Stuck at the Final Round of UX Interviews? Andrew Re-Did His UX Portfolio and Got 3 Offers (Including Blue Origin)

Sarah Doody (00:00)

Andrew, tell us a little bit about yourself, what you do in UX, how you got into UX, and kind of what you’re doing now.

Andrew Milmoe (00:09)

Sure.

primarily work with global organizations that have engineers in the field, and they want to have software that allows those engineers in the field to have access to the enterprise data and gather data and put it back into the system. So people that have dirty, dangerous, and difficult jobs. ⁓ so I’m an interaction designer. I also do research.

And.

That’s

Sarah Doody (00:38)

Andrew, you studied industrial design at Carnegie Mellon, and I’m curious, like, how did you discover user experience and are there any other interesting parallels between the two that kind of jump out to you?

Andrew Milmoe (00:41)

Mm-hmm.

Yeah, for sure. ⁓ Yeah, when I graduated, was a, I think it was the worst year to graduate in 20 years. ⁓ There were no, you know, all the, all the design firms had just been laying people off. And I actually went into pre-press and then ⁓ sort of digital agency types of work. And so I’m kind of a dinosaur, but when the, when the web came along, ⁓ I was able to convince people, said, you hey, as an industrial designer,

you’re thinking about how people are using a physical tool. You’re creating an interface between the engineering of the tool and the person who’s using it. And so it’s like, well, that’s hardware engineering. So if we just translate that over to software engineering, it’s kind of the same thing. There’s still engineering going on. You still need to create interfaces for people to interact with the system and, ⁓ you know. ⁓

put inputs into the system and get feedback from the system. So was very sort of a parallel track for me. I was able to persuade them of that at least and it worked out.

Sarah Doody (01:53)

Yeah, yeah, there’s so many parallels and not just with industrial design, but, you know, architecture, even health related fields. we may have some career switchers here, I’m not sure. But Andrew, I’m curious if you can think back in time to when you ⁓ were thinking about joining Career Strategy Lab, like take us back to that moment in your career, what was going on and how did Career Strategy Lab get on your radar?

Andrew Milmoe (02:22)

Sure. ⁓ I had the good fortune of working at GE, the GE Software Group, for about six years. ⁓ One of my colleagues left for a healthcare startup and hired me, sort of no questions asked. ⁓ And I was there for another two or three years. So I had about eight or nine years since I’d touched my portfolio. The healthcare startup shot up and then crashed. ⁓ So I was faced with…

a portfolio that was geared towards roles that I had long grown out of. And I didn’t really know how to apply for a more senior principal level role. And so I was having a lot of difficulty with that. I ended up applying to a number of positions over the course of a year, actually. And I kept getting to the last round and not getting the job. And was applying. I got into fangs. had, you know, yeah, Facebook.

Amazon, Google, all that, and other companies. just, it kept ⁓ hitting a wall and I couldn’t really figure out what the deal was. ⁓ I can’t remember how I came across CSL, but it seemed to really fit, even though it seemed to be more geared for people who are switching careers or just getting started. ⁓ I still felt like it’d be good to have a sort of a reboot and kind of, you know, throw everything out, start from scratch, work my way through the program and

As a result, I got three interviews at once. So it worked. yeah, had the bones were there. I just wasn’t presenting it in a way that was ⁓ working for recruiters and hiring managers.

Sarah Doody (03:54)

Hahaha!

And remind me, but did you end up in a scenario where you were choosing between multiple job offers?

Andrew Milmoe (04:12)

Yeah, I three offers. It’s a commercial construction company. I guess I can name them. Of course, not CBB, or C, I can’t remember what it’s called. And Cisco, and then Blue Origin Aerospace Company. And I took the lowest of the three offers, but I was like, I can’t not do aerospace. It’s so exciting. And it also, I wanted to get back to…

Sarah Doody (04:35)

Yeah.

Andrew Milmoe (04:41)

the connection between hardware and software. designing software for people working with hardware and not just before I’d worked in finance and areas that were a little more in marketing, which is a little more esoteric. So this is much more connected to the real world.

