCPS01E05)

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Episode Summary

"Interviewing knocks down pretty much everyone's confidence."

With all the lost time and huge frustration that comes with interviewing, it's easy to compromise your values in favor of feeling the relief that comes from getting to the end of the interviewing process and finally landing a job. In the long run, though, you don't want to compromise your values and non-negotiables.

In this episode, we discuss a massive problem everyone in the tech industry faces:

The challenge of finding a company whose values align with yours and navigating the infamous, often confusing and frustrating, interview process the tech industry is known for.

My guest, Alyssa, and I talk about her own experiences interviewing and finding a job that fits her needs and values. Alyssa shares her challenges in finding a company with aligned values, the painful experiences of interviewing, factors to consider in her job search, how to assess fit and requirements, and how to ultimately find what you're looking for.

Chapters

  • 00:00 First Impressions and Reality

  • 05:30 Misalignment of Values

  • 09:20 Painful Interview Experiences

  • 11:39 Challenges in Interviewing for Leadership Roles

  • 16:18 Understanding Company DNA

  • 20:33 Assessing Fit and Requirements

  • 25:42 Prioritizing Requirements and Non-Negotiables

  • 28:34 First Impressions vs. Reality

  • 32:44 Ranking Requirements and Non-Negotiables

  • 33:40 Finding a Company that Fits Your Skills

  • 36:01 Learning and Specific Experiences

  • 37:26 Bridging the Gap Between Values and Work

  • 39:40 Don't Let Bad Experiences Define Your Value

***

We want to hear from you! Email us with feedback, questions, or topic ideas; I can't promise we'll always respond, but I can promise we read every email! At pod@lenareinhard.com.


Full Episode Transcript

Alyssa: And it's like looking for anything meaningful in your life, like an apartment, for example. It's always very, very different from the first impression for me compared to later. My first impression is always a little bit far from reality.

Lena: There's an old fairy tale that talks about having to kiss many frogs in order to find a prince and live happily ever after. The tech job search equivalent of this is probably, you have to speak to many frogs in order to find a job that will help you pay for your bills over the next one to many years.

This is Leadership Confidential with Lena Reinhard. We get to talk on more than two hard things in technology, finding community and becoming the engineering leader you can be. Today, how do you find a company whose value is aligned with yours and how do you deal with the many frogs you have to talk to along the way? 

Interviewing in tech has a reputation for being pretty awful and has had this one for a really long time.

A while ago, my team and I got an email from a candidate who we'd rejected for a position because their skills didn't fit the job. In their email, they thanked us profusely for writing such a kind rejection email. I think of this a lot. I was really glad at the time about the positive feedback, but at the same time, it really stung. 

Man. Where are we at as an industry? The friendly rejection email is what stands out to you. Interviewing knocks down pretty much everyone's confidence. And we also know that many companies really struggle with how to interview for leadership skills and roles. Even worse, many companies still just interview for how to interview well and not for how someone will perform on their actual job. There's a poem called Good Bones by the poet Maggie Smith. I've been thinking a lot about it since my conversation with my guest that I'm sharing with you today.

The last lines of this poem go, any decent realtor walking you through a real shithole trips on about good bones. This place could be beautiful, right? You could make this place beautiful. The poem at its essence is about how to convey to children that the world isn't an all beautiful place, but that they can make it one or at least try. And I've been thinking a lot of this poem because in looking for new leadership roles, there's often a somewhat similar question buried. What state is a place or company in now? And can you make it beautiful or, if not that, at least maybe clear out some of the debris and spider webs. Maybe remodel some parts or add another window or two to get some light in. And ideally do all that without being stung by bees that have moved into the basement? This is why I'm really excited to share with you my conversation with my guest today. Her name is Alyssa. That's not her real name, but what we'll call her in this episode. She's been in the tech industry for over eight years and shifted her career from linguistics and language teaching to software development.

She's now been leading remote teams for four years after being an IC in the same company that she's in now. She also has experience with managing various senior engineers, growing the team through hiring and mentoring junior developers, and also parting ways with employees from time to time. She works in a mid-sized company that's been growing fast until 2023 and has had some difficult times last year, which led to some layoffs and big budget cuts. The company is serving enterprise customers and had to rapidly adopt AI technologies to keep up with the competition.