Sarah Doody (04:58)

Andrew, I’m curious, you you had been applying for a year and after you joined Career Strategy Lab, if you can remember that far back, I think it was two years ago maybe, or maybe more. What, did you…

have any realizations once you got into Career Strategy Lab around like, here is what maybe my, what I wasn’t doing in the one year that I was approaching my job search on my own.

Andrew Milmoe (05:25)

Sure. Yeah, I had spent a lot of time at GE thinking about, know, a lot of times I was sort of acting as the PM in certain roles or spent a lot of time discussing like what the product was, what the product did. And so when I went into an interview, I spent way too much time talking about the intricacies of the industry and why the product was so cool and interesting, because I was very passionate about it. But I did not spend enough time

describing what my contribution was and how that would apply to the role I was applying for. So ⁓ I had kind of gotten in this pattern of explaining the products without really saying, like, OK, this was what I did to move this forward, and this was the outcome, and this is what I can do for your organization or how it aligns with the role. ⁓ So I think that was the major key kind of aha moment that happened. ⁓

And yeah, a lot of my stuff was just way too long. Like my portfolio was like 120 pages or something. It was crazy. Because again, I was really excited about it, but you can’t jam that into an interview and make any sense out of it.

Sarah Doody (06:35)

Yeah.

And earlier you had said like you were making it to the end stage of a lot of interviews, even at Fang, Meng companies. In hindsight, what do you think made the difference in getting those three job offers ⁓ and then ultimately, you know, saying yes to Blue Origin?

Andrew Milmoe (07:03)

A ⁓ big part of it, I had run out of steam a bit because of getting so close and then kind of blowing it in the last interview. And so that really created a lot of anxiety and I was kind of insecure about like, why is this not working? I couldn’t really diagnose what was going

Sarah Doody (07:23)

you said you realized your portfolio was kind of too dense and focused on the intricacies of the product and you weren’t explaining your contributions. And I’m wondering, I guess one of my hunches is in redoing your portfolio through the way that we teach in CSL, do you think that impacted your ability?

to talk about that stuff in interviews and was that maybe one of the things that helped you seal the deal and create, an asset that converts?

Andrew Milmoe (07:56)

Yeah, for sure. By scrapping everything and starting over, I was able to really clarify the message of what it is I have to offer and ⁓ what’s specific about what I enjoy about UX design and the impact I can have. And so once I had that clarified, was able to, ⁓ as I made each, worked on my resume, worked on my LinkedIn, worked on my portfolio, I was able to keep bringing back that same message so that it was baked into everything I presented.

And so there was no way, you at end of an interview people knew exactly who I was and what I was able to do. ⁓ Whereas before things were just kind of all over the place and there wasn’t a lot of cohesion between my LinkedIn and my, you I didn’t have like a core message.

Sarah Doody (08:43)

Right. Right. That through line and core message, as you said, is so important because ⁓ when there is inconsistent messaging and positioning in your resume, your portfolio, your LinkedIn, et cetera, not only does it mean that probably you are unclear about your own positioning, as you kind of alluded to, but definitely that means that recruiter or hiring manager is also going to be confused. And I think that’s

such an important point that you made around that developing that consistency and clarity around that story of who you are and what you’re able to do.

Andrew Milmoe (09:22)

Yeah, it was a good differentiator because they’re talking to a lot of people and if they leave the interview with one core thing about, that’s the guy who did this or he’s good at that, that gives them something to latch onto in their minds.

Sarah Doody (09:36)

Yep. Yeah, it helps you stay top of mind for sure.

Andrew, I’m curious your perspective on the iteration cycles and what about Career Strategy Lab helped you with these iteration cycles in tackling parts of these big portfolio projects that you had and making them be more about what you did and less about the actual product.