Alyssa and I talk about what it means to have values and experience about what good leadership is and what happens when you try to find companies where you can live those values in practice. Alyssa shares her challenges in finding a company with aligned values, the painful experiences of interviewing, factors to consider in her job search, how to assess fit and requirements, and how to ultimately find what you're looking for. Here's Real Talk on more than two hard things in technology with Alyssa.

Lena: I've heard from you that you want to talk about having values of what good engineering leadership is and then figuring out how to find a company where that fits and kind of validating if a company practices those values as well.

So what makes this topic so important for you? 

Alyssa: I'm trying to figure myself out as a specialist, as someone who brings value working for a specific company.

I see myself as a manager and I see myself as a leader and I definitely enjoy working in software development. And from my experience, I really want to be part of a team. It's important to create something really great and not the type of person who could really enjoy working completely alone.

It had some successes and some challenges on my journey. And I would say I'm pretty happy with my place of work, but I feel that I can do more than I'm doing now. So I'm trying to figure out how can I apply in the current job market, and it turns out to be not so easy.

Because having had these good experiences in my current company where I could live some of my important values in this position, of course, I don't want to lose that. I don't want to give up some of my important values in order to just find another job, even like higher paid or in a company that is more well known than my current employer.

So when I started looking into the job market to see what's out there, I was kind of hit with reality. And that reality has shown me that my understanding of what good leadership in engineering is, is not corresponding to companies’ understanding. Let me give you also a specific example of what's happened to me recently. 

So I was interviewed for the job of tech lead. And the interviewing process started. When it started, I was told about how much communication this role entails and how important it is to manage the relationships with stakeholders. And it almost sounded like people tried to scare me with these things to make sure that I was really okay with that.

And then it came to the start of the technical interview. And the technical interview, it was so technical, but I felt like, okay, actually, I can't do anything. I can't be a manager. I can't manage people. It was also so detailed in areas that I've never been very actively working on. And it was just strange for me then that they insisted to have such a detailed technical interview after telling me so much about how important communication is in this role. And even giving me some hints about some strategic task which would come after the technical interview. Oh, and by the way, this company, they shared with me, but they've already been trying to fill this position for nine months.

And at that point, I kind of understood why they couldn't find anybody. So this is my background. At this point, I also, I wasn't sure… Is it really that I have such a bad technical background that doesn't fit for any engineering manager role in this field? Or is it really that the company has those strange expectations and they try to kind of save themselves from bad candidates by putting the high requirements on everything, on every aspect? This was kind of a painful way to find out that my values don't correspond to the values of the company. Because on their website, their values had looked pretty good to me. 

Lena: What did the website say?

Alyssa: That they're ready to meet people where they are and striving for inclusive diverse environments. And they are in the phase of digital transformation where they're looking for new ideas, fresh wind, all this kind of stuff. 

Lena: Wow, that sounds like I mean, what an interviewing experience. Just out of curiosity, how big roughly is that company? Like how, know, what stage are they in? 

Alyssa: Pretty big company. International. Several thousand employees at least. 

Lena: And how did things proceed from after that technical interview? 

Alyssa: I got an email from the person from HR with feedback from the other tech leads who conducted the technical interview about things that I couldn't respond to and their comments about what they think is lacking in my knowledge. And then yeah, there's a comment, “We decided not to proceed to have a nice day.”

Lena: Right. And you mentioned that that was a painful way to have to validate that value alignment you're looking for. What was the thing that made it so painful for you? 

Alyssa: Actually, this whole interview was, yeah, was a bit painful for me because I'm used to being on the other side of things interviewing other people.

And here I was this person who felt literally like in the university at the exam where they are trying to ask you questions and trying to give you hints, but also not too many hints. And start asking me really very specific things, which, as I said, were never important in my work so far. Even when I was a developer, I didn't need these details. And if I needed to, I could look it up. And another thing which was specifically painful for me was a live code analysis exercise. Which I never do in my interviews, never did. And because yes, this is basically an exam situation. I don't know, it kills my mind. It kills all the smartness that I have and just leaves the instincts. 