Andrew Milmoe (10:05)

Yeah, definitely, I feel like by starting over, I was able to really focus on the message and evaluate, know, I’ve got all this, I had all this material and I was able to sort of filter through it and say, okay, these are the sort of the key points that support my message versus telling the entire story in full detail. Because I, yeah, I’m very detail-oriented and so I kind of got caught up in the details and trying to make it perfect and.

lot of the time in the Career Strategy Lab, it’s just like, okay, spend an hour, do the best you can, and then keep going. Don’t spend three weeks on, like you said, honing a bullet point. At the end of the day, they might not even look at it. So ⁓ crafting that sort of higher level message from the top down is much more effective and sort time boxing things and just keeping things moving forward was super helpful.

Sarah Doody (11:01)

I’m curious, know, one of the things that I see with job seekers is oftentimes…

because you’re stuck in these iteration cycles and often not getting a lot of feedback when you’re doing this DIY approach that both of you did before you joined CSL, that DIY approach and lack of feedback can often, and the constant iterations, can often influence your confidence. And I’m

thinking back, where was your kind of confidence at whether it’s,

in your materials, in yourself, in other areas, you know, before you join Career Strategy Lab versus what happened after joining? Does anything come to mind?

Andrew Milmoe (11:49)

Yeah, I think before I joined I like, I’d gotten laid off when the dot com, when the startup crashed. I was like, oh, no big deal. I’ll just hop on apply for a few things. I’ll get another job. And when that didn’t happen, I started freaking out. then, yeah, it’s just.

that.

It was difficult to get the motivation to go back. When I was DIY-ing stuff, I’d come off of a rejection and it was really difficult to get the motivation. they said, OK, well, this didn’t work. So now I have to try to fix it again. And then it didn’t work again. And I was like, I thought I fixed it. But obviously, I didn’t. So then what am I not fixing that needs to be fixed? And just kind of got in this loop of frustration.

And so I was also afraid. I mean, it’s also tricky because it’s like as a designer, you’re like, oh, I should be able to design this. I’m just designing my portfolio. But it. Yeah. I didn’t have, you know, when I’m designing something for as a job, you have access to do like, you know, user research and and and and get feedback from people who are going to use the tool. And so it’s I didn’t have access to like.

Emmanuel Guerra Gunzel (12:59)

worst exercise in my opinion.

Andrew Milmoe (13:18)

get feedback from recruiters necessarily when I was doing that on my own or from hiring managers. so, yeah, it’s a, and the thing that sort of clicked too is like thinking of myself as a product or as a service and packaging that up and selling that instead of. ⁓

Sarah Doody (13:32)

Mm.

Andrew Milmoe (13:39)

trying to sell the, I kind of got into this thing of trying to sell the products that I had worked on, was not, they don’t care about that. They don’t need to know about how a drill ship works or whatever, it’s like they’re a wind farm. just want to know what does Andrew Milmo have to offer as a service to our business to help us improve and getting into the details of some of the project is just, it’s, there’s.

You have to do a little bit of that just to sort of give it some context, but that’s not what you’re telling them. That’s not what they want to hear. And I just got into sort of an iterative cycle that wasn’t bearing any fruit.

Sarah Doody (14:24)

I love how you described the contrast between you previously trying to almost sell the company on the product versus sell you as a service provider to that company that you’re applying to. And it’s almost as though when you’re applying for jobs, if you almost think of it as you’re a freelancer trying to get them to say yes to sign a contract with you, that mindset,

it really forces you to focus on the features of you, right, versus the wind farm or whatever it was.

Andrew Milmoe (15:02)

Yep, for sure.

Sarah Doody (15:03)

I want to just address this question of like, is Career Strategy Lab more geared towards senior or mid-level or senior, et cetera? And when I first started this, I didn’t know, I knew what I was doing. I didn’t know what I was doing marketing wise really. And it was attracting a lot of junior people because at the time in 2021, there was a lot of junior people, right? Over the years that has shifted drastically. And I would say there’s like,

40, 50 % of people who have 10 or more years of experience. And would either of you like to speak to the idea of how does Career Strategy Lab work with people at various levels of their career? Because I think a lot of people assume it can’t work for me if I have 20 years of experience and there’s people with five and one year of experience in there, but.