Lena: Especially the fight-or-flight instincts. 

Alyssa: Mostly flight. Yeah. And so even though I mean, I more or less understood what this task was about. I just needed maybe a little bit more time and not being asked every two seconds, “What do you think? What do you think?” And then they wrote in their analysis that I failed this exercise. And he has this as a kind of validation of knowledge, which I don't like. And yeah, because this is pain of just treating evaluation of knowledge as so important. 

And I definitely don't want to be in a company where these things are really important. And of course, afterwards, I felt pretty bad because I started to have real doubts about myself. I started to have doubts about my level of expertise. And I needed a couple of conversations with my friends, my colleagues, in order to put my level of self-confidence up again to its more movable. 

Lena: Which is very understandable. You know, first of all, I work with so many people who are actively looking for jobs. And one of the first things that I always bring up with them is basically like, this is likely going to knock down your confidence to at least some degree. What do you want to put in place to help with that? Because honestly, no matter what experience level people have, interviewing can be really brutal. I feel like especially for leadership roles. It can be really tough in different ways, at least than for engineering roles. 

And yeah, I have great sympathies for you. Like it's just, it's brutal out there and especially in the current job market. And I kind of honestly, thank you for, you know, for sharing that. That's yeah, it sounds hard. And I kind of, I feel like there's so many different topics going on to, in, into this. I kind of want to name a couple of things that came up for me. And then, you know, you let me know which one or ones you want to dive into a little bit more.

One aspect I find is that companies are just really bad at interviewing, especially interviewing for leadership roles.

That's like true for technical leadership, for people leadership. A big part of that is just the complexity of those roles, but also that companies just really struggle with this. I think that's one aspect. The other aspect, of course, is what you mentioned in terms of what values does a company proclaim they have versus what comes across in the interviews. But then the other component to that is what is the actual job like? I think we all know that interviews are supposed to map as closely as possible to the actual job that people are doing. But a lot of companies are struggling to actually make that happen. 

Which also means for you as a candidate, it becomes even harder to figure out, are these interactions just not great because they don't know how to interview me? Or are the interactions not great because just people suck there? Or I mean, you also described a mismatch between basically an overemphasis on communication and working with people early on in the process. And then suddenly this really like heavy kind of technical interview where it also, as an aside, at least to me, didn't seem like they were super good about the communication practices in the interview.

And then there is a whole other aspect to this in terms of… I like to say that interviewing is a specific skill set and a lot of companies essentially just test for, are people good at performing in interviews and in interview settings versus are they actually good at the job? And as a candidate, you kind of have to prove both, which makes it extra hard. And then there's of course the question essentially what kind of signals is a company sending to you and how do you assess how those translate into what you're looking for and into how you're going to work with them or whether you're just realizing, hopefully early on, and hopefully with your emotional, emotionally intense and just negative experiences. Yeah, but those are a couple of things that kind of I feel like play into this. And I'm quite looking at all of those in my head and like, that's a lot. of course, even just that alone.

I feel it may also make extra tough for you because there's just so much to untangle. What do you think? 

Alyssa: Absolutely. And I really like this matter point that you mentioned about, how do I recognize what companies are actually looking for versus what they proclaim to be looking for. Or what they say that they offer to their employees as opposed to what it actually is. This is a hard question to solve. And I guess this is, it's a hard question to solve because every company has its own DNA, like it's unique. And I also think there might be some cultural differences that play a role here. This company that I was interviewing for, the office is based in the south of Europe. Yeah, my assumption is that there are some subtle differences between, for example, Northern or Western European culture, corporate culture, and the culture in this company, which could have played a role as well.

I mean, is there like any kind of sum of variables that kind of predefined the result? For example, if we put together the country that the company is in besides maybe the age of the engineering department, or how long have they been doing this digital transformation or similar things, and maybe even the main architecture of the product that they have. They have a lot of legacy or do they only have like new stuff, green field work?

Maybe from these variables, I can kind of predict what happens next, like what happens in the interviewing process and what happens when I get hired, if I get hired. Or is it just like a completely random thing? 

Lena: I am honestly a bit torn because I feel like I kind of want to build this matrix with you. And I'm also already scared of what it's going to look like. I would love to kind of take one step back. I'll just share with you and then you let me know if you want to go there with me, which is, you know, I heard from you earlier, this whole topic of like, this is painful. It's knocking down my confidence. It's making me question a lot of things to have these kinds of experiences in interviews. 

And, you know, I love the kind of, like, assessment framework that you just proposed. What is your goal in all of this? You know, in the sense of this whole idea of like you're looking, or you're looking at companies. I'm kind of just going to throw something out there. But, like, it sounds like there is an aspect of kind of wanting to protect yourself, or I might be wrong. 

Alyssa: Protect myself from being sure about that I find a job, or protect myself from poor experiences with companies? 

Lena: The latter, yeah. 

Alyssa: In a way, yes. Because as I said, it is a costly process even to write a CV, adjust it for a specific company, write a summary letter. All the things that already cost time and be good, of course. So you need to have kind of a funnel in order to get one result in the end. But yeah, it would be good to make the tunnel a bit smaller to not think burnout when looking for a job. Although I hear lately a lot about people burning out looking for a job because it's a really hard process. I acknowledge that. 

Lena: So there is an element of it, wanting to at least… I'm going to call it sort of, be strategic or intentional about sort of the, limiting the time and energy that you're spending just on like even getting in, getting a foot in the door with a company initially. That makes a lot of sense. Yeah. What else is important to you there? 

Alyssa: In the job search? Yeah. It's important for me to see how I can grow there. And it can also be kind of horizontal growth. Even me being in a leadership position now, to take on a position with more people than I have now would be growth already. To be responsible for different a set of technologies or to have a different, radius process that would already be growth as well. There are certain communication values that for me, I think they're really crucial, because I'm used to certain values. 

And it's kind of, I experienced it once and I don't think it should be different even though I hear a lot about people working in companies where it's different. For example, where managers are really talking like throwing up to down to their employees, kind of treating them almost like children, like punishing and giving treats. And I mean, this is not the way I want to work with my team or the way that I want managers to work with me. Because I really want to work at this adult level, like on the same level, like have this kind of flat hierarchy.

And first, I recognize that there will be people working with me who have way more experience and also have more responsibilities. And that's why they can make certain decisions that I'm not entitled to make. That's okay. But this kind of cultural setup is really important to me. 

Lena: So it's like basically not a super hierarchical organization where hierarchies may exist in the context of like reporting structure or different contexts or scope of roles. But at the same time, there is a, again, not a hierarchy in the sense of like, yeah, you mentioned some people talking to their reports as if they were children. And to me, it also sounds like there might be an element from what I've heard from you so far in terms of, and it's one thing to look for those things that you mentioned, like having a growth path or learning curve ahead, as well as like that kind of cultural culture in terms of like not a super hierarchical organization. And then of course, not wasting energy in the hiring process itself, but it also sounds like there might be an element of, or at least raised for me, the question of like how much room do you have to work a certain way?

Like for example, if you know, for example, with a large corporation, what's in my experience, what's quite typical is that basically the way the company works is one thing, but a lot in the end hinges on ultimately who are you reporting to, who are the most important stakeholders for your team, and who is on your team. Where essentially, you know, the domain and team that you're in is going to be a much bigger factor than if you're in a startup and it's, you know, a hundred people where kind of everyone who is there is going to shape a lot of your day-to-day experience. I'm curious how you've been thinking about this in your search so far. 

Alyssa: I wasn't really thinking about it too much. And I don't have experience working in huge companies. I only came in touch with some larger corporations being customers of my current company. And what I see there in terms of their communication with us. Honestly, it was a bit alarming for me, alarming in a way that probably that's not how I want to work.

But on the other side, I also think I wouldn't mind to make some experience working in a big company to find out what is it like for me? How does it actually work for me? It's completely different than what I'm used to, but I can imagine that there can be companies which have culture that would still fit with me even though the whole interaction mode is different. 