I have my own thoughts, but I’m curious if either of you have thoughts on how everyone can co-mingle and co-mingle, let’s say that. Co-exist is a better word. How can people co-exist at different levels of their career inside Career Strategy Lab?

Andrew Milmoe (16:16)

I feel like one of the benefits was knowing that there were other sort of principle level people out there who were also struggling and hearing what they were struggling with. Because it’s, you know, there are a lot of materials out there for people who are more junior and it was, I was able to pair off with people who were more junior and give them and sort of mentoring to some extent of, you know, my advice of knowing like what it was like when I was in that.

stage and I think it’s also probably beneficial for them to hear how principle level people are presenting themselves and what challenges they have and selling themselves into a higher level role. So that was kind of the main one of the benefits for me was just having hearing other principle level people discuss the roadblocks they’re running into and understanding like you know I’m not I’m not

I’m not the only person experiencing this frustration and these challenges. And it was interesting to hear sort of their approaches and what they were struggling with and going like, oh, OK, maybe I could help them with that. Or that’s something I could reach out to them and get more nuance or have them get into the details of how they approach something.

Sarah Doody (17:37)

Yeah, I think regardless of the years of experience that you have, a lot of the root problems are still the same, right? Whether it’s ⁓ struggling with writing your case study or what your resume bullet points are or getting clarity around who you are and what you do. mean, that these steps to do that are the same regardless of how many years of experience you have. It’s just that the content of someone like Andrew for your portfolio

will be different than someone who just graduated from University of Washington’s design program, right? So the approach is the same. It’s just the content is different.

Andrew, I’m curious because you’ve been out of CSL, at least like actively ⁓ for a while, but I’m curious, how has the community part of Career Strategy Lab impacted you and have you stayed in touch with people afterwards? like, tell us a little bit more about that.

Andrew Milmoe (18:41)

I guess I was definitely more involved in the community when I was in the program. And it sort of trailed off over time because I sort of found other communities just sort of organically as I was, and I had a lot of, I had to start learning about aerospace so I trying to get involved in all that.

Sarah Doody (18:46)

Yeah.

Yeah.

Andrew Milmoe (19:07)

I do check it back in time to time just to see if like if I hear about something that sounds really cool, I’ll post it as a job just to say like wow, there’s somebody probably really dig this and share that. ⁓ Or if I knew somebody that was looking for a UX designer. ⁓

Yeah, and I guess I wanted to backtrack a little bit. mentioned things I would do differently in CSL. I…

Sarah Doody (19:36)

Yeah.

Andrew Milmoe (19:39)

As I was looking at the progression of my career, didn’t give myself enough… ⁓

Like I had done different things over the course of my career and the job I took was kind of a backtrack and I was like, ah, that’s no big deal. It’s not exactly what I want to do, but it’s something I know I can do and so I’ll give it a shot and it turns out it was really hard to get motivated to do that work because I was like, oh, I’ve already done this before. So I sort of, the CSL really helped me frame what it was I was looking for.

Sarah Doody (20:08)

Hmm.

Andrew Milmoe (20:18)

and I kind of got tempted by the industry and sort of pushed my career back a little bit as a result of that. And in hindsight, that was probably a mistake. ⁓ So yeah, think if I’d have stuck with what I learned a little bit more from CSL, I think I would have benefited from that. But yeah, I don’t know. mean, nobody’s career is perfect. I still learned a ton.

Sarah Doody (20:44)

It’s not linear, that’s for sure.

Andrew Milmoe (20:47)

I still learned a lot and it’s as long as I’m always learning and ⁓ connected to communities that are beneficial and contributing to them. It’s a good habit to get into. It’s just a more fulfilling way because at least me, I tend to be in a job for three to six years and so I know some people I stay in touch with and other people I don’t.

Sarah Doody (21:15)

Yeah.

Andrew Milmoe (21:15)

having communities and being able to jump into a community and get involved and then jump into another community. ⁓ I feel like it’s just a pattern you have to get into.