Lena: Yeah. And so for finding that kind of rolling company that you're looking for, what have you been trying so far to assess that fit for you? 

Alyssa: I mainly tried first of all, what I'm always trying to do is to understand what they actually produce. Like what it is, what is their product and to see also whether I can relate to it in some way. Because I realized that this is also something important for me to feel that I produce something valuable, something impactful, and something that I can relate to at least. And that I usually research also the website of the company in terms of values and mission. Like what do they say is their mission, their values, what do they see as that? What usually attracts my attention to companies is also when they organize some events like meetups on the topics that are interesting to me.

And they also show me that, hey, that's the topic there. So that might get me interested in working there. And I think that's it. And of course, also from conferences, I sometimes get ideas about how the company works inside when some speakers present processes or present some specific examples of projects. That also helps me understand what's going on there and may also attract my attention. 

Lena: And so I'll just try and recap. In addition to what you mentioned earlier in terms of growth, learning, perspective, that hierarchy that's not enforced in communication, there's the product that you can relate to some sort of a colleagues being connected to the community through meetups, for example. And then the values and mission that they're sharing. Also, when you've looked at all of those things that you've just described, kind of your criteria, that next up would be the step when you actually send an application to them or do you already apply beforehand? 

Alyssa: No, I usually take time before I decide to apply somewhere because I'm not in a very active job search. So yeah, I'm collecting some information before I send the application. But I mean, sometimes, for example, as with this previous company where I had the interview, I was just contacted by a recruiter and it was very easy to apply.

That's why I kind of did the research only afterwards, after I sent the CV. And it was mostly just the website evaluation. 

Lena: And what kind of titles or roles are you looking at, or curious about, or looking for? 

Alyssa: I’m usually mainly looking for engineering manager roles or tech lead roles. Anywhere where some leadership position is required on the level of software development.

I’ve also been interested in positions like ambassador for developer knowledge or similar. I've seen it in some huge companies and that sounds very exciting as well. But I didn't dare to apply to such roles yet. Or at least at the time when I seen them, I didn't feel that I was ready. But I've sort of collected enough experiences to do something like that. 

Lena: So basically, as also a tech lead role, where do you want to go from here?

Alyssa: I already had some insights about specifically my requirements to the job because I think I was not aware about the amount of them. Like about the amount of things that are really important to me. Yeah, I would like to go into the direction of this whole process for applying. Like the way I'm doing it now feels pretty chaotic. Does it need to be or does would it help to be more systematic? 

Lena: What would being more systematic look like for you?
Alyssa: A list with the companies and like metrics and list out all my requirements and make the next ticks or notes, and then on the sum of points, decide whether I should apply or not. Yeah, it feels like it's also, it might be too much to just decide whether I send out a CV. But maybe this can happen much faster still. I mean, if it's not fitting, maybe recruiters can also find it out in the beginning. So maybe it's also fine to not make huge Excel tables.
Lena: I mean, I personally love a good Excel table, so here's that. Stating my biases openly.

I have two impulses here and I just want to share them with you.

The one part is that I very much hear you on the effort that applying is. And at the same time, there is also part of me where I'm kind of want to say, hey, don't self-select out of jobs that could be interesting for you, especially because job postings are, you know, we all know the statistics that like, especially women tend to only apply if they're meeting 100% of the criteria and companies, especially for leadership roles, often struggle to actually convey what they're looking for and all that. And so I, and you know, I also, want to honor what you mentioned earlier about not wanting to waste energy and time. 

So there's a part of me where I'm like, maybe the matrix is one thing, but maybe another thing that could be worth looking at is also, can you make the process of applying to jobs easier for yourself? To make it less of a bar, and then focus a bit more on essentially de-risking this whole thing. You know, for example, in the first conversation you have with a recruiter, like what are questions you would really want to ask them? What things are really important to you? 