Sarah Doody (21:22)

Yep.

Yeah, our needs change at various points in our career, right? But the one thing that you said, like you very actively and intentionally post jobs in the community and in the LinkedIn group when you think they might be relevant to other people. And that’s one of ⁓ the benefits of Career Strategy Lab that I literally was not thinking about when I created all this, because now with like 800

little over 800 alumni, we’re at the point where alumni are hiring each other, which blows my mind. But I think it’s a very powerful part of this community because even if you’re not actively in there every week or something, someone might post a job a year from now and it’s like a perfect fit. just like having an in with this community is really powerful in my

what would you tell someone who is on the fence about joining Career Strategy Lab?

Andrew Milmoe (22:25)

know it’s an investment and you have to invest in yourself. And if you don’t and you just wait, then you’re using you’re losing months of salary. So it’s like, I feel like the sooner you invest in yourself and you know, get involved in the program, you can have a bigger impact on your career, you know, in less time or sooner. Because I felt like, you know, if I had to wait another six months to sign up or if I had to

found it earlier, discovered it earlier, realized I needed it earlier. I could have found a job six months earlier. So, you know, no time like the present.

Sarah Doody (23:05)

Well, I’m glad you said that because it answers a question, which was, did you find the investment required daunting when you didn’t have a regular salary? And I think your answer is very relevant. It’s like, yes, it is an investment. And if you think long term and if you get hired three months faster or two months faster or whatever, like, what’s the what’s the cost benefit analysis of that? Right. But I think to.

When you think about the long-term impact of this, meaning you find yourself in an unexpected layoff or some amazing job gets posted in the CSL community, you’re maybe not ready to apply that day, but you’re ready to apply a lot faster because you have all this stuff buttoned up or, and or I guess, you know what you need to do to go quickly update one or two case studies or

your resume, et cetera. it’s kind of like the long-term downstream effect of this too.

Andrew Milmoe (24:12)

Yeah, that brought up another thing. I feel like I was a little too scatter shod when I was applying for things. I was like, well, that sounds kind of cool. I’ll apply for it. And not taking into account that like that takes effort and energy. And if I had just spent more time saying, okay, focus on like three or four roles that sound like, you know, now that I’ve gone through CSL, like these are the roles that are really going to fit what I want to do and really apply for those instead of just like throwing resumes everywhere.

and then you get it anyway if you do get interviewed you’re like well yeah I guess this is not a good fit I wasted everybody’s time like that’s not a good feeling either

Sarah Doody (24:46)

Yeah.

brought up this topic of ⁓ essentially playing the numbers game, right? Applying to high volume of jobs and kind of rolling the dice, so to speak. ⁓ When you changed that approach, was there an impact to your confidence? Because what I find is…

Emmanuel Guerra Gunzel (24:54)

Mm-hmm.

Sarah Doody (25:10)

you know, if you’re applying to tons of jobs, the numbers just say you’re going to get more rejections, right? If you’re applying to some role that needs a decade of mobile experience and you have one year, I mean, you’re probably going to get rejected. was there a confidence shift when you also switched that approach from apply to fewer jobs, but more of the right jobs?

Andrew Milmoe (25:31)

one of the benefits of focusing on a particular industry or a enterprise versus a small business, whatever, the more you can sort of focus yourself in, then there’s probably a pool of companies in that zone. And any research you do or any podcast you listen to or anything you do sort of builds up your knowledge of what they’re looking for and how that space works and how that industry works.