Is something like that too… And I'm just saying that because one, I mean, the hiring market is just really weird right now. You also mentioned it, too, like you mentioned you're not in a rush to look for something. And at the same time, you've also already mentioned the whole point of what companies can present on the outside isn't always necessarily how things work on the inside. And the examples you gave so far are more in a negative way, but that can also happen opposite way. 

Yeah, that’s it, I kind of, I wanted to mention that. Let me know what you think or what that brings up for you. 

Alyssa: Yeah, absolutely. I see your point. Yeah, indeed. All of the companies that I've worked for, they look to me completely differently when I was working there, compared to how they looked when I was just looking at them from the outside. And it's not always for the worse. Sometimes it's better. Sometimes companies just try to be extra protective on the level of what CVs from candidates they accept. And just because they have this soft core, there is a theory of, I don't know, some pitch-type organizations. And so yeah, what is hard on the outside can be very soft and so hidden, and vice-versa.

And it's like looking for anything meaningful in your life, like an apartment, for example. 

It's always very, very different from the first impression for me compared to later. My first impression is always a little bit far from reality. 

Lena: And there's, I love the apartment metaphor because there is, I found, at least in leadership roles for me, there are, it evokes an element of like, well, can I make this place beautiful? Like, are there things that I can do to make this a nice place, even if it's not pretty from the outside?

Which is an interesting kind of criterion to add to the list. You know, like what could your impact be in a place? And in all this, all the criteria you have among those, it might be worth thinking about which ones are really non-negotiable, versus which ones are things that like, yes, are important to you, but okay, if it's not there yet, they can be given. 

I kind of want to share something that was really important to me in my last job search where one of the big reasons why I ended up signing with a company I did, and I'd been interviewing with initially over 50 companies, I was like, I'd made the job search my full-time job. Don't recommend that. 

One of the biggest criteria for me was that that company had a lot of challenges ahead. But everyone I spoke with, regardless of their level and regardless of their role, was pretty much in agreement on what those challenges were. And then they had different opinions on how to tackle them, or at least different ideas. But I often kept coming back to that even as I was working there, in that it made work just so different. If you're working with people that are generally aligned on one, where they want to go and two, what the bigger impediments are to get there. You can then argue and discuss about how exactly that's going to happen. 

But that's very different from an organization where just everyone is in disagreement about, well, are there even any problems in the first place? Let alone how drastic are they? And I kind of, I just want to share that because for me, that became a really interesting point, because especially in the leadership positions I had, like the reality is there's not going to be a perfect organization. And, but there are still things that are really crucial for some of us. 

For you, mentioned for example, like the manager you report to, that can be really important factor. And for me, was the whole thing of having a shared view, at least on what challenges we're having as a company. 

Alyssa: Yeah, absolutely. 

Lena: So, recap so far, you mentioned you have more clarity on your requirements list for a job. What else has come up for you? 

Alyssa: I think the barrier to apply should not be so high, not as high as I have it right now. And the idea that, it's also come up for me, but I need to accept that there will be bad interviews. There will be some processes, like even that whole hiring process experience that I will not like. And that's okay. And that's also because again, companies are very different from one another.

But yeah, I would say that the main insight for me is that I really need, I really have a lot of requirements and I need to rank them somehow to see which are non-negotiable and which are just nice to have. To be honest with myself there, what is the most important? And again, given that this idea that every company is unique and the possibilities that I can find something where that fits exactly my set of skills and where exactly my set of skills is required on a certain position, on a technical leadership position. I actually have the chance to find it. 

Lena: I love that. Yeah. And I also, I kind of want to, kind of, soften some things that I mentioned, like one part being like, I really don't want to basically just tell you to suck it up because hiring is terrible. 

So there is really the element of essentially, if we say that like, yeah, hiring process probably aren't going to be great. How can you protect yourself, prepare yourself at the same time? I also think, you know, ultimately your instincts are good. You have a lot of experience in the industry. And if a company has a terrible hiring process, that is also really good signals. I mean, you, you mentioned it earlier and I want to honor that part. Like I really don't want, want this to become a thing where it's like, you just have to push through hiring process and the job is going to be great. 

Like it's usually a bit of an indicator at least. 

And I think the other part is also, to the fact I kind of accidentally talked you out of the spreadsheet, which is really like, I never want to talk anyone out of a spreadsheet. It might be worth looking at. Like I honestly feel like a full kind of prediction of how companies are going to be is like, really tough.

But at the same time, everything you've been describing to me so far, sounds like there are a couple areas that are probably just not really aligned with what you're looking for. For example, you mentioned mega corporations, at least maybe a bit lower on the priority list because of all the communication challenges and the insight you have from working with them. Same on the other end of the spectrum, of like a really early-stage startup that has maybe 20 to 30 engineers. starting to bring engineering managers who they may want to be really hands-on because it's likely more generalist setup. And then at some point, there may be room to grow. 

Maybe that's a scenario that you're interested in. I mean, you do have the background for it.

So basically looking at some company archetypes might still be worth it. 

Alyssa: Yeah absolutely. It sounds like a nice guideline to make some kind of selection or rating. 

Lena: Yeah, well, there's at least some likelihood of how a certain thing… Like, do you have a sense of what company size or so, or if that's even a factor for you? 

Alyssa: Hmm, I mean, so far, I think that little-sized companies kind of optimal for me because I'm, I like a clear teams organization and I used to work in an engineering department where everyone could program everything. And it was a great hackathon but yes, it's helpful.

At some point, it's also cool to have structures. It's also one of my professional interests, like how teams are organized. And yeah, if you cannot organize a team, yeah, that's problematic for me. 

Lena: That's a great call-on actually, it might be worth thinking about what you're looking to get out of your next job. So we've been talking a lot about, you know, what are you looking for? What are the criteria? But there is also, you know, is there a specific, you know… For example, you mentioned learning, like is there specific knowledge you want to gain a specific angle or experience? Like, you know, for example, if you applied at a midsize company, but they're globally distributed, and they work with a certain organizational structure or so, you know, basically figuring out are there specific things you're looking to learn in this next step of your career, even if the title that you have doesn't necessarily change. 

That might also give you a couple more ideas in terms of what companies might be interesting for you. And I also, other bit I wanted to mention is, I kind of feel like one big challenge in what you described is essentially, what is the interview experience versus what is the actual day-to-day work of someone in this role? You know, how are they spending in the company you're interviewing with? Like, how are they spending their time? What are, how is the success measured of this role?

I feel like the question of basically, what would I be doing every day? That seems like a really important one. And if it's not this one, but basically thinking about what are the things that really matter to you? Because it's one thing, if you feel like you've run into this a couple of times.

It's one thing for companies to put stuff on their website, like, we value inclusivity and collaboration is really important or whatever it is. But then what does that actually mean for your Wednesday afternoon at 2pm?

And I feel like that kind of bridge feels like one where if you get more information or clarity on that early on, it might also be helpful in just helping you assess. I usually say Monday morning at 9am, but I wanted to mix it up a little bit because just this kind of gap or hopefully not gap, but alignment between like, yeah, what we proclaim as companies in values versus like, yeah, the job when you're actually doing it. That seems like an important thing. It's hard for everyone to figure out in interviews. I mean, it's the same thing that companies are struggling with, but they're usually at the longer end of the lever in the hiring process. And yeah, it could be valuable for you as well.

Alyssa: Yeah, sure it is. 

Lena: And I realized we’re at time, and I’ve poorly managed our time today, but I really appreciate your openness. Do you have any last bit that you really want to ask or say? 

Alyssa: I want to thank you for the session because while I was speaking, I realized some things about my approach to job search in general.

Like, what am I looking for? There are a lot of useful questions that I didn't ask myself that you asked me and that will be on my list to think about because I think it's really valuable. And in general, yeah, my thoughts about this are way more organized than they were before. Thank you for listening to my emotional story. 

Lena: My pleasure. Yeah, thank you so much. And yeah, this is giving me a lot to think about as well because I feel like this, complexity of finding a job, and especially in kind of leadership role where you're exposed to the elements of the company environment, so to speak. And at the same time, as we're trying to carve out your place where you can make changes and do good work with people. I feel like that challenge is one that a lot of people face, especially right now. 