And so when you do land an interview with one of those companies, you can speak more knowledgeably about how, you know, how you went to what you have to offer to them. And so not telling a brand new story every time. You know, I had gotten an interview with a social networking company and it was a freak show. Like they didn’t know how to interview me. They were asking me questions that were like, I got interviewed by somebody who was like right out of college and they were asking me like,

very low level UX questions. like, yeah, I’ve been doing this for 20 years. Like, of course I knew that. And I was like, this is like, it was just complete mismatch. And the recruiter was like, oh, sorry about that. I was like, why’d you even, like, why’d you even talk to me in the first place? This is nuts. And yeah, it just, it was really frustrating because I got, and also I got very excited about it. I was like, oh, this would be amazing. But it was, yeah, it was just not a match. So I feel like the more you can…

really apply yourself to a position and really think about, okay, this is what they’re looking for. This is what the industry is doing. Like there’s a company I’m kind of going after right now. And I was able to find like I, they’d interviewed me before. So I reached back out to that interviewer and connected again. And I’m looking at like what their products are and how they’re going to shape the company and their CEO was in a podcast. Like it’s just, the more you can sort of build up like knowledge in a space.

the more you can really nail the interview instead of just kind of, well that looks cool.

Sarah Doody (27:36)

Yeah, and I think too, you you’re a great example of this. Like you had interviews at Fang and Meng companies and everything, but ⁓ there is just such a misconception out there, I think, with job seekers about, you know, there’s all these discussions around is UX going away, et cetera. And I think, do you use the Internet? Do you like live in the world today? Because every day I encounter bad user experience everywhere. And if you think of like

the industries you were describing like aerospace or like energy or hardware software. mean, I think there is such value in kind of becoming a specialist, not in terms of UX, but in an industry as you described, or at least doing the research to become knowledgeable out it for the interviews.

Andrew Milmoe (28:26)

Yeah, they’re starved for, especially like aerospace right now. People get, they’re like, oh my gosh, I don’t know anything about aerospace, but it’s like read a few articles, learn about what their needs are. cause there’s nobody, there are no UX designers that, know, there’s 10 or something. It’s like, there’s a very small pool of people who actually have a lot of experience in that industry. And so they’re, they’re more open to people switching over. But the more you can show an effort of like, hey,

I know I don’t have this industry in my background, but I’ve done a lot of research and I can speak to it and I understand the jargon, the lingo, whatever. That’ll get your foot in the door and then it’s sort of up to you to apply yourself. ⁓

Sarah Doody (29:09)

Yep.

Yeah, we have alumni at Delta Airlines and JetBlue, and I don’t think either of them worked in aviation before, ⁓ but they do now. as you said, like you don’t need to be an expert, but just show that you made an effort, right? Show that you put some amount of work into understanding that business, company or industry before the interview, and you will instantly be ahead of

all the other candidates.

back, what do you wish you could have prioritized during your time in CSL? I think we covered that, but is there any one or two word answers that jump out to you?

Andrew Milmoe (29:48)

I think don’t worry about going forward because you can always circle back. if you, I found it like three steps in, it’s like, you know what? want to tweak my statement. And you do that. You’re not.

Sarah Doody (30:02)

Yeah, it’s, CSL is organized in these sprints, which we recommend you do in a certain order, but it’s not rigid. Like if you get an interview and it’s two weeks from now, obviously go to the interview part of Career Strategy Lab. Like it’s, you know, I give you the tools, I give you the knowledge, but you also have to, you know,

Use your own critical thinking and jump around and work on it linearly when it makes sense. yeah. Okay. When you run out of critiques, ⁓ we currently don’t have a way for you to do one-off, like purchase one-off critiques. That may change in the future, but for now, there are no additional critiques. If you want to stay in Career Strategy Lab after your initial time is over, you can extend your time.

and get additional critiques. But I will say, ⁓ I just released these new AI tools inside of Career Strategy Lab to also help with that challenge in that there is a specific resume AI tool, a specific case study AI tool, and a specific compass statement AI tool. And so I created those so that people could gut check with those if they were nervous about submitting critiques and using critiques or

if you run out of them. Plus the community, like the community is so generous with providing feedback. So you will get awesome feedback from everyone else. And it’s very high quality feedback because everyone is operating from the same, you know, set of instructions. And if you asked your peer for feedback on your resume and it’s one page, they’re going to say, why the hell is your resume one page? Sarah doesn’t tell you to make a one page resume.

And I think that is all. So Andrew again, thank you so much for sharing your