And again, I've learned a couple of things in terms of, one, it's been really helpful to walk through this with you and also in terms of how to get through this for people. Because of course, it's different for everyone. 

And yeah, again, good luck to you with the clarity and at least idea for an Excel file. And I hope that you find what you're looking for and that you're doing okay on the way to get there, or as okay as possible.

Lena: I'm really grateful that Alyssa walked me through her job search experience because I know a lot of people are in a similar position.

If that's you, I want to give you a quick recap and some additions on things that you can do to deal with them. 

First of all, know what you want. And I mean it. Really sort out your criteria for your new job. Stack rank them from one to however many you have. I know it's a really tough exercise, but it can save you a lot of umming and err-ing later on when you're trying to make a decision.

Then based on your criteria, write down questions that you really want to ask or things you really want to understand before making the decision. Also, don't over-engineer your job search. No matter if you're looking on the side or you're currently unemployed, timebox how much time you spend on it and how much energy and track your investments in progress. Job search can be really tiring, especially currently, and it will be helpful to get a bit of a sense of progress at least. Also read the signals that you're getting from a company, but also don't over-interpret them.

There's always going to be a difference in what level you're going for in what company. If you're interviewing to be a VP or even an engineering manager in a startup, you'll likely have much more of a mandate and potential for impact to make things better. Whereas your ability to change the environment is going to be much drastically smaller, the bigger an organization gets. Also, don't make a decision until you have to make a decision. A mentee of mine a while back was looking for a new job and told me, “ Hey Lena, I think I'll withdraw from this hiring process. I don't feel like this job is for me.”

This person had just gotten an invitation to their first interview. Don't do things like that. There are too many variables in hiring for leadership roles or interviewing for leadership roles, especially no matter if it's for technical or people leadership. And as we all know, job postings are often not really reflective of what the job is going to be. And interviewers are often untrained and companies don't know what they want and so forth. That doesn't mean you should take any job, but at least get a clearer sense of what it is before you drop out of the hiring process.

By the way, just as an added bonus, this mentee I mentioned earlier, they actually ended up interviewing with this company and it's the job they took. And it's a really good job for them. 

In addition, always keep your CV up to date. If you, like me, are too lazy to do that, because I know a lot of people really struggle with this, and I do too, at least keep a document where you track your projects that you work on and the impact that you've had. Include some metrics wherever you can and set a reminder for yourself to update it once a month. It's a bit of a tedious exercise, but honestly, it's so much easier to do now than have to figure out what your impact was three years ago in a previous role you had. 

Also, always be interviewing at least once a year. It's a really good way to validate how you're doing and stay in touch with market changes and also form new connections on the side. 

And lastly, don't let bad interview experiences get you down. Remember what you're capable of. It's normal to not feel great after a bad interview experience or rejection, and you can always also give feedback to the company who interviewed you.

Remember that your value as a person isn't determined by an auto-generated applicant tracking system rejection email. 

Next time, we'll get real on how to fix your relationship with your product counterpart. And in another episode, how to assess what a team really needs. 

We've just started making this podcast and would love your feedback. If you have anything to say or any wishes for future episodes, email me at pod@lennareinhard.com

Leadership Confidential was created, produced and presented by me, Lena Reinhard. Our guest's voice was digitally modified. Theme, original composition, and mixing by Esteban Del Pino. Production assistance, guest support, and social media by Sly Stark.

Thank you for listening. I'll hear you next time.

Lena Reinhard

Lena Reinhard (she/her, they/them) is a VP Engineering, leadership coach, mentor, and organizational developer partnering with leaders in the technology space. Having served as VP Engineering with CircleCI and Travis CI, and as a SaaS startup co-founder & CEO, Lena has dedicated her career to helping leaders and their organizations succeed in times of high change and challenging markets.

She has worked with a broad variety of companies at all stages, from startups pre-founding and bootstrapped, scale-ups, to late-stage/pre-IPO and VC-funded ventures, to corporations and NGOs.

https://www.linkedin.com/in/lenareinhard/
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